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
4.96 out of 5 average rating, 23 reviewsCharming Coastal Oasis 2 Bed/2 Bath Cottage
21–28 Jun
Cottage in Holmes Beach
4.91 out of 5 average rating, 45 reviewsKiwi Cottage *Heated Pool+Spa+ walk to the Beach!
2–9 Nov
Cottage in Bradenton
5.0 out of 5 average rating, 4 reviewsCozy Casita Close to Anna Maria Island!
7–14 May
Cottage in Bradenton
4.95 out of 5 average rating, 82 reviewsCoastal Cottage w/ Pool & Hot Tub
6–13 Dec
Cottage in Bradenton
4.87 out of 5 average rating, 31 reviewsShangri-Lodge Cabin on 3 Acres
13–20 May
Cottage in Port Charlotte
5.0 out of 5 average rating, 3 reviewsCute Port Charlotte Home w/ Resort Amenities!
24–31 Oct
Cottage in Sarasota
4.67 out of 5 average rating, 3 reviewsCozy Cottage at Sun Outdoors Sarasota
20–27 Nov
Cottage in Venice
New place to stayCottage near Venice Beach
10–17 Jul
Pet-friendly cottage rentals
Cottage in Gulfport
4.99 out of 5 average rating, 257 reviewsGulfport Art District - One Block From Beach!
24–31 Dec
Cottage in Englewood
4.96 out of 5 average rating, 139 reviewsFamily-Friendly Beach Cottage Manasota Key
9–16 Apr
Cottage in Saint Pete Beach
4.86 out of 5 average rating, 155 reviewsSunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes
12–19 Nov
Cottage in Sarasota
4.81 out of 5 average rating, 154 reviewsDog friendly Cottage
15–22 Dec
Cottage in Sarasota
5.0 out of 5 average rating, 23 reviewsCozy Cottage near Siesta Key Beach
16–23 Oct
Cottage in Siesta Key
4.83 out of 5 average rating, 41 reviewsAwesome spot on Siesta Key - Walk to Everything!
15–22 Jul
Cottage in Sarasota
4.96 out of 5 average rating, 69 reviewsLuxury large cottage-studio/wth kitchen & bathroom
7–14 Aug
Cottage in Holmes Beach
5.0 out of 5 average rating, 26 reviewsOleander Villa by Beach Boutique Rentals
9–16 Oct
Private cottage rentals
Cottage in Sarasota
4.83 out of 5 average rating, 108 reviewsWalk to Beach & St. Armands/Private cottage &grill
30 Aug – 6 Sept
Cottage in Bradenton Beach
4.9 out of 5 average rating, 170 reviewsOhana Gulfside C Historic 1 Bed - 250 ft. to Beach
25 Oct – 1 Nov
Cottage in Gulfport
4.95 out of 5 average rating, 235 reviewsGulfport Cottage STEPS to Beach & Restaurants
22–29 Sept
Cottage in Sarasota
4.87 out of 5 average rating, 131 reviewsCharming Lido Cottage
31 Oct – 7 Nov
Cottage in Bradenton Beach
4.91 out of 5 average rating, 129 reviewsHistoric Beach Cottage with private garden
15–22 Oct
Cottage in Bradenton Beach
4.91 out of 5 average rating, 183 reviewsEbb Tide @ Tides Inn
24–31 Aug
Cottage in Siesta Key
4.94 out of 5 average rating, 67 reviewsSurf Shack- Walk to Village/Boat Dock Included
8–15 Nov
Cottage in Osprey
4.96 out of 5 average rating, 23 reviewsMattie’s Cottage by the Bay
28 Jun – 5 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
£120 before taxes and fees
Destinations to explore
- Sarasota Holiday rentals
- Anna Maria Island Holiday rentals
- Tampa Holiday rentals
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- Rentals with a firepit Siesta Key
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