Cottage holiday rentals in Anna Maria Island
Find and book unique cottages on Airbnb
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 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 Clearwater
4.76 out of 5 average rating, 124 reviewsCorner Cottage Sleeps 5, Steps to Beach, Pets OK.
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 68 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
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
4.83 out of 5 average rating, 64 reviewsTurtle Nest Cottage
Cottage in Palm Harbor
4.8 out of 5 average rating, 60 reviewsHappy Camper Cottage | Cozy Oasis with Hot Tub
Cottage in Siesta Key
4.92 out of 5 average rating, 48 reviewsCozy Cottage 1 block from Beach
Pet-friendly cottage rentals
Cottage in Palm Harbor
4.78 out of 5 average rating, 168 reviewsCrystal Beach Cottage #1
Cottage in Tampa
4.99 out of 5 average rating, 146 reviewsBay Lake Cottage
Cottage in Siesta Key
4.89 out of 5 average rating, 146 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
4.99 out of 5 average rating, 260 reviewsGulfport Art District - One Block From Beach!
Cottage in Bradenton Beach
4.86 out of 5 average rating, 124 reviewsAMI Beach Shack
Cottage in Dunedin
4.99 out of 5 average rating, 274 reviewsWalk to Downtown & Waterfront - Barefoot Parrot 2
Cottage in Indian Rocks Beach
4.99 out of 5 average rating, 156 reviewsCottage w/ Private Patio | 3 Min Walk to the Beach
Private cottage rentals
Cottage in Treasure Island
4.97 out of 5 average rating, 153 reviewsPeacock Beach Cabana beach in 100 steps
Cottage in Indian Shores
4.86 out of 5 average rating, 162 reviews*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*
Cottage in Bradenton Beach
4.91 out of 5 average rating, 184 reviewsEbb Tide @ Tides Inn
Cottage in Sarasota
4.92 out of 5 average rating, 154 reviewsCasa El Sueño - 8 min to Siesta Key - Intracoastal
Cottage in St. Petersburg
4.92 out of 5 average rating, 125 reviewsPrivate Guesthouse- walk to downtown St. Pete!
Cottage in Madeira Beach
4.96 out of 5 average rating, 136 reviewsBEACHFRONT FAIRWINDS Cottage Lower
Cottage in Siesta Key
4.88 out of 5 average rating, 219 reviewsSiesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Cottage in Cortez
4.82 out of 5 average rating, 96 reviewsTy's Canal Cottage
Destinations to explore
- St Petersburg Holiday rentals
- Sarasota Holiday rentals
- Tampa Holiday rentals
- Key West Holiday rentals
- Naples Holiday rentals
- Miami Holiday rentals
- Miami Beach Holiday rentals
- Boca Raton Holiday rentals
- Fort Lauderdale Holiday rentals
- West Palm Beach Holiday rentals
- Kissimmee Holiday rentals
- Orlando Holiday rentals
- Cottage rentals Florida
- Cottage rentals Florida
- Apartment rentals Anna Maria Island
- Rentals with beach access Anna Maria Island
- Rentals with outdoor seating Anna Maria Island
- Rentals with pools Anna Maria Island
- Rentals with a kayak Anna Maria Island
- Waterfront rentals Anna Maria Island
- Rentals with a firepit Anna Maria Island
- Beach house rentals Anna Maria Island
- Villa rentals Anna Maria Island
- Rentals with lake access Anna Maria Island
- Flat rentals Anna Maria Island
- Rentals with a sauna Anna Maria Island
- Rentals with a fireplace Anna Maria Island
- House rentals Anna Maria Island
- Townhouse rentals Anna Maria Island
- Family-friendly rentals Anna Maria Island
- Beach apartment rentals Anna Maria Island
- Family-friendly rentals Anna Maria Island
- Rentals with a washing machine and dryer Anna Maria Island
- Fitness-friendly rentals Anna Maria Island
- Rentals with an EV charger Anna Maria Island
- Wheelchair-accessible rentals Anna Maria Island
- Rentals with a hot tub Anna Maria Island
- Luxury rentals Anna Maria Island
- Resort rentals Anna Maria Island
- Rentals with a patio Anna Maria Island
- Monthly Rentals Anna Maria Island
- Beachfront rentals Anna Maria Island
- Pet-friendly rentals Anna Maria Island
- Cottage rentals Kissimmee
- Cottage rentals Tampa
- Cottage rentals Manatee County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom