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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

SIESTA KEY

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Gulf and Bay Club 409B
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Only $300 to
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Perfect for guests looking for a rental of one month or longer, your time spent at Siesta Key Gulf and Bay Club #409 is guaranteed bliss. Confirmed to be the “Best Sand Beach in America” by the Travel Channel, Siesta Key’s residents and renters alike ... more info
• City: Siesta Key
• View: Gulf View
• Sleeps: 4
Guest Rating: 4.69/5
13 Guest Reviews
Gulf and Bay Club 108D
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Only $300 to
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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
Limited-Time Offer: Stay before 3/24/18 and Save Up to 18%!
Casa Siesta
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Only $300 to
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Casa Siesta makes fun in the sun so easy! The 2-bedroom, ground-floor condo is just a short walk from the powdery white sands of Crescent Beach and the azure waters of the Gulf of Mexico. more info
Only 3 weeks left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
Guest Rating: 5/5
1 Guest Reviews
Gulf and Bay Club 102B
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Only $300 to
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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
Sara Sea #12
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Only $300 to
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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: 6
Limited-Time Offer: Stay before 3/24/18 and Save Up to 18%!
Jamaica Royale Tower Unit T24
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Only $300 to
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Fresh ocean breezes, spectacular sunsets, beautiful gulf view, and rolling waves await you at this Gulfside condo! Enjoy all the luxe comforts of an upscale rental plus the convenience of a private walkway to the beach! more info
Only 3 weeks left in the next 60 days!
• City: Siesta Key
• View: Gulf View
• Sleeps: 6
Limited-Time Offer: Stay before 3/24/18 and Save Up to 18%!
Siesta Dunes Beach 201
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Only $300 to
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This unit has been newly renovated in the fall of 2017. Stunning seaside decor, new kitchen, baths, paint, and luxury vinyl plank flooring throughout. more info
Only 3 weeks left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Guest Rating: 4.59/5
22 Guest Reviews
Limited-Time Offer: Stay before 3/24/18 and Save Up to 18%!
Jamaica Royale Tower T23
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Only $300 to
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Welcome to beach living with gulf views from this breezy, comfortable condo on the shores of Siesta Key! Part of a luxe complex, it offers many amenities just a stone's throw from the surf! more info
Only 2 weeks left in the next 60 days!
• City: Siesta Key
• View: Gulf View
• Sleeps: 4
Limited-Time Offer: Stay before 3/24/18 and Save Up to 18%!
Anchorage 909
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Only $300 to
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Breathtaking Sarasota Bay and Gulf 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
Only 2 weeks left in the next 60 days!
• City: Sarasota
• View: Bay View
• Sleeps: 6
Limited-Time Offer: Stay before 3/24/18 and Save Up to 18%!
Vista Hermosa
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Only $300 to
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Located in Siesta Key’s Vista Hermosa condo complex, this is a 2-bedroom standalone bungalow. That means you don’t have to worry about noisy neighbors next door or on the floor above. more info
Only 2 weeks left in the next 60 days!
• City: Sarasota
• View: Resort View
• Sleeps: 5
Siesta Shores 13
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Only $300 to
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Situated just steps away from the "world's finest, whitest sand" and all of the enjoyment that Siesta Key has to offer, this lovely 3 bedroom/2 bathroom cottage sleeps 8 guests and is the perfect Floridian escape for your next vacation. ... more info
• City: Sarasota
• View: Best Value/Garden
• Sleeps: 8
Limited-Time Offer: Stay before 3/24/18 and Save Up to 18%!
Anchorage 904
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Only $300 to
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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 Intracoastal Waterway to the east and Sarasota just beyond. more info
Only 1 week left in the next 60 days!
• City: Sarasota
• View: Gulf View
• Sleeps: 6
Palm Bay Club G46
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Only $300 to
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With the top-rated beach in the country in your backyard, Palm Bay Club G46 delivers the perfect Gulf-side vacation. Just take an elevator ride down from your fourth-floor condo and you’ll be right at the beach, ready to sink your toes into warm silky ... more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
Guest Rating: 4.45/5
44 Guest Reviews
Limited-Time Offer: Stay before 3/24/18 and Save Up to 18%!
Siesta Dunes Beach 38A
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Only $300 to
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Live the tropical life in this incredible modern condo! From the large wooden deck to the heated pool, and only a few minutes’ walk from the beach, you’ll love every minute of your time in Siesta Key! more info
Only 1 week left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Guest Rating: 4.49/5
71 Guest Reviews
Beachaven 52
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Only $300 to
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Imagine this: You step out your front door, and there, at the end of a walkway flanked by shrubbery on one side and an impeccably manicured lawn on the other, are the twinkling white sands of Crescent Beach and, just beyond, the sparkling Gulf of Mexico. ... more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
Guest Rating: 4.33/5
3 Guest Reviews
Polynesian Gardens Villa P6
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Only $300 to
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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
White Sands Village Unit 205
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Only $300 to
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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
Inlet 21
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Only $300 to
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Are you ready for a great escape? If so, Inlet 21 is the perfect spot for you. more info
• City: Sarasota
• View: Gulf View
• Sleeps: 6
Harbor Towers Yacht & Racquet 324
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Only $300 to
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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 ... more info
• City: Siesta Key
• View: Water View
• Sleeps: 4
Guest Rating: 5/5
1 Guest Reviews
Limited-Time Offer: Stay before 3/24/18 and Save Up to 18%!
Crescent Street 1138 Unit A
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Only $300 to
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When you stay at Crescent Street 1138A, you can walk to the east side of Siesta Key in just minutes to catch the sunrise over the Gulf of Mexico. Then later, just before dusk, you can take an equally brief stroll over to the west side of the barrier ... more info
Only 1 week left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Limited-Time Offer: Stay before 3/24/18 and Save Up to 18%!
Gulf and Bay Club: Bayside 1303-D
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Only $300 to
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When you pull up to the Gulf and Bay Club: Bayside 1303-D you will know right away that you made the perfect decision for your family vacation. Beautiful palms adorn the grounds to give you a totally tropical vibe. more info
Only 1 week left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
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The Longer You Stay - The More You Save! - Save $300 with Code SAVE300 when 1 month stay - Save $100 with Code SAVE100 when 2 week stay - Save $50 with Code SAVE50 when 1 week stay - Offer Ends 1/28 - Browse Rentals Now!
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