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Southwest Florida Vacation Rentals: SIESTA KEY

Florida's Siesta Key has one of the top 10 beaches on Earth! This island gem lies between the Bay and the Gulf of Mexico - enjoy beautiful sunsets nightly. No car needed; ride vacationer-friendly trolleys. Choose one of our oceanfront condos steps from the Gulf. Excellent values with full furnishings, amenities.
Florida Vacation Rentals - Siesta Key
Listings Found: 33

SIESTA KEY

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FLASH SALE! Left to Save 18% 4/21 - 4/28 or Save 18% 4/28 - 5/5!
Anchorage 904
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Was $1,210.65 NOW $989.09
You’ll be living the high life at Anchorage 904—literally and figuratively. Located on the 9th floor of the Anchorage Yacht & Tennis Club, the 2-bedroom condo offers panoramic views of the Gulf of Mexico, Siesta Key & beyond. more info
• City: Sarasota
• View: Gulf View
• Sleeps: 6
FLASH SALE! Left to Save 18% 4/21 - 4/28 or Save 18% 4/28 - 5/5!
Anchorage 909
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Was $1,321.25 NOW $1,079.45
Breathtaking, panoramic views await you at this luxurious penthouse condo on the 9th floor of an elevator building overlooking the Intracoastal Waterway! Enjoy 200+ sq ft of balcony bliss! more info
• City: Sarasota
• View: Bay View
• Sleeps: 6
FLASH SALE! Left to Save 18% 4/28 - 5/5!
Gulf and Bay Club: Bayside 1226
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Was $989.59 NOW $808.48
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 and Bay Bayside is irresistible! more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Guest Rating: 4.65/5
17 Guest Reviews
FLASH SALE! Left to Save 18% 4/21 - 4/28 or Save 18% 4/28 - 5/5!
Gulf and Bay Club: Bayside 1303-D
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Was $989.59 NOW $808.48
Experience Siesta Key from Bayside 1303-D and get ready for the perfect vacation! This beautiful condo features two accommodating bedrooms, two bathrooms and sleeps six. more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
FLASH SALE! Left to Save 18% 4/21 - 5/5!
Sara Sea #12
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Was $1,724.94 NOW $1,409.26
With direct access to the #1 beach in the US, Sara Sea #12 delivers on the promise of an ideal Florida vacation. There are just 12 units in the Sara Sea community, so you never feel overwhelmed with people and activity. more info
• City: Sarasota
• View: Best Value/Garden
• Sleeps: 4
FLASH SALE! Left to Save 18% 4/21 - 5/5!
Harbor Towers Yacht & Racquet 324
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Was $1,757.98 NOW $1,436.26
Discover the power that a change of scenery can have: steal away to this charming pied-a-terre just a stone's throw from the Gulf, with a cozy balcony, heavenly master suite, and resort perks galore. Harbor Towers 324 is located in a beautiful resort just a stroll from the ... more info
• City: Siesta Key
• View: Water View
• Sleeps: 4
Guest Rating: 4.5/5
4 Guest Reviews
FLASH SALE! Left to Save 18% 4/21 - 4/28 or Save 18% 4/28 - 5/5!
Gulf and Bay Club 108D
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Was $1,004.08 NOW $820.32
Want to get away from everyday life and enjoy a month alongside the #1 beach in the USA? Gulf and Bay Club 108D is just what you are looking to find. more info
• City: Siesta Key
• View: Beach Front
• Sleeps: 4
FLASH SALE! Left to Save 18% 4/21 - 5/5!
White Sands Village Unit 205
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Was $1,757.98 NOW $1,436.26
Beat a path to the beach every day from your own breezy lanai when you stay at this ground-floor condo in a lovely resort. The latest technology, comfy furnishings, and the perfect location await you! more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
FLASH SALE! Left to Save 18% 4/28 - 5/5!
Midnight Cove II 432
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Was $1,100.12 NOW $898.79
From the spacious balcony of this 3rd-floor condo, you can enjoy sun or shade, watch exotic birds visit the nearby lagoon, and bask in the balmy air of the Gulf. Enjoy luxury and beauty in Siesta Key! more info
• City: Siesta Key
• View: Lagoon View
• Sleeps: 4
Guest Rating: 5/5
3 Guest Reviews
FLASH SALE! Left to Save 18% 4/21 - 5/5!
Excelsior 306
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Was $2,421.30 NOW $1,978.18
With spectacular views of the beautiful trees, pond, pool and peek a boo view of the Intracoastal, you will be asking yourself why you didn't choose Excelsior 306 sooner. Our 3 bedroom condo sits on a little strip of paradise! more info
• City: Siesta Key
• View: Pool View
• Sleeps: 6
Guest Rating: 5/5
1 Guest Reviews
FLASH SALE! Left to Save 18% 4/21 - 4/28 or Save 18% 4/28 - 5/5!
Bay Oaks D-42
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Was $878.99 NOW $718.13
With 2 bedrooms and 2.5 bathrooms, Bay Oaks D-42 can accommodate a family of 5 or 2 couples with equal ease. more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 5
FLASH SALE! Left to Save 18% 4/21 - 4/28 or Save 18% 4/28 - 5/5!
Beach Walk Unit B
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Was $1,763.58 NOW $1,440.83
Experience Siesta Key from Beach Walk Unit B and enjoy the beautiful gulf view! This beautiful condo features three accommodating bedrooms, two-and-a-half bathrooms and sleeps eight. more info
• City: Sarasota
• View: Gulf View
• Sleeps: 8
Guest Rating: 4.86/5
7 Guest Reviews
FLASH SALE! Left to Save 18% 4/21 - 4/28!
Our House at the Beach 222
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Was $1,210.65 NOW $989.09
There's plenty of room for everyone here at Our House. We have a split-level living/dining area, with a large living room made for a crowd! more info
• City: Siesta Key
• View: Lake View
• Sleeps: 4
Guest Rating: 4.68/5
38 Guest Reviews
FLASH SALE! Left to Save 18% 4/28 - 5/5!
Gulf Holidays 15
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Was $989.59 NOW $808.48
Budget-friendly and just a block from a beach rated #1 in the country, it’s easy to see why Gulf Holidays 15 is a very popular place to vacation in beautiful Siesta Key. Gulf Holidays 15 is one of just 18 condos in the community that offers a beautiful swimming pool surrounded by palm ... more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
FLASH SALE! Left to Save 18% 4/21 - 4/28 or Save 18% 4/28 - 5/5!
Gulf and Bay Club 102B
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Was $1,004.08 NOW $820.32
Ready to spend 28 days or more in paradise? If so, Gulf & Bay Club 102B is waiting for you. more info
• City: Siesta Key
• View: Beach Front
• Sleeps: 6
Guest Rating: 5/5
1 Guest Reviews
FLASH SALE! Left to Save 18% 4/21 - 4/28 or Save 18% 4/21 - 5/5!
Bay Tree Club 106
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Was $878.99 NOW $718.13
With the Gulf of Mexico just steps from your back door and beautiful Sarasota Bay a couple minutes’ drive in the other direction, Bay Tree Club 106 is perfectly situated for fun on Siesta Key. In 2011 Siesta Beach was named the Best Beach in America. more info
• City: Siesta Key
• View: Beach Front
• Sleeps: 6
Guest Rating: 5/5
6 Guest Reviews
FLASH SALE! Left to Save 18% 4/21 - 4/28 or Save 18% 4/28 - 5/5!
Gulf and Bay Club 204C
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Was $1,004.08 NOW $820.32
Come vacation on the white sands of Siesta Beach! When you stay at our condo at Gulf and Bay Club 204C, you'll enjoy luxury and comfort in more than 1,500 sq ft of beachfront property, including a lovely lanai. more info
• City: Siesta Key
• View: Gulf View
• Sleeps: 6
Guest Rating: 4/5
2 Guest Reviews
Limited-Time Offer: Stay before 6/16/18 and Save Up to 18%!
Twin Palms 5
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Only $300 to
Book Now!
You’ll be just a one-block walk from Siesta Key, the #1 rated beach in the USA when you stay at Twin Palms #5. This one-story condo was built in 2003 and retains the wonderful Key West style that is the complex’s hallmark. more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
Guest Rating: 4.5/5
2 Guest Reviews
FLASH SALE! Left to Save 18% 4/28 - 5/5!
Gulf and Bay Club 305C
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Was $1,350.86 NOW $1,103.64
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 renovated unit with a new air conditioning and heating system, Gulf and Bay Club 305C, trumps the ... more info
• City: Siesta Key
• View: Gulf View
• Sleeps: 6
Guest Rating: 4.89/5
9 Guest Reviews
Limited-Time Offer: Stay before 6/16/18 and Save Up to 18%!
Palm Bay Club G34
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Only $300 to
Book Now!
Both TripAdvisor and Dr. Beach named Siesta Beach the country’s best beach. more info
• City: Siesta Key
• View: Gulf View
• Sleeps: 4
Limited-Time Offer: Stay before 6/16/18 and Save Up to 18%!
Polynesian Gardens Villa P6
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Only $300 to
Book Now!
Welcome to your home in paradise! This standalone 2-bedroom villa offers privacy and relaxation for an incredible family vacation. more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
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