Siesta Key vacation rentals

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Top-rated vacation rentals in Siesta Key

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Entire cottage · Siesta Key
Love Shack - steps away from #1 Beach in USA!
Enjoy Amazing sunsets and beautiful mornings at the Love Shack! Located only steps from Beach Access #4 and a minute walk into the heart of Siesta Key Village.
$141 per night
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Entire condo · Siesta Key
On the Beach; Siesta Key SunBum Studio
STEPS TO YOUR OWN PRIVATE BEACH!! NO TRICKS or GIMMICKS LIKE OTHER LISTINGS. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, new gym, boat docks, fishing pier, outdoor grills, tennis courts and not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking! You are sure to enjoy your time here on the #1 U.S. Beach.
$218 per night
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Entire rental unit · Siesta Key
Siesta Key - Poolside Suite - Studio - Free kayaks
Newly remodeled in 2021! Poolside Suite is a hotel room style suite. There is a king sized bed & a 55” smart TV. Cable & Wifi are also included. A private en suite bathroom features a spa like walk in shower, toilet and large vanity with sink & mirror. Also provided in a walk in closet space is a fridge, microwave, freezer, blender, cups, plates, silverware, keurig, iron, mini ironing board & hangers. Simple & stylish! The a/c is a centralized system, set to 73 degrees. Fan provided.
$124 per night
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Vacation rentals for every style

Get the amount of space that is right for you

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Stay near Siesta Key's top sights

Photo of Siesta Key Beach Access 2
Siesta Key Beach Access 24 locals recommend
Photo of South Lido Key Beach Park on the Gulf
South Lido Key Beach Park on the Gulf16 locals recommend
Photo of Siesta Key Drum Circle
Siesta Key Drum Circle32 locals recommend
Photo of Phillippi Estate Park
Phillippi Estate Park9 locals recommend
Photo of Siesta Key Oyster Bar
Siesta Key Oyster Bar84 locals recommend
Photo of Daiquiri Deck Siesta Key Village
Daiquiri Deck Siesta Key Village38 locals recommend

Siesta Key beach vacation rentals

Entire townhouse · Siesta Key
"Safe & Clean"- Honeymoon Suite- Siesta Key Beach
$201 per night
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Entire condo · Siesta Key
Comfy Siesta Key Condo
$82 per night
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Entire rental unit · Sarasota
NEW 2021 - Siesta Shores Studio - King bed - Pool!
$126 per night
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Entire condo · Sarasota
5209A Calle Menorca - Siesta Key Village Condo
$218 per night
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Entire villa · Siesta Key
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
$166 per night
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Entire condo · Siesta Key
Siesta Key Beach across the street ideal location
$140 per night
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Entire condo · Siesta Key
Siesta Key Gulf Coast Condo
$120 per night
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Entire condo · Siesta Key
[Beach Elements] pool view + private beach & bikes
$134 per night
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Entire condo · Sarasota
Beachside Siesta Key Cottage steps from the ocean
$200 per night
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Entire rental unit · Siesta Key
☀️ Beach & Pool Open! Direct Beachfront. Sunset View!
$190 per night
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Entire serviced apartment · Siesta Key
Siesta Key Enjoy your own beach & tennis paradise
$302 per night
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Entire condo · Sarasota
5213B Calle Menorca - Siesta Key Village Condo
$199 per night
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Siesta Key house rentals

Private room · Sarasota
Studio Apartment by Siesta Key beach
$90 per night
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Entire home · Siesta Key
Beachfront Getaway in Siesta Key
$227 per night
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Entire home · Sarasota
Incredible Oasis in the Heart of Downtown Sarasota
$475 per night
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Entire home · Siesta Key
Siesta Beach House
$250 per night
Entire home · Siesta Key
[modern beach bungalow] private patio +bikes
$166 per night
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Entire home · Siesta Key
[lounge like locals]walk to siesta beach +bikes
$149 per night
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Entire home · Sarasota
5Stars Tiki, Heated Pool, Close to Beaches and ALL
$176 per night
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Entire home · Sarasota
Beautifully Remodeled Home with Pool Near Siesta
$170 per night
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Entire home · Sarasota
Heated Pool - Just 1 mile to Beach! Updated/Fun!
$214 per night
Entire home · Siesta Key
Coolest House in Siesta Key Village
$370 per night
Private room · Sarasota
Cheerful beach room in a home with a pool.
$47 per night
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Entire home · Sarasota
Quiet Retreat-Hot Tub Outdoor Shower- 5mi to Beach
$128 per night
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Siesta Key villa rentals

Entire villa · Sarasota
New remodel- 150 Yds to Beach and Restaurants!
$218 per night
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Entire villa · Siesta Key
Siesta Key BEACH SIDE villa/Private beach/pool
$250 per night
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Private room · Sarasota
Tranquil 1 bedroom suite with pool
$79 per night
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Entire villa · Siesta Key
Island House Beach Resort V28
$210 per night
Entire villa · Siesta Key
Island House Beach Resort V16
$210 per night
Entire villa · Siesta Key
*** NEW *** Completely remodeled villa w/ beach and heated pool access
$204 per night
Entire villa · Siesta Key
Island House Beach Resort V17
$210 per night
Entire villa · Sarasota
Siesta Key bungalow at Vista Hermosa
$146 per night
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Entire villa · Siesta Key
Recently Updated Cozy Siesta Key Beach Villa
$150 per night
Entire villa · Sarasota
Siesta Key Oasis
$486 per night
Entire villa · Sarasota
SEALAND 3/2 Modern Villa w/ Pool near Siesta
$163 per night
Entire villa · Lido Key
Entire Standalone Villa,1.2k sf,1 block Lido Beach
$208 per night
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Your guide to Siesta Key

All About Siesta Key

Siesta Key is an eight-mile-long barrier island off the coast of Sarasota, known for its soft quartz beaches, turquoise waters, and abundance of marine life. Due to its location on the western Florida shoreline in the balmy waters of the Gulf of Mexico, the island experiences ideal conditions year-round for swimming, paddling, and watersports. This small coastal community offers a host of recreational opportunities outside of the beach as well. Wander the Siesta Key Village, where you can find the many live music venues, boutique art shops, and souvenir vendors scattered throughout the small but lively downtown area. Check out one of the weekly farmer’s markets, spend an afternoon picking through the gift shops, or just lounge one the one of the white-sand beaches waiting for the sun to set over the Gulf.


When is the best time to stay in a vacation rental in Siesta Key?

Thanks to the island's location in the Gulf of Mexico, weather conditions and water temperatures are favorable for most of the year. Beginning in March, temperatures start to rise, with averages peaking around mid October. You can expect heat and humidity at your Siesta Key rental during this period, but gulf stream breezes help keep things cool. Weekly farmers markets, a musical festival, and a fireworks show are just a few of the notable events happening through the summer season.

In winter, temperatures see a marginal decrease, with January and February being the coldest months. However, many still find both the air and water temperatures suitable for swimming. The winter also happens to be when many of the area’s art festivals take place. Check out the Chalk Art Festival towards the end of October or the sand sculpture competition in November where you can take sculpting classes and vote on your favorite piece of art.


What are the top things to do in Siesta Key?

Point of Rocks

One of the best snorkeling sites on Siesta Key, this limestone rock outcropping is home to abundant marine life and migratory bird populations. Calm waters and clear conditions make this a perfect place for beginners and experienced snorkelers alike. Expect to see schools of tropical fish, crabs, ocean sponges, and manatees during the summer. You may even get lucky and spot some of the area’s resident dolphins.

Siesta Key Drum Circle

The Siesta Key drum circle is a weekly tradition held on Sundays at Englewood and Siesta beaches throughout the year. Beginning about an hour before sunset, local artists and dancers kick off an evening of music and dancing. Large crowds gather to watch the festivities as onlookers are encouraged to dance or grab a drum and beat along.

Deep-sea fishing

Sandwiched between the vast Gulf of Mexico and Roberts Bay, Siesta Key is a year-round fishing destination. The reefs attract cobia and grouper, and if you venture further out you’ll be rewarded with tuna and wahoo. July is peak season for red snapper, while the fall bait migration off the Florida coast is a big draw for anglers from October onward.

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