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.

Guest favorite

Guest suite in Sarasota

4.94 out of 5 average rating, 471 reviews

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 14 – 21

G$29,499 GYD per night
Guest favorite

Guesthouse in Sarasota

4.93 out of 5 average rating, 448 reviews

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.

Oct 13 – 20

G$21,429 GYD per night
Guest favorite

Island in Sarasota

4.97 out of 5 average rating, 298 reviews

*MAY SALE! Sarasota #1 Luxury Villa Pool/Beach!*

Check our nearby sister properties for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Jan 22 – 29

G$123,132 GYD per night

Popular amenities for Siesta Key vacation rentals

Stay near Siesta Key's top sights

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

Siesta Key beach vacation rentals

Guest favorite

Guesthouse in Osprey

4.99 out of 5 average rating, 281 reviews

Cozy Cottage by the Bay

Apr 7 – 14

G$22,969 GYD per night
Guest favorite

Condo in Sarasota

4.96 out of 5 average rating, 119 reviews

Lido-Key- Tiny Studio Holiday Cottage-A

Aug 30 – Sep 6

G$30,594 GYD per night
Guest favorite

Apartment in Siesta Key

4.99 out of 5 average rating, 135 reviews

Siesta Key #1 Beach, pickle ball & tennis paradise

Mar 13 – 20

G$94,918 GYD per night
Guest favorite

Home in Siesta Key

4.93 out of 5 average rating, 104 reviews

Siesta Peace Retreat a private home rental

May 26 – Jun 2

G$122,060 GYD per night
Guest favorite

Guest suite in Sarasota

4.94 out of 5 average rating, 279 reviews

Beach & Town Posh Location! Jungle Paradise Studio

Jul 18 – 25

G$36,093 GYD per night
Guest favorite

Apartment in Sarasota

4.89 out of 5 average rating, 582 reviews

Charming Apt. in old Florida home

Sep 16 – 23

G$21,272 GYD per night
Guest favorite

Guest suite in Siesta Key

4.92 out of 5 average rating, 129 reviews

Cozy Studio - 5 min walk to #1 Siesta Key Beach!

Sep 18 – 25

G$43,346 GYD per night
Guest favorite

Apartment in Sarasota

4.86 out of 5 average rating, 286 reviews

Sarasota Downtown close to Lido Beach

May 29 – Jun 5

G$21,210 GYD per night
Guest favorite

Condo in Siesta Key

4.95 out of 5 average rating, 148 reviews

Walk to Siesta Key Village and Beach

Aug 21 – 28

G$71,867 GYD per night
Guest favorite

Home in Siesta Key

4.92 out of 5 average rating, 138 reviews

Siesta Key Beach & Village 2BR/2BA Steps to Beach

Jul 25 – Aug 1

G$102,813 GYD per night
Guest favorite

Condo in Siesta Key

4.96 out of 5 average rating, 104 reviews

Siesta Key Condo. Checkout our great rates!

Sep 10 – 17

G$32,704 GYD per night
Guest favorite

Home in Bradenton

4.97 out of 5 average rating, 189 reviews

Home near Anna Maria Beach - Hot Tub + Fire Pit

Dec 4 – 11

G$28,270 GYD per night

Siesta Key home rentals

Guest favorite

Home in Sarasota

4.98 out of 5 average rating, 196 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

Oct 15 – 22

G$23,979 GYD per night
Guest favorite

Home in Sarasota

4.91 out of 5 average rating, 142 reviews

Sunshine Suite, Minutes to Beach,Tropical Paradise

Nov 3 – 10

G$20,538 GYD per night
Guest favorite

Home in Sarasota

4.96 out of 5 average rating, 107 reviews

Newly Renovated Ranch Minutes From Beach/Downtown

Sep 10 – 17

G$26,209 GYD per night
Guest favorite

Home in Sarasota

4.96 out of 5 average rating, 127 reviews

Sarasota Florida -Wild Orchid Creek Cottage Home

Jul 19 – 26

G$26,924 GYD per night
Guest favorite

Home in Sarasota

4.96 out of 5 average rating, 238 reviews

Lovely guest house

Jul 22 – 29

G$18,248 GYD per night
Guest favorite

Home in Sarasota

4.87 out of 5 average rating, 201 reviews

The Pineapple Suite.Teal tropical home in Sarasota

May 9 – 16

G$20,528 GYD per night
Guest favorite

Home in Siesta Key

4.89 out of 5 average rating, 102 reviews

Siesta Key, FL - Casa Berano

Jun 7 – 14

G$59,080 GYD per night
Superhost

Home in Siesta Key

4.87 out of 5 average rating, 118 reviews

"Safe & Clean" Palm Oasis - Relax in comfort!

Oct 21 – 28

G$164,595 GYD per night
Guest favorite

Home in Sarasota

4.85 out of 5 average rating, 161 reviews

Authentic Florida Bungalow near Downtown and Beach

Apr 29 – May 6

G$21,564 GYD per night
Guest favorite

Home in Sarasota

4.94 out of 5 average rating, 124 reviews

Ranch 2 blocks from Sarasota Bay

Dec 15 – 22

G$25,887 GYD per night
Guest favorite

Home in Sarasota

4.94 out of 5 average rating, 292 reviews

☀Coastal Gem☀Heated pool & amazing location!☀

Jun 30 – Jul 7

G$61,665 GYD per night
Guest favorite

Home in Sarasota

4.87 out of 5 average rating, 128 reviews

5 minutes to private Siesta Key Beach + 2 pools

Nov 26 – Dec 3

G$77,372 GYD per night

Siesta Key villa rentals

Guest favorite

Villa in Sarasota

4.96 out of 5 average rating, 130 reviews

Newly Renovated- 150 Yards to Beach & Restaurants!

Jan 10 – 17

G$60,345 GYD per night
Guest favorite

Villa in Siesta Key

4.9 out of 5 average rating, 133 reviews

Mermaid Villa Ocean Front!

Sep 21 – 28

G$164,099 GYD per night
Guest favorite

Villa in Sarasota

4.89 out of 5 average rating, 181 reviews

Entire Standalone Villa,1.2k sf,1 block Lido Beach

Sep 13 – 20

G$48,886 GYD per night
Guest favorite

Villa in Sarasota

4.9 out of 5 average rating, 176 reviews

Hansen- Gorgeous 3BR/2BA Villa near Siesta Key

Jul 14 – 21

G$64,581 GYD per night
Superhost

Villa in Sarasota

4.77 out of 5 average rating, 120 reviews

Aloha Villa Pet Friendly 3 miles to Siesta Key #2

Sep 24 – Oct 1

G$43,417 GYD per night
Guest favorite

Villa in Bradenton

4.83 out of 5 average rating, 133 reviews

Elegant private home 3Bdr/3bth

Jun 29 – Jul 6

G$63,013 GYD per night
Guest favorite

Villa in Siesta Key

4.92 out of 5 average rating, 49 reviews

Siesta Key BEACH SIDE villa/Private beach/pool

Sep 3 – 10

G$46,323 GYD per night
Guest favorite

Villa in Sarasota

5.0 out of 5 average rating, 18 reviews

Vacation Luxury Villa/ Heated Pool -Beach Access

Jan 6 – 13

G$141,662 GYD per night
Guest favorite

Villa in Sarasota

4.93 out of 5 average rating, 14 reviews

Relaxation awaits in this bohemian inspired villa

Aug 6 – 13

G$175,380 GYD per night
Guest favorite

Villa in Sarasota

5.0 out of 5 average rating, 18 reviews

NEW-Cheerful 2-bedroom villa-13 min. to Siesta Key

May 2 – 9

G$36,486 GYD per night
Guest favorite

Villa in Sarasota

4.96 out of 5 average rating, 28 reviews

Village Des Pins - 2 bedroom 2 bath villa

Aug 13 – 20

G$35,458 GYD per night
Guest favorite

Villa in Sarasota

4.9 out of 5 average rating, 20 reviews

Beautiful House w/ Pool, 10 Min to Siesta Beach

Aug 5 – 12

G$57,384 GYD per night

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 400 house rentals, over 80 villa rentals to over 790 condo 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