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 Indian Rocks Beach
4.96 out of 5 average rating, 293 reviewsPrivate Heated pool/spa home!
26 Mar – 2 Apr
Cottage in Clearwater
4.77 out of 5 average rating, 123 reviewsCorner Cottage Sleeps 5, Steps to Beach, Pets OK.
19 – 26 Oct
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 63 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
19 – 26 Nov
Cottage in Bradenton
4.95 out of 5 average rating, 82 reviewsCoastal Cottage w/ Pool & Hot Tub
28 Oct – 4 Nov
Cottage in Palm Harbor
4.84 out of 5 average rating, 49 reviewsHappy Camper Cottage | Cozy Oasis with Hot Tub
24 – 31 Jan
Cottage in Treasure Island
5.0 out of 5 average rating, 28 reviewsCasa Sunset by Agua Salá
9 – 16 Sept
Cottage in Largo
4.95 out of 5 average rating, 59 reviewsHidden Oasis #1, just a few minutes to the beaches
7 – 14 Jan
Cottage in Largo
5.0 out of 5 average rating, 18 reviewsFamily FUN~Pool, GameRoom+Bikes, Near Beach/Trail
1 – 8 Aug
Pet-friendly cottage rentals
Cottage in Siesta Key
4.89 out of 5 average rating, 143 reviewsSiesta Key Cozy Cottage across from the beach!
15 – 22 Aug
Cottage in Dunedin
4.96 out of 5 average rating, 304 reviewsWalk to Downtown & Waterfront- Barefoot Parrot 1
16 – 23 Sept
Cottage in Sarasota
4.97 out of 5 average rating, 128 reviewsTropical Oasis SRQ.
25 Aug – 1 Sept
Cottage in Gulfport
4.96 out of 5 average rating, 135 reviewsThe Pelicans Roost / Gulfport
12 – 19 Aug
Cottage in Gulfport
4.99 out of 5 average rating, 257 reviewsGulfport Art District - One Block From Beach!
1 – 8 Oct
Cottage in Tampa
4.99 out of 5 average rating, 140 reviewsBay Lake Cottage
11 – 18 Dec
Cottage in Indian Rocks Beach
4.99 out of 5 average rating, 155 reviewsCottage w/ Private Patio | 3 Min Walk to the Beach
28 July – 4 Aug
Cottage in Tampa
4.97 out of 5 average rating, 265 reviewsHistoric Heights Hideaway *LOW FEES*
18 – 25 Nov
Private cottage rentals
Cottage in Sarasota
4.94 out of 5 average rating, 138 reviewsSea-esta Cottage-cheerful 2bd/1ba w/ free parking
18 – 25 Nov
Cottage in Bradenton Beach
4.9 out of 5 average rating, 170 reviewsOhana Gulfside C Historic 1 Bed - 250 ft. to Beach
21 – 28 Dec
Cottage in Treasure Island
4.91 out of 5 average rating, 114 reviewsHistoric Holly House on Treasure Island
25 Sept – 2 Oct
Cottage in Indian Shores
4.86 out of 5 average rating, 161 reviews*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*
24 Sept – 1 Oct
Cottage in Sarasota
4.83 out of 5 average rating, 150 reviewsCharming Beach Cottage
9 – 16 Nov
Cottage in Madeira Beach
4.96 out of 5 average rating, 134 reviewsBEACHFRONT FAIRWINDS Cottage Lower
13 – 20 Sept
Cottage in Holmes Beach
5.0 out of 5 average rating, 26 reviewsOleander Villa by Beach Boutique Rentals
9 – 16 Oct
Cottage in Cortez
4.82 out of 5 average rating, 94 reviewsTy's Canal Cottage
8 – 15 Jan
Destinations to explore
- St Petersburg Accommodation & holiday rentals
- Sarasota Holiday rentals
- Tampa Holiday rentals
- Key West Holiday rentals
- Naples Accommodation & holiday rentals
- Miami Holiday rentals
- Miami Beach Accommodation & 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
- Beach condo rentals Anna Maria Island
- Family-friendly rentals Anna Maria Island
- Townhouse rentals Anna Maria Island
- Wheelchair accessible rentals Anna Maria Island
- Beach house rentals Anna Maria Island
- Pet-friendly rentals Anna Maria Island
- Rentals with a kayak Anna Maria Island
- Monthly Rentals Anna Maria Island
- Rentals with a hot tub Anna Maria Island
- Waterfront rentals Anna Maria Island
- Villa rentals Anna Maria Island
- Rentals with a washing machine and dryer Anna Maria Island
- Apartment rentals Anna Maria Island
- Kid-friendly rentals Anna Maria Island
- Rentals with a fireplace Anna Maria Island
- Rentals with a fire pit Anna Maria Island
- Fitness-friendly rentals Anna Maria Island
- Rentals with an EV charger Anna Maria Island
- Rentals with lake access Anna Maria Island
- Beachfront rentals Anna Maria Island
- Rentals with outdoor seating Anna Maria Island
- Rentals with a patio Anna Maria Island
- Rentals with a sauna Anna Maria Island
- Condo rentals Anna Maria Island
- Rentals with pools Anna Maria Island
- House rentals Anna Maria Island
- Rentals with beach access 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