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