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Vacation Rentals & Beach Rentals in Siesta Key

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1,580 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

$203

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. 2 hours 3 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

$189

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. 26 minutes

Price per night from

$285

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

$195

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 57 minutes

Price per night from

$114

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$291

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. 3 minutes

Price per night from

$290

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

$262

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

$326

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. 41 minutes

Price per night from

$126

Walk to Crescent Beach, Wifi, Bay Views From Lanai, Heated Pool, Tennis, On Trol

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 minutes

Price per night from

$98

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. 3 minutes

Price per night from

$136

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. 3 minutes

Price per night from

$118

Complex on the Bay, Walk to Beaches, Heated Pool, Wifi, Ground Floor, Renovated,

Siesta Key condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 minutes

Price per night from

$99

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. 3 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. 3 minutes

Price per night from

$110

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

$501

Holiday House 1

Siesta Key apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$91

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

$548

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

$103

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. 3 minutes

Price per night from

$271

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. 3 minutes

Price per night from

$144

Charming Siesta Key Condo, Walk to Beach, Pool

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 53 minutes

Price per night from

$107

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. 3 minutes

Price per night from

$114

Sea Club II

Siesta Key condo

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$114

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 28 minutes

Price per night from

$245

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

Siesta Key apartment

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 minutes

Price per night from

$156

Chinaberry 436 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$239

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 24 minutes

Price per night from

$215

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

Siesta Key hotel apartment

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$138

Beautiful, Affordable Close to famous Siesta Beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 4

“It was wonderful!” Everything about the trip and condo was great! Mike met us to give us the keys and we called him for suggestions about restaurants, etc. and he was very helpful. The condo was very clean and had everything we needed. It was also great that we were able to use the beach chairs and umbrella. I am already trying to figure out when we can go again.

Price per night from

$162

The Shells Villa - Next to Beach & Village

Siesta Key house

3 bedrooms / 3 bathrooms / sleeps 10

“Great Experience and Location!” We could not have been happier with our Experience at Shell Villa. Location to the Village was super close as described. Access to the beach was great both through the private walkway or the public access about two block away. The house was well stocked and the floor plan was perfect for our two families. Best place I have rented on SK in 5 years.

Price per night from

$286

Responds fast! avg. 3 minutes

Price per night from

$152

The Perfect 2Bedroom/2Bath Steps Away From Siesta Key Beach- BiancoSands

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$540

Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front

Siesta Key house

2 bedrooms / 2 bathrooms / sleeps 6

“What a great view” We usually rent a house one block from the main Siesta Key beach area. This year friends rented the house and my husband and I stayed in this condo for a week. Loved the view of the beach from the living room! Loved the lani! Location was great. Pool was massive compared to our usual house pool, however we did have to walk thru parking lot to get there. The noise from the hall was annoying. And I did miss my temperpedic mattress, but had a great relaxing time.

Responds fast! avg. 2 hours 11 minutes

Price per night from

$220

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

$263

Buttonwood 462 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$255

Viewing 38 of 1,580
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

Deluxe 3-BR Siesta Key Townhouse - Heated Pool - Siesta Key Village
Wonderful Location with wonderful amenities!!

Best location, close to town, grocery, and beach!!! No car needed!! Spacious condo with an amazing pool area! The condo was super clean and it was nice to have a washer and dryer! This is my second stay in this condo and plan many more!!! Thank YOU!!!! … 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 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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