Vacation Rentals & Beach Rentals in Siesta Key

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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. 55 minutes

Price per night from

$222

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. 55 minutes

Price per night from

$314

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. 1 hour 9 minutes

Price per night from

$275

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

$256

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. 2 hours 51 minutes

Price per night from

$170

Walk to Crescent Beach, Wifi, Bay Views From Lanai, Heated Pool, YTube TV, Tenni

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 minutes

Price per night from

$141

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

$237

Siesta Key Beach is Across the Street, Partial Water Views, WiFi, Renovated, Ove

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 minutes

Price per night from

$128

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

$137

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful condo” Great location with beach access and walking access to great restaurants. Only downside it was listed as 2 bathrooms when there were only 1 and 1/2

Responds fast! avg. 3 minutes

Price per night from

$180

New Owners & Superbly Renovated, Walk to Crescent Beach, Free Cable/Wifi, Heate

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 minutes

Price per night from

$170

Holiday House 1

Siesta Key apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$90

Canal Home on Siesta Key w/ Pool, Wifi, Authentic 1950 Sarasota School of Archit

Siesta Key house

4 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 minutes

Price per night from

$327

Walk to Siesta Beach, Heated Pool, Ground Floor Unit, Parking

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 minutes

Price per night from

$154

Sea Club II

Siesta Key condo

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$133

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 38 minutes

Price per night from

$354

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

$194

Chinaberry 436 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$263

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$359

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 36 minutes

Price per night from

$440

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

Responds fast! avg. 3 minutes

Price per night from

$204

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.

Price per night from

$333

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. 3 hours 15 minutes

Price per night from

$299

Buttonwood 462 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$289

Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.

Responds fast! avg. 1 hour 29 minutes

Price per night from

$188

Private Beach, Full Gulf Views, Wifi/Cable, Heated Swimming Pool Overlooking Oce

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 minutes

Price per night from

$231

LuLu's Leatherback Walk to Beach & Village, Heated Pool, WiFi, Barbecue Station,

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 minutes

Price per night from

$276

Responds fast! avg. 3 hours 7 minutes

Price per night from

$182

Doveplum 621 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$167

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 4

“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.

Price per night from

$86

Buttonwood 477 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$289

“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 15 minutes

Price per night from

$147

Firethorn 320 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$248

Firethorn 333 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$248

Siesta Key Beach : 2 Bedroom, 3 Beds, 3 Bathroom Duplex & Heated Pool

Siesta Key apartment

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$318

Walk to Beach, WiFi, Heated Pool, Screened Lanai Overlooks Pool, Fishing Pier, T

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 minutes

Price per night from

$139

Beach Across the Street, Partial Gulf Views, Wifi, Tennis Courts, Community Poo

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 minutes

Price per night from

$164

Viewing 38 of 1,312
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
Midnight Cove II - Doveplum
Great deal

The best of three places I have stayed at . The house was clean and smelled good. Overall very happy .plan to stay here again sometime … see more
Beachfront Getaway in Siesta Key
Wonderful beach

The unit was very very clean. Short walk to beach with comfortable lounge chairs. Nice community patio with grills and picnic tables. The unit was well stocked in the kitchen with just one exception of just one dish towel and no dish cloths. Easy fix at dollar store. Loved that the supplies of soaps were of the good quality mrs Meyer and not cheap stuff. Nicely decorated but not the most comfy furniture. If you are working, the bar stools can be uncomfortable after a period of time. The table is very small too for someone working but the photos do show this. The bathroom sink area is a bit tight but very nice. Loved the shower rainwater shower head. Great pressure. The bed was too soft for us but maybe others would like that. Music at captain curt’s can be loud at night but sound machines are provided on both sides of the bed. Genius! We met nice neighbors and the community all seemed very nice including the office staff. Walked across the street to captain curt’s in mornings for a cappuccino and croissant a couple of times. Croissants were great! Dior was very nice to work with and quick to respond. His attention to detail was appreciated. … 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 CONDO!
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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