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Vacation Rentals & Beach Rentals in Siesta Key

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156 beach rentals

Gorgeous Direct gulf Front 2 Bedroom Condo on Siesta Keys... JUST REMODELLED

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$188

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$276

Luxury Villa, Sleeps 6 Comfortably Located on Siesta Key Beach, Sarasota Florida

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 8 minutes

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Price per night from

$205

5 Bedroom Beachfront Home on Siesta Beach!! 49 Beach Rd

Siesta Key house

5 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$672

Beachfront- Gulf View! 2 BR/BA Crescent Arms 603S, #1 Beach in the US.

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 36 minutes

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Price per night from

$179

Elegant Condo with Gulf Views - Walk to Beach and Siesta Village

Siesta Key condo

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$438

Luxury Village Townhouse w/ Gulf and Beach Views

Siesta Key townhouse

2 bedrooms / 2 bathrooms / sleeps 8

“A wonderful home in an equally wonderful location.” The home provides a truly enjoyable family situation. The quality of the furnishings is very nice, the living space is very well maintained and clean and my interaction with the owner was always timely and courteous. My wife and I shared the home with our 14 year old granddaughter during our stay and the quiet enjoyment of the pool and the easy 1-2 minute walk to the Gulf of Mexico and the 5 minute walk to the heart of Siesta Key Village made the location hard to beat. Except for our day trips no car was needed. This is our second stay in the home and we will look to reserving it for our next visit. There were absolutely no disappointments only wonderful experiences.

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Price per night from

$384

Siesta Key Condo, Crescent Arms, unit 605 South

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 20 minutes

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Price per night from

$221

Siesta Key - #1 Beach in USA

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$143

WOW Factor Siesta Key Beach Gulf Front Condo in Siesta Dunes on #1 Beach in USA

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 19 minutes

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Price per night from

$277

Crescent Arms 703S, Beachfront Penthouse, Gulf View from Every Room! 2BR-BA

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 5

“vacation excellence” Room is great. View is outstanding. We really enjoyed our stay. Room is quiet no outside noise. We recommend

Responds fast! avg. 36 minutes

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Price per night from

$182

Siesta Key Paradise! 4 Bedroom Beachfront Home

Siesta Key house

4 bedrooms / 2 bathrooms / sleeps 10

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Price per night from

$672

Renovated 2 bedroom with beach views and pool access!!-Living the Dream, Mermaid

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$216

Excellent Location - Gulf/Beach View - Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 39 minutes

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Price per night from

$227

Siesta Key Oceanfront on Gulf with western sunsets, 1250 sq ft Townhome

Siesta Key villa

2 bedrooms / 3 bathrooms / sleeps 4

“Absolutely Perfect---one Kodak sunset after another” This townhome was gorgeous! We totally enjoyed our 3 week stay and hated to leave. Kelley (owner) could have not been more helpful. We fished off the dock and enjoyed watching the birds fish then dry their wings. Town is a short, enjoyable jaunt. Just a few blocks further are the most gorgeous beaches with sand like flour! If you are adventureous, walk to Point of Rocks at beach access 13 for the best shelling ever (only at very low tide)!!! We would come back in a heartbeat. The views from the lanai and upstairs balcony were awesome. Townhome was beautifully maintained and fully stocked. Thanks to Kelley and her daughter for a never-to-be-forgotten vacation.

Responds fast! avg. 2 hours 13 minutes

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Price per night from

$142

Spectacular Siesta Key Beachfront Condo, Sarasota Surf & Racquet Club

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$245

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 6

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Price per night from

$164

EP-301 Gulf View Spacious Condo on Siesta Key Beach #1 in USA

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$282

Amazing Beachfront Condo, Siesta Key, 100ft+ Beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 53 minutes

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Price per night from

$195

Fully renovated pool home directly across from Siesta Beach!!-Ocean Blue

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$544

Beachfront Siesta Key Home directly on the white sands of Siesta Beach!!

Siesta Key house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$531

Enjoy Sounds of the Surf and Gorgeous Sunsets from Your Lanai

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Great Place for a relaxing vacation!” The place has everything you need to feel like home and relax. Perfect for family vacation. And the location is awesome - the beach two feet of the balcony.

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Price per night from

$170

Another Day in Paradise

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$314

Direct Beachfront 2 BR/2BA, Sunset View!

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 36 minutes

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Price per night from

$219

2BR2BA 800sqft 2nd Floor Siesta Key Crescent Beach Condo + WiFi No Road to Cross

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 7

“Wonderful Vacation - great place, great location, perfect beach !” We make this trip every year and have stayed in other units owned by this owner, and as per usual everything was perfect. Location is awesome, reason we come every year. Private beach is just steps away, or private pool in the opposite direction. Laundry facilities available and the unit itself has all the amenities of home. Would definitely recommend to anyone with children, master bedroom has own private bath. Currently trying to figure out a date closer to summer to book another week !!

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Price per night from

$111

Renovated Beach Front 2BR/2BA Condo, Steps to beach, Gulf of Mexico Views

Siesta Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 11 minutes

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Price per night from

$209

Beachfront. Gulf View from Every Room, 2BR/2BA, Pool, Beach Chairs, Sunsets

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 36 minutes

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Price per night from

$179

Gulf and Bay Club 3bdrm “E” Luxury Penthouse Unit - RIGHT ON BEACH

Siesta Key condo

3 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$588

Brand new with rooftop terrace. Directly across from Siesta Beach! 641 Beach Rd

Siesta Key house

4 bedrooms / 4 bathrooms / sleeps 12

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Price per night from

$675

Beachfront Condo Directly Across the Street From the Beautiful Siesta Beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$250

Newly Renovated Condo Near SK Beach and Village

Siesta Key condo

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$502

Direct Beachfront Siesta Key condo on the Gulf of Mexico ~ Breathtaking Views!

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 28 minutes

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Price per night from

$143

Ocean view beachfront 2BD2BA Sleeps 7 New furniture Walk to grocery/restaurants

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 7

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Price per night from

$182

Gulf & Bay Paradise: Luxury Beach Condo; Pool, Tennis, Direct Beach Access

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 55 minutes

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Price per night from

$132

4 Bedroom with Gulf View Siesta Key FL Beach Fun

Siesta Key apartment

4 bedrooms / 4 bathrooms / sleeps 10

“Fantastic Location and Beautiful Accomodations” Our daughters and their families stayed here in February. The condo was everything we expected and more. It has a breathtaking view of the Gulf from the screened in lani which runs the width of the unit. The four bedrooms were perfect for our group of nine and the kitchen / dining area was well stocked with appliances , pots & pans , dishes , glassware , etc. Condo has easy access to heated pool and ample parking. Owner made the rental process smooth as silk , and we all felt right at home as soon as we had checked in. Right across street from world famous Siesta Beach. Would highly recommend.

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Price per night from

$350

Beachfront Condo Siesta Key

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!

Responds fast! avg. 1 hour 53 minutes

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Price per night from

$189

Siesta Key Beachfront Condo with Gulf View!

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 7 minutes

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Price per night from

$158

Midnight Cove #714 in Siesta Key, FL- Sun, Sand & *Save 9% to 25% per Week*

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$122

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rentals in Siesta Key

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