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Siesta Key Vacation Rentals

Grab a Piece of Paradise -- Reserve Your Vacation in Fabulous Siesta Key Today!

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SIESTA KEY

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Only $300 to
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The Palm Bay Club offers all of the amenities of the finest resort hotels in a unique condo environment. Enjoy great comfort and value in this gulf-side suite that sleeps 4, with all the first class resort amenities you can image to relax and enjoy. more info
Only 3 weeks left in the next 60 days!
2 Heated Pool, Gym, Tennis
• City: Siesta Key
• View: Best Value/Garden View
• Sleeps: 4
Guest Rating: 4.42/5
33 Guest Reviews
Limited-Time Offer: Stay before 10/18/14 and Save Up to 26%!
Only $300 to
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Siesta Key Florida House of Sun 307 rentals condos is very family-friendly, was recently renovated and has sensational sunset and Gulf views. In the living room, cushioned sofas, arm chairs and foot stools sit around a fine area rug. more info
Only 2 weeks left in the next 60 days!
Heated Pool, Tennis
• City: Siesta Key
• View: Ocean View
• Sleeps: 6
Guest Rating: 4.53/5
57 Guest Reviews
Limited-Time Offer: Stay before 10/18/14 and Save Up to 26%!
Only $300 to
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Decked in pure tropical style, Siesta Dunes Beach 201 in Siesta Key, Florida is an ideal choice for families planning to spend all their daytime hours at the pool or the gorgeous on-site beach. more info
Only 3 weeks left in the next 60 days!
Heated Pool, Heated Spa
• City: Siesta Key
• View: Best Value/Garden View
• Sleeps: 6
Guest Rating: 4.67/5
12 Guest Reviews
Only $300 to
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Featuring new living room furniture, and tile floors - life at this condo is luxe. Sleeping 6 people in 2 bedrooms, Jamaica Royale 91 is a great family retreat for long or short stays. more info
2 Heated Pools
• City: Siesta Key
• View: Best Value/Garden View
• Sleeps: 6
Guest Rating: 4.5/5
38 Guest Reviews
Only $300 to
Book Now!
The Palm Bay Club offers all of the amenities of the finest resort hotels in a unique condo environment. Enjoy great comfort and value in this gulf-view suite that sleeps 4, with all the first class resort amenities you can image to relax and enjoy. more info
2 heated pools, gym, tennis
• City: Siesta Key
• View: Ocean View
• Sleeps: 4
Guest Rating: 4.32/5
22 Guest Reviews
Only $300 to
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Decked in tropical style, Siesta Dunes 104 is an ideal choice for families to spend their daytime hours at the pool or the gorgeous on-site beach. And, this gulf-side property is a great for relaxing evenings and memorable chats under the stars. more info
Heated Pool, Heated Spa
• City: Siesta Key
• View: Best Value/Garden View
• Sleeps: 6
Guest Rating: 4.78/5
63 Guest Reviews
Only $300 to
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An idyllic ocean side condo perfect for energetic kids or families seeking added privacy, Siesta Dunes Beach 38A is your perfect vacation rentals condo in Siesta Key, Florida. Siesta Key resort features Gulf Front pool and tennis courts. more info
Heated Pool, Heated Spa
• City: Siesta Key
• View: Best Value/Garden View
• Sleeps: 6
Guest Rating: 4.48/5
62 Guest Reviews
Savings Alert: Left to Save 26%! Reserve 8/23/14 - 8/30/14 Now!
Was $795 NOW $591
Just steps from a private walkway to the beach, our townhouse overlooking the beach Siesta Key is the ideal beach retreat for a family, group of friends, or 2 couples. With a pool, tennis, and picnic area, the complex is nearly as fun as the beach! more info
Heated Pools, Tennis
• City: Siesta Key
• View: Ocean View
• Sleeps: 6
Guest Rating: 4.5/5
6 Guest Reviews
Limited-Time Offer: Stay before 10/18/14 and Save Up to 29%!
Only $300 to
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Guests rate the Palm Bay Club Bayside #328 as a perfect destination for romantic getaways and family vacations. Treat yourself to an idyllic holiday on Florida’s Gulf Coast, at this 2 bedroom condo with intracoastal water views from your outdoor patio. more info
heated pool, tennis
• City: Sarasota
• View: Best Value/Garden View
• Sleeps: 4
Guest Rating: 4.25/5
4 Guest Reviews
Limited-Time Offer: Stay before 10/18/14 and Save Up to 24%!
Only $300 to
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Just steps from the bay, our newly remodeled condo in a gated Key West-style community is the perfect destination for your Siesta Key vacation. With resort amenities and the ideal location for beach and bay access, Gulf & Bay Bayside is irresistible! more info
2 Pools, Tennis, Gym
• City: Siesta Key
• View: Best Value/Garden View
• Sleeps: 6
Guest Rating: 4.67/5
6 Guest Reviews
Only $300 to
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Nestled on the southern tip of Siesta Key is our ground-floor condo, Bay Tree Club 106. Located in an oceanfront complex, it will pamper you with brand-new HDTVs, spacious and well-appointed rooms, and a sunny lanai overlooking grassy grounds. more info
2 Pools
• City: Siesta Key
• View: Beach Front
• Sleeps: 6
Guest Rating: 5/5
2 Guest Reviews
Limited-Time Offer: Stay before 10/18/14 and Save Up to 26%!
Only $300 to
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Just steps from a private walkway to the beach, our townhouse overlooking the lake at Siesta Key is the ideal beach retreat for a family, group of friends, or 2 couples. With a pool, tennis, and picnic area, the complex is nearly as fun as the beach! more info
Heated Pool, Tennis
• City: Siesta Key
• View: Best Value/Garden View
• Sleeps: 4
Guest Rating: 4.67/5
33 Guest Reviews
Only $300 to
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With beautiful lagoon views from both the big lanai and the master bedroom, our condo at Castaway Cove is ideal for your Siesta Key vacation. Spacious and well equipped, the condo offers everything from bikes to a boat dock. Come play here very soon! more info
on Lagoon, near Beach
• City: Siesta Key
• View: Best Value/Garden View
• Sleeps: 5
Guest Rating: 4.64/5
11 Guest Reviews
Savings Alert: Left to Save 29%! Reserve 8/23/14 - 8/30/14 Now!
Was $595 NOW $421
Aloha Kai is a 5 acre Oceanside (Gulfside) vacation retreat tucked away on the powder sand shores of Siesta Key. Featuring the largest heated outdoor pool on Siesta Key, this private villa awaits you with all of the comforts of home. more info
Heated Pool
• City: Siesta Key
• View: Best Value/Garden View
• Sleeps: 6
Guest Rating: 4.39/5
36 Guest Reviews
Only $300 to
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Every sunset is a memorable experience at our condo at Crystal Sands 406 in Siesta Key. Overlooking the placid Gulf of Mexico, our 4th-floor condo on the shores of Crescent Beach is a great venue for your next sun, sea, and sightseeing vacation! more info
2 Heated Pools
• City: Siesta Key
• View: Ocean View
• Sleeps: 4
Guest Rating: 4.32/5
19 Guest Reviews
Only $300 to
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With the Bay in back and the Gulf in front, our condo at Excelsior 107 sits on a little strip of paradise! Located in a luxurious resort with everything from heated pools to private beach access, it's a tropical getaway on one of the world's finest beaches more info
2 Heated Pools, Tennis
• City: Siesta Key
• View: Best Value/Garden View
• Sleeps: 6
Guest Rating: 4.6/5
10 Guest Reviews
Only $300 to
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Roll into the lap of luxury and enjoy a unit that’s still sparkling new. Siesta Key Gulf and Bay Club is known to be the finest long-stay resort in the area - and this newly renvoated unit, Gulf and Bay Club 305C, trumps the competition. more info
3 Heated Pools, Tennis, Gym
• City: Siesta Key
• View: Ocean View
• Sleeps: 6
Guest Rating: 5/5
7 Guest Reviews
Only $300 to
Book Now!
Perfect for guests looking for a rental of one month or longer, your time spent at Siesta Key Gulf & Bay Club #409 is guaranteed bliss. At 1630 square feet, it is the largest 2 BR condo available at Gulf & Bay Club Resort. more info
3 Heated Pools, Tennis, Gym
• City: Siesta Key
• View: Beach Front
• Sleeps: 4
Guest Rating: 4.78/5
9 Guest Reviews
Only $300 to
Book Now!
Love sunsets? How about white sand, plush beds, a choice of three pools, swans ... and a little shuffleboard? If this sounds like a month or more of paradise, you’ll immediately love life at Siesta Key Gulf and Bay Club #102B. Book now for a stay of 28 or more info
3 Pools, Gym, Tennis
• City: Siesta Key
• View: Beach Front
• Sleeps: 6
New Property, Be One of Our First Guests!
Only $300 to
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Come vacation on the white sands of Siesta Beach! When you stay at our condo at Gulf & Bay Club 204C, you'll enjoy luxury and comfort in more than 1,500 sq ft of beachfront property, including a lovely lanai. And use of resort amenities is included! more info
3 Heated Pools, Tennis, Gym
• City: Siesta Key
• View: Beach Front
• Sleeps: 6
New Property, Be One of Our First Guests!
Only $300 to
Book Now!
Gulf and Bay 502D will perfectly suit six nice people who deserve a month of total reward and relaxation on Crescent Beach. The resort club is unrivalled for repeat guest satisfaction and its location is in the middle of the best sand beach in America. more info
3 pools, gym, spa, tennis
• City: Siesta Key
• View: Beach Front
• Sleeps: 6
New Property, Be One of Our First Guests!
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Siesta Key, Florida

Siesta Key Vacation Rentals

Gorgeous White Sand Beaches, Sparkling Water, and Perfect Accommodations!

Vacation rental properties are available for short-term and long-term visits to Siesta Key, Florida. We have oceanfront condo rentals in Gulf and Bay Club, Palm and Bay Club, Excelsior Condos, Siesta Dunes, Jamaica Royale, and more, as well as vacation rental home properties such as House of Sun, Our House at the Beach, and Aloha Kai. whatever size your group or budget, you can find the perfect vacation rental property here!

Every vacation rental condo, townhouse, or home we manage is fully furnished, with all linens and towels provided, a washer and dryer, a fully equipped kitchen, and free wireless Internet. Our properties are nicely furnished and spotlessly maintained. Pack light and rely on your vacation rental to have what you need -- you won't be disappointed!

Siesta Key is just off the west coast of Florida, between the Bay and the Gulf of Mexico. Its beach, Siesta Beach, has been named one of the Top 10 Beaches in the World. Pure white sands and sparkling waves await you here, not to mention spectacular sunsets!

Siesta Key is a small community with plenty for vacationers to do. Filled with several streets of shopping, galleries, and restaurants, it even offers a trolley to help you find your way around the island. Siesta Key Beach is at the southern end of the island, while the shopping district is at the northern.

Browse our vacation rental properties now and find your Siesta Key dream getaway. You will find the scenery breathtaking (right down to the wild parrots on the island!), the attractions fascinating, and the beach simply heavenly. We've got the perfect home-away-from-home just waiting for you to rent. Book today, and begin planning your stay in paradise!

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Vacation Rental Pros, 151 Sawgrass Corners Suite 200, Ponte Vedra Beach, FL 32082 - . Florida beach front vacation rentals homes, condos and villas from$100+ a night. We manage over 650 ocean front rentals in St Augustine Beach, Palm Coast, Venice Beach, Siesta Key FL. Browse over 10,000 guest reviews.