CONTACT US
Showing 12 of 59 properties



Condo

704N Crescent Arms

704N Crescent Arms

Beautiful 7th Floor Penthouse Condo with Gulf Front View * 2 bedroom, 2 bath * Shared Resort amenities, private beach access, heated pool, bbq area, beach chairs provided * Fully updated unit * Private screened-in lanai with Gulf view * Located on Siesta Key Enjoy every moment of your vacation to sunny Florida in style at this stylishly renovated unit overlooking the Gulf of Mexico! The bright and welcoming living and dining area offers water views and comfortable seating to relax, while the new kitchen features all-new appliances for your convenience. It’s a great combination for casual home-cooked dinners at sunset without even leaving the comfort of your own “home away from home”. Able to accommodate up to 6 guests, the new primary bedroom features an ensuite bathroom, and the second bedroom has 2 Queen beds. All are decorated in a chic coastal style with new furnishings. Unit layout:
Primary bedroom - King bed with ensuite bathroom with walk-in shower
Bedroom 2 - 2 Queen beds Second hallway bathroom with walk-in shower Resort amenities are available for guest use, including private beach access, beach chairs, a bbq area and a heated pool, plus covered parking. Located in South Village on Siesta Key, this condo is perfectly situated close to restaurants, shopping and happy hour hotspots. Inquire today! *1 week minimum stay required

2 2 6
BOOK NOW

Condo

Sea Club II Unit 2B

Sea Club II Unit 2B

Sea Club II Unit 2B by Tropical Sands Accommodations 5955 Midnight Pass Rd, Unit 2B Siesta Key, FL Welcome to Sea Club II Unit 2B! This one-bedroom, one-bath bayfront condo is a perfect couple's beach escape. Located on the ground level and just steps from Siesta Key Beach, you'll also be a quick trolley ride from Siesta Key Village, where you can explore coastal boutiques, ice cream parlors, coffee shops, and top-rated restaurants. Highlights • Private beach access • Front porch with seating • 1 parking spot • Community pool • Community fishing pier • Community boat basin (up to 24’) • Community grills and tiki hut • Laundry facility onsite • 4-minute walk to trolley stop As a guest at Sea Club II, you'll have exclusive access to some amazing amenities designed to make your stay unforgettable, including a swimming pool, BBQ grills, and a poolside tiki hut. For water enthusiasts, there’s private beach access just across the street, along with a fishing pier and dock, perfect for your aquatic adventures. Upon arriving at Unit 2B, you'll be greeted by a charming front patio with seating—ideal for enjoying your morning coffee or mingling with fellow travelers. Inside, you'll find a cozy seating area with a sofa, side chair, and TV, perfect for relaxing after a day at the beach. The fully equipped kitchen includes all the appliances, dishware, utensils, and cookware you need for preparing quick meals, and a charming kitchen table for two adds a touch of convenience. The main bedroom has a King bed, a TV, a dresser, and a desk. The hall bath has a shower and tub combo. Book your stay at Sea Club II Unit 2B today and enjoy community amenities, beach access, and close proximity to top attractions! We can’t wait to have you as our guest!

1 1 4
BOOK NOW

Condo

Siesta Beach House #102

Siesta Beach House #102

Siesta Beach House #102 by Tropical Sands Accommodations 5950 Midnight Pass Rd, #102 Siesta Key, Florida Welcome to Siesta Beach House #102! This ground-level beach condo features one bedroom and one bath, making it perfect for a small family beach getaway. With private beach access just a two-minute walk from your doorstep and the Siesta Key trolley only a four-minute walk away, you and your loved ones can easily explore local attractions. Enjoy the vibrant Siesta Key Village, offering a variety of dining options and live entertainment, or visit the South Village Shopping District for some leisurely shopping. Highlights • Ground-floor condo • Private beach access • 2-minute walk to the beach • Community pool • Community shuffleboard • Shared BBQ grills • 4-minute walk to Trolley stop • 2 miles to Siesta Key Village • 7-night minimum stay Siesta Beach House offers fantastic community amenities, including private beach access for sun-soaked days, a sparkling community pool to cool off, and shuffleboard for some friendly competition. Inside, you’ll find a simple, modern living space with a comfy sofa and a TV, perfect for unwinding after a day at the beach. The updated kitchen boasts a full suite of appliances and essential cookware for preparing quick meals, along with a cozy kitchen table set for two. In the bedroom, parents can enjoy the Queen bed while the child sleeps comfortably in the Twin bed. The hall bath features a convenient walk-in shower. Ready for your next beach adventure? Book your stay at Siesta Beach House #102 today and start making memories that will last a lifetime!

1 1 3
BOOK NOW

Condo

15 SS Cottage

15 SS Cottage

Located directly across the street from Siesta Key Beach access 7 and only two blocks to the village! This adorable beach cottage has been newly furnished - island style and has a cozy home feel. There is a private outdoor patio, equipped with table and chairs with umbrella, a brand new gas grill to enjoy the evening breezes. Updated kitchen has full size refrigerator, stove, dishwasher and Keurig coffee maker. The Living Room has a full size sleep sofa, LCD TV and wireless internet is provided. The Master bedroom has a King size bed with a LCD TV as well. The best feature is the location, directly across the street from the beach, and only 2 blocks to the Siesta Key Village and all it has to offer--Siesta Key Oyster Bar (SKOB), Daiquiri Deck, and of course, the Broken Egg. You can leave your worries and your car behind. One stay and you will never want to leave! It's that perfect! This cottage is pet friendly with a 45 lb weight limit. Additional pet fee applies.

1 1 4
BOOK NOW

Condo

Vista Hermosa Sun N Fun

Vista Hermosa Sun N Fun

Vista Hermosa Sun N Fun by Tropical Sands Accommodations 110 Vista Hermosa Cir #304B Sarasota, Florida Experience the perfect Siesta Key getaway at Vista Hermosa Sun N Fun, a modern and inviting two-bedroom and two-bathroom coastal condo designed for families seeking a relaxing retreat in paradise. Nestled just a 5-minute walk from the beautiful Crescent Beach and the trolley stop is conveniently in front of the complex giving you easy access to Siesta Village, offering an array of restaurants, ice cream parlors, boutiques, and so much more to make the perfect family vacation. Highlights • 5-minute walk to the Beach • Siesta Key Breeze Trolley Stop In Front of Building • Espresso Machine • Near Shopping and Dining • Beach Chairs and Cart • Community Pool • Community Shuffleboard • Community Clubhouse • Shared Washer and Dryer The open-concept layout ensures an inviting atmosphere where everyone can unwind after a fun-filled day at the beach. The bright living space features comfortable seating, stunning views, a dining table set for four, and remote control shades. The modern, fully-equipped kitchen boasts stainless steel appliances, a spacious island with bar seating for four, and an espresso machine to keep you energized. Retreat to the primary bedroom with a luxurious king bed, promising a restful night’s sleep. The second bedroom comes with two twin beds, providing ample space for the kids. Guests can indulge in the ensuite bathroom attached to the primary bedroom, complete with a refreshing walk-in shower. The shared hallway bathroom features a convenient shower and tub combination, perfect for rinsing off after a day in the sun. A coin-operated washer and dryer are located across from this unit. Room Details -Primary Bedroom: King bed and ensuite bathroom with walk-in shower -Second Bedroom: Two Twin Beds Don’t miss out on your dream vacation! Book your stay at Vista Hermosa Sun N Fun today and create unforgettable memories in Siesta Key! - This home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. This property does not allow pets of any kind. 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 see our Tropical Sands Accommodations Rental Policies for full details. 1 car 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 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.

2 2 4
BOOK NOW

Condo

Siesta Beach House #312

Siesta Beach House #312

If you're looking for a great vacation location on beautiful Siesta Key, then look no further. This people friendly complex is the perfect place to bring the family for a true holiday get-away at the beach! You can enjoy swimming in the heated pool, take up a game of shuffleboard, stroll along gorgeous white sandy beaches, or swim in the crystal clear waters of the Gulf of Mexico. Come join us for the perfect vacation.

2 2 7
BOOK NOW

Condo

Bay Oaks E-14

Bay Oaks E-14

Bay Oaks E-14 by Tropical Sands Accommodations 6157 Midnight Pass Rd #E 14 Sarasota, Florida Welcome to your perfect family getaway at Bay Oaks Condominium, a delightful two-bedroom, two-bath vacation rental located on beautiful Siesta Key, Florida. Nestled among tropical foliage and serene pathways, this condo offers a relaxing atmosphere just minutes away from the world-renowned Siesta Beach. Enjoy strolls under coconut palms and oak trees while taking advantage of nearby attractions, including restaurants and shopping. Highlights • 10-minute Walk to the Beach • Community Fishing Pier • Private Washer and Dryer • Private Balcony • Heated Community Pool • 1 Covered Parking Space • Tennis and Pickleball Court • Easy Access to Siesta Key Breeze Trolley Stop At Bay Oaks, family fun awaits! Enjoy sunny days at the heated pool, challenge each other on the tennis courts, and share delicious meals at the BBQ area. Don’t forget to catch stunning sunsets from our private fishing pier—perfect for creating cherished memories and enjoying quality time together! Step inside Bay Oaks E-14 and discover a beautifully designed open floor plan that exudes a light and inviting beachy charm. The cozy seating area is perfect for family movie nights with a Smart TV that makes streaming favorites a breeze. The fully equipped kitchen features a variety of appliances and all the cookware necessary for delicious family meals. Enjoy casual breakfasts at the kitchen island, gather for more formal dinners at the dining table, or unwind on the balcony with a glass of wine as the island breeze gently surrounds you after the kids are fast asleep. Each bedroom at Bay Oaks E-14 is designed for comfort and entertainment, featuring smart and direct TVs for endless viewing options. The primary suite offers a plush king-size bed, a spacious walk-in closet, and an ensuite bath with a walk-in shower. Perfect for kids or guests, the second bedroom includes twin beds and its own private bath, complete with a newly tiled bathtub shower combo. Room Details -Primary Bedroom: King bed and ensuite bathroom with walk-in shower -Second Bedroom: Two Twin beds Ready for Your Next Family Adventure? Pack your swimsuit and toothbrush, and get ready for a memorable family vacation at Bay Oaks Condominiums on Siesta Key! - This home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. This property does not allow pets of any kind. 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 see our Tropical Sands Accommodations Rental Policies for full details. 1 car 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 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.

2 2 4
BOOK NOW

House

3360 Higel Avenue

3360 Higel Avenue

3360 Higel Avenue by Tropical Sands Accommodations 3360 Higel Ave Siesta Key, Florida VR23-00029 Welcome to 3360 Higel Avenue! This gorgeous ground-level home boasts four bedrooms and three bathrooms and is nestled on a serene street, offering the ultimate peaceful escape. The backyard is adorned with lush tropical plants and highlights a glistening pool complete with an in-ground spa. You'll also find an outdoor living area with comfy lounge chairs, a dining table, and a BBQ grill for relaxing and entertaining. Highlights • Less than a 10-minute walk to the beach • 2-minute walk to trolley stop • Private pool with in-ground spa • BBQ grill • Washer and dryer Step inside this beautiful space and be transported to a world of elegance with a charming nautical theme and a variety of seating areas for guests to unwind, watch a movie, or catch up with loved ones. The kitchen has a full suite of stainless steel appliances, an assortment of essentials, and a kitchen island with seating for four. In the formal dining room, you’ll discover a dining table set for six and a bar with a built-in fridge - great for hosting! The primary room boasts beautiful ocean-themed decor with a soothing blue color scheme and features an ensuite bathroom with a double vanity and a convenient walk-in shower. There are two queen guest bedrooms (one with an ensuite bathroom!) and a cozy bunk bedroom available for use. The home also includes a hall bathroom with a shower and tub combo and a complete laundry room with a washer and dryer for your convenience. Room Details -Primary Bedroom: King bed and ensuite bathroom with a walk-in shower -Second Bedroom: Queen bed and ensuite bathroom with a walk-in shower -Third Bedroom: Queen bed -Fourth Bedroom: Two Twin over Twin bunks Hop on a bike, golf cart, or snag a ride on the free trolley to experience the stunning Gulf beaches and charming Siesta Key Village. The village boasts an array of one-of-a-kind boutiques, locally owned restaurants, cozy coffee shops, and delightful ice cream parlors. Your stay at 3360 Higel Ave will be nothing short of awesome! - This property has an active Ring doorbell at the main entrance. No pets are allowed in this home. This home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. 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 see our Tropical Sands Accommodations Rental Policies for full details. 3 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 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.

4 3 10
BOOK NOW

Condo

Gulf Holiday Unit 12

Gulf Holiday Unit 12

This beautifully renovated, well-appointed one bedroom condo is perfect for a romantic getaway!!. Gulf Holiday is just a short walk to Siesta Key Beach voted #1 beach in the U.S and the Siesta Key Village shops, restaurants, and nightlife. This 2nd floor unit has a newly renovated kitchen with custom cabinets, new appliances, including dishwasher. Bedroom is Newly furnished with a King sized bed with pillow top mattress. New furnishings in living room include a queen sized sleeper sofa bed (children only please). Flat screen TV in family room / kitchen as well as bedroom. Perfect location and size for a beach vacation.

1 1 2
BOOK NOW

House

Casa Mango

Casa Mango

Highlights • Shared Dock • Screened-in Private Pool • 2-mile drive from Siesta Key Beach • Ping Pong Table • Kayak Casa Mango by Tropical Sands Accommodations 7123 Roland Oaks Circle Sarasota, FL 34231 Welcome to Casa Mango! This vibrant three-bedroom, two-bath vacation home has a stunning pool and a shared dock just down the street where your friends and family can enjoy kayaking and paddleboarding on Sarasota Bay. The world-famous Siesta Key sunsets and white powdery sand beaches are just a short drive away. Pack your bags and get ready to soak up the Florida sunshine! Instantly feel the vacation vibe as you watch the palm trees gently sway as you pull into your private driveway. Once you open the door, you will be welcomed into an inviting seating room that boasts spectacular pool and lanai views, creating a seamless indoor-outdoor living experience. The kitchen has stainless steel appliances, cooking basics including pots and pans, and opens to the kitchen table. This Old Florida-style home offers a split-bedroom layout perfect for multiple groups or families. traveling together. The primary bedroom is a beautiful light blue to provide a calming ambiance and features a bright ensuite bathroom with double vanity, walk-in shower, and a standalone tub. The second bedroom is appointed with a King bed and a closet to store vacation essentials. The third bedroom has a Full over Queen bunk bed, making it ideal for kids or a small family. There is a hallway bathroom with a shower and tub combination. To ensure every guest has a comfortable stay, there is a bonus room with a twin trundle daybed. A washer and dryer are available for guest use. Room Details -Primary Bedroom: King bed and ensuite bathroom with walk-in shower and standalone tub -Second Bedroom: King bed -Third Bedroom: Full over Queen bunk -Bonus: Twin daybed with trundle Step into the private oasis where the possibilities for relaxation are endless. Take a dip in the pool, refresh with a drink in one of the chairs by the pool, swing in the hammock, or play yard games with friends, family, and even your pets! A three-person kayak, with paddles in the shed and paddle boards in the garage, is excellent for exploring the deeded water access and shared dock. - This home requires a 30-night minimum stay. This property only allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated, see our Tropical Sands Accommodations Rental Policies for full details. 3 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. This home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. 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 see our Tropical Sands Accommodations Rental Policies for full details.

3 2 10
BOOK NOW

Condo

Oasis Beach Villa S-1

Oasis Beach Villa S-1

Beautiful 2 bedroom 2 bath condo right on Beach Rd! It's just a short walk across the street to the beach, and only a block away from the Village. Beach chairs, umbrella and beach cart included for your use. This gated community offers private balconies off the living room and the master bedroom. Enjoy your mornings overlooking the pool area, or the evenings taking in our gorgeous sunsets! Nicely appointed with updated Kitchen, laundry room, and all the comforts of a 5 star resort! 1 week minimum rental *inside garage parking only max 2 cars*

2 2 6
BOOK NOW

Condo

Siesta Beach House #201

Siesta Beach House #201

If you're looking for a great vacation location on beautiful Siesta Key, then look no further. This people friendly complex is the perfect place to bring the family for a true holiday get-away at the beach! You can enjoy swimming in the heated pool, take up a game of shuffleboard, stroll along gorgeous white sandy beaches, or swim in the crystal clear waters of the Gulf of Mexico. Located on a private lane that leads right to the beach . . . no through traffic and no streets to cross – just a short stroll to the famed white sands of Crescent Beach. 1 WEEK MINIMUM RENTAL REQUIRED

2 1.5 4
BOOK NOW

    Skip to content