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Siesta Key Vacation Rentals

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Excelsior 107, 1st Floor, 2 heated pool, spa, wifi, beach access
Guest rating:4.5/5
( Read 4 reviews )
2 Heated Pools, Tennis
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Only $300!

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Jamaica Royale 91 Rental, heated pool, beach access,wifi
Guest rating:4.53/5
( Read 17 reviews )
2 Heated Pools
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Only $300!

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House of Sun 307 Siesta Key, Large Heated Pool, Gulf View, Wifi
Guest rating:4.66/5
( Read 44 reviews )
Heated Pool, Tennis
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Gulf and Bay Club 305C GulfView 3 pools, fitness room, spa, wifi
Guest rating:4.83/5
( Read 6 reviews )
3 Heated Pools, Tennis, Gym
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Our House at the Beach 222, with Heated Pool, Tennis
Guest rating:4.83/5
( Read 18 reviews )
Heated Pool, Tennis
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Gulf and Bay 207F, Siesta Key Beach Front, 3 pools, spa, wifi
Guest rating:4.56/5
( Read 9 reviews )
3 Heated Pools, Tennis, Gym
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Aloha Kai 50 heated pool & beach access
Guest rating:4.41/5
( Read 22 reviews )
Heated Pool
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Only $300!

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Siesta Dunes 38A, Gulf Side, Large Heated Pool, Wifi
Guest rating:4.41/5
( Read 37 reviews )
Heated Pool, Heated Spa
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Only $300!

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Siesta Dunes 104, Siesta Key Gulf, Spa, Heated Pool, Wifi
Guest rating:4.89/5
( Read 36 reviews )
Heated Pool, Heated Spa
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Only $300!

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Bay Tree Club 106, 2 bedrooms, 2 heated pools, spa, wifi,
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2 Pools
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Only $300!

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Excelsior 107, 1st Floor, 2 heated pool, spa, wifi, beach access

Guest Rating: 4.5/5
4 Guest Reviews
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
  • City: Siesta Key Florida
  • View: Best Value/Garden View
  • Sleeps: 6

2 Heated Pools, Tennis

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Only $300!


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Jamaica Royale 91 Rental, heated pool, beach access,wifi

Guest Rating: 4.53/5
17 Guest Reviews
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
  • City: Siesta Key Florida
  • View: Best Value/Garden View
  • Sleeps: 6

2 Heated Pools

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Only $300!


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House of Sun 307 Siesta Key, Large Heated Pool, Gulf View, Wifi

Guest Rating: 4.66/5
44 Guest Reviews
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
  • City: Siesta Key Florida
  • View: Ocean View
  • Sleeps: 6

Heated Pool, Tennis

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Only $300!


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Gulf and Bay Club 305C GulfView 3 pools, fitness room, spa, wifi

Guest Rating: 4.83/5
6 Guest Reviews
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
  • City: Siesta Key Florida
  • View: Ocean View
  • Sleeps: 6

3 Heated Pools, Tennis, Gym

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Only $300!


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Our House at the Beach 222, with Heated Pool, Tennis

Guest Rating: 4.83/5
18 Guest Reviews
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
  • City: Siesta Key Florida
  • View: Best Value/Garden View
  • Sleeps: 4

Heated Pool, Tennis

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Only $300!


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Gulf and Bay 207F, Siesta Key Beach Front, 3 pools, spa, wifi

Guest Rating: 4.56/5
9 Guest Reviews
A large and comfortable condo, Siesta Key Gulf and Bay 207 rentals boasts 1,525 square feet of Mediterranean style. Enjoy gorgeous gulf views from your second-floor balcony and luxury tucked into every corner. Your stay will be first-class. more info
  • City: Siesta Key Florida
  • View: Beach Front
  • Sleeps: 6

3 Heated Pools, Tennis, Gym

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Only $300!


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Aloha Kai 50 heated pool & beach access

Guest Rating: 4.41/5
22 Guest Reviews
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
  • City: Siesta Key Florida
  • View: Best Value/Garden View
  • Sleeps: 6

Heated Pool

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Siesta Dunes 38A, Gulf Side, Large Heated Pool, Wifi

Guest Rating: 4.41/5
37 Guest Reviews
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
  • City: Siesta Key Florida
  • View: Best Value/Garden View
  • Sleeps: 6

Heated Pool, Heated Spa

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Only $300!


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Siesta Dunes 104, Siesta Key Gulf, Spa, Heated Pool, Wifi

Guest Rating: 4.89/5
36 Guest Reviews
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
  • City: Siesta Key Florida
  • View: Best Value/Garden View
  • Sleeps: 6

Heated Pool, Heated Spa

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Only $300!


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Bay Tree Club 106, 2 bedrooms, 2 heated pools, spa, wifi,

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Ground Floor Gulf Unit with 2 pools and a fishing dock on the bay side. Open the sliding doors and let the sea breeze in. Completely updated. Tile in living room areas. Includes a huge 52" HDTV in the living room and a 52" HDTV in the master bedroom. more info
  • City: Siesta Key Florida
  • View: Beach Front
  • Sleeps: 6

2 Pools

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Only $300!


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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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