Siesta Key Vacation Rentals

(238 rentals)
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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Enjoy our 2br 2 bathroom ground floor condo. 30’ to the pool, tennis courts, Weber gas grills, and picnic table . Or cross the street to private deeded beach access on the #1 beach in the US. Enjoy bayside fishing on the fishing deck. 1280 square feet of living space. Roku tv’s and ...

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Property Type

Siesta Key Condo

"Cold escape"

We always enjoy our stay at Gulf and Bay Bayside!!! Condos are perfect! We always meet new people who have become friends and can’t wait to see them again next year!!!

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos ...

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Property Type

Siesta Key Condo

"GREAT!!"

These people are great , have stayed there before and will again.clean good service nice pool right on the gulf.

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2 BR | 1 BA | Sleeps 6 | Quick View

$290

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

Our guests always comment on how clean our units are and we take pride in this.2 bedroom / 1 bath with direct access to pool through back door, one of our favorites for families! 1 King Bed + 1 Queen Bed

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Property Type

Siesta Key Apartment

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1 BR | 1 BA | Sleeps 4 | Quick View

$311

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

1 Bedroom / 1 bath with its own private pool walled in for complete privacy. Vaulted ceilings — spacious inside and out, with flat screen TVs in bedroom and living room. Great get-away unit…with pull-out sofa, great for families or even two couples. Pool and patio area is entirely ...

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Property Type

Siesta Key Apartment

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2 BR | 2 BA | Sleeps 5 | Quick View

5

Distance to beach: 0.0 miles to Siesta Key beach also known as "Crescent Beach"

$393

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Unit 404's furnishings were updated in November 2022.The million dollar five star view you want and can now enjoy.Fully equipped modern, clean kitchen with a big beach view, stainless steel appliances, ice maker, dish washer, granite counters and back splashes and custom cabinets. Two types ...

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Property Type

Siesta Key Condo

"A wonderful stay at Siesta Key"

We had a wonderful time at Charley and Nancy's condo. His condo is beautiful and very well maintained. They have recently purchased all new living room furniture, it was very pretty as well as comfortable. ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

SIESTA BREAKERS - Siesta Key Beachfront Vacation Rental Condo on Crescent Beach (Two Bedroom Vacation Units for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL BEAUTIFUL NEW LISTING: This beautiful, two bedroom, two bath, luxury Villa is located directly on the ...

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Property Type

Siesta Key Condo

"good place"

Comfortable and quiet at that time. I recommend it to everybody.. Please have more explanation to find the place to unlock the gate

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

NEWLY RENOVATED IN 2023!!VERY SPACIOUS 4 BEDROOM 2 BATHROOM DETACHED VILLA IN HIGHLY SOUGHT AFTER POLYNESIAN GARDENS COMMUNITY ON BAY SIDE OF THE ROAD. PUBLIC BEACH ACCESS AT CRESCENT BEACH AND ACCESS TO HEATED POOL AND COMMUNITY CENTER. WIRELESS INTERNET ACCESS,VILLA SLEEPS 8, 1 KING, 1 QUEEN, ...

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Property Type

Siesta Key Villa

"AMAZING"

This villa was very spacious, clean, homey and comfortable. It was well stocked in all areas. The garage was filled with anything you would need to go to the beach. The beds were the most comfortable beds ...

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3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 20 yards to Crescent Beach, Siesta Key

$440

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

Unit 608 is a large 3 bedroom, 2 bath high-rise unit in Horizons West, Siesta Key, Florida. The unit has recently undergone a complete makeover by a Chicago designer. The interior was fully demolished and rebuilt. No detail or expense was spared in completing the perfect beach condo: large panoramic ocean ...

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Property Type

Siesta Key Condo

"Stunning Condo"

My family stayed in this stunning condo and absolutely loved it. Beautiful views, fabulous modern furniture, high tech TVs and sound system, awesome high end kitchen and baths.

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

You will fall in love with this condo! Everything you would possibly need is provided. Enjoy relaxing on the lanai in the morning with your coffee or a glass of wine in the evening. Nice beach chairs, beach umbrellas, straw mats, small cooler, swim noodles and a beach bag are all in the condo for your ...

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Property Type

Siesta Key Condo

"What a Fantastic Little Gem!"

Siesta Key have become our favorite vacation spot and #409 at Crescent Royale was where my wife and I got to experience the very best thanks to Karen who accepted us in her beautiful and awesomely appointed ...

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3 BR | 3 BA | Sleeps 6 | Quick View

8

Distance to beach: 0.3 miles to Crescent Beach

$450

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Welcome to your perfect vacation home on Siesta Key! Our turnkey townhouse is located just a few minutes' walk from the #1 ranked Crescent Beach, where you can enjoy the crystal-clear waters and powdery white sand that have made Siesta Key world famous.Our townhouse features a spacious courtyard ...

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Property Type

Siesta Key Townhome

"Paradise!"

The place was immaculate and had everything we needed. It was so nice to have beach towels, chairs, and sand toys provided. The location is perfect. It's a very short walk to the beach. Some restaurants ...

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2 BR | 2 BA | Sleeps 6 | Quick View

63

Distance to beach: 0.0 feet to We are directly on the beach and direct oceanfront

$358

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Our condo is directly on the beach and is direct oceanfront (Gulf-front). Unfortunately, there are properties on this site that falsely claim to be beachfront / oceanfront. We encourage travelers to ask property owners to verify those claims.When we travel over 1,000 miles to enjoy a beach vacation ...

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Property Type

Siesta Key Condo

"Love it had everything you need."

Love the whole place so clean. I like the recycle idea. We will be back every year here. Was not at all tourist place so nice. Everyone there was very helpful and friendly. Beautiful place to stay. Ty mrs ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

VILLAGE WEST - Deluxe Ground Floor Vacation Condo in Siesta Key Village with Heated PoolLocated right in the Heart of Siesta Village, Sarasota FL - Short Walk to Crescent BeachVILLAGE WEST: This Siesta Key one bedroom ground floor condo vacation rental is located right in the heart of Siesta Village ...

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Property Type

Siesta Key Condo

"Great location!"

The location of this rental was perfect. We were able to walk into the village to shop and eat within a few minutes. Drive time to local attractions was minimal.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Welcome to Siesta Sunset, a breathtaking beachfront home located right on the pristine shores of Siesta Key Beach. This gorgeous condo not only offers direct beach access but also stunning panoramic views of the Gulf of Mexico, ensuring your island getaway is nothing less than spectacular!As you step ...

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Property Type

Siesta Key House

"Peaceful family getaway"

We loved the house. It was perfect for my husband and I and our two young kids. The pool was the perfect temp and having the back of the house covered in windows was great b/c we could keep and eye on ...

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2 BR | 2 BA | Sleeps 7 | Quick View

12
last minute deal
LAST MINUTE DEAL 11/20 - 12/30: Please inquire about discounts for any remaining weeks in Nov-Dec!

$338

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

The Gulf of Mexico is only 100 ft. from your private sand beach and lanai entrance. Listen to the surf from your master bedroom. Enjoy dining on the lanai while watching the sunset. During the day you can see dolphins, kite boarding and sea birds. This unit has all the comforts of home plus a full size ...

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Property Type

Siesta Key Condo

"Comfortable unit"

We enjoyed our stay, unit was clean, in good repair, and steps to the beach. Nice outdoor chairs and toys. Beds were comfortable. Good size for our adult group of 3. Close to a park. Felt safe. Only downside ...

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DEAL

1 BR | 1 BA | Sleeps 4 | Quick View

$263

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

1 bedroom / 1 bath with full kitchen and walled private patio off living room…one of our largest 1 bedroom units with a very private, walled patio with table/chairs/umbrella for morning breakfast or evening dinner on the patio! Just steps to the pool, grills, hammock…a great unit! 1 King ...

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Property Type

Siesta Key Apartment

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2 BR | 1.5 BA | Sleeps 4 | Quick View

28
owner special
Owner special: December dates available! Enjoy all the Christmas decorations on our beautiful island!

Distance to beach: 200 yards to Crescent Siesta Key Beach

$266

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool
  • Rentals by owner

About this property

Located in beautiful Siesta Key, Fl (consistently ranked #1 beach in the US!!) in Midnight Cove 1, this bayside condo spoils its occupant with all the amenities and luxuries needed for a relaxing, tropical vacation. Nestled amid lush landscaping in this gated community, our unit is newly remodeled and ...

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Property Type

Siesta Key Condo

"Great location, clean property"

My husband and I stayed here with our two toddlers and a baby. This was the perfect location. We were able to walk to the beach and the pools with ease. The condo had everything you possibly needed. We ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Enjoy easy living and carefree days on Siesta Key! This modern bungalow is steps away from the private, deep, white sand beach of Aloha Kai and the only solar-heated, Olympic-sized pool on the Key. Have your morning coffee or afternoon cocktails on the airy lanai or relax in the bright mid-century modern ...

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Property Type

Siesta Key Bungalow

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2 BR | 1 BA | Sleeps 6 | Quick View

1

$290

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

2 bedroom / 1 bath with private patio, spacious kitchen and living room. Enjoy eating outside on your private patio. Every bedroom and the living room have flat screen televisions; this is true for every unit at Sea Spray Resort! One of our favorite 2 bedroom units and one of the closest to the beach ...

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Property Type

Siesta Key Apartment

"Oh ya"

Great place oh boy oh ya. Get there this year terrific place. Wonderful experience. Will donut again

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1 BR | 1 BA | Sleeps 4 | Quick View

$238

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

This is a 3rd floor, 1 bedroom / 1 bath furnished unit with kitchen area but no “baking oven.” (You’ll have to save baking for another time!) However, you will find everything else you need in your unit, including your very private 3rd floor balcony off the living room. This is a great ...

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Property Type

Siesta Key Apartment

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2 BR | 2 BA | Sleeps 7 | Quick View

1

Distance to beach: 0.0 miles to Cresent Beach

$334

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Siesta Key condo with heated pool. One of the best locations in Siesta Key. Updated with fun designs, feature walls, smart TVs, functional kitchen. Minutes’ walk to white sands of Siesta Beach ranked #2 beach in the US and #14 in the world. Walk to Tiki bar, Captain Curt’s, bike, boat, kayak, ...

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Property Type

Siesta Key Condo

"Perfect Getaway!"

This condo has it ALL! It's all about location in Siesta Key & this condo is a very short walk to the beach, stores & restaurants! I loved walking down the lush path to see the picture perfect sunsets on ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos ...

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Property Type

Siesta Key Condo

"Beautifully renovated beach condo"

The condo contained anything and everything need to have a wonderful vacation. The view of the ocean was spectacular.

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3 BR | 2 BA | Sleeps 8 | Quick View

4.9 rating on other travel sites

$395

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FLTop beachfront unit at Fisherman's Cove!! Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

1

$394

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

RENOVATED 2020!!! From the lanai and your private patio, you are directly on the beach where it is easy to keep an eye on the children playing, or walk down to the Gulf of Mexico for a swim. Located on Turtle Beach, Siesta Key's quiet south end - this lovely Gulf front first floor unit with large ...

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Property Type

Siesta Key Condo

"Beautiful Condo!"

This Condo is well appointed and is in the perfect spot right on the beach of the Gulf! We we're ableto walk out to the beach from our back door and see the canal out the front. We cooked in the kitchen ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos ...

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Property Type

Siesta Key Condo

"Beautiful Condo in a nice quiet area a stone's throw from the beach."

We loved this condo. It was beautiful, newly refurbished and so comfortable. More like a nice family home than just a rental. We loved sitting in the sun on the lanai watching the birds and the beach. ...

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2 BR | 2 BA | Sleeps 6 | Quick View

4

Distance to beach: 50 feet to Turtle Beach

$338

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Pool

About this property

Direct Beachfront Condo on the Gulf of Mexico located on Siesta Key. 2 bed, 2 bath condo loaded with amenities. Just remodeled, completely new, finished with tile flooring, granite counters, stainless appliances, washer and dryer and all new furniture. Both Bedrooms have king beds and separate baths. ...

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Property Type

Siesta Key Condo

"Closest View and Walk to Beach We've Ever Had!!"

3 Moms, 2 young adult all girl getaway to Siesta Key, which we've never been before. We like Sanibel, Captiva, Madeira Beach, Destin, so we thought we'd try SK. LOVE IT! Adorable, clean, nice 15 minute ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

There is no way you can get closer to the water than this! Sitting outside and having your morning coffee listening to the waves is so relaxing. Having a glass of wine and watching the sun set is the perfect way to end the day. This amazing unit has it all! The Primary bedroom has a king bed and its ...

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Property Type

Siesta Key Condo

"Life on the Beach"

The location was what I wanted which was to be near the gulf so I could easily swim and enjoy the serenity of the gulf at my fingertips. The accommodations met my needs with plenty of kitchen supplies ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

This magnificent unit has been completely remodeled and is on the ground floor with beautiful water views and spectacular sunsets. Walk out the rear lanai door directly onto the beach where children can play within view or walk over the boardwalk to the blue-green waters of the Gulf of Mexico within 100 ...

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Property Type

Siesta Key Condo

"Relaxing beach front getaway"

We once again thoroughly enjoyed our stay in A108 at Fisherman's Cove on Siesta Key. Russ and Dina have supplied everything needed for an enjoyable vacation experience. The kitchen is well stocked. The ...

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2 BR | 2 BA | Sleeps 4 | Quick View

16

Distance to beach: 0.1 miles to Siesta Key Beach

$300

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

NEWLY UPGRADED - BEAUTIFUL LAKEFRONT CONDO FOR THE PERFECT GETAWAY FROM THE COLD Right across from Siesta Key Beach, minutes from Siesta Key Village - or the South VIllage - shopping, top restaurants, live music, and entertainment. Walk , bike or take the free trolley.Sit on the balcony for a ...

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Property Type

Siesta Key Condo

"Gorgeous Siesta Key Condo"

I could rave about this condo and Cristina for days! The condo itself was everything we hoped it would be and more. It was so absolutely comfortable and charming, with every amenity you could wish for. ...

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1 BR | 1 BA | Sleeps 4 | Quick View

$227

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

1 Bedroom / 1 bath with TWO private patios, one off the dining/living room and the other off the bedroom. Both patios are walled for privacy. With a pull-out sofa on one end of the unit and the bedroom on the other side it makes a great unit for up to four people, even though it is a one bedroom unit. 1 ...

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Property Type

Siesta Key Apartment

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

THE BEACH IS CALLING AND I MUST GO!! *We invite you to come stay with us in the Crescent Arms South Tower--Condo 601S--directly on the #1 famous Crescent Beach with a FULL view of the Gulf on a private 32 foot lanai.*Decorated in a "beachy motif" with granite counter tips in the kitchen ...

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Property Type

Siesta Key Condo

"Beauty at the Beach"

I highly recommend condo 601 South/ Beauty at the Beach! Elaine was very accommodating and her condo was the most coziest, beautiful, and relaxing place that I have stayed in a very long time. It had everything ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

A millionaire's retreat! This completely remodeled first floor unit with view of the Gulf of Mexico and amazing sunsets awaits you on Siesta Key. Walk out the lanai door directly to the beach where children can play within view or walk over the boardwalk to the blue-green waters of the Gulf within ...

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Property Type

Siesta Key Condo

"Fantastic location"

Steps away from the beach, this condo is modern and very well equipped and certainly met all our needs for a great vacation. Dina and Russ were great hosts! We are already planning to return next November.

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1 BR | 1 BA | Sleeps 4 | Quick View

6

Distance to beach: 100 yards to Crescent Beach

$280

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Simply relaxing one bedroom condo with a king bed facing the pool area and just a few steps to the private entrance to" Siesta Key #1 beach" white quartz sand beach . Additionally a Lazyboy queen memory foam sofa sleeper for separate sleeping area if needed Unit includes a full kitchen for ...

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Property Type

Siesta Key Condo

"Sea Crest #26"

Great people. Great weather. Great beach access, loved the sunsets. TV had no directions on how to navigate. Loved being close to Captain Curt’s restaurant. Loved the Old Florida charm.

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2 BR | 2 BA | Sleeps 6 | Quick View

$290

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

2 bedroom / 2 bath unit with direct back door access to main pool! There you can grill on one of the barbeques, relax in the hammock, swim in the pool and later in the evening have a campfire and enjoy the starry night sky! 1 King Bed + 1 Queen Bed

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Property Type

Siesta Key House

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2 BR | 2 BA | Sleeps 5 | Quick View

5

Distance to beach: 100 feet to Crescent Beach

$400

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

Relax and listen to the waves while sitting on your private lani. You're on the top floor (6th) of the Siesta Breakers Condominium, a private, gated facility with direct access to Crescent Beach, the #1 Top Rated beach in the USA.This luxury 2 bedroom 2 bath apartment, has been kept up to date ...

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Property Type

Siesta Key Condo

"Perfect"

Siesta Breakers is the perfect place to get away. This condo was wonderful and had everything we needed! You couldn’t ask for more beauty, comfort, and relaxation! This is the perfect place.

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2 BR | 2 BA | Sleeps 6 | Quick View

6

$361

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

This colorful custom2rd floor unit has a commanding view of the Gulf of mexico.This special unit has been decorated by a pro, and shows it! unit, perfect for people who can take excellent care of things and appreciate the fine nature of this unit.From the modern kitchen, you will enjoy Siesta ...

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Property Type

Siesta Key Condo

"Wonderful Vacation"

This was a terrific place to stay with wonderful views of the gulf. It was a very pleasant and peaceful trip. Carrie was great to work with. Once she found out about a beach project date changing, she came ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

My ground floor rental is directly on the beach on the Gulf of Mexico, with incredible views and sunsets!The lanai has a back door directly out to the Beach. The front of my unit faces the Lagoon where we have a FREE DOCK for your boat or other water craft. (So you have water views in both directions)! ...

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Property Type

Siesta Key Condo

"Amazing"

This unit offers an amazing view of the ocean and sunsets. Perfect get away spot, great location, clean and has everything you need to enjoy your stay. We will be back in 2014!

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1 BR | 1 BA | Sleeps 4 | Quick View

$238

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

This second floor 1 bedroom / 1 bath is beautifully furnished with everything you need, including beach towels. Kitchen has everything except “baking oven”…think you can make it without baking a turkey while you relax in paradise? Private patio for romantic setting while enjoying drinks ...

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Property Type

Siesta Key Apartment

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to Bay Isle Bliss, a luxurious 3 bedroom, 2 bathroom vacation home that offers a serene retreat from the hustle and bustle of everyday life. Located just 0.3 miles from Shell Beach and 1.7 miles from Siesta Key Village, this exquisite property provides the perfect vacation getaway for families, ...

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Property Type

Siesta Key House

"Perfect pet-friendly property"

Great location close to the beach and Sarasota downtown. The property is completely fenced, and located in a very quiet neighborhood. My kids enjoyed the pool and the hot tub...We will visit again.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to Floritas Key, a vibrant yet coastal bungalow located on the northern end of Siesta Key. This delightful retreat offers an unforgettable experience, with its stunning private heated pool and prime location that puts you just moments away from the best attractions and natural beauty this area ...

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Property Type

Siesta Key House

"Fabulous Place"

Excellent Location close to the Crescent Beach and Restaurants. I would stay there again the next time I visit Siesta Key.

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1 BR | 1 BA | Sleeps 4 | Quick View

$290

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

1 bedroom / 1 bath has a full kitchen, private patio off bedroom and lovely walkway to pool. The world will never find you in this sultry hideaway located on our tropical, brick paver walkway just steps from the pool or the beach!

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Property Type

Siesta Key Apartment

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3 BR | 2 BA | Sleeps 8 | Quick View

4.8 rating on other travel sites

$606

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Escape to Baydream Bungalow, a charming 3 bedroom villa nestled on the northern end of Siesta Key. This quaint home offers a peaceful island retreat, ensuring a memorable stay for you and your loved ones.Situated a short distance of only 0.6 miles, Shell Beach welcomes you to indulge in the serenity ...

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Property Type

Siesta Key House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

The Siesta Key vacation condo rental is a one bedroom / one bathroom individually owned condominium at the Gulf and Bay Club Bayside and is furnished with the basic household items necessary for normal living. This unique Old Key West style condo is fully equipped with an emphasis on vacation living. ...

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Property Type

Siesta Key Condo

"March Getaway!"

Siesta Key was very beautiful and a great place to visit. The accommodations were very nice, clean and comfortable. We hope to visit this area again next year.

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Our Condo is on beautiful Turtle Beach at the southern and most private end of Siesta Key directly on the Gulf of Mexico. When we say directly, we mean directly and not merely a Gulf “View” or a long car ride or a long walk to the Gulf. We call it “Paradise” and you could not ...

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Property Type

Siesta Key Condo

"Excellent Condo A306"

We stayed at A306 the third week of April 2023. Our stay was well beyond expectation and this location & Unit is the best overall rental we’ve experienced in 25+ years of Florida vacationing. Everything ...

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2 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to beach: 0.1 miles to Crescent Beach Siesta Key

$245

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to The Anchorage Yacht and Tennis Club across from the beautiful sands of Crescent Beach on Siesta Key. Sitting directly on the intercoastal waterway where you can park your boat, jet ski, kayak, and paddleboard. This complex has an Olympic size pool, three lighted tennis courts, pickleball nets. ...

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Property Type

Siesta Key Condo

"June Trip"

Check in was easy. Clean unit. Management staff were friendly and helpful. Beach area use could be more clear. The beach accessories were good.

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1 BR | 1 BA | Sleeps 4 | Quick View

$238

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

This is a 3rd floor walk-up with 1 bedroom / 1 bath. It is turn-key furnished with everything you need — except “baking oven”…you will have to hold off on baking until you return home! A balcony off the bedroom overlooks the lush grounds. You can enjoy total privacy in your 3rd ...

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Property Type

Siesta Key Apartment

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach (Two Bedroom Beachfront Unit for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL Crescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront ...

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Property Type

Siesta Key Condo

"Beach and ocean waves"

The condo was super nice. The master bedroom mattress was amazing for a rental. So often I feel like they are hard as rocks but this one wasn’t. The second bedroom had similar mattress but they were not ...

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1 BR | 1 BA | Sleeps 4 | Quick View

$255

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

1 Bedroom/1 bath with full kitchen, pool view and private patio area adjacent to the pool. This 1 bedroom unit has a comfy king bed as well as a pull-out sofa bed in the living room. Enjoy a mid-day refreshment on your private patio with table, chairs, and umbrella for your comfort and relaxation. An ...

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Property Type

Siesta Key Apartment

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2 BR | 2 BA | Sleeps 6 | Quick View

5

Distance to beach: 0.2 miles to Siesta Key

$293

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

NEWLY REMODELED - LUXURY WATERVIEW CONDO FOR COUPLES or Families GETAWAY - POOLS, GYM, TENNIS - Walk to beach, town, shopping, top restaurants, live music, and entertainment.Walk out of the front door of this fantastic condo, grab your beach gear and take a short walk and you'll hit the beach ...

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Property Type

Siesta Key Condo

"Palm Bay review"

Oscar is a super guy. The place he’s renting is even better. Very easy walk to multiple pools and the beach. In a prime location for many shopping and dining amenities. You’re not gonna find any better ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

A front row seat for the famous sands and sunsets of Siesta Key Step barefoot directly on to the award-winning, powdery sand of Crescent Beach Two of four bedrooms have gulf views Ideal for families or small groups of up to 8 people Enjoy access to an Olympic-sized pool Fully equipped kitchen Screened ...

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Property Type

Siesta Key House

"Beautiful View Great Location"

Perfect oceanfront stay! Group of 8 (4 adults and 4 children under 10). Fit our 2 families perfectly and is only steps from the beach making it easy to run back and forth. Close to all shops/ice cream/restaurants. ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to Casa Leone, a luxurious home nestled on the northern end of Siesta Key. This exquisite property offers an array of amenities and comforts to ensure a memorable and relaxing stay.As you ascend up the stairs to the main level of the home, you will be greeted by a spacious and elegantly decorated ...

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Property Type

Siesta Key House

"Casa Tegula Review..."

We LOVED Casa Tegula!!! The house was very clean and stocked with everything we needed. Location was wonderful, only a short walk to the ocean and shops. Sara at The Cottages on the Key was AMAZING and ...

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Siesta Key Vacation Rentals

Siesta Key Weather

 | 

7122°  5111°
JANUARY
Ocean 6418°
7423°  5412°
FEBRUARY
Ocean 6518°
7725°  5814°
MARCH
Ocean 6719°
8127°  6217°
APRIL
Ocean 7323°
8630°  6820°
MAY
Ocean 7826°
8932°  7323°
JUNE
Ocean 8228°
9133°  7423°
JULY
Ocean 8530°
9133°  7524°
AUGUST
Ocean 8730°
8932°  7323°
SEPTEMBER
Ocean 8529°
8529°  6719°
OCTOBER
Ocean 8228°
7926°  6016°
NOVEMBER
Ocean 7524°
7423°  5412°
DECEMBER
Ocean 6921°

Find the Beach Vacation of a Lifetime with Siesta Key Vacation Rentals


Interested in a beach vacation for your next spring break or a long weekend away? Though the great state of Florida is known for its many scenic beach towns, there are some that cater more to those looking for a quiet, relaxing trip and some that are perfect for an exciting vacation full of non-stop fun in the sun. What if you could find a beach city that offers the best of both worlds for a truly well-rounded vacation? Enter Siesta Key vacation rentals. 

Nestled just south of Sarasota, Siesta Key, FL, is a spirited city along the Gulf Coast that offers just as many opportunities for R&R as it does for nightlife, watersports, and unforgettable adventures in the great outdoors. Though the island of Siesta Key itself is only about eight miles long, it’s jam-packed with enticing restaurants, unique shops, and glittering white sand beaches as far as the eye can see. 

As a major vacation destination along Florida’s Gulf Coast, there are many hotel options to choose from during your stay, with varying proximities to the beach. However, if you’re looking for a truly immersive experience during your trip to Siesta Key, you won’t get it at a crowded commercial hotel! 

Browse Siesta Key vacation rentals from FloridaRentals to find the perfect rental home for your beach vacation. Whether you’re looking for a sunny, romantic getaway for you and a loved one, or you’re bringing the whole family along, you’re sure to find an incredible property. Look for one that offers authentic local architecture, plenty of space to spread out during your downtime, and close proximity to all of the best features the city has to offer.

Siesta Key, Florida Travel Tips


There’s a reason why oceanside Florida cities like Siesta Key tend to be popular destinations during springtime. While temperatures may be warmest on average in the summer months, this time of year also has the highest levels of precipitation and humidity. Unfortunately, this makes it more difficult to enjoy outdoor activities. 

In mid to late spring, temperatures in the air and water are warm and comfortable without too much rain or humidity expected. This makes it easy to take part in all of your favorite pastimes, including surfing, boating, wakeboarding, or simply catching some rays on the sand. 

The closest airport to Siesta Key is the Sarasota/Bradenton International Airport, which lies around 11 miles north of the city center. Most visitors will fly into this airport for its easy access, though the area can also be reached relatively quickly by way of the Tampa International Airport.

How to Spend Your Vacation to Siesta Key House Rentals


It’s no surprise that most Siesta Key vacationers spend more time at the beach than anywhere else during their visits. The most popular beach destination is Siesta Key Beach, which was ranked the #1 Beach in the U.S. by TripAdvisor’s Traveler’s Choice Awards in 2020. The gentle waves, powdery white sand, ample parking, and plentiful concession stands are just some of the reasons why many visitors choose to lounge their day away at Siesta Key Beach. 
Those who are interested in an unforgettable outdoor experience shouldn’t miss out on a trip out on the water with Adventure Kayak Outfitters. You’ll have the choice of a guided kayak tour of the nearby Exotic Mangrove Tunnels or a kayak rental to make your own adventure. You’re sure to spot some incredible wildlife like dolphins, exotic birds, and manatees along the way.

Yearly Events in Siesta Key


Siesta Key is closely linked with the nearby city of Sarasota. The two cities share many of their annual events, creating even bigger and better celebrations for locals and tourists alike to enjoy. 

One annual event that’s already become a mainstay in the local culture is the Annual Downtown Sarasota Craft Festival. This unique arts and crafts show features a wide variety of media, including pottery, paintings, jewelry, photography, and much more, alongside the scenic white-sand beaches. Visitors can peruse and purchase unique wares from local artisans, including soaps, spices, plants, and even kettle corn. 
Runners visiting Siesta Key can get in a great workout while supporting a great cause at the Annual Andrew Monroe Memorial Scholarship 5K Run/Walk. All funds raised during this event are donated to the Sarasota Community Foundation Scholarship, which helps local athletes train to their full potential and achieve their goals.  

Best Eats Near Siesta Key Rentals


Whether you’re in need of some casual seaside grub for the family after a long day at the beach or looking forward to a romantic date night with your significant other, Siesta Key has a huge variety of delicious and eclectic eateries fit for every taste and occasion. 

For a hearty steak, you can’t do much better than Summer House Steak & Seafood. This stylish eatery offers sustainably sourced steaks alongside a variety of unique sides, salads, beverages, and desserts that are sure to satisfy. Additionally, Summer House offers a full menu of seafood dishes. It takes full advantage of the city’s close proximity to fresh seafood and offers plenty of surf and turf options for hungry visitors. 

Island House Tap and Grill is a local favorite for casual yet memorable eats in Siesta Key. With a varied menu that includes everything from tacos to burgers to ceviche, as well as plenty of refreshing cocktails, you’re sure to enjoy a delicious and satisfying dinner with your family.


FAQ

How many vacation rentals are there in/around Siesta Key?

There are 238 Siesta Key vacation rentals available on FloridaRentals.com. From condo rentals to house rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Siesta Key?

There are vacation rentals available in Siesta Key for as low as $144 per night with an average price per night of $338.

Can I find a vacation rental in Siesta Key?

Yes, you can find vacation rentals in Siesta Key close to Sieta Beach, Turtle Beach and Crescent Beach. Don't forget to stop in to Point of Rocks or Siesta Farmer's Market.

Do any vacation rentals in Siesta Key have a pool?

Yes, there are 61 vacation rentals with a pool in Siesta Key on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Siesta Key vacation rentals on the ocean?

There are 48 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!