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Siesta Key Vacation Rentals

(174 rentals)
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
6 reviews

Key Amenities

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

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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Featured review

"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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$362
avg per night
Last Minute Deal
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
47 reviews

Key Amenities

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

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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Featured review

"Little piece of heaven"

I can't say enough about this property absolutely heaven out your front door is a beautiful Bay with manatees playing in it pretty much every day we were able to be there!! out the back door you're about...

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$396
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

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

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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Featured review

"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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$399
avg per night
Siesta Key Condo
Sleeps 8, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to the gorgeous 2BR 3Bath beachfront townhouse nestled in the tranquil complex on Siesta Key, FL. Escape the big-city crowds and enjoy the lovely ambiance from the patio while being just a few steps from the pristine sandy beach, swimming pool, local restaurants, shops, and attractions. 2 Comfortable...

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$508
avg per night
Siesta Key Condo
Sleeps 7, 2 bedrooms, 2 bathrooms
15 reviews

Key Amenities

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

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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Featured review

"Clean & Well Stocked"

Three very important things to make your vacation complete; cleanliness is number one of course, location and is the rental property well stocked so you have everything that is needed for a vacation of...

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$365
avg per night

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Siesta Key Townhome
Sleeps 6, 3 bedrooms, 3 bathrooms
12 reviews

Distance to beach: 0.3 miles to Crescent Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Discover the ultimate Siesta Key getaway with this beautifully appointed, smoke free, 3-bedroom Townhouse, perfectly situated just 300 steps from the world-famous Crescent Beach. Enjoy the best of both worlds with Turtle Beach only 2.4 miles away, offering endless opportunities for seaside relaxation...

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Featured review

"Dream Spot"

Our stay at this Siesta Key Airbnb was absolutely amazing. The location couldn’t have been better—just a short walk to the beach with that famous powder-soft white sand. The home was spotless, beautifully...

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$449
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 0.1 miles to Crescent Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This amazing condo offers a Gourmet Kitchen and island. Granite counter tops, high ceilings and stainless steel appliances (including super quiet Bosch dishwasher and French door refrigerator with two ice-makers).Removed and replaced all forty year old Duct-work with brand new Flex Duct-work for improved...

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$414
avg per night
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 100 feet to Crescent Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

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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Featured review

"Siesta Key"

The area: The general area of the condo was a fun place to visit. Plenty of stores within walking distance (just across the street). More than ample restaurants from which to choose. If you are heading...

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$482
avg per night
New
Siesta Key House
Sleeps 16, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Key Differentiators & Amenities•360 steps to Siesta Key Beach (#1 beach in the US) •Ample parking for RV, boat, and multiple vehicles •EV charging station onsite •Private saltwater pool (fenced backyard) •Pet-friendly: beds, crates, bowls, blankets, waste bags •4...

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$1,392
avg per night
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
2 reviews

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

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

Best beachfront view on Siesta Key from remodeled two bedroom and two bathroom beachfront condo. Stay for the unbelievably beautiful beachfront balcony views. Enjoy the modern open floor plan with beach views from most rooms. Beautifully furnished apartment you will be proud of.Upgraded, secure WiFi.Spectacular...

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Featured review

"Any last minute availability for February"

Hello I was looking to see if you had any last minute availability for February ? Sorry to contact through the review I could not find an email address to send a request. Thank you for your time best Joann

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$479
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
8 reviews

Key Amenities

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

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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Featured review

"Amazing Stay"

My family and I had the most amazing stay in Don & Elaine’s condo! We have been coming to Siesta Key for 6 years and this was our favorite room- best location and best view ever! We look forward to returning....

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$450
avg per night
Siesta Key House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Very private - empty lot across the canal and fenced in. Walk to the islands best restaurants, bars, shops and ice cream parlors. The beach is a short stroll (8 min), use free golf cart taxi or ride provided bikes with tow behind cart! Siesta is well known for its #1 beach in the USA!

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$449
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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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$388
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

This tropical island get-away offers everything you desire for a magical, effortless vacation. Sunny, spacious second floor condo with easy indoor-outdoor living space including two queen bedrooms, each with an ensuite bathroom. Just steps to private, quiet powder-sand gulf beach and private fishing...

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Featured review

"Just perfect - a beautiful condo in a natural setting"

This is a lovely immaculate condo in a lush green setting. From my window i watched birds, ducks, and turtles on the lake . On the sweet private beach i saw pelicans, dolphins and egrets. It's tempting...

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$327
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This first floor colorful unit sleeps 6 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 America. A lovely spot to watch sunsets. The unit is upgraded and comfortable for couples traveling together or with...

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$372
avg per night
Siesta Key House
Sleeps 10, 4 bedrooms, 3 bathrooms

Distance to beach: 0.6 miles to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to your slice of paradise on Siesta Key—where coastal charm meets everyday convenience. This beautifully maintained single-family pool home offers the perfect blend of privacy, comfort, and proximity to the island’s natural beauty. Step outside and enjoy the lush, landscaped backyard,...

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$460
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Summer Cove on Siesta Key is life at its finest. This gated community on Little Sarasota Bay offers a spacious 2 bedroom, 2 1/2 bath unit of luxury with the sophistication and conveniences of the finest resort located on the Key within minutes to the #1 beach in the US - Siesta Key Beach. The unit is...

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$408
avg per night
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
8 reviews

Key Amenities

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

About this property

Crystal Sands, Siesta Key, SarasotaAmazing Views!! Our property is right on the beach. Take the elevator down and you're at the ocean. The views are amazing as you can see in the pics. Sit on the lanai for breakfast and watch the activities on the beach, or have a glass of wine and watch...

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Featured review

"AMAZING 2-Weeks!!!!!"

We loved every minute of our 2-week stay at Crystal Sands, the unit was beautiful and views breathtaking. We were a stones throw from the beach and it couldn't have been any better. I highly recommend!

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$625
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 100 yards to Turtle Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

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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$374
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful 2 Bedroom, 2 Full bath condo. Close to everything, right on Crescent Beach, voted #1 beach twice in the last 5 years. King in the master, 2 full size beds in the second.

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Featured review

"Fantastic location"

Our family loved staying here and have already looked into coming back! The location can’t be beat as it is on the first floor of the tower which makes the beach just steps from your door. We enjoyed...

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$328
avg per night
Siesta Key Condo
Sleeps 3, 1 bedroom, 1 bathroom
4 reviews

Distance to beach: 0.0 miles to Siesta Key Main Beach

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Water views everywhere from this Penthouse condo on Siesta Key! Taxes (13%) already included in my rates. Walk to beach. King bed in bedroom (and a Queen bed in living room if needed). Come and enjoy beautiful weather at the best beach in Florida! Heated Pools, Lighted Har-Tru Tennis Courts, Fitness...

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Featured review

"Penthouse Paradise"

what a great find! A bright and lovely penthouse condo in a resort on Siesta Key. Easy walk to the beach, and the new Pickleball courts at the Main beach. Harbor Towers itself had a great pool, marina,...

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$242
avg per night
Siesta Key Condo
Sleeps 6, 3 bedrooms, 3 bathrooms
5 reviews

Distance to beach: 0.1 miles to Siesta Key

Key Amenities

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

About this property

Fully renovated penthouse unit! This property seamlessly melds state of the art amenities with casual beachfront living with privacy. Step off of the sugary sands of Siesta Key Beach and right in to this beautifully renovated beachfront condominium with surprisingly expansive gulf views. Sea and sky...

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Featured review

"Heaven"

I think this is what Heaven must be like.. Our stay here was wonderful! This is a beautifully renovated, clean, and comfortable unit. It is the whole top floor of a two unit building (no elevator; 27 steps...

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$800
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
11 reviews

Distance to beach: 0.3 miles to Crescent Beach on Siesta Key

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Siesta Key Condo - Siesta Key ParadiseLooking for a vacation rental in Siesta Key? Look no further... we have a two bedroom first floor condo located on the spacious, gorgeous landscaped grounds of Midnight Cove ii.Enjoy great views from our lanai watching boats, yachts, and wildlife on the Intracoastal...

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Featured review

"Loved the View!"

You wouldn’t think a ground level condo could have a great view, but think again! The living room looks out onto the inter coastal, so you can watch the boats go by. So picturesque and relaxing. The condo...

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$242
avg per night
Siesta Key Villa
Sleeps 5, 2 bedrooms, 2 bathrooms
16 reviews

Distance to beach: 400 yards to Crescent Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

The Sand Dollar is a private villa located at the quiet, well run and exceedingly clean "beach to bay" community of Horizons West. A maximum of 50% of Horizons West properties are rented so the community has a more residential feel than many others on the island. The villa has been recently...

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Featured review

"Perfect Stay!"

This E-8 villa is in the perfect location for a family visit. It’s just steps from the bay and a short walk to the pools and beach. The villa itself is very clean and spacious. It’s located in a residential...

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$325
avg per night
Siesta Key Townhome
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 600 yards to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Our House on Siesta Key!There’s plenty of room for everyone here at Our House. The split-level living area features a large-screen HDTV, perfect for movie nights with popcorn and frosty drinks after a day of outdoor fun. Just steps away, the fully equipped kitchen has everything you...

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Featured review

"Great Stay"

We had a great stay at this condo. We would definitely stay here again. It was clean and spacious. It was also very close to siesta beach and near siesta village. Overall great experience!

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$300
avg per night
Siesta Key Condo
Sleeps 10, 4 bedrooms, 4.5 bathrooms
3 reviews

Distance to beach: 0.3 miles to Siesta Beach

Key Amenities

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

About this property

This 4 bedroom 4.5 bathroom condo with elevator, pool and private beach access. No need to look any further as luxury awaits! This unit can be combined with the adjoining unit for 8 bedrooms total. There is a wonderful outdoor living space with dining table and lounging area, living room, dining area,...

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Featured review

"Great condo and location"

Thanks to Stephanie for excellent communication and special thanks to MJ who was very helpful and quickly available during our stay. This condo is beautiful and has an excellent location. It's a 3 minute...

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$698
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
7 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Our little piece of paradise is a one bedroom condominium ideal for couples or young families. We are located at 73 Avenida Messina in unit #7 on the ground floor of the Gulf Holiday Apartments. We are 300 ft. from the Gulf of Mexico and about a five minute walk from the village - known for its shops,...

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Featured review

"Condo #6"

We enjoyed staying in Condo #6 for two nights before Hurricane Helene arrived. We evacuated and weren’t able to return. We hope to stay here again in the future. We have stayed in these condos for...

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$171
avg per night
Last Minute Deal
Siesta Key House
Sleeps 7, 3 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 0.7 miles to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

**Completely Renovated February 2025** Welcome to island life! Enjoy your own private resort in the heart of the #1 beach in America, Siesta Key!Indulge in the pinnacle of island living at this pristine waterfront home on Siesta Key—a haven where luxury meets natural beauty. In the heart of...

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Featured review

"Beautiful and comfy"

5 stars. Wish I could give 10. Beautiful and comfy cozy home, comfortable beds, gorgeous pool, so kid friendly and lovely views from the fire pit. The decor is top notch!! Danielle and Jeb were great-...

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$668
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 3 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Great house as is renovate december-2024 with new kitchen, toilets, furniture and everything is painted inside the house on Siesta key with pool and kanal. You can do fishing on the backside or have a jetski, boat there. Sometime you can see manates on the kanal. 3 bedroom with 3 bath and a nice heated...

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Featured review

"Perfect Location"

Located close to the village and within walking distance of the beach. Plenty of room for families and amenities which included bikes for all ages. The pool is heated and such a great perk!

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$371
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
6 reviews

Distance to beach: 100 yards to Crescent Beach

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

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 queen memory foam sofa sleeper for separate sleeping area if needed Unit includes a full kitchen for your...

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Featured review

"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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$314
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 0.3 miles to Siesta

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy resort amenities at the Harbor Towers tennis and Yacht club in Siesta key. The building has completed a $13 million dollar structural and cosmetic renovation and is a beautiful building highlighting Siesta key and Midnight Pass. This condo offers the option to play tennis, swim at the pool exercise...

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$346
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
14 reviews

Distance to beach: 1 miles to Crescent Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

AFTER 2 HURRICANES E91 IS READY FOR GUESTS!! We thank God that our condo was spared! E91 is a completely renovated, First floor Condo, steps to the pool. Master bedroom has a King bed with on-suite bathroom and walk-in closet. Second bedroom has a Queen bed and twin bunk beds. Fully equipped kitchen...

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Featured review

"Great place"

The owner thought of everything. Beach and restaurants are within walking distance. Would definitely rent the condo again.

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$277
avg per night
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
5 reviews

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

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

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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Featured review

"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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$395
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 800 feet to Siesta Key Beach

Key Amenities

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

About this property

Brand New Condo, completely renovated. 2 Bedroom, 2 Bath large condo with granite kitchen and baths. Tile deck flooring. Full water views from our 6th floor location. See all the way to end of Anna Marie on clear day. Ringling bridge, downtown Sarasota, Lido and Bird Key views. King bed in master...

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$182
avg per night
Siesta Key Condo
Sleeps 5, 2 bedrooms, 1.5 bathrooms

Distance to beach: 250 feet to Siesta Key

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

On Siesta Key - Quick walk to Siesta Key's world famous beach. Beautiful and private, this updated condo with granite kitchen and tile floors overlooks the bay inlet and boat basin. Across street from world famous beach. Fully amenitied condo in amentied condo complex. Large community pool, tennis...

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$240
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Distance to beach: 30 yards to Turtle Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Bright and inviting, this popular unit has floor to ceiling sliding glass doors from the lanai, offering breathtaking third floor views. Beautiful white porcelain tile leads to new bamboo laminate flooring, which is just one of the many recent upgrades. The open kitchen has comfortable counter seating...

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Featured review

"Holmes Beach Rental"

We loved our visit and loved the condo. The views were amazing . The only compliant would be the living room furniture was not comfortable. And the kitchen could use more kitchen items. But we dealt with...

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$374
avg per night
Last Minute Deal
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
16 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Located on siesta Key in Sarasota, FL. The Palm Bay Club has two heated pools both Bayside and Gulfside. A private marina, dock, spa, tennis courts, fitness rooms and is located on Crescent Beach voted number one beach USA 2014Sarasota is located approximately 40 minutes South of Tampa. 1 1/2 hour...

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Featured review

"Really great hosts which made the stay"

Great location, short walk to the No 1 beach in Siesta Key.We had an absolutely fantastic stay! Roy was a wonderful host—friendly, accommodating, and incredibly easy to work with. The property itself...

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$273
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Beautiful 4th floor condo with gulf views, a private beach, and a private fishing pier. This space was completely renovated in 2020 with all new features (including central AC) and furniture throughout. The fully-stocked kitchen is equipped with everything you need for a home-cooked meal. With a king...

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Featured review

"Modern Beach Condo: Hidden Gem of Siesta Key"

This modern beach condo is one of the best kept secrets of Siesta Key. While I had hoped to keep it that way, all I can offer is a ringing endorsement and review for the owners (who are incredibly kind...

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$294
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Distance to beach: 0.3 miles to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Renovated 2BR (one queen size & 2 single beds) 2 Bathrooms 2nd floor condo and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings & paved stones drive and covered parking, newly installed luxury wood-like flooring a comfortable...

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Featured review

"Beautiful condo"

We spent a month at this beautiful condo. It was very well equipped with everything we needed. Lovely warm pool and such a short walk to Siesta Key Beach. Thank you Lynette (the owner) for making this...

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$214
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 0.7 miles to Turtle Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Welcome to Bayside Haven at the Pointe, your perfect getaway nestled along the serene shores of Sarasota Bay. This charming vacation rental features two spacious bedrooms and two full bathrooms, ensuring ample comfort and privacy for you and your guests.The fully equipped kitchen is perfect for preparing...

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$229
avg per night
Siesta Key House
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 0.4 miles to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Location, location, location!! New pool and spa just completed! Waterfall edge from spa to pool and deck jets. New landscaping with additional seating areas near pool and canal. Also, lots of green space to enjoy too!Canal home in heart of the Siesta Key Village, no need for a car! Steps away...

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Featured review

"Excellent"

The house was extremely clean and nothing was missing. Loved my stay from beginning to end. Melissa checked in a few times to make sure I was happy. I would stay at this home again. It has raised my bar...

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$640
avg per night
Siesta Key House
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 0.9 miles to Siesta key

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Comfortable private 3bedroom 2 bath home, open concept floor plan. The master suite is large and open with a sitting area and views of the tropical garden in the back of the house, a full walk in closet and step down shower bath with dual vanities. The next bedroom consist of 2 twin beds with additional...

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Featured review

"Definitely more than 5 stars for this property"

I’ve rented several Siesta Key properties, but this is definitely my favorite. The home is located very close to the public beach down a quiet cul de sac. The neighbors were all friendly and the area...

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$445
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
12 reviews

Distance to beach: 200 feet to across street

Key Amenities

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

About this property

2 bedroom gorgeous condo overlooking Siesta Key Beach and Gulf of Mexico. Complex with large community pool, sauna, covered parking, secure gated area. Gas grills, party room, beautiful property. 2 full bathrooms with granite walk in showers and basin, etc. King bed in master with ensuite full bath,...

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Featured review

"Crescent Royale 4b Siesta Key,FL"

We had a great time. Condominium was wonderful. It had everything we needed. The owners were very helpful.

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$301
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This cozy beach house awaits your visit! Magnificent view of the Gulf of Mexico and evening sunset from lanai.... Peaceful Intercoastal inlet views and sunrise from front door...This little nest has been newly "stem to stern" furnished and equipped for your comfort. Coastal Living as its...

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Featured review

"Perfect sunsets, great lanai and best location"

Nice quiet location on Turtle Beach. Best sunset views, right on the beach and all the amenities one needs for a perfect beach holiday. Added bonus of docks for boats/kayaks, heated pool and gated entry....

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$374
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Your private Siesta Beach escape! Walk or bike to sand, unwind in the heated saltwater pool or Sauna and bring your furry friends along!Key Differentiators & AmenitiesSought-after Siesta Key Family & Pet friendly location—easy access to the beach, village, shops, restaurants, coffee...

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Featured review

"Paradise"

The home on Siesta Key is totally amazing in every aspect. The completely updated modern architecture combined with the lush tropical landscape make this an excellent choice to relax and experience...

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$860
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 30 feet to Turtle Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

We are ready to welcome guests back to Fisherman's Cove! While we have made tremendous progress recovering from Hurricane Helene, some construction is still underway. but he sun is still shining and the Gulf is still as refreshing. We look forward to hosting you and your guests!Within just...

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Featured review

"Oldie but Goodie"

We’ve traveled many places in our lives ( especially all over Florida) and this is one of our favorites. From the moment we requested more info on Bill and JoAnn’s condo until today at check out the...

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$374
avg per night
Siesta Key House
Sleeps 13, 5 bedrooms, 4 bathrooms
14 reviews

Distance to beach: 400 feet to Siesta Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Excellent location at only 120 Yards To The Cool White Quartz Sand Of Siesta Beach! ?This Home Has Water Frontage on a Navigable Canal to the Bay And Then The Gulf of Mexico , Pool, Hot Tub And BBQ Area Within A Screen Enclosure. There Is A Nice Sized Sunning Patio As Well With Views Down The Waterway....

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Featured review

"What a fantastic home and location?!!"

We just spent a full week at 5589 Cape Letye and had a wonderful experience. We had a total of 6 adults and 4 teenagers and we had more than enough space in the home. The home is gorgeous both inside and...

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$936
avg per night
Siesta Key Villa
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Discover your own slice of paradise in this brand new 100% fully renovated 2-bedroom, 2-bathroom villa, with vaulted ceilings and an open floor plan. This villa is located in the vibrant heart of Siesta Key. This charming retreat blends modern amenities with a prime location, ensuring an unforgettable...

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$359
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 200 yards to Siesta Key Crescent Beach

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

SIESTA SUMMER SAVINGS! UP TO 20% OFF YOUR SUMMER STAY BETWEEN 5/31/25 AND 9/1/25 WHEN BOOKING DIRECTLY ONLINE Online booking: Click link in Host information section of this listing and use promo code Anchor6415 at checkoutWe invite you to stay in our spacious 2 bed 2 bath condo, 'Siesta Chillin',...

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Featured review

"Siesta Central - The Anchorage!!"

We stayed at the Anchorage in unit 305. It faces the city and the inner coastal lagoon. We were treated to a dolphin show one evening when they entered the lagoon searching for food!! This location...

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$319
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Gorgeous unit and beautifully furnished with an incredible 2nd floor view of the Gulf of America. Sleeps six comfortably with a king master and a full-size bed along with a twin in the guest room, plus a queen sleeper sofa. beach chairs and toys for your enjoyment. You will not want to leave once you...

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Featured review

"Amazingly Fantastic."

The beach, Turtle Beach, not so great, but good to soak up the sun and be close by. Amenities were very good, staff exceptional, condo was awesome. Everything needed was there. Very clean, neat,

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$374
avg per night
Full map
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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°

FAQ

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

There are 174 Siesta Key vacation rentals available on FloridaRentals.com. From condo rentals to apartment 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 $157 per night with an average price per night of $367.

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 89 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 43 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!