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Vacation Rentals & Beach Rentals in Siesta Key

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166 beach rentals

Siesta Key Villa A - Only 150 yards to Crescent Beach and heated pool!

Siesta Key villa

2 bedrooms / 1 bathroom / sleeps 4

“This place was absolutely perfect!” This place was amazing. We stayed here just a week:( but we will definitely be back. The condo was clean, fully equipped, comfortable and perfectly located. The beautiful beach was a very short walk away and the lovely heated pool was even closer. I came here with 2 of my daughters 18 and 22. They loved it also. The restaurant “ The Toastd Mango” right across the street had delicious omelettes and friendly staff. The trolley stop is also right across the street and it takes you into the village. And back free! So park your car because everything is right here:) ENJOY

Responds fast! avg. 1 hour 23 minutes

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$149

Remodeled 2br 2ba with private patio, beautiful water views, walk to #1 beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 11 minutes

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$107

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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$188

Siesta Key Villa B - Only 150 yds. to Crescent Beach and heated pool!

Siesta Key villa

2 bedrooms / 1 bathroom / sleeps 4

“Another great stay!” Location is great and owners are awesome to work with! Clean and fully furnished! Thanks for another great stay Derek and Marina! Look forward to next time!

Responds fast! avg. 1 hour 23 minutes

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$149

Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.

Responds fast! avg. 1 hour 29 minutes

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$160

Best Deals on Siesta Key

Siesta Key apartment

1 bedroom / 1 bathroom / sleeps 4

“Nice and easy to get around” You have a wonderful neighbor. I was able to access all the amenities you described. Navigated through out the area with ease.

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$103

The Shells Villa - Next to Beach & Village

Siesta Key house

3 bedrooms / 3 bathrooms / sleeps 10

“Great Experience and Location!” We could not have been happier with our Experience at Shell Villa. Location to the Village was super close as described. Access to the beach was great both through the private walkway or the public access about two block away. The house was well stocked and the floor plan was perfect for our two families. Best place I have rented on SK in 5 years.

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$261

"Safe & Clean" -Honeymoon Suite - Gulf views - next to Siesta Key Beach

Siesta Key apartment

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 50 minutes

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$194

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 4

“It was very cozy and comfortable apartment!” We loved to spend our vacation at this place. Really close to the beach, to different restaurants, and all kind of stores.

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$63

Large Modernized Home a Short Walk to Beach

Siesta Key house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 2 hours 17 minutes

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$398

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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$277

Crystal Sands Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$405

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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$142

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 6

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$164

Ringling Bungalow - Lagoon View

Siesta Key hotel apartment

1 bedroom / 1 bathroom / sleeps 2

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$235

Newly discounted rates! Maximum safety-smaller community, distancing compliant!

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 3

“Anniversary Trip” Had a wonderful time at LA Siesta Condominiums for our anniversary vacation. Beautifully furnished and do close to the best beach in the USA

Responds fast! avg. 22 minutes

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$151

Siesta Key beach & sunsets - 2018 Spring & Summer openings!

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 4

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$135

Beach, Village, Dock, Private Heated Pool... Fantastic Location, No Car Needed!

Siesta Key house

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 40 minutes

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$455

"Safe & Clean" Key West Suite next to Siesta Key Beach

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

“Awesome property and location!” Our 3 teenagers loved the beach right across the street and taking the trolley to the Village. Our 5 year old lived in the beautiful pool. The kitchen was fully equipped and the unit was impeccably clean. A bonus was the use of beach toys, chairs and umbrellas. We'll definitely stay at Gumbo Limbo again.

Responds fast! avg. 50 minutes

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$227

BEAUTY ON THE BEACH! Crescent Arms 601S FULL FRONT VIEW

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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$252

"Safe & Clean" Royal Palm Suite, Exceptional, Beach Views from all 3 balconies!!

Siesta Key apartment

3 bedrooms / 3 bathrooms / sleeps 6

“Fabulous” Last summer My Wife myself and our three daughters stay in the honeymoon suite and had such a wonderful experience we decide to give the Royal Palm Suite a try, and we were really impressed everything was neat and clean, the pre teen girls 4 of them lived in the pool I enjoyed the new gas grill put it to use everyday of our 5 day 4 night stay Thanks Virginia for such a fabulous time, also thanks to Daniel for his diligence in ensuring we had wifi. WE plan on returning next year,and by the way it is exactly 60 steps to the beach I counted.

Responds fast! avg. 50 minutes

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$343

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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$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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$209

OPEN 5/22/20 LIMITED OFFER! BOOK IN ADVANCE- 2020/-21 Siesta Key Beach /HOUSE

Siesta Key house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 1 minutes

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$171

Unique Siesta Key Pool Home

Siesta Key house

4 bedrooms / 3 bathrooms / sleeps 10

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$201

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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$182

Siesta Key 2/2 Pools, Fitness Center, Tennis Courts, Walk to Beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 44 minutes

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$177

Pineapple Bungalow - Courtyard View

Siesta Key hotel apartment

1 bedroom / 1 bathroom / sleeps 4

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$163

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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$350

Dolphin Bungalow - Courtyard View

Siesta Key hotel apartment

1 bedroom / 1 bathroom / sleeps 4

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$176

Coconut

Siesta Key hotel apartment

1 bedroom / 1 bathroom / sleeps 4

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$174

Mermaid

Siesta Key hotel apartment

1 bedroom / 1 bathroom / sleeps 4

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$212

Coquina Bungalow - Courtyard View

Siesta Key hotel apartment

1 bedroom / 1 bathroom / sleeps 4

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$176

Sunset Bungalow - Courtyard View

Siesta Key hotel apartment

1 bedroom / 1 bathroom / sleeps 4

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$176

Catamaran

Siesta Key hotel apartment

1 bedroom / 1 bathroom / sleeps 2

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$212

Tortoise

Siesta Key hotel apartment

1 bedroom / 1 bathroom / sleeps 4

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$211

Come to the Sea and Stay on the Key!

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 4

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$138

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN, UPDATED KITCHEN!

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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$235

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