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Vacation Rentals & Beach Rentals in Siesta Key

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125 beach rentals

Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 16 minutes

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Price per night from

$196

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 30 minutes

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Price per night from

$245

Siesta Key Condo, Crescent Arms, unit 605 South

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 50 minutes

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Price per night from

$229

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

$431

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

$572

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

$606

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

$344

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

$162

Amazing Beachfront Condo, Siesta Key, 100ft+ Beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$196

Another Day in Paradise

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 32 minutes

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Price per night from

$439

Watch Sunsets From Your Lanai ON THE BEACH plus FREE Boat Docks!

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

$175

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

Siesta Key house

4 bedrooms / 6 bathrooms / sleeps 10

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Price per night from

$1,764

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

$249

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 14 minutes

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Price per night from

$208

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

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 5 minutes

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Price per night from

$169

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

Siesta Key condo

3 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$635

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

$361

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. 2 hours 13 minutes

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Price per night from

$205

Midnight Cove #532 in Siesta Key, FL- Sun, Sand & *Save 10% to 25% per Week*

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 4

“Clean comfortable Siesta Key Condo with all the comforts of home...Perfect!” The condo is walking distance to shops, restaurants and quaint local tiki bar! The beach is a short walk across the street and through the beach-front section of the complex with lounge chairs and umbrellas available, very nice! I didn't mention the 2 pools (one beachside) and nice gym facilities also just downstairs of the unit. The covered parking space was an added plus! The condo was clean and very comfortable with all of the amenities of home which is greatly appreciated! You can even enjoy the view of the bayside inlet and beautiful landscaping from the kitchen through the entire wall of glass doors in the living/dining room! We had a wonderful week! The property owner Vic supplied more than enough information on the condo, local businesses and area maps! He was such a pleasure to work with! Thanks again Vic! We are already planning our next trip to Siesta Key in May!!

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Price per night from

$130

Midnight Cove #714 in Siesta Key, FL- Sun, Sand & *Save 10% to 25% per Week*

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$130

Siesta Key Beachfront Condo with Gulf View!

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 40 minutes

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Price per night from

$172

Siesta Breakers #603 in Siesta Key, FL- Sun, Sand & *Save 10% to 25% per Week*

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$200

Beautiful Condominium In Great Location !

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

“A vacation place that meke you feel like home” Sarasota is a great city, siesta beach a wonderful beach, but everything is better when you stay in this apartment. The owners made a great effort to make your stay comfortably. They think in everything,it is very organized, clean and complete. You are near restaurants, shoppes and fun. I went whit three teens and they like it so much.

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Price per night from

$92

Siesta Key - 2bdrm on the beach - amazing views!!

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 5

“Escape from reality” We had an amazing vacation. Accommodations were great and very comfortable. Breakfast on the lanai and sunset fishing on the beach were 2 of our families favorite things to do. You also have the bay right behind you where you can kayak or paddle board. The community was quiet which was prefect for our getaway. We will definitely be staying here again.

Responds fast! avg. 1 hour 49 minutes

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Price per night from

$423

Beautiful Crescent Beach on Siesta Key One of the

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$246

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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Price per night from

$257

Three bedroom house directly on beach with gulf vi

Siesta Key house

3 bedrooms / 4 bathrooms / sleeps 7

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Price per night from

$373

3BR/4BA TOWNHOUSE - POOL VIEW PARADISE - PRIVATE BEACH ACCESS

Siesta Key townhouse

2 bedrooms / 4 bathrooms / sleeps 6

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Price per night from

$206

THE BEST SPOT ON SIESTA KEY BEACH & VILLAGE! !

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 12

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Price per night from

$572

Stunning 2 Bed/ 2 Bath with Best Siesta Key Beach View, Our House at the Beach!!

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$240

Stunning 2 Bedroom/ 2 Bath by Siesta Key Beach, Sunlight Sensation!!

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$274

Newly Renovated Condo with Gulf Views and a Private Beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$195

Siesta Key townhouse steps away from the beach and the village

Siesta Key townhouse

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 21 minutes

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Price per night from

$470

THE BEST LOCATION ON SIESTA KEY BEACH & VILLAGE! !

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 12

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Price per night from

$570

Siesta Oceanview House

Siesta Key townhouse

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$146

Great rentals within 20 miles that match your search

GULF FRONT 2 BR 2 BATHROOM CONDO

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$222

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$385

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