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 Safety Harbor
4.96 out of 5 average rating, 156 reviewsHarbor Oasis with Hot Tub
Jun 5 – 12
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
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 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
Cottage in Anna Maria
4.96 out of 5 average rating, 24 reviewsSnail's Pace: On Canal, Kayaks & Dog Friendly
May 25 – Jun 1
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- Rentals with a washer and dryer Anna Maria Island
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- Rentals with a patio Anna Maria Island
- Rentals with pools Anna Maria Island
- Wheelchair accessible rentals Anna Maria Island
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- Rentals with lake access Anna Maria Island
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