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 cottage rentals in Anna Maria Island
Cottage rentals with a hot tub
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 300 reviewsPrivate Heated pool/spa home!
Cottage in Safety Harbor
4.96 out of 5 average rating, 162 reviewsHarbor Oasis with Hot Tub
Cottage in Clearwater
4.77 out of 5 average rating, 169 reviewsTiki Cottage Sleeps 6, Pets OK, Steps to Beach
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 72 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
Cottage in Holmes Beach
4.91 out of 5 average rating, 47 reviewsKiwi Cottage *Heated Pool+Spa+ walk to the Beach!
Cottage in Indian Rocks Beach
4.83 out of 5 average rating, 64 reviewsTurtle Nest Cottage
Cottage in Treasure Island
5.0 out of 5 average rating, 30 reviewsCasa Sunset by Agua Salá
Cottage in Palmetto
5.0 out of 5 average rating, 21 reviewsCharming Home w/ Hot Tub, 20 min to Beach + Garden
Pet-friendly cottage rentals
Cottage in Dunedin
4.97 out of 5 average rating, 273 reviewsWalk to Downtown & Waterfront- Barefoot Parrot 3
Cottage in Bradenton Beach
4.86 out of 5 average rating, 124 reviewsAMI Beach Shack
Cottage in Gulfport
4.99 out of 5 average rating, 260 reviewsGulfport Art District - One Block From Beach!
Cottage in Tampa
4.99 out of 5 average rating, 147 reviewsBay Lake Cottage
Cottage in Siesta Key
4.89 out of 5 average rating, 148 reviewsSiesta Key Cozy Cottage across from the beach!
Cottage in St. Petersburg
4.95 out of 5 average rating, 101 reviewsArtsy guest house; near downtown w/ private patio
Cottage in Gulfport
4.96 out of 5 average rating, 138 reviewsThe Pelicans Roost / Gulfport
Cottage in Tampa
4.96 out of 5 average rating, 275 reviewsHistoric Heights Hideaway *LOW FEES*
Private cottage rentals
Cottage in Dunedin
4.95 out of 5 average rating, 101 reviewsBeachBunkies Cottage 2. Four miles to the beach!
Cottage in Madeira Beach
4.78 out of 5 average rating, 167 reviewsQuaint Madeira Beach Cottage with Heated Pool
Cottage in Bradenton Beach
4.91 out of 5 average rating, 185 reviewsEbb Tide @ Tides Inn
Cottage in Treasure Island
4.97 out of 5 average rating, 156 reviewsPeacock Beach Cabana beach in 100 steps
Cottage in St. Petersburg
4.92 out of 5 average rating, 126 reviewsPrivate Guesthouse- walk to downtown St. Pete!
Cottage in Indian Shores
4.86 out of 5 average rating, 163 reviews*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*
Cottage in Sarasota
4.83 out of 5 average rating, 152 reviewsCharming Beach Cottage
Cottage in Cortez
4.83 out of 5 average rating, 98 reviewsTy's Canal Cottage
Destinations to explore
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- Rentals with a kayak Anna Maria Island
- Villa rentals Anna Maria Island
- Rentals with a sauna Anna Maria Island
- Rentals with beach access Anna Maria Island
- Rentals with pools Anna Maria Island
- Flat rentals Anna Maria Island
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- Beach house rentals Anna Maria Island
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- Rentals with a firepit Anna Maria Island
- Apartment rentals Anna Maria Island
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- Rentals with a fireplace Anna Maria Island
- Family-friendly rentals Anna Maria Island
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- Monthly Rentals Anna Maria Island
- Rentals with a hot tub Anna Maria Island
- Rentals with an EV charger Anna Maria Island
- Beachfront rentals Anna Maria Island
- Pet-friendly rentals Anna Maria Island
- Beach apartment rentals Anna Maria Island
- Rentals with a washing machine and dryer Anna Maria Island
- House rentals Anna Maria Island
- Rentals with a patio Anna Maria Island
- Rentals with lake access Anna Maria Island
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