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Vacation Rentals & Beach Rentals in Siesta Key

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1,632 beach rentals

Siesta Key 2 Bedroom 1 Bath Modern/Contemporary Decor Apartment

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 5

“Amazing!” I stayed here with my husband and we had a great time! We were in Orlando visiting family and we decided to arrange some us time. The condo was excellent and very clean! Kathy and her husband were very informative, respond quickly,and available when we needed them. What was great was that we had all beach items available to us and were very useful. We were in close proximity to everything and the beach and restaurants were great! Everyone in the area was very friendly and my husband and I want to definitely come back!

Responds fast! avg. 36 minutes

Price per night from

$202

WE LIKE BLUE, SIESTA BLUE! 2 BED BAYSIDE CONDO ON SIESTA KEY

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 4

“Considering the Corona Influences It Was A Nice Stay” We stayed on Siesta Key and other than the traffic it's a lovely area. We were to stay 3 weeks but actually returned a week early since we were so concerned with the health risks. There were a number of nice sea-food restaurants where we stayed which we enjoyed the first week we were there until we began social distancing. The condo altho fairly small was confortable and the complex very quiet.

Responds fast! avg. 3 hours 25 minutes

Price per night from

$140

Walk to the beach from this adorable condo. Beachside. Perfect location. Bikes,

Siesta Key house

1 bedroom / 1 bathroom / sleeps 2

“Book with Island Time!” We really lucked out with our first Flipkey booking. My husband and I traveled to Siesta Key last year for our honeymoon, and we returned this year to celebrate our anniversary. The property had everything we could possibly have wanted -- a very short and easy walk to beach access 13, Point of Rocks, and many restaurants (aaaaand the liquor store), a very comfortable bed with the appropriate amount of pillows (EIGHT), a fully equipped kitchen with everything we needed to eat in when we wanted, a large covered porch, and everything was CLEAN. Angel was a fantastic host -- quick to respond and clear and concise with his communication. The price was more than right. I cannot say enough great things about this property and Angel. Recommended so very highly.

Responds fast! avg. 1 hour 29 minutes

Price per night from

$159

Siesta Key Villa A - Only 150 yards to Crescent Beach and heated pool!

Siesta Key villa

2 bedrooms / 1 bathroom / sleeps 4

“Awesome owners and location” The location is great, only 3 minutes walking to a private beach. The house offers all the essentials you might need. This is our second time stay and we were not dissapointed again. The owners are very responsive and helpful.

Responds fast! avg. 29 minutes

Price per night from

$190

Siesta Key- Beach Chic Retreat, Siesta Key 3 Bedroom 2 Bath Apartment

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 7

“This was the definition of home away from home” great value for your money...very cozy, with lots of new upgrades. Easy access to the beach and restaurants.

Responds fast! avg. 36 minutes

Price per night from

$286

Siesta Key Villa B - Only 150 yds. to Crescent Beach and heated pool!

Siesta Key villa

2 bedrooms / 1 bathroom / sleeps 4

“Another great stay!” Location is great and owners are awesome to work with! Clean and fully furnished! Thanks for another great stay Derek and Marina! Look forward to next time!

Responds fast! avg. 29 minutes

Price per night from

$196

Remodeled 2br 2ba with private patio, beautiful water views, walk to #1 beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 51 minutes

Travelers’ Choice award

Price per night from

$114

Top Floor End Unit Directly Across the Street from Siesta Key public beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

“Awesome Condo Unit” There were 4 in our party and nothing that we were disappointed with. We absolutely loved every moment!! We will definitely rent this unit again!!

Responds fast! avg. 3 hours 57 minutes

Price per night from

$148

Jamaica Royale #92 on the #1 Beach in the USA!

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$289

600 ft. to Shell Beach, Pool/Spa, Fire Pit, New & Custom Nantucket Style Home,

Siesta Key house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 4 minutes

Price per night from

$291

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 15 minutes

Price per night from

$197

Jamaica Royale #100-Peaceful Gulf Side Condo

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

“Spring break” This unit was beautifully done; recently renovated, impeccably clean and very close to the beach! The owner was e trendy helpful and accommodating. She made it easy and if you are headed to Siesta Key, you must stay here!

Responds fast! avg. 2 hours 6 minutes

Price per night from

$252

Beachfront Getaway in Siesta Key

Siesta Key townhouse

1 bedroom / 1 bathroom / sleeps 4

“Very comfortable, nice amenities and well run.” Loved the beach and the nearby restaurants. The free trolly ride was easy to use and a great way to go into the village.

Responds fast! avg. 1 hour 24 minutes

Price per night from

$328

Quiet and Comfortable Condo Near Turtle Beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 5

“Siesta sweet spot” Great value for location. Nice pool, visits with the manitees. Close to everything. This time of year ocean water was amazing

Responds fast! avg. 3 hours 6 minutes

Price per night from

$128

Walk to Beach, Wifi, Water view from patio, Heated Pool, On Trolley Line

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 4 minutes

Price per night from

$115

WHAT A VIEW !! 2 BED BAYSIDE CONDO ON SIESTA KEY

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Beautiful and memorable vacation with our son,wife and grandchil” My husband and I rented unit B41,it was beautifull, tastefully decorated stainless steel appliances and new furniture. The owners thought of everything.Very pleased to have a washer and dryer in unit. The layout of this rental was spacious,the bed was very comfortable I slept like a baby which is rare when I'm away from home.The view of the intercostal water way and tropical landscaping were breathtaking whether relaxing in living room or dinning.It was very peaceful ,walking distance to Siesta keys famous beach and close to all amenities. Would recommend Bay Oaks!Thanks Barbara Okin.

Responds fast! avg. 3 hours 25 minutes

Price per night from

$165

Across the street from Siesta Key Beach, Gulf View, Pool, Tennis, Parking, Balco

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 4 minutes

Price per night from

$177

Siesta Key Beach is Across the Street, Partial Bay Views, WiFi, Renovated, Overl

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 4 minutes

Price per night from

$124

Complex on the Bay, Walk to Beaches, Wifi, Ground Floor, Renovated, Enclosed Pat

Siesta Key condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 4 minutes

Price per night from

$113

Siesta Key Condo w/Private Beach Access, Wifi Included, Heated Pool, Tennis & B

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

Price per night from

$131

Only 6 Minute Walk to Crescent Beach, Free Wifi, Private Lanai, Heated Pool, Fis

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 4 minutes

Price per night from

$112

3 Bedroom/ 2 Bath unit across from Siesta Key Beach Access.- Islamorada

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$252

Seagrove

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$127

Holiday House 1

Siesta Key apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$126

Perfect Getaway-2Bedroom/2Bath Steps from Beach with Pool Access!!- La Estrella

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$298

Best Deals on Siesta Key

Siesta Key apartment

1 bedroom / 1 bathroom / sleeps 4

“Nice and easy to get around” You have a wonderful neighbor. I was able to access all the amenities you described. Navigated through out the area with ease.

Price per night from

$104

Canal Home on Siesta Key w/ Pool, Wifi, Renovated 1950 Style Sarasota School of

Siesta Key house

4 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

Price per night from

$272

Fido Friendly, Saltwater Pool, Only 1 mile to SK Beach, Close to the Village, Sh

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 4 minutes

Price per night from

$175

Charming Siesta Key Condo, Walk to Beach, Pool

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 1 hour 57 minutes

Price per night from

$115

Walk to Siesta Beach, Heated Pool, Wifi, Fido friendly, Renovated Ground Floor U

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 4 minutes

Price per night from

$115

Sea Club II

Siesta Key condo

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$114

Luxury Condo Ground Floor Across the Street

Siesta Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$181

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 22 minutes

Price per night from

$246

Beautifully Renovated & Modern, Wifi, Harbor Towers, 3 bedroom with den

Siesta Key apartment

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 4 minutes

Price per night from

$157

Chinaberry 436 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$227

Recently updated, Crescent Beach resort, Heated Pool, Jacuzzi, Tennis, Barbeques

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 31 minutes

Price per night from

$213

Tiny House Siesta - Tiny Aqua Oasis- Tiny House that sleeps 6 comfortably

Siesta Key hotel apartment

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 52 minutes

Price per night from

$115

Viewing 37 of 1,632
rentals in Siesta Key

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About Siesta Key

What was once a secret gem known to only a few, has rapidly become America's darling beach town.

Siesta Key, located in Sarasota County and about an hour south of the Tampa Bay Area, is an eight-mile island accessible by two bridges from the mainland. Sandals and swimming suits are accepted - even expected in virtually all of the restaurants and boutiques that populated the island - especially so of those located in Siesta Key Village. The atmosphere is as cool as the white quartz sands in the daytime, and while libations and celebrations can warm up the evening, you are never to far from a tiki-esque style bar and the quiet sounds of ocean waves gliding up and down the beach.

In 2011, Dr. Beach named Siesta Beach No. 1 in the nation for its sugary white sand. Siesta Key beach is, in fact, almost entirely composed of crushed quarts crystal. This unique composition not only makes this sand sparkle under the Florida sun, but also keeps the sand cool on even the hottest of Florida summer days. The sand is perfect for sculpting, and every year Siesta Key is home to world-class sand sculpting competitions.

Despite its popularity, there are still quiet corners of Siesta to sneak off to and explore.

Turtle Beach located at the southern end of Siesta Key has sand that's a bit coarser. This beach is a great fishing and snorkeling hot spot. The beach has a steeper incline and carries more shells. After a storm beachcombers might even find a petrified shark's tooth. Nearby are restaurants, shopping and a few local nightspots.

Crescent Beach is another quieter spot, just south of Siesta Key Beach. Enjoy the same blue waters in a secluded atmosphere. This area contains coral formations and bright marine life - perfect for diving.

Siesta Key is perfectly fit for families, singles, and couples alike. Lodging accommodations can be found throughout the key, including hundreds of vacation rentals. Though active year round, Siesta Key's peak season runs January through April. Plan to book your stay as soon as possible if your vacation is planned within that duration.

Information provided by:Visit Sarasota County

Top Destination reviews

Palm Bay on Private Beach w/Private Access, Full Beach Views from 7th Fl, Pool
Great condo

Loved it. Modern, beachy, clean, well equipped. Excellent location on the beach. Would definitely stay again. … see more
Seaside Villas Unit 3BR 5241
Perfect Stay

This place was amazing! We had two families stay and it was perfect! We will definitely book again soon! … see more
Just Minutes from the White Sandy Siesta Beach
Amazing!!!!

Bea’s rental in Sienna Park was an amazing place to stay. The new free form pool is just steps from your door. She has everything you need for a luxurious vacation. Best place we have stayed..... It is also only minutes from Siesta Key beach. I will definitely book with her again. … see more
2 BR, 2 Bath, Siesta Key Village Condo with Pool
Amazing Location; property and customer service

This property is so well maintained! Every thing is immaculately clean and maintained. Property maintenance stops by everyday to make sure the outside is perfect for your stay. Pool company comes twice a week. Location is within walking distance of restaurants and beach! We will definitely stay here again!see more
A Siesta Tropical Retreat - Island Pool Oasis -super close to Village & #1 beach
Clean, pet friendly and as close to the village as it gets!

Great spot within a 30 second walk into the village. The village is about a five minute walk to the beach as well. The house was very clean and has a nice pool area. The house was very equipped with beach and pool equipment. No need to bring your chairs, coolers, or toys, very nice touch! All the instructions for speakers and TV's are lined up nicely for you. Overall a great place to stay.see more
FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN, UPDATED KITCHEN!
Siesta Dunes

The condo was really nice,the beach is close by and the location was perfect,really had wonderful time. … see more

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