Cottage holiday rentals in Siesta Key
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Top-rated cottage rentals in Siesta Key
Guests agree: these cottages 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 cottage rentals in Siesta Key
Cottage rentals with a hot tub
Cottage in Sarasota
4.82 out of 5 average rating, 34 reviewsSiesta Key Cottages Crescent 1C Beach/Pool/Hot Tub
4–11 Oct
Cottage in Siesta Key
4.91 out of 5 average rating, 46 reviewsCozy Cottage 1 block from Beach
2–9 Feb
Cottage in Sarasota
4.96 out of 5 average rating, 23 reviewsCharming Coastal Oasis 2 Bed/2 Bath Cottage
29 Sep – 6 Oct
Cottage in Holmes Beach
4.91 out of 5 average rating, 45 reviewsKiwi Cottage *Heated Pool+Spa+ walk to the Beach!
15–22 Mar
Cottage in Bradenton
4.95 out of 5 average rating, 82 reviewsCoastal Cottage w/ Pool & Hot Tub
28 Oct – 4 Nov
Cottage in Treasure Island
5.0 out of 5 average rating, 28 reviewsCasa Sunset by Agua Salá
9–16 Sep
Cottage in Holmes Beach
Yacht Rock Ranch
14–21 Dec
Cottage in Bradenton
4.87 out of 5 average rating, 31 reviewsShangri-Lodge Cabin on 3 Acres
26 Feb – 5 Mar
Pet-friendly cottage rentals
Cottage in Gulfport
4.96 out of 5 average rating, 135 reviewsThe Pelicans Roost / Gulfport
12–19 Aug
Cottage in Gulfport
4.99 out of 5 average rating, 257 reviewsGulfport Art District - One Block From Beach!
1–8 Oct
Cottage in Englewood
4.96 out of 5 average rating, 138 reviewsFamily-Friendly Beach Cottage Manasota Key
19–26 Oct
Cottage in Saint Pete Beach
4.86 out of 5 average rating, 155 reviewsSunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes
9–16 Dec
Cottage in Bradenton Beach
4.86 out of 5 average rating, 123 reviewsAMI Beach Shack
2–9 Dec
Cottage in Sarasota
4.81 out of 5 average rating, 154 reviewsDog friendly Cottage
23–30 Jul
Cottage in Sarasota
5.0 out of 5 average rating, 23 reviewsCozy Cottage near Siesta Key Beach
8–15 Oct
Cottage in Siesta Key
4.83 out of 5 average rating, 41 reviewsAwesome spot on Siesta Key - Walk to Everything!
7–14 Sep
Private cottage rentals
Cottage in Treasure Island
4.97 out of 5 average rating, 150 reviewsPeacock Beach Cabana beach in 100 steps
29 Jul – 5 Aug
Cottage in Sarasota
4.84 out of 5 average rating, 154 reviewsHeated Pool! Beach! Drift Inn Unit B Siesta Key!
14–21 Apr
Cottage in Bradenton Beach
4.91 out of 5 average rating, 183 reviewsEbb Tide @ Tides Inn
21–28 Sep
Cottage in Gulfport
4.95 out of 5 average rating, 235 reviewsGulfport Cottage STEPS to Beach & Restaurants
23–30 Jun
Cottage in Sarasota
4.87 out of 5 average rating, 131 reviewsCharming Lido Cottage
22–29 Sep
Cottage in Bradenton Beach
4.91 out of 5 average rating, 129 reviewsHistoric Beach Cottage with private garden
12–19 Oct
Cottage in Siesta Key
4.94 out of 5 average rating, 67 reviewsSurf Shack- Walk to Village/Boat Dock Included
3–10 Nov
Cottage in Osprey
4.96 out of 5 average rating, 23 reviewsMattie’s Cottage by the Bay
16–23 Jul
Quick stats about cottage rentals in Siesta Key
Total rentals
20 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
2K reviews
Nightly prices starting at
€ 140 before taxes and fees
Destinations to explore
- Sarasota Holiday rentals
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