CONTACT US
STAYCATION PROMO
Escape, retreat, and indulge with Siesta Key Luxury Rental Properties. Take advantage of our exclusive offer for locals and save 10% off your dream getaway. Book now by calling 941-349-1125! *Offer valid for residents of Manatee, Sarasota, Pinellas, and Hillsborough counties.

Celebrate the holiday season with our deal of the year! Book any new Siesta Key Luxury Rental Properties reservation with an arrival date now through December 31, 2024 and save 15% off the rental rate. Minimum night stay will vary by property and date of stay. Book now with promo code: BLACKFRIDAY2023
Offer ends at MIDNIGHT, November 26, 2023. Book your vacation directly on our website or call us now at 941-349-1125 to receive this promotion.

*Subject to availability. Blackout dates may apply. This promotion cannot be applied to an existing reservation or combined with any other offers.

Showing 53 of 53 properties



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

Duplex

Salty Summer

Salty Summer

Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key! Salty Summer by Siesta Key Luxury Rental Properties 310 Canal Rd Siesta Key, Florida Welcome to Salty Summer, a fantastic duplex with a shared pool perfectly located minutes from the turquoise waters and powder-soft sands of the Gulf and steps from Siesta Village, which offers a variety of shops and restaurants. With two bedrooms and two bathrooms, this home is perfect for your beach getaway, so pack your bags and enjoy a dream island vacation at Salty Summer! You will love the beach decor and colors as you enter the open living space. The family room has inviting conversational seating, perfect for watching a show after a day at the beach. In the kitchen, you will find stainless steel appliances, cooking essentials, and granite countertops with seating. Dine at the kitchen table or head outside for a lovely BBQ on the shared grill. Rest and refresh in the primary bedroom, with a colorful seaside decor, a king bed, and an ensuite bathroom with a walk-in shower. The second bedroom has a queen bed and a double over double bunk bed, and the hallway bathroom has a shower and bathtub combination. Room Details Primary bedroom: King bed and ensuite bathroom with a walk-in shower Second bedroom: Queen bed and double over double bunk bed 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. 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. This home is also part of our Property Manager Program, so one of our dedicated Property Managers will assist you during the entire reservation and vacation process. We are here to help you vacation the right way and ensure you have everything you need, including any recommendations or advice to help improve your vacation! A Siesta Key Luxury Rental Properties vacation is the best type of vacation! 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 a 10-minute walk to the beach • Shared Pool • 2-minute walk to restaurants and shops • Dog Friendly • Shared Outdoor Seating and BBQ grill

2 2 8
BOOK NOW

House

Sea Spray

Sea Spray

Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key! Sea Spray by Siesta Key Luxury Rental Properties 538 Canal Rd Siesta Key, Florida Welcome to Sea Spray, a beach and boaters paradise with a private dock across the street and just a block from the famous Siesta Key beach! This eight-bedroom and six-and-a-half-bathroom home boasts a spectacular backyard built like a private waterpark with a Private Resort Style Heated Pool featuring a Rock Water Slide, Waterfall, Grotto, Swim-up bar, Sun Shelf, and Spa. Pack your bags for the best vacation ever! Take the elevator up to the main living floor, where you’ll find a lovely living area with plenty of seating for all your guests and large sliding doors leading to the furnished balcony; this is where you can access the rooftop deck. The kitchen highlights stainless steel appliances, cookware essentials, and two island seating options; the dining table and nook seating are adjacent, great for large parties. The primary bedroom is a dream! It’s spacious with a walk-in closet, a private balcony with Adirondack chairs, an ensuite bathroom with a delightful baby blue double vanity, a large walk-in shower, and a premium standalone tub. The second/third bedroom has a unique setup with a King bed and a bunk bed with a curtain to separate the two, an ensuite bathroom with a walk-in shower, making it a perfect room for parents and kids! There are two King bedrooms with ensuite bathrooms and two King bedrooms that share a Jack-n-Jill bathroom with a walk-in shower. The last bedroom is the bunk room with easy access to the hall bath with a walk-in shower. The living room has a sleeper sofa and a laundry room on the second floor. Room Details -Primary Bedroom, 3rd floor: King bed, private balcony, and ensuite bathroom with walk-in shower and standalone tub -Second Bedroom, 3rd floor: King bed and shared ensuite bathroom with the third bedroom -Third Bedroom, 3rd floor: Twin over Full Bunk Bed with a Twin Pull Out Trundle and shared ensuite bathroom with the second bedroom -Fourth Bedroom, 3rd floor: King bed, balcony access, and an ensuite bathroom with a walk-in shower -Fifth Bedroom, 2nd floor: King bed, balcony access, and an ensuite bathroom with a walk-in shower -Sixth Bedroom, 2nd floor: King bed, balcony access, and Jack-n-Jill bathroom with walk-in shower -Seventh Bedroom, 2nd floor: King bed and Jack-n-Jill bathroom with walk-in shower -Eighth Bedroom, 2nd floor: Two Twin bunk beds and ensuite bathroom with walk-in shower The Outdoor space has a covered patio with lounge chairs, a dining room table, a BBQ grill, a TV, and an incredible pool area! The game room is located just off the pool area with a ping pong table, a foosball table, and a refrigerator. Throw in a line and try your luck at fishing, or explore the bay by boat, kayaks, or paddleboards! This home is a short walk to Siesta Key Beach and within walking distance to Downtown Siesta Key Village Area. So, catch some sunshine at the beach or great live music, dining, or shopping in the Village. Book your dream vacation 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. 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 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 • Private Dock • Rooftop Deck with Gulf Views • Less than a 5-minute walk to the beach • Private Pool with Waterslide and In-ground Spa • Ping Pong and Foosball table

8 6.5 22
BOOK NOW

House

Siesta Palooza

Siesta Palooza

Siesta Palooza by Siesta Key Luxury Rental Properties 332 Avenida De Mayo Siesta Key, Florida Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key! Resort island living awaits at Siesta Palooza! This eight-bedroom and eight-bath home is a true masterpiece with a picture-perfect backyard with a sparkling pool, large spa, and covered patio with high-end seating, dining table, grill, and a game room with a TV and ping pong table! Guests can unwind and enjoy their stay, whether lounging in the coastal indoor seating area with a large TV, sitting on the rooftop deck and soaking up the sun, or indulging their culinary passions in the fully-equipped kitchen with high-end appliances and essential amenities. With seating for up to six people, the kitchen island seamlessly connects to the main dining area and deck, featuring modern dining room tables. Siesta Palooza boasts five king rooms, including the primary suite, a queen room, and two bunk rooms, all of which are beautifully decorated to exude beach vibes. Each room is furnished with dressers and televisions, and has either an ensuite bathroom or easy access to a hall bath. Additionally, we have provided a washer and dryer for your convenience. On the fourth floor, you'll find an excellent hang-out spot with video games and a large sofa that can be easily converted into a sleeper sofa. There's also a sleeper sofa in the main living room. Room Details -Primary Bedroom, 3rd floor: King bed, balcony, and ensuite bathroom with a shower and tub combination -Second Bedroom, 3rd floor: King bed, balcony, and ensuite bathroom with double vanity and walk-in shower -Third Bedroom, 3rd floor: King bed, balcony, and jack-n-jill bathroom with shower and tub combo -Fourth Bedroom, 3rd floor: Queen bed and jack-n-jill bathroom with shower and tub -Fifth Bedroom, 4th floor: King bed, balcony, and ensuite bathroom with a shower and tub combination -Sixth Bedroom, 2nd floor: King bed, balcony, and ensuite bathroom with a shower and tub combination -Seventh Bedroom, 3rd floor: Full over Full bunk bed with Twin trundle and ensuite bathroom with walk-in shower -Eighth Bedroom, 2nd floor: Twin over Full bunk bed with Twin trundle -Bonus, 4th floor: Queen sleeper sofa -Bonus, 2nd floor: Queen sleeper sofa The location is unbeatable, just a few steps away from the grocery store, restaurants, shops, and vibrant nightlife. Plus, with the nearby Siesta Key Beach access points just a short walk or bike ride away, you'll be able to take in the stunning surroundings with ease. Book now and start planning your remarkable getaway! - This property has 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 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. 5 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 • Less than a 10-minute walk to the beach • Private pool and in-ground spa • Rooftop deck • Ping Pong table • Elevator

8 8 25
BOOK NOW

House

Siesta Sun

Siesta Sun

Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key! Siesta Sun by Siesta Key Luxury Rental Properties 559 Beach Rd A Siesta Key, FL 34242 Live out your vacation dreams at Siesta Sun, a fantastic three bedroom and three-and-a-half bath home with a rooftop deck that boasts spectacular Gulf views, which is right across the street! This duplex has a shared backyard with a sparkling pool, lounge seating, and even a ground-floor game room! Take the stairs up to your private side of the duplex and immediately feel the vacation vibes as you walk in. There is a beautiful nautical seating area with two sofas, side chairs, and a large TV. The kitchen boasts stainless steel appliances, counter seating, basic cookware, adjacent is the formal dining table set for eight guests. If you can’t get enough of the Florida weather, head out to the balcony and take advantage of the grill provided and the outdoor table. The primary bedroom has beautiful coastal décor, a TV, and access to the screened-in lanai that has cute outdoor seating. In the primary ensuite bathroom, you will find a double vanity, a walk-in shower with unique tile, and a spacious walk-in closet. Similar to the primary, the second bedroom has a comfy bed, balcony access, and an ensuite bathroom with a shower and tub combination. The third bedroom has a TV, closet space and access to the hall bath with a shower and tub combination. On your way to the rooftop deck is a den with a daybed. Room Details -Primary Bedroom, 2nd floor: King bed, balcony, and ensuite bathroom with walk-in shower -Second Bedroom, 2nd floor: King bed, balcony, and ensuite bathroom with shower and tub combo -Third Bedroom, 2nd floor: King bed -Den, 3rd floor: Twin bed with Twin Trundle Pull Out Are you traveling with friends and family? Siesta Sun’s neighboring duplex is available for rent and has three bedrooms and three and one half bath, totaling six bedrooms and five-and-a-half bathrooms. These vacation rentals share a game room with a foosball table and a 3-1 table, it is a pool table on one side, air hockey on the other side, with a table to put on top with the net for ping pong! Search for Island Sun on our Browse Rentals search page. - 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. At A Glance • 2-minute walk to the beach • Rooftop Deck • Shared Pool • Shared Game Room • Dog Friendly

3 3.5 10
BOOK NOW

    Skip to content