Siesta Key vacation rentals

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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
Phillippi Estate Park17 locals recommend
Siesta Key Drum Circle62 locals recommend
Siesta Key Oyster Bar167 locals recommend

Other great vacation rentals in Siesta Key

Guest favorite

Home in Sarasota

4.9 out of 5 average rating, 131 reviews

The lovely place getaway-SRQ

May 1 – 6

G$20,939 GYD per night
Guest favorite

Home in Sarasota

4.96 out of 5 average rating, 111 reviews

Newly Renovated Ranch Minutes From Beach/Downtown

Jul 27 – Aug 3

G$23,677 GYD per night
Guest favorite

Home in Sarasota

4.99 out of 5 average rating, 130 reviews

Adorable Bungalow Fire pit/outdoor shower 2/1 Cute

Oct 13 – 20

G$27,833 GYD per night
Guest favorite

Home in Siesta Key

4.92 out of 5 average rating, 141 reviews

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

Aug 18 – 25

G$84,016 GYD per night
Guest favorite

Home in Sarasota

4.94 out of 5 average rating, 106 reviews

Hyde Park/Southside Village Modern 5 Star Home

Sep 3 – 10

G$28,668 GYD per night
Guest favorite

Home in Siesta Key

5.0 out of 5 average rating, 123 reviews

One-of-a-kind*Beach, Village, Dock & Private Pool!

Jul 14 – 21

G$147,623 GYD per night
Guest favorite

Home in Sarasota

5.0 out of 5 average rating, 278 reviews

Stunning Luxe Casita- Gateway to Siesta Beach

Mar 2 – 9

G$58,558 GYD per night
Guest favorite

Home in Sarasota

4.89 out of 5 average rating, 103 reviews

Quiet Retreat-5mi to Beach-Hot Tub, Outdoor Shower

Aug 25 – Sep 1

G$36,096 GYD per night

Private vacation rentals in Siesta Key

Guest favorite

Guest suite in Sarasota

4.92 out of 5 average rating, 258 reviews

Two Miles to Siesta Key

Jul 3 – 10

G$481,836 GYD per night
Guest favorite

Guesthouse in Osprey

4.99 out of 5 average rating, 286 reviews

Cozy Cottage by the Bay

Jun 5 – 12

G$16,589 GYD per night
Superhost

Guest suite in Sarasota

4.78 out of 5 average rating, 232 reviews

Sarasota Escape: Perfect Studio Near the Beach

Aug 14 – 21

G$19,883 GYD per night
Guest favorite

Guest suite in Sarasota

4.97 out of 5 average rating, 350 reviews

Adorable studio close to Siesta beach!

Sep 23 – 30

G$19,145 GYD per night
Guest favorite

Cottage in Sarasota

4.94 out of 5 average rating, 137 reviews

Sea-esta Cottage-cheerful 2bd/1ba w/ free parking

Sep 4 – 11

G$23,727 GYD per night
Superhost

Cottage in Sarasota

4.83 out of 5 average rating, 150 reviews

Charming Beach Cottage

Jul 14 – 21

G$28,477 GYD per night
Guest favorite

Apartment in Sarasota

4.85 out of 5 average rating, 291 reviews

Sarasota Downtown close to Lido Beach

Jun 22 – 29

G$20,508 GYD per night
Guest favorite

Tiny home in Sarasota

4.89 out of 5 average rating, 171 reviews

@Tiffanythetinyhome| island | netflix|bike|hammock

Jul 24 – 31

G$32,228 GYD per night

Siesta Key beach vacation rentals

Guest favorite

Condo in Sarasota

4.96 out of 5 average rating, 119 reviews

Lido-Key- Tiny Studio Holiday Cottage-A

Aug 1 – 8

G$30,852 GYD per night
Guest favorite

Condo in Siesta Key

4.85 out of 5 average rating, 131 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

Oct 15 – 22

G$31,228 GYD per night
Guest favorite

Condo in Siesta Key

4.96 out of 5 average rating, 275 reviews

On the Beach; Siesta Key SunBum Studio

Mar 14 – 21

G$95,463 GYD per night
Guest favorite

Cottage in Nokomis

4.98 out of 5 average rating, 123 reviews

Staycation Sanctuary - 100% Smoke-Free Property

Aug 11 – 18

G$24,907 GYD per night
Superhost

Condo in Siesta Key

4.83 out of 5 average rating, 286 reviews

[Sunny in Siesta] King bed+5 minute walk to beach

Oct 10 – 17

G$47,708 GYD per night
Guest favorite

Condo in Siesta Key

4.96 out of 5 average rating, 105 reviews

Siesta Key Condo. Checkout our great rates!

Sep 13 – 20

G$32,565 GYD per night
Guest favorite

Apartment in Sarasota

4.89 out of 5 average rating, 587 reviews

Charming Apt. in old Florida home

Sep 7 – 14

G$21,182 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

Jun 3 – 10

G$75,234 GYD per night

Quick stats about vacation rentals in Siesta Key

  • Total rentals

    1.7K properties

  • Rentals with dedicated workspaces

    770 properties have a dedicated workspace

  • Rentals with a pool

    1.3K properties have a pool

  • Pet-friendly rentals

    350 properties allow pets

  • Family-friendly rentals

    1.4K properties are a good fit for families

  • Total number of reviews

    29K 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 820 condo rentals to over 410 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 770 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