Cottage vacation 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.
Vacation 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
4.96 out of 5 average rating, 155 reviewsHarbor Oasis with Hot Tub
Sep 28 – Oct 5
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 292 reviewsPrivate Heated pool/spa home!
Sep 12 – 19
Cottage in Clearwater
4.76 out of 5 average rating, 164 reviewsTiki Cottage Sleeps 6, Pets OK, Steps to Beach
Oct 8 – 15
Cottage in Holmes Beach
4.91 out of 5 average rating, 44 reviewsKiwi Cottage *Heated Pool+Spa+ walk to the Beach!
Nov 9 – 16
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 61 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
Mar 3 – 10
Cottage in Siesta Key
4.91 out of 5 average rating, 46 reviewsCozy Cottage 1 block from Beach
Aug 14 – 21
Cottage in Bradenton
4.95 out of 5 average rating, 81 reviewsCoastal Cottage w/ Pool & Hot Tub
Dec 12 – 19
Cottage in Largo
4.95 out of 5 average rating, 58 reviewsHidden Oasis #1, just a few minutes to the beaches
Oct 7 – 14
Pet-friendly cottage rentals
Cottage in Siesta Key
4.89 out of 5 average rating, 140 reviewsSiesta Key Cozy Cottage across from the beach!
Jul 24 – 31
Cottage in Tampa
4.99 out of 5 average rating, 139 reviewsBay Lake Cottage
Oct 18 – 25
Cottage in Bradenton Beach
4.86 out of 5 average rating, 123 reviewsAMI Beach Shack
Dec 11 – 18
Cottage in Saint Pete Beach
4.86 out of 5 average rating, 154 reviewsSunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes
Nov 1 – 8
Cottage in Dunedin
4.97 out of 5 average rating, 259 reviewsWalk to Downtown & Waterfront- Barefoot Parrot 3
Aug 6 – 13
Cottage in Sarasota
4.97 out of 5 average rating, 127 reviewsTropical Oasis SRQ.
Jun 22 – 29
Cottage in Gulfport
4.99 out of 5 average rating, 256 reviewsGulfport Art District - One Block From Beach!
Aug 23 – 30
Cottage in Indian Rocks Beach
4.99 out of 5 average rating, 155 reviewsCottage w/ Private Patio | 3 Min Walk to the Beach
Jul 19 – 26
Private cottage rentals
Cottage in Siesta Key
4.88 out of 5 average rating, 214 reviewsSiesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Dec 2 – 9
Cottage in Largo
4.94 out of 5 average rating, 124 reviewsFall special 3rd night free! “The Sweet”
Mar 4 – 11
Cottage in Indian Shores
4.86 out of 5 average rating, 159 reviews*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*
Jun 10 – 17
Cottage in Madeira Beach
4.96 out of 5 average rating, 134 reviewsBEACHFRONT FAIRWINDS Cottage Lower
Nov 21 – 28
Cottage in Dunedin
5.0 out of 5 average rating, 225 reviewsDowntown Dunedin Historic Orange Blossom Cottage 1
Dec 29 – Jan 5
Cottage in Treasure Island
4.91 out of 5 average rating, 113 reviewsHistoric Holly House on Treasure Island
Mar 1 – 8
Cottage in Cortez
4.82 out of 5 average rating, 94 reviewsTy's Canal Cottage
Jun 27 – Jul 4
Cottage in Holmes Beach
5.0 out of 5 average rating, 26 reviewsSailfish Gulf Suites #4, Garden Views, Steps from
Sep 14 – 21
Destinations to explore
- St Petersburg Vacation rentals
- Sarasota Vacation rentals
- Tampa Vacation rentals
- Key West Vacation rentals
- Naples Vacation rentals
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Boca Raton Vacation rentals
- West Palm Beach Vacation rentals
- Kissimmee Vacation rentals
- Orlando Vacation rentals
- Cottage rentals Florida
- Cottage rentals Florida
- Fitness-friendly rentals Anna Maria Island
- Pet-friendly rentals Anna Maria Island
- Rentals with lake access Anna Maria Island
- Beach condo rentals Anna Maria Island
- Villa rentals Anna Maria Island
- Wheelchair accessible rentals Anna Maria Island
- Rentals with a washer and dryer Anna Maria Island
- Monthly Rentals Anna Maria Island
- Rentals with a hot tub Anna Maria Island
- Rentals with beach access Anna Maria Island
- Rentals with a fireplace Anna Maria Island
- Rentals with a kayak Anna Maria Island
- Rentals with a patio Anna Maria Island
- Rentals with a fire pit Anna Maria Island
- Rentals with pools Anna Maria Island
- Beachfront rentals Anna Maria Island
- Apartment rentals Anna Maria Island
- Rentals with outdoor seating Anna Maria Island
- Beach house rentals Anna Maria Island
- Condo rentals Anna Maria Island
- Townhouse rentals Anna Maria Island
- Family-friendly rentals Anna Maria Island
- Rentals with an EV charger Anna Maria Island
- Rentals with a sauna Anna Maria Island
- Waterfront rentals Anna Maria Island
- Kid-friendly rentals Anna Maria Island
- House 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