Holiday rentals in Siesta Key

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Top-rated holiday rentals in Siesta Key

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

Guest favourite

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!

14–21 Nov

€ 153 per night
Guest favourite

Guest house 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.

13–20 Oct

€ 112 per night
Guest favourite

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!

22–29 Jan

€ 625 per night

Popular amenities for Siesta Key holiday 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

Other great holiday rentals in Siesta Key

Guest favourite

Guest house in Sarasota

4.93 out of 5 average rating, 363 reviews

Clean and Modern Sarasota Studio w/ Beach Gear!

1–8 Sep

€ 108 per night
Guest favourite

Flat in Sarasota

4.98 out of 5 average rating, 164 reviews

Gillespie On The Park, Walk to Downtown

21–28 May

€ 99 per night
Guest favourite

Guest suite in Sarasota

4.96 out of 5 average rating, 101 reviews

Cozy little guest suite- 6 miles from Siesta Beach

24 Apr – 1 May

€ 120 per night
Guest favourite

Apartment in Sarasota

4.96 out of 5 average rating, 119 reviews

Lido-Key- Tiny Studio Holiday Cottage-A

30 Aug – 6 Sep

€ 162 per night
Guest favourite

Guest suite in Sarasota

4.94 out of 5 average rating, 254 reviews

Two Miles to Siesta Key

21–28 Oct

€ 145 per night
Guest favourite

Guest house in Osprey

4.99 out of 5 average rating, 281 reviews

Cozy Cottage by the Bay

7–14 Apr

€ 122 per night
Guest favourite

Flat in Siesta Key

4.99 out of 5 average rating, 135 reviews

Siesta Key #1 Beach, pickle ball & tennis paradise

13–20 Mar

€ 484 per night
Guest favourite

Home in Siesta Key

4.93 out of 5 average rating, 104 reviews

Siesta Peace Retreat a private home rental

26 May – 2 Jun

€ 630 per night
Guest favourite

Home in Sarasota

4.98 out of 5 average rating, 196 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

15–22 Oct

€ 129 per night
Guest favourite

Guest suite in Sarasota

4.98 out of 5 average rating, 184 reviews

The Sapphire Suite 1Bed/1Bath

4–11 Nov

€ 123 per night
Guest favourite

Cottage in Siesta Key

4.94 out of 5 average rating, 66 reviews

Surf Shack- Walk to Village/Boat Dock Included

19–26 Sep

€ 164 per night
Guest favourite

Apartment in Siesta Key

4.95 out of 5 average rating, 61 reviews

The Honeymoon Suite on Siesta Key Beach

8–15 Sep

€ 220 per night

Quick stats about holiday 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

Destinations to explore

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