Cottage vacation rentals in Siesta Key
Find and book unique cottages on Airbnb
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 pool
Cottage in Sarasota
4.91 out of 5 average rating, 33 reviewsLa Casita ~ Charming Pool Cottage ~ Tropical Oasis
Oct 21 – 28
Cottage in Sarasota
4.96 out of 5 average rating, 69 reviewsLuxury large cottage-studio/wth kitchen & bathroom
Aug 7 – 14
Cottage in Sarasota
4.95 out of 5 average rating, 39 reviewsSarasota Home with pool in resort community
Oct 12 – 19
Cottage in Bradenton
4.96 out of 5 average rating, 97 reviewsCoastal Style 2BR cottage near Anna Maria Island
Aug 20 – 27
Cottage in Nokomis
5.0 out of 5 average rating, 49 reviewsNew Pool Tropical Waterfront Dock & Optional Boat
Aug 17 – 24
Cottage in Sarasota
5.0 out of 5 average rating, 33 reviewsBee Keepers Cottage
Jun 22 – 29
Cottage in Bradenton
4.85 out of 5 average rating, 59 reviewsCozy! near restaurants, beaches, airport & more
Nov 12 – 19
Cottage in Bradenton
4.96 out of 5 average rating, 71 reviewsPool home on water. Fish from dock! Close to beach
Nov 16 – 23
Beachfront cottage rentals
Cottage in Sarasota
4.83 out of 5 average rating, 108 reviewsWalk to Beach & St. Armands/Private cottage &grill
Aug 30 – Sep 6
Cottage in St Pete Beach
4.98 out of 5 average rating, 158 reviewsPass-a-Grille Historic Cottage Unit 1
Aug 22 – 29
Cottage in Saint Pete Beach
4.86 out of 5 average rating, 155 reviewsSunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes
Nov 12 – 19
Cottage in Siesta Key
4.94 out of 5 average rating, 67 reviewsSurf Shack- Walk to Village/Boat Dock Included
Nov 8 – 15
Cottage in Sarasota
4.82 out of 5 average rating, 82 reviewsThe Best Villa on Siesta Key
Dec 10 – 17
Cottage in Nokomis
4.92 out of 5 average rating, 84 reviewsThe "Turtle Cottage" - a charming beachy retreat.
Nov 24 – Dec 1
Cottage in Holmes Beach
5.0 out of 5 average rating, 26 reviewsOleander Villa by Beach Boutique Rentals
Oct 9 – 16
Cottage in Sarasota
5.0 out of 5 average rating, 18 reviewsLido Key Beach Bungalow with Private Heated Pool!
Dec 16 – 23
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
Jan 18 – 25
Cottage in Sarasota
4.96 out of 5 average rating, 23 reviewsCharming Coastal Oasis 2 Bed/2 Bath Cottage
Jun 21 – 28
Cottage in Siesta Key
4.91 out of 5 average rating, 46 reviewsCozy Cottage 1 block from Beach
Feb 2 – 9
Cottage in Holmes Beach
4.91 out of 5 average rating, 45 reviewsKiwi Cottage *Heated Pool+Spa+ walk to the Beach!
Nov 2 – 9
Cottage in Bradenton
5.0 out of 5 average rating, 4 reviewsCozy Casita Close to Anna Maria Island!
May 7 – 14
Cottage in Bradenton
4.95 out of 5 average rating, 82 reviewsCoastal Cottage w/ Pool & Hot Tub
Dec 6 – 13
Cottage in Holmes Beach
Yacht Rock Ranch
Dec 7 – 14
Cottage in Bradenton
4.87 out of 5 average rating, 31 reviewsShangri-Lodge Cabin on 3 Acres
May 13 – 20
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
$150 before taxes and fees
Destinations to explore
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