CONTACT US
Showing 12 of 15 properties



House

Southern Exposure (SKLRP)

Southern Exposure (SKLRP)

This gorgeous five-bedroom, four-bath home on Siesta Key is a must-see! Ideally located steps from the Siesta Key Village with all of the best shopping, dining, and entertainment. It is only minutes from the soft sands at the World-Famous Siesta Key Beach! This Beach Home is filled with Modern Personality! You will be amazed when you walk inside this home away from home. The fresh white interior feels extremely spacious. The living room is filled with an abundance of natural light and also boasts an incredible white brick faux fireplace! The open floor plan flows into the cozy dining area and then into the spacious kitchen with granite countertops and all stainless steel appliances. There is additional counter seating for three. Just off the kitchen is the laundry room equipped with large front loading washer and dryer. Every inch of this home has been meticulously maintained and expertly updated! Home Layout: • Bedroom #1 - King Bed w/ ensuite bathroom • Bedroom #2 - King Bed w/ ensuite bathroom and sitting area • Bedroom #3 - King Bed • Bedroom #4 - Queen Bed • Bedroom #5 - 2 Twin Beds Step outside into your private backyard oasis that features a soft turf yard and inground pool complete with an in water sundeck for relaxing. There are additional loungers for a quick cat nap in the sun! Finally, there is a grill and outdoor table with umbrella to enjoy an island bar-b-que! Come enjoy some island time at Southern Exposure! You may never want to leave this paradise! This property allows pets - there will be an additional pet fee associated. Siesta Key Luxury Rental Properties Pet Policy: Dogs are allowed under certain conditions and ALL animals, including service animals, must be disclosed and approved prior to arrival. We cannot accept cats. *Please note that there will be an additional non-refundable pet fee charged upon approval by Siesta Key Luxury Rental Properties.* Weight limit of 50 lbs max total for 1 or 2 dogs combined. No dangerous breeds allowed. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. This home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

5 4 10
BOOK NOW

House

On The Rocks (SKLRP)

On The Rocks (SKLRP)

On The Rocks by Siesta Key Luxury Rental Properties 309 Calle Miramar Siesta Key, Florida Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key! Let the fun begin at On The Rocks! This spectacular five-bedroom and five-bathroom home is just minutes from the world-renowned Siesta Key Beach and is a short block from Siesta Key Village, offering guests a wide selection of restaurants, bars, and shops! The getaway offers amazing amenities, including a private pool with a waterslide, a putting green, and a private balcony. So, pack your bags and head to On The Rocks for an unforgettable vacation experience! As you step into the living area, you'll immediately be greeted by the coastal atmosphere with its dynamic shades of blue and beach-inspired decor. The kitchen has stainless steel appliances, custom cabinetry with ample storage space for your groceries and a gorgeous dining table right in the center that can comfortably seat all your guests. Right beyond the seating area, equipped with a sofa, side chairs, and TV, lies the deck which offers a high-top table and overlooks the pool area. The luxurious primary bedroom has bright decor, access to the inviting upstairs deck, and a stunning ensuite bathroom complete a walk-in shower. Your guests will love the three guest rooms, each equipped with a luxurious King bed and its own ensuite bathroom featuring a walk-in shower. The fifth bedroom is a whimsical dream for kids, adorned with Sea Life artwork and equipped a bunk bed and a TV. Conveniently located nearby is the hall bathroom, featuring a shower and tub combination. The laundry room down the hallway includes a washer and dryer for your convenience. Room Details -Primary Bedroom, 2nd floor: King bed, balcony access, and ensuite bathroom with walk-in shower -Second Bedroom, 2nd floor: King bed an ensuite bathroom with walk-in shower -Third Bedroom, 2nd floor: King bed an ensuite bathroom with walk-in shower -Fourth Bedroom, 2nd floor: King bed an ensuite bathroom with walk-in shower -Fifth Bedroom, 2nd floor: Full over Full bunk bed with Twin trundle -Bonus, Living Room: Queen Sleeper Sofa The backyard of this house is truly amazing. It features a premier pool with a sunshelf, a waterslide, and an in-ground spa. On the side of the house, you'll find a grassy area where kids and dogs can play, as well as a putting green. The covered patio is perfect for relaxing, with a cozy seating area, a TV, a BBQ grill, and an outdoor dining table. Siesta Key Beach Complex is located just South of the house. It has concessions, volleyball courts, bathrooms, showers, and a playground for kids. Plan your dream escape to On The Rocks today! - This property participates in our Professional Linen Program. This ensures high quality linens and towels are Always included for your stay. These are professionally laundered at a commercial facility for every guest. This property has an active Ring doorbell and additional video surveillance on the pool equipment only. This property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated, see our Siesta Key Luxury Rental Properties Rental Policies for full details. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. This home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund. At A Glance • Private Pool with Waterslide and In-Ground Spa • Less than a 5-minute walk to the beach • Putting Green • Dog Friendly • Near restaurants and boutiques

5 5 15
BOOK NOW

House

High Tide (SKLRP)

High Tide (SKLRP)

High Tide by Siesta Key Luxury Rental Properties 141 Avenida Veneccia Siesta Key Siesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key! Welcome to High Tide, a spectacular home with six bedrooms and six-and-a-half bathrooms just a two-minute walk from the Gulf of Mexico beaches! Nothing will beat the attention to detail and incredible amenities in this home, and best of all, this home has a rooftop deck with mesmerizing water views and a backyard oasis with a top-notch pool. The main living floor features a comfortable seating area with premium sofas, a TV, and wooden accents that enhance the beach atmosphere. You will find a fully equipped kitchen with top-of-the-line stainless steel appliances, cookware, utensils, and a breakfast bar with six chairs. The spacious dining room table is perfect for indoor meals, while the large deck, furnished with a dining table and rocking chairs, invites you to enjoy al fresco. The primary bedroom offers a serene and calming vibe, complete with gorgeous blue hues, a personal balcony, and a chic ensuite bathroom featuring two vanities and a walk-in shower. You will love the tropical vibes that every room exudes, not to mention the ample storage space and TV in each one. The four King-sized bedrooms come with their own ensuite bathrooms that boast walk-in showers, while the sixth bedroom is perfect with two bunk beds, a cozy sitting area, and a lovely ensuite bathroom that features a shower and tub combo. For your convenience, a washer and dryer are available for guest use. Room Details -Primary Bedroom, 2nd floor: King bed, balcony, and ensuite bathroom with walk-in shower and two vanities -Second Bedroom, 2nd floor: King bed, balcony access, and ensuite bathroom with walk-in shower -Third Bedroom, 2nd floor: King bed and ensuite bathroom with walk-in shower -Fourth Bedroom, 1st floor: King bed and ensuite bathroom with walk-in shower -Fifth Bedroom, 1st floor: King bed and ensuite bathroom with walk-in shower -Sixth Bedroom, 2nd floor: Two full over full bunk beds and ensuite bathroom with shower and tub combo This home offers a variety of amenities suitable for all ages! You can enjoy a stunning heated pool, an in-ground spa, and a thrilling slide that leads into the pool. There's also an excellent island bar where you can make delicious drinks, a grill to cook tasty meals, a cozy sitting area with a TV, and a ping pong table for some fun. If you head upstairs to the game room, you'll find a poker table along with a wet bar, wine fridge, and a mini fridge! Explore the island and enjoy boutiques, coffee shops, fresh ice cream, and restaurants at Siesta Key Village. Soak in the beautiful waters at Siesta Key Beach and make the perfect vacation happen at High Tide! - This property participates in our Professional Linen Program. This ensures high quality linens and towels are always included for your stay. These are professionally laundered at a commercial facility for every guest. This property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated, see our Siesta Key Luxury Rental Properties Rental Policies for full details. 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. This home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund. At A Glance • 2-minute walk from the beach • Heated private pool with spa and waterslide • Rooftop deck • Game room • BBQ grill

6 6.5 18
BOOK NOW

Townhouse

Dry Dock

Dry Dock

Siesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key! Dry Dock by Siesta Key Luxury Rental 515 Canal B Siesta Key Welcome to Dry Dock, a desirable canal-front townhouse with a shared dock only a block from the white sands of Siesta Key Beach. Your guests will love boating, kayaking, paddle boarding, and fishing from the backyard in modern coastal comfort. The elevator makes move-in a breeze. Enjoy refreshments and watch a stunning sunset over the Gulf on the rooftop deck before relaxing in the private pool and hot tub. Restaurants, boutiques, coffee shops, and ice cream are three blocks away at Siesta Key Village. Because you are centrally located near all the major island attractions in a home with such desirable amenities, hosting a fantastic stay will be a breeze. Dry Dock has two levels of living space over the garage, easily accessed with the elevator. It accommodates up to eighteen guests with six bedrooms and six and a half baths for eighteen guests. The living room features an oversized sectional for guests to gather and connect over a conversation, a movie, or relax after a day of island adventures. It also provides access to the second-level balcony, where guests can sit at the bistro table and read or sip coffee while overlooking the canal. The kitchen offers generous counter space for preparing delicious island meals and snacks in an updated, fully equipped kitchen with stainless steel appliances that will delight your family chef. The kitchen island seats six for quick snacks and breakfasts. The adjacent banquette-style dining table seats 12 comfortably for your guests to enjoy home-cooked meals, take-out, or board games. The seating co-location allows all eighteen guests to dine together in a shared space. The primary bedroom offers peace and relaxation with spa hues, featuring generous closet space and an ensuite bathroom with a shower/tub combination. Guests in the second bedroom will enjoy relaxing on their private balcony after freshening up in the ensuite bathroom. The third and fourth bedrooms each have ensuite bathrooms with walk-in showers and share access to a balcony overlooking the canal, which has access to the rooftop deck. The fifth bedroom’s nautical hues will delight younger guests. It has an ensuite bathroom, a shower/tub combination, and a closet for storage. Finally, the sixth bedroom is excellent for teens or singles to relax and unwind, and it has a convenient ensuite bathroom with a shower/tub combination. This fantastic offering has a little something for everyone. Host refreshments and enjoy endless ocean views from the rooftop deck. The covered patio has an outdoor bar with seating for five, a conversational seating area where guests can watch a movie on the outdoor TV, and ping-pong for the more competitive friends. Cool off, relax in the backyard pool and hot tub, and rest in the surrounding lounge chairs while watching boats and wildlife on the canal. A paddleboard and kayak are included with the rental, just sign the waiver, and you are ready to explore. To double your party, consider renting the unit next door that shares a common wall and has a mirrored layout. Sleeping Arrangement (Sleeps 18) Primary Bedroom, Second Level – King Bed, ensuite bathroom with shower/tub combination Second Bedroom, Third Level – King Bed, ensuite bathroom with walk-in shower, private balcony Third Bedroom, Third Level – King Bed, bathroom with walk-in shower, shared balcony Fourth Bedroom, Third Level – King Bed, ensuite bathroom with walk-in shower, shared balcony Fifth Bedroom, Third Level – Two Sets of Twin Bunk Beds, ensuite w bathroom with shower/tub combination Sixth Bedroom, Second Level – Full over Full Bunk Beds, ensuite w/ bathroom with shower/tub combination Siesta Key Luxury Rental Properties Pet Policy: Dogs are allowed under certain conditions and ALL animals, including service animals, must be disclosed and approved before arrival. We cannot accept cats. *Please note that an additional non-refundable pet fee will be charged upon approval by Siesta Key Luxury Rental Properties.* Weight limit of 50 lbs max total for 1 or 2 dogs combined. No dangerous breeds are allowed. Please see our Siesta Key Luxury Rental Properties Rental Policies for complete details. This property has an active Ring doorbell, active video surveillance on the exterior public approach areas, and the pool equipment. This property participates in our Professional Linen Program. This ensures high-quality linens and towels are always included in your stay. These are professionally laundered at a commercial facility for every guest. If you have any questions concerning our home, rates, amenities, policies, or anything else, please send us an inquiry. One of our professional reservationists and property managers would be happy to help answer your questions. You are a couple of clicks away from paradise, and we look forward to seeing you soon. At A Glance • Canal Front Home with Dock Access • 2-minute walk from the beach • Private Pool and Hot Tub • Pet Friendly • Ping Pong Table • Elevator • Professional Linen Program

6 6.5 18
BOOK NOW

House

Shell-Abrate Good Times

Shell-Abrate Good Times

Siesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key! Shell-Abrate Good Times by Siesta Key Luxury Rental Properties 85 Avenida Messina Sarasota FL 34232 Welcome to Shell-Abrate Good Times, a brand-new luxury home just a one-minute walk to Siesta Key Beach and four minutes to Siesta Key Village. This six-bedroom, eight-bathroom, new construction home can sleep up to twelve guests. The open living design gives guests sunny and airy space to sit back and relax, gather for a movie night, and connect over fun conversations. The fully equipped kitchen is a chef’s dream, with brand-new appliances and a generous counter space that makes meal prep a breeze. There is a large kitchen island with seating and a dining table. After dinner, grab your favorite drink and head to the 2nd-floor balcony to watch a breathtaking Siesta Key sunset. The primary, second, and third bedrooms are on the 2nd level. Let all your worries disappear as you drift off to sleep in the primary bedroom that features a private deck! Other primary bedroom features include an ensuite bathroom with a double vanity, a spacious tub, a walk-in shower, and an oversized walk-in closet. The second and third bedrooms have ensuite bathrooms with walk-in showers and have access to the uncovered deck, where they can relish in the island breeze before heading to bed. The fourth, fifth, and sixth bedrooms are on the main level. The fourth bedroom has a covered patio perfect for a quiet getaway and an ensuite bathroom with a walk-in shower. The fifth bedroom has ample closet space for storage and an ensuite bathroom with a walk-in shower. The sixth bedroom is perfect for younger guests after a long day of exploring, as they can refresh in the ensuite bathroom shower/tub combo. Additionally, there are half bathrooms on the main level and 2nd floor. Enjoy a relaxing day at Siesta Key Beach, where the soft sand covers your feet, the water is warm, and the waves are calm. Return to this incredible backyard oasis, swim in the gorgeous new pool or bask in the sun on one of the lounge chairs. Stroll to Siesta Key Village to enjoy boutiques, coffee shops, fresh ice cream, and restaurants. Investigate the island with a Siesta Key tour, kayak, or paddleboard the calm intercoastal waterway and beautiful Tampa Bay, where you might encounter a dolphin or manatee, or charter a fishing trip to see who brings in the biggest catch. The possibilities are endless! Sleeping Arrangements: Primary Bedroom, 2nd Floor: King bed, private deck, and ensuite bathroom with walk-in shower and tub Second Bedroom, 2nd Floor: King bed, deck access, and ensuite bathroom with walk-in shower. Third Bedroom, 2nd Floor: King bed, deck access, and ensuite bathroom with walk-in shower. Fourth Bedroom, 1st Floor: King bed and ensuite bathroom with walk-in shower. Fifth Bedroom, 1st Floor: King bed and ensuite bathroom with walk-in shower. Sixth Bedroom, 1st Floor: Full over full bunk bed with ensuite bathroom. This property allows pets - there will be an additional pet fee associated. Siesta Key Luxury Rental Properties Pet Policy: Dogs are allowed under certain conditions and ALL animals, including service animals, must be disclosed and approved prior to arrival. We cannot accept cats. *Please note that there will be an additional non-refundable pet fee charged upon approval by Siesta Key Luxury Rental Properties. * Weight limit of 50 lbs max total for 1 or 2 dogs combined. No dangerous breeds are allowed. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. This property participates in our Professional Linen Program. This ensures high-quality linens and towels are always included in your stay. These are professionally laundered at a commercial facility for every guest. If you have any questions concerning our home, rates, amenities, policies, or anything else, please send us an inquiry, and one of our professional reservationists and property managers would be happy to help answer your questions. You are a couple of clicks away from paradise, and we look forward to seeing you soon. At A Glance • 1-minute walk from the beach • 4-minute walk from Siesta Key Village • Private Pool, Hot Tub, and Waterslide • Elevator • Professional Linen Program

6 7 14
BOOK NOW

House

Summer House

Summer House

Summer House by Siesta Key Luxury Rental Properties 99 Avenida Messina Siesta Key, Florida Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key! Welcome to Summer House! This amazing, ground-level vacation home has six bedrooms and six bathrooms and is sure to become your friends and family's go-to vacation spot. The outdoor entertainment area is truly exceptional, with a magnificent pool and three seating areas that are ideal for hosting gatherings and creating unforgettable memories. Upon entering, you will be greeted by a stylish and spacious living area with cozy seating, a beautiful dining space, and a fully equipped kitchen. You'll have everything you need to feel comfortable and at ease. You can relax and watch your favorite TV shows on the large screen, grab a quick bite at the kitchen island, and cook delicious meals, as the kitchen is equipped with stainless steel appliances and essential cooking tools. The indoor dining area features a comfortable breakfast nook-style dining table and a bar-top seating area for your pleasure. Wake up refreshed in one of the six dreamy bedrooms, each with an ensuite bathroom, ready to explore Siesta Key and the surrounding barrier islands. The primary bedroom radiates a delightful beach theme and offers the largest ensuite bathroom, complete with a double vanity and walk-in shower. We have three additional rooms designed with the adults in mind, as well as two bedrooms with bunk beds, perfect for the kids to unwind and play. Every room has a television and ample storage space, ensuring comfort and convenience. And to make your stay even easier, the home has a washer and dryer. Room Details -Primary Bedroom: King bed and ensuite bathroom with walk-in shower and double vanity -Second Bedroom: King bed and ensuite bathroom with walk-in shower -Third Bedroom: King bed and ensuite bathroom with walk-in shower and double vanity -Fourth Bedroom: King bed, porch access, and ensuite bathroom with walk-in shower -Fifth Bedroom: Two Full over Full bunk beds and ensuite bathroom with walk-in shower -Sixth Bedroom: Full over Full bunk and ensuite bathroom with a shower and tub combo Let's kick off this vacation! Summer House boasts a spectacular pool with a breathtaking grotto, a rock waterslide for the kids (and the young at heart), and a spa where you can relax and soothe your muscles after exciting days of exploring. The backyard has two seating areas: a covered porch with plush wicker seats and the second offers a fantastic atmosphere with unique swings, outdoor television, and bartop seating. Break out the cards and some drinks, and let the good times and reminiscing begin. Within a short walk, you will discover the vibrant collection of shops and restaurants in Siesta Key Village. You'll also find the beach, which has been voted the best beach in the USA several times. We can't wait for you to experience the beauty and relaxation of Summer House! - This property participates in our Professional Linen Program. This ensures high quality linens and towels are Always included for your stay. These are professionally laundered at a commercial facility for every guest. This property has an active Ring doorbell and additional video surveillance on the pool equipment. This property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated, see our Siesta Key Luxury Rental Properties Rental Policies for full details. 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. This home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund. At A Glance • 2-minute walk to the beach • 2-minute walk to Siesta Key Village • Pool with spa and waterslide • Outdoor living space • BBQ grill

6 6 22
BOOK NOW

Townhouse

Village Time

Village Time

Village Time by Siesta Key Luxury Rental Properties 355 Calle Miramar Sarasota, FL 34242 Welcome to Village Time, a terrific choice for multi-family groups booking accommodation together, as each can enjoy their own separate space while staying close. Offering a total of six bedrooms, six full baths, and two half baths in two unique living areas, this home is a quick walk to Florida's prettiest beach and near Siesta Key village, which offers a wide variety of restaurants and shops. On each unit's main living floor are coastal living rooms with plush sofas and fully equipped kitchens, including utensils, pots, and pans, and they have their own dining tables and bar-top seating. Additionally, each unit has a half bath and a washer and dryer. This beautiful duplex offers six bedrooms, six full baths, and two half baths. Each side has three bedrooms and three- and one-half baths. A primary bedroom with a King bed, a balcony overlooking the sparkling pool, and an ensuite bathroom with a walk-in shower. The King guest bedrooms have tasteful beach décor, a balcony, and an ensuite bathroom with a walk-in shower. Across the hall is the bunk bedrooms, which are appointed with two bunk beds, a TV, and an ensuite bathroom with a shower and tub combo. Room Details Island Time West -Primary Bedroom, 2nd floor: King bed, balcony, and ensuite bathroom with walk-in shower -Second Bedroom, 3rd floor: King bed, balcony, and ensuite bathroom with walk-in shower -Third Bedroom, 3rd floor: Two Full over full bunk beds and ensuite bathroom with a shower and tub combo Island Time East -Primary Bedroom, 2nd floor: King bed, balcony, and ensuite bathroom with walk-in shower -Second Bedroom, 3rd floor: King bed, balcony, and ensuite bathroom with walk-in shower -Third Bedroom, 3rd floor: Two Full over full bunk beds and ensuite bathroom with a shower and tub combo Enjoy the Florida sunshine in the comfort of either backyard that features a dazzling pool and hot tub and open the gates to create a sense of togetherness. Guests can sunbathe and read their favorite book on one of the loungers. Complete the evening with a freshly grilled BBQ meal and share it at the covered picnic table, then head to the ground-level game rooms for some friendly rounds of Ping Pong and Foosball. This property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated, see our Siesta Key Luxury Rental Properties Rental Policies for full details. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. This home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund. At A Glance • Two separate living spaces perfect for groups • Less than a 5-minute walk to the beach • Two pools with in-ground spas • Balconies • Near Siesta Key Village restaurants and shops

6 7 28
BOOK NOW

House

Sugar Sand Cottage

Sugar Sand Cottage

Sugar Sand Cottage by Siesta Key Luxury Rental Properties 105 Beach Rd Siesta Key, Florida Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key! Welcome to Sugar Sand Cottage! This five-bedroom, three-and-a-half-bathroom Siesta Key home is located directly across the street from the Gulf of Mexico. This bright and sunny getaway boasts a serene backyard with a sparkling pool, and an incredible wraparound patio with deluxe seating and non-stop Gulf views. Inside is a fantastic open living space with a cozy seating area with a sofa, side chairs, and a TV. Get ready to cook up a storm in the dreamy kitchen, complete with sleek stainless steel appliances, beautiful tiling, and ample storage space. The dining area is truly the heart of the home, offering a combination of bar-top seating and a large dining table, making it the ideal place to gather with loved ones and entertain guests. This home has spacious bedrooms and a variety of sleeping options in a split floor plan. One side features the primary bedroom, which offers a comfortable night's sleep and an ensuite bathroom with a walk-in shower. The other two rooms have soothing blue tones and easy access to a beautifully detailed hall bathroom with a walk-in shower. Further down the hall is a second living space with an additional living room, a king bedroom, a bunk bedroom, and the third bathroom with a shower and tub combo. Each of the sofas can easily convert to sleeper sofas, providing even more sleeping options for guests. Room Details -Primary Bedroom: King bed and ensuite bathroom with a walk-in shower -Second Bedroom: Queen bed -Third Bedroom: Full over Full bunk with Twin trundle -Fourth Bedroom: King bed and jack-n-jill bathroom with shower and tub combo -Fifth Bedroom: Full over Full bunk and jack-n-jill bathroom with shower and tub combo While being right across the street from the beach, this home is also only moments away from the vibrant Siesta Key Village. Discover a plethora of dining options, shopping destinations, and entertainment venues that will make your vacation unforgettable. We can't wait for your stay at Sugar Sand Cottage! - Professional Linen Program: We ensure high quality linens and towels are professionally laundered at a commercial facility for every guest. Mid Stay Cleans and Linen Exchange is available for an additional cost. This property has an active Ring doorbell and additional video surveillance on the pool equipment only. At A Glance • 2-minute walk to the beach • Private Pool • Gulf views • Near restaurants and shops • Washer and dryer

5 3.5 19
BOOK NOW

House

The Pool House

The Pool House

Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key! The Pool House Siesta Key Luxury Rental Properties 98 Avenida Messina Siesta Key, Florida Welcome to The Pool House, a gorgeous Sunset Pointe home where you can lounge by the sparkling pool in year-round sunshine, enjoy easy access to Siesta Beach, and dine in Siesta Village steps away. With five bedrooms and four bathrooms, there is plenty of space for your beach-loving crew to unwind and enjoy paradise. Pack your sunglasses and flip-flops and get ready for fun. When you enter the home, you'll notice the luxe coastal decor and open and airy spacious feel. Gather guests for a movie night and grab a seat on one of the serene-colored sofas. Cooking is a breeze in the chef's kitchen with stainless steel appliances, a large island with countertop seating, and an open layout to allow for multiple cooks in the kitchen, and there is a formal dining table with a custom distressed-look top and seashell chandelier. You and your guests will love the three primary bedrooms on the first floor, each with a king bed, and some have ensuite bathrooms with walk-in showers. The second-floor bedrooms are arranged for the ultimate slumber party or multiple families traveling with two bedrooms, a loft area, a private balcony, and a shared bathroom with a walk-in shower. Room Details: First bedroom, 1st floor: King bed and ensuite bathroom with walk-in shower Second bedroom, 1st floor: King bed and ensuite bathroom with walk-in shower Third bedroom, 1st floor: King bed Fourth bedroom, 2nd floor: Twin over full bunk bed with a twin trundle bed Fifth bedroom, 2nd floor: King bed, Twin bunk bed, and furnished balcony. This home's unique backyard gives unlimited outdoor living options to entertain guests. Loungers surround the inviting pool and hot tub, providing a resort ambiance in the lush tropical landscape. A tiki hut with ping pong and ring toss complete the outdoor theme, and the covered patio has conversational seating, a bistro table, and a television and is fenced for pool safety. This desirable location is within walking distance of all the best spots on Siesta Key. You are just a few houses from the beach and less than a five-minute walk to Siesta Village, where you will find boutique shops, fantastic local restaurants, and amazing dessert stands. The Pool House is your perfect getaway for a dream vacation with nightly sunsets on the beach and daily fun activities. *Please note- the fireplace is not a working fireplace and is for decorative purposes only. This home is located on property at the Tropical Breeze Resort, but it is a stand alone home, rented separately from the Resort. This property participates in our Professional Linen Program. This ensures high quality linens and towels are Always included for your stay. These are professionally laundered at a commercial facility for every guest. This property has an active Ring doorbell, active video surveillance on the exterior public approach areas, and the pool equipment and gate. Want to stay with us longer than 2 weeks? Great! We just ask that you coordinate a day and time with us so we can have an additional clean done during your stay. There is an additional cleaning fee required for this and we would be happy to provide you with a quote. If you want to have your linens and towels replaced during this clean, we can do that too, just let us know. We are passionate about maintaining our homes and keeping them clean so we appreciate your cooperation on this. We will require an additional clean for every 2 weeks that you are in our home. Beach Towels and Beach Chairs are included. Don't forget to check out our Preferred Vendors for rentals, activities, tours, and more. Through our preferred vendors list, we offer Rental equipment: golf carts, mopeds, mini cars, umbrellas, bikes (daily/weekly), kayaks, paddleboards, fishing charters, adventure tours, sunset cruises, eco-tours and more. Our preferred vendors recommend some Services, Tours, and Equipment be reserved in advance due to limited space and high demand. After you've made your vacation rental reservation, feel free to inquire with your Property Manager on how you can secure your spot for these services, tours, and amenities. Or, if you would like to wait, you can check out these services when you arrive. Most of our preferred vendors offer our guests discounted services and priority status. Discounts vary between vendors, and our list of preferred vendors is being updated daily. Inquire today for more information and for instructions on how to add these packages to your stay. If you have any questions concerning our home, rates, amenities, policies, or anything else, please send us an inquiry and one of our professional reservationists and property managers would be happy to help answer your questions. You are a couple of clicks away from paradise, and we look forward to seeing you soon. At A Glance • Less than 5-minute walk to Siesta Beach • Private heated pool and hot tub • Tiki hut with Ping-Pong table • Dog Friendly • Near restaurants and shops

5 4 16
BOOK NOW

House

Bahama Mama

Bahama Mama

Bahama Mama by Siesta Key Luxury Rental Properties 5227 Calle Menorca Siesta Key, Florida Siesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key! Welcome to Bahama Mama, a stunning vacation home boasting five bedrooms and five bathrooms, located just a five-minute walk away from the picturesque Gulf of Mexico beaches! The backyard of this home is a true tropical paradise, featuring a sparkling pool with a spa, comfortable loungers, and a charming covered patio that includes an outdoor dining table, a television, and a BBQ grill. We can't wait to welcome you to this unforgettable retreat! As you step inside your dream beach vacation home, you will be greeted with a modern living space adorned with coastal touches that create a relaxing ambiance. The cozy seating area boasts a large TV, perfect for streaming your favorite shows. The fully equipped kitchen has stainless steel appliances, a spacious kitchen island that serves as an ideal spot for preparing large meals, seating for six guests to keep the cook company, and a unique banquette-style table that adds character to the dining area. What makes this home's bedrooms so delightful and unique is that each one has an ensuite bathroom! You'll appreciate the thoughtful design that prioritizes both comfort and elegance, along with convenient amenities like televisions and plenty of storage space. The King and Queen rooms boast walk-in showers, while the bunk room features a shower and tub combo. Room Details -Primary Bedroom: King bed and ensuite bathroom with walk-in shower -Second Bedroom: King bed, pool access, and ensuite bathroom with walk-in shower -Third Bedroom: King bed, pool access, and ensuite bathroom with walk-in shower -Fourth Bedroom: Queen bed and ensuite bathroom with walk-in shower -Fifth Bedroom: Full over full bunk bed and ensuite bathroom with shower and tub combo. This lovely home is situated in the heart of Siesta Key Village, merely one block away from Ocean Boulevard's fabulous boutiques and restaurants. You can enjoy a peaceful outing at Siesta Key Beach, famous for its shimmering white sand and warm waters. Whether you want to rest, relax, or embark on an adventure, this place has everything you need for the perfect vacation! - This property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated, see our Siesta Key Luxury Rental Properties Rental Policies for full details. This property has an active Ring doorbell and additional video surveillance on the pool equipment only. This property participates in our Professional Linen Program. This ensures high-quality linens and towels are always included in your stay. These are professionally laundered at a commercial facility for every guest. 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. This home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund. At A Glance • 5-minute walk to the beach • Near restaurants and boutiques • Pool with in-ground spa • BBQ • Outdoor shower

5 5 12
BOOK NOW

House

Courtyard Castle

Courtyard Castle

Siesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key! Courtyard Castle By Siesta Key Luxury Rental Properties 147 Avenida Veneccia Sarasota, FL 34242 Welcome to Courtyard Castle, a stunning vacation home with six bedrooms each with their own ensuite bathroom, and two additional half baths. Watch the mesmerizing Siesta Key sunsets from the rooftop deck or from one of the other two decks, and relax in the private pool and hot tub. The nearest access to the pristine Gulf of Mexico beaches and Siesta Key Village are just a quick walk away from this serene getaway. On the third floor, you’ll find the main living area that offers a peaceful seating area and a large TV for movie nights after long days spent at the beach. The gourmet kitchen is packed with cooking essentials, stainless steel appliances, and has a vast kitchen island with island seating. Guests can choose to have dinner at the formal dining table or head out the sliding glass doors that lead to the outdoor dining table that overlooks the pool. On the second floor is an additional living space with a tv and a second patio with plush seating perfect for conversing and having a drink with friends and family. The primary bedroom offers a peaceful place with a private balcony and an ensuite bathroom with a shower and tub combination. Four of the six bedrooms are appointed with King beds, and each have an ensuite bathroom with a walk-in shower. The sixth bedroom has two bunk beds, the perfect place for a slumber party and has ensuite bathroom with a walk-in shower. Room Details -Primary Bedroom, 2nd floor: King bed and ensuite bathroom with shower and tub combination. -Second Bedroom, 2nd floor: King bed and ensuite bathroom with a walk-in shower. -Third Bedroom, 2nd floor: King bed and ensuite bathroom with a walk-in shower. - Fourth Bedroom, 3rd floor: King bed and ensuite bathroom with a walk-in shower. -Fifth Bedroom, 3rd floor: King bed and ensuite bathroom with a walk-in shower. -Sixth Bedroom, 2nd floor: Full over Full bunk bed + Twin XL over Twin XL bunk bed and ensuite bathroom with walk-in shower. The backyard oasis has a sparkling pool, hot tub, and plenty of lounge chairs for basking in the Florida sunshine. The covered patio has two TV’s and high top seating, perfect for enjoying BBQ favorites. Head to Siesta Key Village to enjoy boutiques, coffee shops, fresh ice cream, and restaurants. Explore the island with a Siesta Key tour, kayak, or paddleboard the calm intercoastal waterway and beautiful Tampa Bay, where you might encounter a dolphin or manatee or charter a fishing trip to see who brings in the biggest catch. Book Courtyard Castle today! This property has an active Ring doorbell. If you have any questions concerning our home, rates, amenities, policies, or anything else, please send us an inquiry, and one of our professional reservationists and property managers would be happy to help answer your questions. You are a couple of clicks away from paradise, and we look forward to seeing you soon. This property does not allow pets. At A Glance • Less than a 5-minute walk to the beach • Rooftop Deck • Private Pool and Hot Tub • Less than a 5-minute walk from Siesta Key Village • Elevator

6 7 16
BOOK NOW

House

Salty Dog (SKLRP)

Salty Dog (SKLRP)

Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key! Boater's Paradise! Canal front home, about 1 block (2 minute walk) to the beach and about 3 blocks (7 minute walk or 2 minute bike ride) to Siesta Key Village. This home's location is fantastic, and your family will love it. There is so much to do on Siesta Key, and this home makes it easy to enjoy the beautiful weather. Provided with your rental is 1 kayak, a 1 paddleboard, and USCG approved life vests (waiver must be signed to use). Your family will love paddling through the canal, and out into the intercoastal waterway. There is tons of marine life to see, beautiful sights and sounds to enjoy, and the opportunity to catch snook, redfish, snapper, and more from your shared dock or your kayak. Or, feel free to bring your own boat, or rent one from one of the local vendors that we work with. Regardless of what you choose, just grab a seat by the pool, or on the dock, and enjoy watching your family have a blast at this amazing vacation rental. We also just added new fencing to add additional privacy and security between both units and the canal waters. Or, go up to your private roof top deck for some Sunset and Gulf Views. You are a couple of clicks away from paradise, and we look forward to seeing you soon and showing you why a Siesta Key Luxury Rental Properties vacation is the best type of vacation! The Home itself is almost as special as the location. You'll enter the home on the ground level, where you'll find a large 2+ car garage, a foyer, an Elevator to ALL floors, and direct access to the covered patio and pool area. The pool and spa are both heated and offer year-round use. There is plenty of outdoor seating and dining space, a TV so you can enjoy the game while you swim, and a ping pong table. Heading up stairs via the stairs or elevator, you'll find the first level of living. This floor features the main living area of the home, with an expansive great room that includes the kitchen, dining, living room, and a half bath. The kitchen is very large, and it is fully stocked with all the normal items that our guests could need. It includes high end stainless steel appliances, and your family will love the openness of the space so everyone can get together in one place. Speaking of that, the kitchen has an oversized island that doubles as the dining table for 14 people. It is a very unique design that allows for everyone to get together in one place and it provides dual functionality. The living room has plenty of seating as well, with a large HDTV and WiFi throughout the home, you'll be able to kick back and relax anywhere you'd like. There is also a nice balcony off the living room, so with just a quick step outside, you can enjoy views of the pool and canal, and a canopy view of the island. On the first level of living you'll also find the Master Bedroom. This room has a King Bed, and it has access to an outdoor balcony. It features a large bathroom with dual vanities, a private water closet, and an open walk in shower with a stand alone tub inside the walk in shower space. This is perfect for bubble baths, and you'll never have to worry about the bath overflowing because the tub is located in the shower space. Whoever gets this room will love this feature. Traveling upstairs to the Second Level of Living, or the top floor of the home, you'll find the remaining 5 bedrooms of this home. 3 of these 5 bedrooms feature en suite bathrooms, while the final 2 bedrooms feature a Jack N Jill style shared bathroom. There is also another balcony on this level that 3 of the bedrooms have access too, and you'll have even more expanded views of the pool, canal, and Siesta Key area. This home and location is absolutely amazing. Your family will love the fun that all things offer, and the close proximity to the #1 Beach in the USA - Siesta Key Beach. Take the paddleboard or kayak to the beach, or just make the short walk and enjoy the large playgrounds, volleyball courts, calm Gulf waters, or the pure white sand beach. This home offers it all and you won't be disappointed. Oh ya, and if you need more than 6 bedrooms that sleep a total of 17 in beds, then feel free to rent the home next door - 515 Canal Road Unit B, which is another 6 Bedroom home sleeping 18 people, with a private heated pool and spa, shared dock, and it's own paddleboard, kayak, outdoor games, and more. These two homes are set up very similar to 2 townhomes, with a shared wall. They were built to provide privacy for people renting the homes separately, while also providing the availability for a larger group to rent both sides. When you rent both sides you'll have a 12 bedroom home, with 2 kitchens, 2 dining spaces, 2 living rooms, multiple balconies and covered patios, 2 pools and 2 spas, and the ability to sleep 35 people all under the same roof. This property participates in our Professional Linen Program. This ensures high quality linens and towels are Always included for your stay. These are professionally laundered at a commercial facility for every guest. This property has an active Ring doorbell, active video surveillance on the exterior public approach areas, and the pool equipment. Beach Towels and Beach Chairs are available for guest use. At A Glance • Cozy 6 Bed/4.5 Bath, CANAL FRONT Townhome, Sleeps 17 • Property Manager Program - Let us help you Vacation the Right Way • Sleeps 17 - 5 Kings, a Full over Full Bunk Bed, and Queen Sleeper Sofa • Part of our Professional Linen Program • 2 Minute Walk to Siesta Key Beach and 7 minute walk to Siesta Key Village • Shared Dock, able to accommodate up to an 18' boat • Private Heated Pool and Spa - paddleboard, kayak launch • Rooftop Deck with Expansive Views - Gulf, Sunset, Canal, Downtown Siesta Views • Great Room - Full Kitchen with Supplies, Living and Dining • Multiple Balconies with Waterfront Views, Covered Patio Space • Beach Chairs and Beach Towels Included - Inquire for More Details • Parking for 2+ Cars, Free WiFi, TV, BBQ Grill Included

6 5.5 17
BOOK NOW

    Skip to content