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
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!
3–10 Nov
₹10,160 per night
4.94 out of 5 average rating, 470 reviews
Guest favourite
Guest house 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.
7–14 Aug
₹7,012 per night
4.93 out of 5 average rating, 448 reviews
Guest favourite
Apartment 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.
11–18 Nov
₹21,473 per night
4.96 out of 5 average rating, 267 reviews

Popular amenities for Siesta Key holiday 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

Other great holiday rentals in Siesta Key

Guest favourite
Flat in Siesta Key
Siesta Key #1 Beach, pickle ball & tennis paradise
16–23 Sep
₹32,749 per night
4.99 out of 5 average rating, 135 reviews
Guest favourite
Guest suite in Sarasota
Sweet Hideaway Minutes from Siesta Key!
14–21 Apr
₹8,220 per night
4.95 out of 5 average rating, 228 reviews
Guest favourite
Guest suite in Sarasota
Cozy little guest suite- 6 miles from Siesta Beach
29 Apr – 6 May
₹8,664 per night
4.96 out of 5 average rating, 100 reviews
Guest favourite
Apartment in Siesta Key
New: Cozy 1BR Beach Condo on Siesta Key!!!
9–16 Jul
₹12,436 per night
4.83 out of 5 average rating, 186 reviews
Guest favourite
Guest house in Sarasota
Sarasota guest house only 8 miles to Siesta Key
8–15 Jun
₹7,163 per night
4.96 out of 5 average rating, 243 reviews
Guest favourite
Cottage in Siesta Key
Surf Shack- Walk to Village/Boat Dock Included
6–13 Nov
₹10,364 per night
4.94 out of 5 average rating, 66 reviews
Guest favourite
Apartment in Siesta Key
The Honeymoon Suite on Siesta Key Beach
24–31 Oct
₹14,094 per night
4.95 out of 5 average rating, 60 reviews
Superhost
Apartment in Sarasota
Beautiful condo near Siesta Key beach
1–8 May
₹6,550 per night
5.0 out of 5 average rating, 4 reviews
Guest favourite
Apartment in Sarasota
Sea Club II: Paradise w/ Private Beach Access!
28 Sep – 5 Oct
₹10,115 per night
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Sarasota
Siesta Key Fully-Renovated Unit 5 min to the beach
1–8 Sep
₹8,069 per night
5.0 out of 5 average rating, 22 reviews
Guest favourite
Guest suite in Sarasota
Mid-Century Modern Beach Getaway
19–26 Oct
₹8,219 per night
4.98 out of 5 average rating, 99 reviews
Guest favourite
Flat in Siesta key
Siesta Key Bungalow - Pineapple, Queen unit!
21–28 Aug
₹7,809 per night
4.88 out of 5 average rating, 34 reviews

Quick stats about holiday rentals in Siesta Key

Total rentals

1.6T properties

Rentals with dedicated workspaces

680 properties have a dedicated workspace

Rentals with a pool

1.2T properties have a pool

Pet-friendly rentals

340 properties allow pets

Family-friendly rentals

1.3T properties are a good fit for families

Total number of reviews

28T reviews

Destinations to explore

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