Vacation rentals in Siesta Key

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Top-rated vacation rentals in Siesta Key

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

Guest favorite
Guest suite in Sarasota
Studio Apartment. Priv Yard. 5 min to Siesta Key!
Self checkin. Includes kayak and bikes! You’ll love my place because of the coziness, the high ceilings, and the location. My place is good for couples, solo adventurers, and business travelers. Converted garage space. Your own private fenced back yard, kitchenette, fridge, private bathroom, Amazon Firestick with Netflix, Hulu and dock/boat ramp just 30 sec from your door and in a beautiful neighborhood. Just a 10 min bike ride to Siesta Key. The #1 beach in America! What more could you ask for!
Nov 3 – 10
$123 per night
4.94 out of 5 average rating, 470 reviews
Guest favorite
Guesthouse in Sarasota
La Casetta: "the little house" near to the beaches
La Casetta means, in Italian, a tiny house. Set in a private, peaceful, mature Florida tropical garden, a real hideaway. I am proud of the cleanliness of our property, however in this new reality that we live in, we do carry out enhanced cleaning and sanitizing between guests. We also practice social distancing, insofar as guests have their own part of our luscious back garden as well as your own entrance. La Casetta has 1 queen sized bed, bathroom & kitchenette. Wifi & Netflix available.
Aug 7 – 14
$85 per night
4.93 out of 5 average rating, 448 reviews
Guest favorite
Condo in Siesta Key
On the Beach; Siesta Key SunBum Studio
STEPS TO YOUR OWN PRIVATE BEACH!! NO TRICKS or GIMMICKS LIKE OTHER LISTINGS on the KEY. 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/pickle ball courts; 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.
Nov 11 – 18
$259 per night
4.96 out of 5 average rating, 267 reviews

Popular amenities for Siesta Key vacation rentals

Stay near Siesta Key's top sights

The Cottage68 locals recommend
Phillippi Estate Park17 locals recommend
PARASAIL SIESTA24 locals recommend
Siesta Beach Pavillion3 locals recommend
Siesta Key Oyster Bar167 locals recommend
South Lido Key Beach Park on the Gulf25 locals recommend

Condo rentals in Siesta Key

Guest favorite
Condo in Siesta Key
New: Cozy 1BR Beach Condo on Siesta Key!!!
Jul 9 – 16
$150 per night
4.83 out of 5 average rating, 186 reviews
Guest favorite
Condo in Siesta Key
Walk to Siesta Key Village and Beach
Aug 28 – Sep 4
$256 per night
4.95 out of 5 average rating, 148 reviews
Guest favorite
Condo in Siesta Key
Siesta Key Ground Floor Condo 2BR On Trolley Line
Oct 20 – 27
$141 per night
4.84 out of 5 average rating, 129 reviews
Guest favorite
Condo in Siesta Key
*A Stones Throw from #1 Voted Siesta Key Beach*
Dec 5 – 12
$250 per night
4.92 out of 5 average rating, 128 reviews
Guest favorite
Condo in Siesta Key
Siesta Key Condo. Checkout our great rates!
Aug 12 – 19
$134 per night
4.96 out of 5 average rating, 104 reviews
Superhost
Condo in Siesta Key
Private Beach Siesta Key Resort Jamaica Royale
Oct 7 – 14
$299 per night
4.88 out of 5 average rating, 121 reviews
Guest favorite
Condo in Siesta Key
2 Bed/2 Bath Condo Resort View on Siesta Key Beach
Sep 1 – 8
$310 per night
4.96 out of 5 average rating, 102 reviews
Guest favorite
Condo in Siesta Key
Bright and Beachy - Steps to the Water!
Sep 5 – 12
$263 per night
4.92 out of 5 average rating, 178 reviews
Guest favorite
Condo in Sarasota
Beachside Siesta Key Cottage steps from the ocean
May 22 – 29
$266 per night
4.91 out of 5 average rating, 117 reviews
Superhost
Condo in Siesta Key
[Sunny in Siesta] King bed+5 minute walk to beach
May 19 – 26
$342 per night
4.82 out of 5 average rating, 281 reviews
Guest favorite
Condo in Siesta Key
Sarasota Surf & Racquet Club Siesta Key Condo
Aug 1 – 8
$358 per night
4.82 out of 5 average rating, 119 reviews
Guest favorite
Condo in Siesta Key
Sea Club 2 Condo Siesta Key
Aug 27 – Sep 3
$200 per night
4.9 out of 5 average rating, 200 reviews

House rentals in Siesta Key

Guest favorite
Home in Siesta Key
Siesta Key Beach & Village 2BR/2BA Steps to Beach
Jan 16 – 23
$356 per night
4.92 out of 5 average rating, 136 reviews
Guest favorite
Home in Siesta Key
Siesta Key, FL - Casa Berano
Sep 4 – 11
$244 per night
4.89 out of 5 average rating, 101 reviews
Guest favorite
Home in Sarasota
Lovely guest house
Jul 18 – 25
$75 per night
4.96 out of 5 average rating, 236 reviews
Guest favorite
Home in Sarasota
Stunning Luxe Casita- Gateway to Siesta Beach
Jun 23 – 30
$222 per night
5.0 out of 5 average rating, 273 reviews
Guest favorite
Home in Sarasota
Cottage Getaway 2 miles from Beach
May 5 – 12
$125 per night
4.92 out of 5 average rating, 189 reviews
Guest favorite
Home in Sarasota
Authentic Florida Bungalow near Downtown and Beach
May 18 – 25
$74 per night
4.85 out of 5 average rating, 161 reviews
Guest favorite
Home in Sarasota
The Pineapple Suite.Teal tropical home in Sarasota
Sep 8 – 15
$87 per night
4.87 out of 5 average rating, 201 reviews
Guest favorite
Home in Sarasota
Sunshine Suite, Minutes to Beach,Tropical Paradise
Dec 21 – 28
$98 per night
4.91 out of 5 average rating, 141 reviews
Superhost
Home in Siesta Key
"Safe & Clean" Palm Oasis - Relax in comfort!
Dec 8 – 15
$750 per night
4.87 out of 5 average rating, 117 reviews
Guest favorite
Home in Sarasota
☀Coastal Gem☀Heated pool & amazing location!☀
Oct 30 – Nov 6
$222 per night
4.94 out of 5 average rating, 292 reviews
Guest favorite
Home in Sarasota
Your private retreat near Siesta Key Beach.
Oct 26 – Nov 2
$282 per night
4.97 out of 5 average rating, 200 reviews
Guest favorite
Home in Sarasota
Ranch 2 blocks from Sarasota Bay
Dec 15 – 22
$106 per night
4.95 out of 5 average rating, 123 reviews

Siesta Key beach vacation rentals

Guest favorite
Guest suite in Siesta Key
Cozy Studio - 5 min walk to #1 Siesta Key Beach!
Aug 1 – 8
$172 per night
4.92 out of 5 average rating, 128 reviews
Guest favorite
Apartment in Siesta Key
Siesta Key #1 Beach, pickle ball & tennis paradise
Sep 16 – 23
$395 per night
4.99 out of 5 average rating, 135 reviews
Guest favorite
Guest suite in Sarasota
Sweet Hideaway Minutes from Siesta Key!
Apr 14 – 21
$99 per night
4.95 out of 5 average rating, 228 reviews
Guest favorite
Apartment in Sarasota
No Subzero Temps Here
Jun 13 – 20
$91 per night
4.99 out of 5 average rating, 106 reviews
Guest favorite
Apartment in Sarasota
Modern Private Apartment 1 Block from Sarasota Bay
Oct 11 – 18
$102 per night
4.96 out of 5 average rating, 198 reviews
Guest favorite
Bungalow in Sarasota
Mid Century Gem, west of the trail.
Aug 2 – 9
$151 per night
4.85 out of 5 average rating, 193 reviews
Guest favorite
Island in Sarasota
*MAY SALE! Sarasota #1 Luxury Villa Pool/Beach!*
Nov 5 – 12
$494 per night
4.98 out of 5 average rating, 296 reviews
Guest favorite
Cottage in Nokomis
Staycation Sanctuary - 100% Smoke-Free Property
Jul 19 – 26
$102 per night
4.98 out of 5 average rating, 123 reviews
Guest favorite
Apartment in Sarasota
Charming Apt. in old Florida home
Jul 22 – 29
$89 per night
4.89 out of 5 average rating, 581 reviews
Guest favorite
Cottage in Siesta Key
Siesta Key Cozy Cottage across from the beach!
Jul 18 – 25
$261 per night
4.88 out of 5 average rating, 137 reviews
Guest favorite
Guest suite in Sarasota
Private, cozy, studio 2 miles from Siesta Key!
Jul 26 – Aug 2
$111 per night
4.89 out of 5 average rating, 326 reviews
Guest favorite
Cottage in Siesta Key
Surf Shack- Walk to Village/Boat Dock Included
Nov 6 – 13
$125 per night
4.94 out of 5 average rating, 66 reviews

Quick stats about vacation rentals in Siesta Key

Total rentals

1.6K properties

Rentals with dedicated workspaces

680 properties have a dedicated workspace

Rentals with a pool

1.2K properties have a pool

Pet-friendly rentals

340 properties allow pets

Family-friendly rentals

1.3K properties are a good fit for families

Total number of reviews

28K reviews

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.


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.


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.

Frequently Asked Questions

  • How is the weather in Siesta Key?

    Siesta Key enjoys a tropical climate with warm weather throughout the year. Summer temperatures can rise up to 90°F (32°C) while winter temperatures rarely drop below 50°F (10°C). The island gets a significant amount of rainfall, especially during the summer months.

  • What are some of the best things to do in Siesta Key?

    Activities in Siesta Key often revolve around its beautiful beaches, where you can swim, sunbathe, or play beach volleyball. You can also explore the local shops and restaurants in Siesta Village, or take a boat tour to spot dolphins.

  • What is the best time of year to visit Siesta Key?

    The most popular time to visit Siesta Key is during the winter and spring months when the weather is warm and comfortable. A notable local event is the Siesta Key Crystal Classic, an international sand sculpting festival that takes place every November.

  • What are the best places to stay in Siesta Key?

    Popular areas to stay in Siesta Key include Siesta Village for its proximity to dining and shopping, Crescent Beach for its quiet atmosphere, and Turtle Beach for its family-friendly environment.

  • What are the best places to visit in Siesta Key?

    Siesta Key is known for its stunning beaches such as Siesta Beach and Turtle Beach. You might also find exploring the Siesta Key Village and Point of Rocks interesting. The latter is a limestone formation on Crescent Beach attracting snorkeling enthusiasts.

  • What are some hiking trails in Siesta Key?

    While Siesta Key is more known for its beautiful beaches, you can still explore walking trails such as the Palmer Point Beach trail or Turtle beach trail. These paths provide an opportunity to enjoy the island's natural beauty and spot local wildlife.

  • What are some family activities to do in Siesta Key?

    Families can have fun exploring the Siesta Key beaches, perfect for swimming and building sandcastles. The Siesta Key Water Sports provide opportunities to engage in safe marine activities. For nature lovers, the Siesta Key Marina has dolphin watching tours.

  • What are some of the best day trip ideas in Siesta Key?

    Popular day trips from Siesta Key include visiting the vibrant city of Sarasota, which has a lively arts scene, or exploring the Myakka River State Park, known for its diverse wildlife and hiking trails.

  • What types of vacation rentals are available in Siesta Key?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Siesta Key. From over 790 condo rentals to over 400 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Are there vacation rentals with a dedicated workspace in Siesta Key?

    Yes! Work meets play with ease at over 680 vacation rentals in Siesta Key featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Sarasota County
  5. Siesta Key