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Siesta Key Vacation Rentals

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

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Awesome 1st Floor Beachfront! Just outside your sliding doors is the #1 rated Crescent Beach. Condo features sweeping ocean view and super easy access to the beach while maintaining privacy of corner unit. Two bedrooms, two baths. Washer/dryer, Flat screen TVs in bedrooms 60" Ultra High Def 4k TV ...

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$305
avg per night
Siesta Key Apartment
Sleeps 25, 9 bedrooms, 9 bathrooms
3 reviews

Key Amenities

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

About this property

Our seven apartment beach house is located 100 yards from the beach at Access #7 and one-block from the tropical Village of Siesta Key. Heated pool and spa along with our poolside surfboard bar and barbecue give our guests many choices to very their daily routine. Our 1st and 2nd floor above ground level ...

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Featured review

"Best place in the keys"

This place is one of a kind. It has everything you need. Our family rents out the entire place every couple years. The location is amazing...right by the village and beach. The rooms are clean and bug free!!! ...

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$315
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - UpscaleLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FLRe-opening of 2nd and 3rd floor units on 6/28/25. Property restoration from Hurricane Helene has not been completed and there may be some ongoing construction ...

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Featured review

"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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$263
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
8 reviews

Distance to beach: 0.2 miles to Siesta Key

Key Amenities

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

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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Featured review

"Great place!"

This was our first time back to Siesta Key in 20 years and we loved this condo! The location is right between the two villages, so super easy to grab a trolly to dine or shop. The beach is a pretty short ...

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$203
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Experience luxurious living in one of the largest units on Siesta at this stunning 2 bedroom, 2 bathroom condo. This immaculate condo features porcelain tile flooring in the living areas, brand new plush carpeting in both bedrooms, and beautiful crown molding throughout. The kitchen is a chef's dream, ...

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$193
avg per night

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Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Pool
  • WiFi

About this property

Beautiful ground floor unit with screened porch at White Sands located just a few blocks from Siesta Key public beach. Unit sleeps 4, 2 Cable TV's , wireless internet ( Siesta 4 Rent is not responsible for tech support), community coin laundry right outside the door, covered parking, community pool ...

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$126
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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$263
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Located in beautiful Siesta Key, Fl. this bayside condo is full of amenities needed for a relaxing beach vacation. Two tennis courts with Pickleball available, two heated pools, covered private parking, outdoor gas grills, boat docks, outdoor bathrooms within this private, gated community.Walk to ...

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Featured review

"Fantastic"

Very family friendly, had beach toys and beach towels available, along with a beach tote. Host provided us a pack and play on request. Beautiful bay facing condo and easy walk to gulf side.

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$211
avg per night
Siesta Key Villa
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

This updated Villa is on the beach side of Siesta Key, with private beach!!! It does not get better than this!! Fully renovated private villa on beachside. In 1 to 2 mins you can have your feet in the sand. Parking directly in front of villa. (Updated pics coming soon) There is an amazing huge pool,, ...

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Featured review

"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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$254
avg per night
Siesta Key Townhome
Sleeps 6, 2 bedrooms, 2.5 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

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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Featured review

"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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$221
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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$275
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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$346
avg per night
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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$278
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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$167
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 Mexico. A lovely spot to watch sunsets. The unit is upgraded and comfortable for couples traveling together or with ...

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$263
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
7 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

"Great location"

We enjoyed our stay at Our House at the Beach. It was in a great location. You can walk across the street to siesta key Beach. You can’t see the ocean from the Balcony however because it’s on a lower ...

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$253
avg per night
Special Offer
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
10 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

"Siesta key condo"

Absolutely loved our stay at Siesta Key. The condo is clean, well equipped with everything you need, easy access to food and the beach. Would definitely stay here again

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$149
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 Lazyboy queen memory foam sofa sleeper for separate sleeping area if needed Unit includes a full kitchen for ...

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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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$230
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

There's plenty of room for everyone here at Our House. We have a split-level living area facing a large screen HDTV, so anytime you need a little down time from all the outdoor fun, settle in with your favorite movie, a bowl of popcorn, and frosty drinks. The kitchen's just a few steps away, ...

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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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$208
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool

About this property

You will love the grounds with 7 acres of lush tropical landscaping. Our unit is complete with coastal décor, newer appliances and washer/dryer. Walk to Siesta Key Beach or swim in the heated pool. We have several grills, a clubhouse with library, and a peaceful lagoon. Siesta Key Village is filled ...

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$112
avg per night
Siesta Key Condo
Sleeps 10, 4 bedrooms, 4.5 bathrooms

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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$509
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 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 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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$309
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
12 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

"Luxurious layout,100% return there,home from home."

Arrived late at night,found the instruction's from Ana very helpful .Delighted with the layout and condition.Not a thing out of place. It was a pleasure to stay there.Would recommend this condo to everyone.

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$178
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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$255
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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$150
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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$353
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

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

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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Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
15 reviews

Key Amenities

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

About this property

Roomy 2 bedroom, 2 full bath condo in prime Siesta Key location. Comfortably furnished living room, dining area, all linens and fully equipped kitchen included, ceiling fans in all rooms, Flat screen tv in living room with DVD player and a flat screen in the master bedroom. Master bedroom has queen-size ...

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Featured review

"Comfortable unit"

The property was nice and comfortable. The children enjoyed the pool that was close to the unit. Owner promptly responds if we had questions.

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$268
avg per night
New
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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$110
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

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

About this property

MONTHLY RENTAL. Introducing our BEAUTIFUL NEW LISTING! Nestled within this premier condominium complex, our home offers direct access to the highly acclaimed Siesta Key Beach without the need to cross any streets.Our home away from home is perfect for those seeking a winter retreat or anyone seeking ...

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Featured review

"CASARINA on Siesta Key Beach-#1 Beach, Place to Visit, Hosts"

To start off with Chris and Jeannie are the best hosts to deal with. Easy going, prompt if anything is needed! They share their lovely home with us vacation lovers visiting literally the #1 Beach-Siesta ...

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$283
avg per night
Siesta Key House
Sleeps 13, 5 bedrooms, 4 bathrooms
13 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

"Amazing home!"

We had an amazing time with our family at this home in SK! David (property manager) was incredibly responsive to our questions and even stopped by to introduce himself when we arrived!The space was ...

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$815
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

This colorful and well cared for unit has a new owner! The view from your lanai will include sunset and will be magnificent! No other property on Siesta Key is built this close to the Gulf of Mexico where you can hear the waves from your lanai and master bedroom windows. The furnishings are very comfortable ...

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$263
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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$263
avg per night
Siesta Key Condo
Sleeps 2, 1 bedroom, 1 bathroom
10 reviews

Distance to beach: 0.5 miles to Siesta Key Main Beach

Key Amenities

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

About this property

Sweet Siesta Key Condo walking distance to #1 Beach in America! Spacious and Quiet One Bedroom with King Bed, Screened Lanai, Wireless Internet, Flat screen TV’s, full kitchen with amazing water filtration system. Easy Walk right over to Siesta Key Main Beach, and their 6 new lighted Pickleball ...

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Featured review

"Great place to stay"

Perfect location, situated right in the middle of the village and the south bridge. Restaurants and entertainment either way. It's a 2 min walk to the beach. The condo had everything I needed to make my ...

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$125
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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$263
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 Mexico. 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. Two DVD players with movie collection; a CD player and CD collection; & beach ...

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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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$263
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 20 feet to Turtle Beach, Siesta Key

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Beautiful beach inspired decor...Fresh, airy and calm...perfect relaxing unit with all the comforts of home and more to enjoy a fun filled time at the beach!!!!!

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$263
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Gorgeous totally remodeled 2 bed (both brand new kings) 2 full bath condo in the highly desirable gated Gulf and Bay Club on the world-renowned Siesta Key Beach, a luxury community sitting on 32 acres and offering 3 pools, a fitness center, pickleball, tennis, saunas, hot tub, and its own 800 ft of private ...

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$333
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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$517
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
15 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

"Great Stay"

We cannot say enough about how great our stay was, Roy was a great host and super nice guy. Very easy to work with. We loved the pool and hot tub and location of the property. We preferred this private ...

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$200
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

We invite you to stay in our spacious 2 bed 2 bath condo, 'Siesta Chillin', across from the beautiful crystal sands of Crescent Beach on Siesta Key. Siesta Chillin has been recently updated and has all the conveniences of home in an amazing vacation spot at The Anchorage Yacht and Tennis Club.When ...

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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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$197
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
4 reviews

Distance to beach: 400 feet to Siesta Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Prime location, being only two minutes walk to Siesta Beach entrance from this attractive three bedroom, two bath florida ranch! You live around the ground level pool with large patio doors openings from the two living areas and kitchen/dinning area. The home has been freshened with a very nice decor ...

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Featured review

"A Perfect Getaway!"

Our recent stay at the Siesta Key Beach Vacation Home was nothing short of incredible! The 3-bedroom home is ideally located from the world-renowned Siesta Key Beach, making it easy to enjoy the soft white ...

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$567
avg per night
Special Offer
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

Within just a few feet of the beach, our condominium home features a well equipped kitchen with granite counter tops, luxury vinyl flooring, a leather sectional couch, recliner chairs, teak furnishings, ceiling fans in all rooms, a 55 inch smart TV in the living room and a flat screen TV in each bedroom ...

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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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$263
avg per night
Siesta Key Condo
Sleeps 3, 1 bedroom, 1 bathroom
11 reviews

Distance to beach: 0.5 miles to Siesta Key Main Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Sweet and spacious one bedroom condo in a Siesta Key Luxury Resort Building - Harbor Towers Yacht & Racquet Club. Great view of the historic waterfall in front of building, Palm Trees and Blue Skies and Great Sun Sets. 2 Pools (1 for kids), Fitness Room, , 3 lighted Tennis courts, boat marina, gazebo, ...

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Featured review

"We love Harbor Towers!!"

Thank you Barbara and Angelo for providing a beautiful "home away from home" for our spring vacation. We have rented on Siesta Key several times and this was definitely our favorite location. Your renovations ...

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$99
avg per night
Siesta Key Studio
Sleeps 2, 0 bedrooms, 1 bathroom
5 reviews

Distance to beach: 0.3 miles to Siesta Key Beach access 10

Key Amenities

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

About this property

*Calendar month rentals only*******SPECIAL - April 2025 - $150 per night plus utilities - 10-night minimum****May - November (three-month lease) - $2000 per month plus utilities December - $3900 per month plus utilities January, February, & March- $6500 per month plus utilities April - ...

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Featured review

"Perfect peaceful pet friendly bungalow"

I recently had the pleasure of staying for three months in this cozy bungalow on Palm Island in the heart of Siesta Key. Nestled amidst lush vegetation and just a short walk from the beach and Siesta Key ...

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$67
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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$155
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

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

About this property

This two bedroom(master King bed), second bedroom double bed/ single bed (with pull out trundle) full kitchen, dining, living room and lanai open into living space. Out back you sit on the bay and across the street is number 1 beach in the U.S. Pool heated year round 80 degrees, grill areas and laundry ...

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Featured review

"Very nice host and home. Home needs work."

The owner could not have been nicer. The home is beautiful but does need attention to details like, no ice from icemaker, hot water takes forever to get to kitchen and master bath. Carpet in bedroom needed ...

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$140
avg per night
Siesta Key Bungalow
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 0.4 miles to Beach access 10 of Siesta Beach

Key Amenities

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

About this property

*Calendar month rentals only*May-October (six-month lease) - $3900 per month plus utilities November & December - $6900 per month plus utilities January, February, & March - $9800 per month plus utilities April - $7900 per month plus utilities50% deposit upon booking, balance 90 prior ...

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Featured review

"We Keep Coming Back"

It's all about The Lily Patch on Palm Island in the village of Siesta Key!!! We've love it so much that we've signed up again for 2021 (Winter #3) and sent in a donation to the neighborhood HOA this time. Bring ...

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$117
avg per night
Full map
Map

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 169 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 $67 per night with an average price per night of $263.

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 47 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 50 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!