Siesta Key Vacation Rentals

(238 rentals)
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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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Key Amenities

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

About this property

The condo benefits from its own private pool. The living room, master bedroom, kitchen, and lanai (balcony) all have stunning ocean views. The lanai, with over $10,000 of new doors and windows, is furnished with a table and chairs to enable you to dine al fresco. There is also a beautiful couch to curl ...

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Property Type

Siesta Key Condo

"Fisherman’s Cove Condo 208A"

If you’re looking for a place to unwind and decompress this is the place. We came down from Indiana and i made a call to owner to see if we could check-in early,after asking where we was he said don’t ...

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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 3 | Quick View

8

Distance to beach: 150 yards to Crescent Beach

$320

avg/night

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Key Amenities

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

About this property

1 Week Minimum Stay Required except during Feb 1 to the first Saturday after Easter when 2 weeks are required. Newly Upgraded 1BR/1 BA condo with full sleeper sofa and twin sleeper chair in LR. Updated Kitchen fully remodeled with premium appliances. Top of the Line King Size Bed will give you a great ...

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Property Type

Siesta Key Condo

"Georgious Siesta Key Condo"

This condo is perfectly located in the middle of Siesta Key, on the beach. It is a short distance to Siesta Key Village, that has shopping and restaurants. The condo is very comfortable, with up to date ...

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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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2 BR | 1 BA | Sleeps 6 | Quick View

$291

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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3 BR | 2 BA | Sleeps 10 | Quick View

Distance to beach: 0.7 miles to Siesta Key Beach

$567

avg/night

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Key Amenities

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

About this property

Hard to find home near #1 Siesta Key Beach and Village with all the amenities. The space Welcome to island life!Luxurious 3 bed/2 bath with spectacular water view and walking distance to the village restaurants, shopping, and #1 beach in America!Enjoy your heated pool, hot tub, fire pit, and ...

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Property Type

Siesta Key House

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2 BR | 1 BA | Sleeps 6 | Quick View

$291

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

2 bedroom / 1 bath with private patio plus pull-out sofa (in all units); from your doorway you can see the beach access just across the street – it’s that close! Flat screen televisions in each bedroom and the living room (in all units at Sea Spray Resort). Dine on your private patio! All ...

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Property Type

Siesta Key Apartment

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Key Amenities

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

About this property

If you are looking for a terrific vacation spot tastefully decorated, clean, and comfortable, you just found it. You can be as lazy as the sun and free as the Gulf breeze. We are not underselling ourselves when we say we have the 'Best Location' on 'Crescent Beach.' Experience the ...

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Property Type

Siesta Key Condo

"Owner"

This condo Crescent Arms 501 North is a Direct Front 180 Degree View of the Beach & Gulf of Mexico Some of the Reviews are not our Condo Joan

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2 BR | 2 BA | Sleeps 7 | Quick View

1

Distance to beach: 0.0 miles to Cresent Beach

$258

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
  • 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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1 BR | 1 BA | Sleeps 4 | Quick View

$259

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

1 Bedroom / 1 bath on first floor with private front patio (“no baking oven” discount). Open kitchen and dining area, and like all our units, turn-key furnished, including beach towels. You will like this one! First floor and very spacious! Nice private patio at front door and back door leads ...

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Property Type

Siesta Key Apartment

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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 8 | Quick View

4.9 rating on other travel sites

$398

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

4

Distance to beach: 50 feet to Turtle Beach

$340

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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1 BR | 1 BA | Sleeps 4 | Quick View

$239

avg/night

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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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1 BR | 1 BA | Sleeps 4 | Quick View

$239

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

1 Bedroom / 1 bath on ground floor with patio off bedroom (“no baking oven” discount). This is a first floor unit with a patio off the bedroom. From your patio it is just steps to pool area where you can grill, kick back in the hammock, relax by the pool, or later in the evening have a campfire….you ...

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Property Type

Siesta Key Apartment

Show less

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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2 BR | 2 BA | Sleeps 6 | Quick View

1

$395

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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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

$360

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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1 BR | 1 BA | Sleeps 3 | Quick View

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

$321

avg/night

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Key Amenities

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

About this property

Unit 113 is one of the largest, 1 bedroom hi-rise units in Horizons West, Siesta Key, Florida and has recently undergone a full renovation 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

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2 BR | 1 BA | Sleeps 6 | Quick View

1

$291

avg/night

View Details

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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3 BR | 3.5 BA | Sleeps 8 | Quick View

5.0 rating on other travel sites

$204

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Serenity Cottage, a tranquil cottage located on the southern end of Siesta Key. This remarkable vacation home offers a serene escape where you can unwind, relax, and create cherished memories in a beautiful coastal setting.Step inside and discover a recently renovated kitchen that will ...

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Property Type

Siesta Key House

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3 BR | 2 BA | Sleeps 8 | Quick View

5.0 rating on other travel sites

$1185

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Escape to Bali Hai House, a stunning waterfront home located on the tropical island of Siesta Key. This exceptional property offers a truly blissful retreat with an array of exciting amenities and convenient proximity to Siesta Key Village and Siesta Key Public Beach Access.Situated less than 1 mile ...

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Property Type

Siesta Key House

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Key Amenities

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

About this property

Welcome to Casa Ohana, a stunning vacation home that promises to exceed all your expectations. Nestled in the heart of Siesta Key Village, this extraordinary retreat offers an abundance of luxurious amenities and unparalleled convenience for an unforgettable getaway.Located just a two-minute walk ...

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Property Type

Siesta Key House

"Great place!"

Nice pool! Beautiful area and nice area. We will Be visiting soon and bringing the family. Smooth time.

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4 BR | 3 BA | Sleeps 8 | Quick View

5.0 rating on other travel sites

$453

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Siesta Soul, a captivating retreat located just steps from the vibrant Siesta Key Village. This enchanting vacation home offers an ideal location and a backyard oasis, providing the perfect blend of convenience and relaxation for your Siesta Key getaway.Siesta Soul features four bedrooms ...

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Property Type

Siesta Key House

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4 BR | 3 BA | Sleeps 12 | Quick View

2

Distance to beach: 5 miles to Siesta Key Beach

$433

avg/night

View Details

Key Amenities

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

About this property

Welcome to Casa Mahalo, a stunning vacation home that promises to exceed all your expectations. Nestled in the heart of Siesta Key Village, this extraordinary retreat offers an abundance of luxurious amenities and unparalleled convenience for an unforgettable getaway.Located just a two-minute walk ...

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Property Type

Siesta Key House

"Very comfortable and Clean"

Lily Casita is truly a Cozy Sarasota Home . We were greeted to the home with lights on and music playing the home was very clean and equipped with anything you may need. This was our first time in the ...

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4 BR | 3 BA | Sleeps 12 | Quick View

2

Distance to beach: 1 miles to Siesta Key Beach

$345

avg/night

View Details

Key Amenities

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

About this property

Welcome to Casa Stolida, your luxurious tropical oasis on the Southern end of Siesta Key. This stunning beach house offers an unparalleled experience for large groups seeking both privacy and space. With 4 bedrooms and 3 full baths, it is the perfect choice for family reunions, group getaways, or special ...

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Property Type

Siesta Key House

"Bliss"

Home was fantastic! Maintenance was speedy on my TV problem and fixed it while I was out at the beach. I stayed with three couples. Beds were comfortable for all. Unit had everything we needed. Steps from ...

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2 BR | 2 BA | Sleeps 4 | Quick View

10

Distance to beach: 0.2 miles to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Our adorable unit – Casita Siesta - is located at Gulf & Bay Bayside on Siesta Key, on the bay just south of Sarasota and with private beach access to world-famous Siesta Key Beach. It is a lovely 2 bdr/2 bath unit with a spacious living room and sunny lanai. The master bedroom has full bathroom ...

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Property Type

Siesta Key Condo

"Girls Vacation 2023"

Another amazing week in Siesta Key. This condo is an amazing community, Clean, comfortable with everything needed for a great vacation. This is my third year at this condo and it won’t be my last. Already ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Welcome to Sea Esta, a coastal villa that offers the perfect blend of luxury, convenience, and relaxation. This remarkable property can be rented separately or as a whole, known as Siesta Salt Life, allowing you to choose the ideal accommodation to suit your needs. With a shared heated pool, an unbeatable ...

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Property Type

Siesta Key House

"Ultimate getaway"

The moment you walk in your in vacation mode. Pure relaxation plus a outdoor space that puts it over the top. There’s nothing to want for The lazy river pool is fabulous

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Key Amenities

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

About this property

Welcome to Island Escape, a breathtaking haven located within the heart of Siesta Key! This gorgeous 4-bedroom, 2.5-bathroom home has just undergone a stunning renovation, ensuring that every moment of your stay is filled with comfort and luxury.Step inside and be greeted by a beautifully designed ...

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Property Type

Siesta Key House

"Great Vacation Home"

Very nice house with many amenities. Short walk to the beach. Great place for a family vacation!Carla

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4 BR | 3 BA | Sleeps 12 | Quick View

4.9 rating on other travel sites

$345

avg/night

View Details

Key Amenities

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

About this property

Welcome to Casa Tegula, your luxurious tropical oasis on the Southern end of Siesta Key. This stunning beach house offers an unparalleled experience for large groups seeking both privacy and space. With 4 bedrooms and 3 full baths, it is the perfect choice for family reunions, group getaways, or special ...

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Property Type

Siesta Key House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Welcome to Sea la Vie, a coastal villa that offers the perfect blend of luxury, convenience, and relaxation. This remarkable property can be rented separately or as a whole, known as Siesta Salt Life, allowing you to choose the ideal accommodation to suit your needs. With a shared heated pool, an unbeatable ...

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Property Type

Siesta Key House

"Great location"

Excellent location. Walk across the street to the beach or around the corner to Siesta Village. The place was very clean and most everything was supplied for us. The company made the process so easy. I ...

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3 BR | 3 BA | Sleeps 10 | Quick View

4.7 rating on other travel sites

$223

avg/night

View Details

Key Amenities

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

About this property

Escape to Casita Morning Star, a magnificent retreat that offers nothing but luxury and relaxation. This coastal villa can be rented separately or as a whole as The Solaster, providing you with the flexibility to choose the perfect accommodation for your vacation. With its prime location just a short ...

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Property Type

Siesta Key House

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Key Amenities

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

About this property

Welcome to Crescent Cottage, a charming villa nestled on the southern end of Siesta Key. With its luxurious backyard oasis and perfect location, this delightful retreat is the perfect accommodation for your next island getaway.As you step inside Crescent Cottage, you will find 4 bedrooms and 3 full ...

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Property Type

Siesta Key House

"Vacation 2020"

I visited siesta key and loved my stay. Stayed in the village Evey thing was In walking distance.beach was walking distance

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1 BR | 1 BA | Sleeps 4 | Quick View

4.8 rating on other travel sites

$177

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Welcome to Sea Angel, the perfect destination for small families or couples looking for an intimate yet unforgettable vacation experience. Located within the heart of Siesta Key Village and less than 400 feet to the world-renowned Siesta Key Beach, this property offers the ultimate combination of convenience ...

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Property Type

Siesta Key House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Welcome to Endless Views, a luxurious 3 bedroom 3 bathroom vacation rental located in the heart of Siesta Key, Florida. This stunning property is just a 3 minute walk away from the world-famous Siesta Key Beach, and is conveniently located within walking distance to Siesta Key Village, where you can find ...

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Property Type

Siesta Key House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Welcome to Seahorse Cottage, a beautiful home nestled between the quiet streets of south Siesta Key. This charming duplex offers the perfect retreat for your vacation, featuring a spacious outdoor lanai and a shared heated swimming pool. Whether you choose to rent Seahorse Cabana as a standalone retreat ...

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Property Type

Siesta Key House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Welcome to Sandy Cabana, a beautiful home nestled between the quiet streets of south Siesta Key. This charming duplex offers the perfect retreat for your vacation, featuring a spacious outdoor lanai and a shared heated swimming pool. Whether you choose to rent Sandy Cabana as a standalone retreat or opt ...

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Property Type

Siesta Key House

"Quiet and close to the beach"

Our family had a wonderful spring break staying at Sandy Cabana. Quick walk to the beach and close enough you can walk to local market, shops and restaurants. Condo was clean and well stocked. The neighborhood ...

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Key Amenities

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

About this property

Welcome to Villa Castile, a luxurious retreat located just outside the vibrant Siesta Key Village. This stunning vacation home offers the perfect blend of sophistication and comfort, providing an unforgettable experience for your stay. Whether you're seeking relaxation by the private heated pool, ...

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Property Type

Siesta Key House

"Excellent Property"

Super close to Siesta Village’s shops and restaurants, plus an easy walk to the beach. Very comfortable home, well equipped with everything you need for a great stay.

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3 BR | 3 BA | Sleeps 10 | Quick View

5.0 rating on other travel sites

$335

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Latitude Adjustment, your ultimate waterfront retreat on the beautiful island of Siesta Key! Prepare to be enchanted by the beauty of this captivating home, combining stunning canal and an unbeatable location, ensuring an unforgettable stay for every guest.Upon arrival, you'll be greeted ...

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Property Type

Siesta Key House

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3 BR | 3 BA | Sleeps 8 | Quick View

5.0 rating on other travel sites

$251

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Welcome to Peacock Villa, an exquisite Siesta Key retreat that offers a unique opportunity for a customizable vacation experience. This magnificent property can be rented separately or as a whole - Casa De Mariposa. Whether you're traveling with a large group or looking for a more intimate stay, ...

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Property Type

Siesta Key House

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Key Amenities

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

About this property

This first floor colorful unit sleeps 4 and you will love the sandy beach just outside the lanai door with comfortable patio chairs. Walk past the dune to enjoy more beach and the Gulf of Mexico. A lovely spot to watch sunsets. The unit is upgraded and comfortable for couples traveling together or with ...

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Property Type

Siesta Key Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

This spacious, beautifully decorated and updated 2 BR/2.5 bath townhome overlooks the canal and boat basins and is located directly across the street from the gorgeous Siesta Beach. The kitchen and all baths have been renovated and the newly furnished living room features a sofa bed and 55” smart ...

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Property Type

Siesta Key Townhome

"Had a great vacation."

The townhouse was in a perfect location overlooking an inlet and very close to the beach. Unit well maintained, beautifully furnished. Would stay again!

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Key Amenities

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

About this property

This updated Villa is on the beach side of Siesta Key, with private beach!!!Newly renovated private villa! Beautiful brand new kitchen with quartz countertops and stainless steel appliances. All new flooring through out and newly decorated!Be one of the first guests in this newly renovated clean ...

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Property Type

Siesta Key Villa

"Highly Recommend!"

I would highly recommend renting through Ruth. Her villa was in the perfect location, with great beach access and it was newly renovated! Ruth was easily accessible and answered every question I had. The ...

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Key Amenities

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

About this property

This 5th floor two bedroom, two bath condo is totally and completely renovated. Be one of the first guests to stay in this beautifully renovated condo. New tile throughout. There are two bedroom suites with private baths. Each bedroom has new slider doors that open to screened in lanai with beautiful ...

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Property Type

Siesta Key Condo

"Relaxing getaway"

We had a really nice week in this condo just steps to the beach. The powdery white sand never gets hot.The condo has all of the essentials and more. Very comfortable. And there’s a nice pool if want to ...

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Key Amenities

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

About this property

Our condominium is in the beautiful, gated complex of Gulf and Bay Club on Siesta key Beach, one of the top beaches in America! It has a very large kitchen, 2 King bedrooms and 2 bathrooms. It has been updated with a new King bed and gel mattress, updated bathrooms, new kitchen quartz counter tops and ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 100 yards to Turtle Beach

$340

avg/night

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Key Amenities

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

About this property

Enjoy your home away from home in beautiful Siesta Key! This great 2-bedroom, 2-bath has everything you need for a wonderful, relaxing vacation. This prime location makes it convenient to get to the beach. Just walk a single flight of stairs (or elevator) and you're on the beach where you can enjoy ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

13

Distance to beach: 0.0 miles to Siesta Key Public Beach

$381

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

This 2-bedroom, 2 bath Siesta Key condo can sleep 6 comfortably with a pull-out queen sofa bed and total square feet of 1,773! The beautifully decorated updated condo, with newly tiled bathrooms offers a comfortable, home-away-from-home feel. Sit on your private 20 ft deck and enjoy the view of a lake ...

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Property Type

Siesta Key Condo

"Siesta Key get away"

We loved the beautiful condo. It was our first trip to Siesta Key and we enjoyed it thoroughly. The condo was well kept, fully furnished for the most part and the Mgmt team was there to help us when we ...

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2 BR | 2 BA | Sleeps 5 | Quick View

2
last minute deal
LAST MINUTE DEAL 12/9 - 1/2: Siesta Key Private Villa - Available Dec 9 to Dec 20! January 2024 availability, too!

$248

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Your dream vacation awaits! Your spacious and private single-level house is a perfect getaway for a peaceful and relaxing vacation. Enjoy all the comforts of home while being just a short walk away from bars, restaurants, and Siesta Key's beautiful white sand beaches. Nestled on a quiet tree-lined ...

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Property Type

Siesta Key House

"The Most Well-Appointed Villa"

Snowbird here! We have found the BEST winter getaway! My hubby and I love living close to our kids and grandkids, especially for the holidays. But then the cold and snow in the Northeast has us running ...

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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 $145 per night with an average price per night of $334.

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!