Cottage holiday rentals in Anna Maria Island
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Top-rated cottage rentals in Anna Maria Island
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 Anna Maria Island cottage rentals
Cottage rentals with a hot tub
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 293 reviewsPrivate Heated pool/spa home!
3–10 Mar
Cottage in Safety Harbor
4.96 out of 5 average rating, 157 reviewsHarbor Oasis with Hot Tub
3–10 Apr
Cottage in Clearwater
4.77 out of 5 average rating, 123 reviewsCorner Cottage Sleeps 5, Steps to Beach, Pets OK.
10–17 Aug
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 Indian Rocks Beach
4.97 out of 5 average rating, 63 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
6–13 Jan
Cottage in Bradenton
4.95 out of 5 average rating, 82 reviewsCoastal Cottage w/ Pool & Hot Tub
25 Apr – 2 May
Cottage in Palm Harbor
4.85 out of 5 average rating, 52 reviewsHappy Camper Cottage | Cozy Oasis with Hot Tub
1–8 Dec
Cottage in Bradenton
5.0 out of 5 average rating, 4 reviewsCozy Casita Close to Anna Maria Island!
8–15 May
Pet-friendly cottage rentals
Cottage in Indian Rocks Beach
4.99 out of 5 average rating, 155 reviewsCottage w/ Private Patio | 3 Min Walk to the Beach
9–16 Nov
Cottage in Dunedin
4.97 out of 5 average rating, 264 reviewsWalk to Downtown & Waterfront- Barefoot Parrot 3
1–8 Aug
Cottage in Siesta Key
4.89 out of 5 average rating, 143 reviewsSiesta Key Cozy Cottage across from the beach!
16–23 Aug
Cottage in Sarasota
4.97 out of 5 average rating, 128 reviewsTropical Oasis SRQ.
9–16 Sep
Cottage in Tampa
4.99 out of 5 average rating, 144 reviewsBay Lake Cottage
9–16 Jan
Cottage in Gulfport
4.96 out of 5 average rating, 135 reviewsThe Pelicans Roost / Gulfport
5–12 Sep
Cottage in Tampa
4.97 out of 5 average rating, 267 reviewsHistoric Heights Hideaway *LOW FEES*
13–20 Jul
Cottage in Gulfport
4.99 out of 5 average rating, 257 reviewsGulfport Art District - One Block From Beach!
24–31 Dec
Private cottage rentals
Cottage in Dunedin
4.92 out of 5 average rating, 166 reviewsDowntown Keylime Cottages 3
17–24 Jun
Cottage in Bradenton Beach
4.91 out of 5 average rating, 183 reviewsEbb Tide @ Tides Inn
6–13 Oct
Cottage in Indian Shores
4.86 out of 5 average rating, 161 reviews*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*
20–27 Aug
Cottage in Treasure Island
4.91 out of 5 average rating, 114 reviewsHistoric Holly House on Treasure Island
28 Aug – 4 Sep
Cottage in Sarasota
4.83 out of 5 average rating, 150 reviewsCharming Beach Cottage
13–20 Nov
Cottage in Sarasota
4.92 out of 5 average rating, 152 reviewsCasa El Sueño - 8 min to Siesta Key - Intracoastal
19–26 Jun
Cottage in Dunedin
5.0 out of 5 average rating, 227 reviewsDowntown Dunedin Historic Orange Blossom Cottage 1
12–19 Jul
Cottage in Cortez
4.82 out of 5 average rating, 94 reviewsTy's Canal Cottage
12–19 Nov
Destinations to explore
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