House holiday rentals in Siesta Key
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Top-rated house rentals in Siesta Key
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Siesta Key
House rentals with a pool
Home in Sarasota
4.97 out of 5 average rating, 206 reviewsYour private retreat near Siesta Key Beach.
6–13 Aug
Home in Siesta Key
4.89 out of 5 average rating, 141 reviewsSiesta Beach House
7–14 Nov
Home in Sarasota
4.97 out of 5 average rating, 109 reviewsGorgeous Home / Heated Pool and Spa
7–14 Nov
Home in Sarasota
4.95 out of 5 average rating, 410 reviewsThe Cottage At Central Park
16–23 Mar
Home in Sarasota
4.87 out of 5 average rating, 132 reviews5 minutes to private Siesta Key Beach + 2 pools
5–12 Apr
Home in Siesta Key
4.91 out of 5 average rating, 122 reviewsSea Club II Garden House
30 Sep – 7 Oct
Home in Siesta Key
4.9 out of 5 average rating, 105 reviewsSiesta Key, FL - Casa Berano
19–26 Oct
Home in Sarasota
4.98 out of 5 average rating, 130 reviewsBeautiful 3 Bd, 2 bth Pool Home Near Siesta Key!
8–15 Jul
Weekly house rentals
Home in Sarasota
5.0 out of 5 average rating, 22 reviewsThe Mango House Beach Cottage
9–16 Aug
Home in Sarasota
5.0 out of 5 average rating, 6 reviewsCute 2 bedroom home close to it all.
26 May – 2 Jun
Home in Sarasota
5.0 out of 5 average rating, 29 reviewsSiesta Key Fully-Renovated Unit 5 min to the beach
24–31 Dec
Home in Sarasota
4.89 out of 5 average rating, 47 reviewsCentrally Located Cozy Home
23–30 Oct
Home in Siesta Key
5.0 out of 5 average rating, 7 reviewsVintage Coastal
21–28 Sep
Home in Siesta Key
5.0 out of 5 average rating, 45 reviewsCoolest House in Siesta Key Village
6–13 Oct
Home in Sarasota
4.93 out of 5 average rating, 54 reviews1 Bed 1 bath 7 mins to the beach
7–14 Jun
Home in Siesta Key
5.0 out of 5 average rating, 22 reviewsBeachfront 180-Degree View, Walk to Village!
8–15 Mar
Private house rentals
Home in Siesta Key
5.0 out of 5 average rating, 20 reviewsIn Village, Steps to Beach, Pool, Ocean-view.
10–17 Dec
Home in Bradenton Beach
5.0 out of 5 average rating, 10 reviewsNew! Sunset Beach View/Trolley/Bridge Street!
21–28 Sep
Home in Anna Maria
4.96 out of 5 average rating, 51 reviewsSteps to the Beach! Pool/spa! Golf Cart Included!!
10–17 Dec
Home in Siesta Key
5.0 out of 5 average rating, 14 reviewsParadise In Siesta!
4–11 Apr
Home in Sarasota
5.0 out of 5 average rating, 6 reviewsCozy Heaven Studio III
3–10 Oct
Home in Sarasota
4.96 out of 5 average rating, 45 reviewsSandy Feet Retreat- Cozy Bungalow & Outdoor living
10–17 Oct
Home in Sarasota
4.98 out of 5 average rating, 62 reviewsQuaint Cottage,150 steps away from Crescent Beach!
12–19 Nov
Home in Sarasota
4.98 out of 5 average rating, 58 reviewsCheerful cottage, fenced private patio, near beach
2–9 Nov
Quick stats about house rentals in Siesta Key
Total rentals
410 properties
Rentals with dedicated workspaces
270 properties have a dedicated workspace
Rentals with a pool
290 properties have a pool
Pet-friendly rentals
190 properties allow pets
Family-friendly rentals
370 properties are a good fit for families
Total number of reviews
6.1K reviews
Destinations to explore
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