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
Jul 30 – Aug 6
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 293 reviewsPrivate Heated pool/spa home!
Feb 23 – Mar 2
Cottage in Clearwater
4.77 out of 5 average rating, 129 reviewsPink Gulfside Cottage, Steps to Beach, Pets OK
Nov 16 – 23
Cottage in Holmes Beach
4.91 out of 5 average rating, 45 reviewsKiwi Cottage *Heated Pool+Spa+ walk to the Beach!
Sep 21 – 28
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 63 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
Feb 11 – 18
Cottage in Indian Rocks Beach
4.82 out of 5 average rating, 62 reviewsTurtle Nest Cottage
Sep 12 – 19
Cottage in Bradenton
4.95 out of 5 average rating, 82 reviewsCoastal Cottage w/ Pool & Hot Tub
Aug 21 – 28
Cottage in Largo
4.95 out of 5 average rating, 58 reviewsHidden Oasis #1, just a few minutes to the beaches
Jul 12 – 19
Pet-friendly cottage rentals
Cottage in Siesta Key
4.89 out of 5 average rating, 142 reviewsSiesta Key Cozy Cottage across from the beach!
Oct 28 – Nov 4
Cottage in Tampa
4.99 out of 5 average rating, 139 reviewsBay Lake Cottage
Aug 21 – 28
Cottage in Sarasota
4.97 out of 5 average rating, 128 reviewsTropical Oasis SRQ.
Sep 13 – 20
Cottage in Gulfport
4.96 out of 5 average rating, 134 reviewsThe Pelicans Roost / Gulfport
Aug 12 – 19
Cottage in Dunedin
4.99 out of 5 average rating, 268 reviewsWalk to Downtown & Waterfront - Barefoot Parrot 2
Jul 29 – Aug 5
Cottage in Gulfport
4.99 out of 5 average rating, 257 reviewsGulfport Art District - One Block From Beach!
Oct 1 – 8
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*
Mar 22 – 29
Private cottage rentals
Cottage in Sarasota
4.83 out of 5 average rating, 150 reviewsCharming Beach Cottage
Jul 15 – 22
Cottage in Madeira Beach
4.8 out of 5 average rating, 162 reviews20% OFF Quaint Madeira Beach Cottage w Heated Pool
Dec 28 – Jan 4
Cottage in Treasure Island
4.91 out of 5 average rating, 114 reviewsHistoric Holly House on Treasure Island
Sep 19 – 26
Cottage in Indian Shores
4.86 out of 5 average rating, 161 reviews*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*
Aug 13 – 20
Cottage in Madeira Beach
4.96 out of 5 average rating, 134 reviewsBEACHFRONT FAIRWINDS Cottage Lower
Oct 31 – Nov 7
Cottage in Largo
4.94 out of 5 average rating, 124 reviewsFall special 3rd night free! “The Sweet”
Mar 4 – 11
Cottage in Holmes Beach
5.0 out of 5 average rating, 25 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 fire pit Anna Maria Island
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