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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.

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.
Dec 15 – 22
$169 per night
Superhost
Condo · Siesta Key
Siesta key getaway!
perfect and very comfortable 4th floor condo with elevator, screened in lanai, fully stocked kitchen and full bath. laundry facilities on the premises, a tennis court. We supply beach chairs, umbrellas, a rolling cooler and big beach bag. There is a beautiful dock on the intercoastal side of us with picnic chairs, grills, and you may even see dolphins playing !
Oct 19 – 26
$115 per night
Superhost
Private room · Sarasota
Studio Apartment by Siesta Key beach
Looking for a private, quiet, and cozy place to rest after a long day of enjoying the #1 beach in the U.S. –Siesta Key Beach? ☀️🏖 Well look no further, this is the perfect place for you! My studio is approximately a 30 minute walk to the beach, and just a short 5 minute drive.
Oct 17 – 24
$90 per night
Superhost

Vacation rentals for every style

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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

Condo · Siesta Key
Comfy Siesta Key Condo
Sep 15 – 22
$97 per night
Superhost
Condo · Siesta Key
Sea Shell Ocean views 2BE2BA Walk everywhere Pool
Jan 7 – 14
$225 per night
Superhost
Home · Siesta Key
Siesta Beach House
Jul 26 – Aug 2
$250 per night
Apartment · Siesta Key
Siesta Key ~New Waterview studio ~ sleeps 4 ~ pool
May 18 – 25
$164 per night
Superhost
Cottage · Siesta Key
Surf Shack- Walk to Village/Boat Dock Included
Jun 21 – 28
$150 per night
Superhost
Condo · Siesta Key
On the Beach; Siesta Key SunBum Studio
Aug 10 – 17
$299 per night
Superhost
Guest suite · Siesta Key
Cozy Studio - 5 min walk to #1 Siesta Key Beach!
May 16 – 23
$171 per night
Superhost
Condo · Siesta Key
SIESTA KEY GROUND FLOOR CONDO ON TROLLEY LINE
Jun 7 – 14
$144 per night
Superhost
Condo · Siesta Key
Vacation Condo on Siesta Key, FL
Apr 27 – May 4
$162 per night
Condo · Siesta Key
Siesta Key Oasis with Gulf Views
Aug 24 – 31
$399 per night
Superhost
Townhouse · Siesta Key
"Safe & Clean"- Honeymoon Suite- Siesta Key Beach
Sep 29 – Oct 6
$212 per night
Superhost
Condo · Siesta Key
Heat of Siesta Village Walk to Beach w heated Pool
May 6 – 13
$216 per night
Superhost

Siesta Key house rentals

Home · Siesta Key
Siesta Key Quaint Beach House
Nov 28 – Dec 5
$199 per night
Superhost
Home · Sarasota
5Stars Tiki, Heated Pool, Close to Beaches and ALL
May 11 – 18
$294 per night
Superhost
Home · Sarasota
Quiet luxury on the Northern end of Siesta Key! Available after being off the market for several months! Enjoy a stress free vacation at this 3BR paradise.
Dec 9 – 16
$301 per night
Superhost
Home · Sarasota
Renovated Ranch near Downtown Sarasota and Siesta
Nov 30 – Dec 7
$266 per night
Superhost
Home · Sarasota
The Dunes-Heated Private Pool Hot Tub-5mi to beach
Dec 5 – 12
$315 per night
Superhost
Home · Sarasota
Lovely guest house
Nov 12 – 19
$70 per night
Superhost
Home · Sarasota
SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!
Oct 23 – 30
$273 per night
Superhost
Home · Sarasota
Ideal vacation, steps to private Siesta Key beach
Jun 23 – 30
$260 per night
Superhost
Home · Siesta Key
🔥Shark🐋 Top Village,Walk to Beach,Pet-Friendly
Aug 23 – 30
$595 per night
Superhost
Private room · Siesta Key
Airy room on Siesta Key with private bathroom.
Mar 11 – 18
$150 per night
Superhost
Home · Sarasota
Great Vacation Home by Siesta Key Beach
Aug 11 – 18
$224 per night
Private room · Sarasota
Walk to Siesta! Private mini-efficiency w/patio
Oct 20 – 27
$76 per night
Superhost

Siesta Key villa rentals

Villa · Siesta Key
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Dec 27 – Jan 3
$521 per night
Superhost
Villa · Siesta Key
Siesta Key BEACH SIDE villa/Private beach/pool
Aug 5 – 12
$335 per night
Superhost
Villa · Siesta Key
Mermaid Villa Ocean Front!
Sep 26 – Oct 3
$682 per night
Superhost
Villa · Sarasota
Siesta Key Oasis
Oct 19 – 26
$500 per night
Superhost
Villa · Siesta Key
Island House Beach Resort V26
Aug 20 – 27
$210 per night
Villa · Siesta Key
Siesta Key Pineapple 🏖 Beach House Beach view!
May 27 – Jun 3
$950 per night
Superhost
Villa · Siesta Key
Island House Beach Resort V16
Aug 27 – Sep 3
$210 per night
Villa · Sarasota
Newly Renovated- 150 Yards to Beach & Restaurants!
Nov 13 – 20
$221 per night
Superhost
Villa · Siesta Key
Penthouse Mermaid Villa
Jul 5 – 12
$714 per night
Superhost
Villa · Sarasota
Downtown Sarasota Villa, Sleeps 6, WiFi. All *NEW*
Jan 3 – 10
$200 per night
Superhost
Villa · Sarasota
🌴🐬Bay Haven- Resort style Backyard 🏊‍♀️🔥 & Game Rm⚽️
May 17 – 24
$899 per night
Superhost
Villa · Sarasota
SEALAND 3/2 Modern Villa w/ Pool near Siesta
Jul 30 – Aug 6
$303 per night

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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