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Limited Offer! Stay Before 9/16 and Save up to 40% - CLICK HERE NOW!

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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Limited-Time Offer: Stay before 9/23/17 and Save Up to 16%!
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
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Harbor Towers Yacht & Racquet 324
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Only $300 to
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Harbor Towers 324 is a cozy 1 bedroom/ 1 bath Siesta Key condo that sleeps 2-4. Guests will feel right at home thanks to the comfy, newly renovated, very modern furnishings and amenities. more info
• City: Siesta Key
• View: Bay View
• Sleeps: 4
Guest Rating: 5/5
1 Guest Reviews
Vista Hermosa
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Only $300 to
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Beautiful, updated villa in desirable Vista Hermosa – condo on Siesta Key in Sarasota. One of the finest crystal-quart sand beaches in the world, siesta key is definitely a place for you to vacation. more info
• City: Sarasota
• View: Resort View
• Sleeps: 5
Gulf and Bay Club 305C
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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 renovated unit with a new air conditioning and heating system, Gulf and Bay Club ... more info
• City: Siesta Key
• View: Ocean View
• Sleeps: 6
Guest Rating: 4.89/5
9 Guest Reviews
Limited-Time Offer: Stay before 9/23/17 and Save Up to 16%!
Twin Palms 5
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Only $300 to
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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
Limited-Time Offer: Stay before 9/23/17 and Save Up to 16%!
Our House at the Beach 222
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Only $300 to
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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: Best Value/Garden
• Sleeps: 4
Guest Rating: 4.68/5
37 Guest Reviews
Limited-Time Offer: Stay before 9/23/17 and Save Up to 16%!
Bay Oaks D-42
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Only $300 to
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Enjoy the simple pleasures of life by doing anything and everything that you could possibly care to do at the Bay Oaks D-42, Siesta Key Florida where heaven becomes real! The Bay Oaks D-42 is fully equipped with every amenity you can think of! more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 5
Polynesian Gardens Villa P6
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Only $300 to
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Looking for a home away from home as you embark upon your upcoming vacation, Polynesian Gardens Villa P6 is an impeccable choice. Located on the tropical border island of Siesta Key, Florida, Polynesian Gardens is an impressive community. more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
Jamaica Royale Tower Unit 24
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Only $300 to
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Fresh ocean breezes, spectacular sunsets, 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
• City: Siesta Key
• View: Gulf View
• Sleeps: 6
Limited-Time Offer: Stay before 9/23/17 and Save Up to 16%!
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
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
Guest Rating: 5/5
1 Guest Reviews
Jamaica Royale Tower 23
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Only $300 to
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Welcome to beach living with peekaboo 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
• City: Siesta Key
• View: Gulf View
• Sleeps: 4
Limited-Time Offer: Stay before 9/23/17 and Save Up to 16%!
Excelsior 306
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Only $300 to
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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
Only 3 weeks left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Limited-Time Offer: Stay before 9/23/17 and Save Up to 16%!
Midnight Cove II 432
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Only $300 to
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Sun seekers Delight! Enjoy your morning coffee looking at the palms and oaks lining the boat basin from your own private, sunny, 3rd-floor balcony. more info
Only 3 weeks left in the next 60 days!
• City: Siesta Key
• View: Lagoon View
• Sleeps: 4
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: 4.5/5
2 Guest Reviews
Siesta Dunes 8-205
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Only $300 to
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Featuring beautiful wood floors, Siesta Dunes Beach 205 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. As a gulf-side property, it’s easy on the wallet while its ... more info
• City: Siesta Key
• View: Gulf View
• Sleeps: 4
Limited-Time Offer: Stay before 9/23/17 and Save Up to 16%!
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
Bay Oaks B-52
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Only $300 to
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Featured on HGTV's Beachfront Bargain Hunt TV show! With views over a sunny, peek a boo view of the Intracoastal Waterway, a stay at Bay Oaks B-52 provides great value for a vacation filled with anything and everything you care to do. more info
Only 2 weeks left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Limited-Time Offer: Stay before 9/23/17 and Save Up to 16%!
Gulf and Bay Club: Bayside 1226
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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 and Bay Bayside is irresistible! more info
Only 2 weeks left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Guest Rating: 4.69/5
16 Guest Reviews
Bay Tree Club 106
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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
Only 1 week left in the next 60 days!
• City: Siesta Key
• View: Bay View
• Sleeps: 6
Guest Rating: 5/5
5 Guest Reviews
 Jamaica Royale 101
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Only $300 to
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A beach holiday doesn’t get any better when you combine good food and a great place to stay in the mix. This is exactly why you must come over to Jamaica Royale 101 the next time you’re visiting Siesta Key. more info
Only 1 week left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Palm Bay Club G46
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Only $300 to
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The accolades keep pouring in. Guests and media alike rate the Palm Bay Club as a perfect destination for romantic getaways and family vacations. more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
Guest Rating: 4.45/5
44 Guest Reviews
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