Cottage vacation 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.
Vacation 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 Safety Harbor
4.96 out of 5 average rating, 157 reviewsHarbor Oasis with Hot Tub
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 293 reviewsPrivate Heated pool/spa home!
Cottage in Clearwater
4.77 out of 5 average rating, 166 reviewsTiki Cottage Sleeps 6, Pets OK, Steps to Beach
Cottage in Holmes Beach
4.91 out of 5 average rating, 45 reviewsKiwi Cottage *Heated Pool+Spa+ walk to the Beach!
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 63 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
Cottage in Bradenton
4.95 out of 5 average rating, 82 reviewsCoastal Home w/ Pool & Hot Tub
Cottage in Indian Rocks Beach
4.82 out of 5 average rating, 62 reviewsTurtle Nest Cottage
Cottage in Bradenton
5.0 out of 5 average rating, 4 reviewsCozy Casita Close to Anna Maria Island!
Pet-friendly cottage rentals
Cottage in Treasure Island
4.93 out of 5 average rating, 102 reviewsTreasure Island Beach Cottage
Cottage in Indian Rocks Beach
4.99 out of 5 average rating, 155 reviewsCottage w/ Private Patio | 3 Min Walk to the Beach
Cottage in Dunedin
4.97 out of 5 average rating, 264 reviewsWalk to Downtown & Waterfront- Barefoot Parrot 3
Cottage in Siesta Key
4.89 out of 5 average rating, 143 reviewsSiesta Key Cozy Cottage across from the beach!
Cottage in Sarasota
4.97 out of 5 average rating, 128 reviewsTropical Oasis SRQ.
Cottage in Gulfport
4.96 out of 5 average rating, 135 reviewsThe Pelicans Roost / Gulfport
Cottage in Tampa
4.99 out of 5 average rating, 144 reviewsBay Lake Cottage
Cottage in Gulfport
4.99 out of 5 average rating, 257 reviewsGulfport Art District - One Block From Beach!
Private cottage rentals
Cottage in Indian Shores
4.86 out of 5 average rating, 161 reviews*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*
Cottage in Sarasota
4.83 out of 5 average rating, 150 reviewsCharming Beach Cottage
Cottage in Madeira Beach
4.96 out of 5 average rating, 135 reviewsBEACHFRONT FAIRWINDS Cottage Lower
Cottage in Sarasota
4.92 out of 5 average rating, 152 reviewsCasa El Sueño - 8 min to Siesta Key - Intracoastal
Cottage in Siesta Key
4.84 out of 5 average rating, 132 reviewsAdorable Cozy Silver Sands Cottage on Siesta Key!!
Cottage in Cortez
4.82 out of 5 average rating, 94 reviewsTy's Canal Cottage
Cottage in Holmes Beach
5.0 out of 5 average rating, 26 reviewsOleander Villa by Beach Boutique Rentals
Cottage in Holmes Beach
5.0 out of 5 average rating, 26 reviewsSailfish Gulf Suites #4, Garden Views, Steps from
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