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
4.74 out of 5 average rating, 109 reviewsSiesta Key Cottages Crescent 1B Beach/Pool/Hot Tub
27 Nov – 4 Dec
Cottage in Sarasota
4.96 out of 5 average rating, 23 reviewsCharming Coastal Oasis 2 Bed/2 Bath Cottage
30 Sep – 7 Oct
Cottage in Siesta Key
4.91 out of 5 average rating, 46 reviewsCozy Cottage 1 block from Beach
16–23 Feb
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
4.95 out of 5 average rating, 82 reviewsCoastal Cottage w/ Pool & Hot Tub
25 Apr – 2 May
Cottage in Bradenton
5.0 out of 5 average rating, 4 reviewsCozy Casita Close to Anna Maria Island!
8–15 May
Cottage in Holmes Beach
Yacht Rock Ranch
7–14 Dec
Cottage in Bradenton
4.87 out of 5 average rating, 31 reviewsShangri-Lodge Cabin on 3 Acres
14–21 May
Pet-friendly cottage rentals
Cottage in Englewood
4.96 out of 5 average rating, 139 reviewsFamily-Friendly Beach Cottage Manasota Key
5–12 Sep
Cottage in Gulfport
4.99 out of 5 average rating, 257 reviewsGulfport Art District - One Block From Beach!
24–31 Dec
Cottage in Gulfport
4.96 out of 5 average rating, 135 reviewsThe Pelicans Roost / Gulfport
5–12 Sep
Cottage in Sarasota
4.81 out of 5 average rating, 154 reviewsDog friendly Cottage
19–26 Sep
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
5.0 out of 5 average rating, 23 reviewsCozy Cottage near Siesta Key Beach
25 Oct – 1 Nov
Cottage in Sarasota
4.96 out of 5 average rating, 69 reviewsLuxury large cottage-studio/wth kitchen & bathroom
7–14 Aug
Cottage in Siesta Key
4.94 out of 5 average rating, 68 reviewsSiesta Key Two Bedroom Cottage
24–31 Aug
Private cottage rentals
Cottage in Sarasota
4.83 out of 5 average rating, 108 reviewsWalk to Beach & St. Armands/Private cottage &grill
25 Aug – 1 Sep
Cottage in Gulfport
4.95 out of 5 average rating, 237 reviewsGulfport Cottage STEPS to Beach & Restaurants
29 Jul – 5 Aug
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
11–18 Aug
Cottage in Bradenton Beach
4.9 out of 5 average rating, 170 reviewsOhana Gulfside C Historic 1 Bed - 250 ft. to Beach
3–10 Feb
Cottage in Siesta Key
4.94 out of 5 average rating, 67 reviewsSurf Shack- Walk to Village/Boat Dock Included
27 Jul – 3 Aug
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
€ 140 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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