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 Siesta Key
4.91 out of 5 average rating, 46 reviewsCozy Cottage 1 block from Beach
2–9 Feb
Cottage in Sarasota
4.82 out of 5 average rating, 34 reviewsSiesta Key Cottages Crescent 1C Beach/Pool/Hot Tub
18–25 Nov
Cottage in Sarasota
4.96 out of 5 average rating, 23 reviewsCharming Coastal Oasis 2 Bed/2 Bath Cottage
10–17 Nov
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 Holmes Beach
Rock Ranch Yacht
14–21 Dec
Cottage in Bradenton
4.87 out of 5 average rating, 31 reviewsShangri-Lodge Cabin on 3 Acres
27 Jan – 3 Feb
Cottage in Sarasota
4.67 out of 5 average rating, 3 reviewsCozy Cottage at Sun Outdoors Sarasota
20–27 Nov
Pet-friendly cottage rentals
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, 139 reviewsFamily-Friendly Beach Cottage Manasota Key
22 Feb – 1 Mar
Cottage in Saint Pete Beach
4.86 out of 5 average rating, 155 reviewsSunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes
31 Aug – 7 Sep
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
17–24 Oct
Cottage in Siesta Key
4.83 out of 5 average rating, 41 reviewsAwesome spot on Siesta Key - Walk to Everything!
7–14 Sep
Cottage in Sarasota
4.55 out of 5 average rating, 11 reviewsCharming Bungalow | Close to Beach | 2 Beds
18–25 Oct
Cottage in Sarasota
4.96 out of 5 average rating, 69 reviewsLuxury large cottage-studio/wth kitchen & bathroom
8–15 Jun
Private cottage rentals
Cottage in Bradenton
4.94 out of 5 average rating, 301 reviewsHistoric Private King Bed Suite-Near Beach-D’Town.
1–8 Apr
Cottage in Bradenton Beach
4.91 out of 5 average rating, 183 reviewsEbb Tide @ Tides Inn
22–29 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 Bradenton Beach
4.9 out of 5 average rating, 170 reviewsOhana Gulfside C Historic 1 Bed - 250 ft. to Beach
21–28 Dec
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
2T reviews
Nightly prices starting at
₹12,516 before taxes and fees
Destinations to explore
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