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 Clearwater
4.77 out of 5 average rating, 169 reviewsTiki Cottage Sleeps 6, Pets OK, Steps to Beach
Cottage in Safety Harbor
4.96 out of 5 average rating, 160 reviewsHarbor Oasis with Hot Tub
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 298 reviewsPrivate Heated pool/spa home!
Cottage in Holmes Beach
4.91 out of 5 average rating, 46 reviewsKiwi Cottage *Heated Pool+Spa+ walk to the Beach!
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 67 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
Cottage in Palm Harbor
4.79 out of 5 average rating, 58 reviewsHappy Camper Cottage | Cozy Oasis with Hot Tub
Cottage in Largo
4.95 out of 5 average rating, 60 reviewsHidden Oasis #1, just a few minutes to the beaches
Cottage in Indian Rocks Beach
4.83 out of 5 average rating, 64 reviewsTurtle Nest Cottage
Pet-friendly cottage rentals
Cottage in Bradenton Beach
4.86 out of 5 average rating, 123 reviewsAMI Beach Shack
Cottage in Dunedin
4.97 out of 5 average rating, 270 reviewsWalk to Downtown & Waterfront- Barefoot Parrot 3
Cottage in Tampa
4.99 out of 5 average rating, 145 reviewsBay Lake Cottage
Cottage in Siesta Key
4.89 out of 5 average rating, 145 reviewsSiesta Key Cozy Cottage across from the beach!
Cottage in Gulfport
4.99 out of 5 average rating, 260 reviewsGulfport Art District - One Block From Beach!
Cottage in Sarasota
4.97 out of 5 average rating, 129 reviewsTropical Oasis SRQ.
Cottage in St. Pete Beach
4.79 out of 5 average rating, 245 reviewsSunny PaG Island rental w/bikes-just steps2beach
Cottage in Gulfport
4.96 out of 5 average rating, 137 reviewsThe Pelicans Roost / Gulfport
Private cottage rentals
Cottage in Treasure Island
4.97 out of 5 average rating, 152 reviewsPeacock Beach Cabana beach in 100 steps
Cottage in Bradenton Beach
4.9 out of 5 average rating, 171 reviewsOhana Gulfside C Historic 1 Bed - 250 ft. to Beach
Cottage in Indian Shores
4.86 out of 5 average rating, 162 reviews*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*
Cottage in Treasure Island
4.89 out of 5 average rating, 121 reviewsHistoric Holly House on Treasure Island
Cottage in Sarasota
4.83 out of 5 average rating, 151 reviewsCharming Beach Cottage
Cottage in St. Petersburg
4.92 out of 5 average rating, 125 reviewsPrivate Guesthouse- walk to downtown St. Pete!
Cottage in Madeira Beach
4.79 out of 5 average rating, 165 reviewsQuaint Madeira Beach Cottage with Heated Pool
Cottage in Bradenton Beach
4.91 out of 5 average rating, 184 reviewsEbb Tide @ Tides Inn
Destinations to explore
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- Waterfront rentals Anna Maria Island
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