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Vacation Rentals & Beach Rentals in Siesta Key

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1,435 beach rentals

Siesta Sandals Siesta Key

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 13 minutes

Price per night from

$400

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.

Price per night from

$327

Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa

Siesta Key house

5 bedrooms / 4 bathrooms / sleeps 13

Price per night from

$654

The Residence at Siesta Key - Luxury Premier 3BR... Ocean View (May 25-30)

Siesta Key condo

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$1,008

Siesta Key/Derby Bay

Siesta Key villa

3 bedrooms / 2 bathrooms / sleeps 6

“Perfect!” Our family really enjoyed staying here! The villa was very well maintained and cleaned. It was stocked with everything you would need. The owner was very responsive to any concerns. We had a super nice neighbor and my boys loved fishing off the dock. I would recommend renting a golf cart to go to the beach if you have children (with toys etc) or elderly people with walking concerns. It is quite a walk to get to the beach (because you also have to walk down to the cross walk then across the street). The beach in front of the Aloha Kai property is very wide (great because it was never crowded like in front of other resorts) but it was an even farther walk to the water. We have always stayed beach front but needed more rooms than were available in my booking time frame this year. This property has changed the way I will book on siesta in the future. My boys LOVED fishing everyday off the dock. They caught lots of cool fish right off the back. The street that this villa is on was very quiet for our stay. Everyone was very kind & the property is very beautiful! We hope to come back very soon! It was a wonderful experience.

Price per night from

$229

2Bd/2Bath NEW Remodeled Villa just steps away from Siesta Beach!

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$233

Another Day in Paradise

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 29 minutes

Price per night from

$430

Siesta Key Gulf View Condo

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 38 minutes

Price per night from

$355

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 16 minutes

Price per night from

$276

* SPECIAL RATES at Harbor Towers * April 16 - April 30

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 43 minutes

Price per night from

$102

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 20 minutes

Price per night from

$263

Crystal Sands Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$328

Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Renovated!

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Great Experience” This condo is well kept, clean and looks directly onto the Gulf of Mexico. We liked it because the furniture is up to date and replaced when it becomes worn. We also love the fact it is within walking distance of a good restaurant. In fact there is nothing about this rental that we don't like and that is why we return there year after year. A great choice for you to start a great experience!

Price per night from

$261

Siesta key beach house.

Siesta Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$390

Condo wOcean view on Siesta

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 38 minutes

Price per night from

$321

Beach Walk Townhouse

Siesta Key townhouse

3 bedrooms / 3 bathrooms / sleeps 6

“Great vacation and Great Accomations” We loved the accommodations. Great location close to beach access and to the village.The pool was wonderful with lovely landscaping. The house was spacious and very clean. Virginia the manager was also great! We would definitely stay here again.

Responds fast! avg. 2 hours 6 minutes

Price per night from

$264

“gracious and spacious” Lovely home and great location to walk throughout Siesta Key Village and the beautiful sands of the beach!! We were able to have everyone together for a great vacation.

Responds fast! avg. 1 hour 27 minutes

Price per night from

$125

Siesta Key Beachfront 3 Bedroom Home, Sarasota

Siesta Key house

3 bedrooms / 3 bathrooms / sleeps 9

“Beautiful House!” Beautiful house, perfect location, great communication with owner. Lots of dishes/pots/pans for cooking, it was extremely clean and well maintained house. Our family loved our stay and will definitely rent this house again. Thank you David for sharing your gorgeous place with us.

Price per night from

$796

Siesta Breakers #603 in Siesta Key, FL- Sun, Sand & *Save 10% to 25% per Week*

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$205

Siesta Key Crescent Beach 2/2 Sleeps 6 Renovated

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$182

Charming Siesta Key Village Unbeatable Location

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$147

Stunning 2 Bedroom/ 2 Bath by Siesta Key Beach, Sunlight Sensation!!

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$308

Firethorn 712 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$136

Chinaberry 453 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$239

Doveplum 623 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$159

Chinaberry 454 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$239

Firethorn 310 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$236

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$288

Doveplum 112 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$416

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$999

Palm Oasis - Relax in Comfort - 1 rental per calendar month

Siesta Key house

4 bedrooms / 3 bathrooms / sleeps 10

“Beautiful home for a quiet -relaxing getaway!” Fantastic location! House had all you could ever need and the space was perfect! The only downside was not being able to maximize the outside into the evening. Our first full day it had rained but it was humid! We spent the entire day shopping and dining out. We returned around 10:30pm & the rain stopped so we took full advantage of the outside, which is just as lovely at night. There were only 4 of us, and at 11;30 it was just my sister N law and I, no music -just taking & laughing and thats when the neighbor directly behind us loudly announced for us to "keep it down and that we were in a residential area!" The other neighbor to the right didn't hear a thing! After a long, cold, Maine winter... being outside is the #1 goal, so that was unfortunate. Virginia was very pleasant to work with.

Responds fast! avg. 2 hours 6 minutes

Price per night from

$630

Buttonwood 472 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$255

Buttonwood 417 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$255

Buttonwood 950 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$194

Buttonwood 422 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$255

Buttonwood 427 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$255

Buttonwood 432 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$255

Buttonwood 467 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$255

Viewing 38 of 1,435
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

Cathy's Crescent Condos-Siesta Key, FL GULF FRONT
Walking through the door, the view was breathtaking and condo was everything I wanted.

I searched for months for the perfect condo and it paid off with Kathy's condo #201S. Was a 2 bedroom, 2 bathroom, living room and couches facing the ocean which was ON THE BEACH. In my research so many say on the beach and they aren't you have to walk over sea grass etc to get to the beach. This condo is exactly what it says it is. Our balcony was to die for, was the length of the condo, felt like you were sitting on the beach. Had lounge chairs, rocking chair other chairs and tables. It was screened in but did not affect the view. When we didn't need the air on we left doors open in bedrooms and went to sleep listing to the waves. Also each bedroom had glass sliding doors to the balcony and the living room had a 3 panel sliding door to balcony. Had a dining room off the living room. Washer and dryer were right down the hall which was so convenient. Our parking spot was right by the door to condo building, People are so friendly as was Kathy whenever we needed something and especially while booking-very very cooperative, she gave us a list of restaurants they liked and we went to a lot of them. Never had a bad meal anywhere. Capt Curts right down the road had the best Clam Chowder, The Hub Bahia Grill had great Lobster bisque. Carrabas had excellent Italian food and we loved our waiter "Donnie". The Daiqiuiri Deck was good. All seafood was great but would say the Fish Market was the best-had daily special appetizer that was porgie fish with lime, lemon juices, red pepper, onion and other things and ate with chips which were delicious. Alligator bites were excellent and the Ilamarada Piccata was fantastic. If at all possible we would love to go back to Kathy's because she was great and her place was the best beach condo we've ever stayed in. We rented umbrellas and the guy had your chairs and umbrellas set up by the water every day before 8:00 and put them back around 6 (I think). Kathy also had all the start ups, beach towels was a plus too, and kitchen had everything you needed. I would definitely recommend this place for a fun relaxing vacation, not to mention how "friendly" the people are you meet there. Thank you so much Kathy for giving us a much needed vacation.see more
Palm Bay on Private Beach w/Access, WiFi, Full Beach Views from 7th Fl, Pools, B
Great condo

Loved it. Modern, beachy, clean, well equipped. Excellent location on the beach. Would definitely stay again. … 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 in Village & 2 blocks to 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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