Cottage vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Siesta Key cottage rentals
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
Sep. 29 – Oct. 6
Cottage in Bradenton
4.95 out of 5 average rating, 82 reviewsCoastal Cottage w/ Pool & Hot Tub
Aug. 21 – 28
Cottage in Treasure Island
5.0 out of 5 average rating, 28 reviewsCasa Sunset by Agua Salá
Sep. 9 – 16
Cottage in Bradenton
4.87 out of 5 average rating, 31 reviewsShangri-Lodge Cabin on 3 Acres
Feb. 26 – Mar. 5
Cottage in Sarasota
4.67 out of 5 average rating, 3 reviewsCozy Cottage at Sun Outdoors Sarasota
Nov. 20 – 27
Cottage in Port Charlotte
5.0 out of 5 average rating, 3 reviewsCute Port Charlotte Home w/ Resort Amenities!
Oct. 20 – 27
Cottage in Sarasota
Sun Outdoors Sarasota-1 Bedroom Cottage w/Loft
Jul. 30 – Aug. 6
Cottage in Sarasota
Sunny Landings *Florida*
Feb. 19 – 26
Pet-friendly cottage rentals
Cottage in Gulfport
4.96 out of 5 average rating, 135 reviewsThe Pelicans Roost / Gulfport
Aug. 12 – 19
Cottage in Gulfport
4.99 out of 5 average rating, 257 reviewsGulfport Art District - One Block From Beach!
Oct. 1 – 8
Cottage in Englewood
4.96 out of 5 average rating, 138 reviewsFamily-Friendly Beach Cottage Manasota Key
Oct. 19 – 26
Cottage in Saint Pete Beach
4.86 out of 5 average rating, 155 reviewsSunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes
Dec. 9 – 16
Cottage in Bradenton Beach
4.86 out of 5 average rating, 123 reviewsAMI Beach Shack
Dec. 2 – 9
Cottage in Sarasota
4.81 out of 5 average rating, 154 reviewsDog friendly Cottage
Jul. 23 – 30
Cottage in Sarasota
5.0 out of 5 average rating, 23 reviewsCozy Cottage near Siesta Key Beach
Oct. 8 – 15
Cottage in Siesta Key
4.83 out of 5 average rating, 41 reviewsAwesome spot on Siesta Key - Walk to Everything!
Sep. 7 – 14
Private cottage rentals
Cottage in Sarasota
4.84 out of 5 average rating, 154 reviewsHeated Pool! Beach! Drift Inn Unit B Siesta Key!
Apr. 14 – 21
Cottage in Bradenton Beach
4.91 out of 5 average rating, 183 reviewsEbb Tide @ Tides Inn
Sep. 21 – 28
Cottage in Gulfport
4.95 out of 5 average rating, 235 reviewsGulfport Cottage STEPS to Beach & Restaurants
Jun. 23 – 30
Cottage in Sarasota
4.87 out of 5 average rating, 131 reviewsCharming Lido Cottage
Sep. 22 – 29
Cottage in Bradenton Beach
4.91 out of 5 average rating, 129 reviewsHistoric Beach Cottage with private garden
Oct. 12 – 19
Cottage in Siesta Key
4.94 out of 5 average rating, 67 reviewsSurf Shack- Walk to Village/Boat Dock Included
Nov. 3 – 10
Cottage in Osprey
4.96 out of 5 average rating, 23 reviewsMattie’s Cottage by the Bay
Jul. 16 – 23
Cottage in Sarasota
5.0 out of 5 average rating, 13 reviewsBamboo Cottage, minutes from the beach.
Oct. 6 – 13
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
$205 CAD before taxes and fees
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