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 Anna Maria Island cottage rentals
Cottage rentals with a hot tub
Cottage in Safety Harbor
Harbor Oasis with Hot Tub
Cottage in Indian Rocks Beach
Private Heated pool/spa home!
Cottage in Clearwater
Tiki Cottage Sleeps 6, Pets OK, Steps to Beach
Cottage in Indian Rocks Beach
NEW! Updated Stilt Home STEPS TO BEACH!
Cottage in Holmes Beach
Kiwi Cottage *Heated Pool+Spa+ walk to the Beach!
Cottage in Indian Rocks Beach
Turtle Nest Cottage
Cottage in Palmetto
Charming Home w/ Hot Tub, 20 min to Beach + Garden
Cottage in Treasure Island
Casa Sunset by Agua Salá
Pet-friendly cottage rentals
Cottage in Dunedin
Walk to Downtown & Waterfront- Barefoot Parrot 1
Cottage in Gulfport
Gulfport Art District - One Block From Beach!
Cottage in Siesta Key
Siesta Key Cozy Cottage across from the beach!
Cottage in Tampa
Bay Lake Cottage
Cottage in St. Petersburg
Artsy guest house; near downtown w/ private patio
Cottage in Gulfport
The Pelicans Roost / Gulfport
Cottage in Indian Rocks Beach
Vintage Florida Beach Cottage B
Cottage in St. Petersburg
Homey Cottage Close To It All
Private cottage rentals
Cottage in Treasure Island
Peacock Beach Cabana beach in 100 steps
Cottage in Madeira Beach
Flipper's @ Mad Beach Cottage
Cottage in Indian Shores
*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*
Cottage in Sarasota
Charming Beach Cottage
Cottage in Siesta Key
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Cottage in Anna Maria
Snail's Pace: On Canal, Kayaks & Dog Friendly
Cottage in Holmes Beach
Oleander Villa by Beach Boutique Rentals
Cottage in Holmes Beach
Ann’s cottage close to the beach.
Destinations to explore
- St Petersburg Accommodation & holiday rentals
- Sarasota Holiday rentals
- Tampa Holiday rentals
- Key West Holiday rentals
- Naples Accommodation & holiday rentals
- Miami Beach Accommodation & holiday rentals
- Miami Holiday rentals
- Fort Lauderdale Accommodation & holiday rentals
- Boca Raton Accommodation & holiday rentals
- West Palm Beach Holiday rentals
- Kissimmee Holiday rentals
- Orlando Holiday rentals
- Cottage rentals Florida
- Cottage rentals Florida
- Wheelchair accessible rentals Anna Maria Island
- Rentals with a fire pit Anna Maria Island
- Apartment rentals Anna Maria Island
- Rentals with pools Anna Maria Island
- Resort rentals Anna Maria Island
- Kid-friendly rentals Anna Maria Island
- Villa rentals Anna Maria Island
- Rentals with a fireplace Anna Maria Island
- Rentals with a hot tub Anna Maria Island
- Condo rentals Anna Maria Island
- Rentals with beach access Anna Maria Island
- Rentals with lake access Anna Maria Island
- Townhouse rentals Anna Maria Island
- Luxury rentals Anna Maria Island
- Beach house rentals Anna Maria Island
- Rentals with a sauna Anna Maria Island
- Family-friendly rentals Anna Maria Island
- Rentals with an EV charger Anna Maria Island
- Beachfront rentals Anna Maria Island
- Pet-friendly rentals Anna Maria Island
- Rentals with a patio Anna Maria Island
- Waterfront rentals Anna Maria Island
- Monthly Rentals Anna Maria Island
- House rentals Anna Maria Island
- Rentals with a washing machine and dryer Anna Maria Island
- Fitness-friendly rentals Anna Maria Island
- Beach condo rentals Anna Maria Island
- Rentals with outdoor seating Anna Maria Island
- Rentals with a kayak 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