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, 157 reviewsHarbor Oasis with Hot Tub
Aug 7 – 14
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 293 reviewsPrivate Heated pool/spa home!
Oct 20 – 27
Cottage in Clearwater
4.77 out of 5 average rating, 166 reviewsTiki Cottage Sleeps 6, Pets OK, Steps to Beach
Dec 18 – 25
Cottage in Holmes Beach
4.91 out of 5 average rating, 45 reviewsKiwi Cottage *Heated Pool+Spa+ walk to the Beach!
Sep 28 – Oct 5
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 64 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
Feb 28 – Mar 7
Cottage in Bradenton
4.95 out of 5 average rating, 82 reviewsCoastal Home w/ Pool & Hot Tub
Oct 9 – 16
Cottage in Indian Rocks Beach
4.82 out of 5 average rating, 62 reviewsTurtle Nest Cottage
Nov 10 – 17
Cottage in Palm Harbor
4.85 out of 5 average rating, 52 reviewsHappy Camper Cottage | Cozy Oasis with Hot Tub
Dec 25 – Jan 1
Pet-friendly cottage rentals
Cottage in Treasure Island
4.93 out of 5 average rating, 102 reviewsTreasure Island Beach Cottage
Aug 7 – 14
Cottage in Siesta Key
4.89 out of 5 average rating, 143 reviewsSiesta Key Cozy Cottage across from the beach!
Sep 22 – 29
Cottage in Indian Rocks Beach
4.99 out of 5 average rating, 155 reviewsCottage w/ Private Patio | 3 Min Walk to the Beach
Nov 9 – 16
Cottage in Tampa
4.99 out of 5 average rating, 144 reviewsBay Lake Cottage
Aug 3 – 10
Cottage in Sarasota
4.97 out of 5 average rating, 128 reviewsTropical Oasis SRQ.
Aug 11 – 18
Cottage in Dunedin
4.97 out of 5 average rating, 265 reviewsWalk to Downtown & Waterfront- Barefoot Parrot 3
Jul 22 – 29
Cottage in Gulfport
4.99 out of 5 average rating, 257 reviewsGulfport Art District - One Block From Beach!
Dec 3 – 10
Cottage in Gulfport
4.96 out of 5 average rating, 135 reviewsThe Pelicans Roost / Gulfport
Jul 20 – 27
Private cottage rentals
Cottage in Treasure Island
4.9 out of 5 average rating, 115 reviewsHistoric Holly House on Treasure Island
Sep 6 – 13
Cottage in Madeira Beach
4.8 out of 5 average rating, 163 reviewsQuaint Madeira Beach Cottage with Heated Pool
Nov 3 – 10
Cottage in Sarasota
4.92 out of 5 average rating, 152 reviewsCasa El Sueño - 8 min to Siesta Key - Intracoastal
Sep 15 – 22
Cottage in Madeira Beach
4.96 out of 5 average rating, 135 reviewsBEACHFRONT FAIRWINDS Cottage Lower
Sep 28 – Oct 5
Cottage in Sarasota
4.83 out of 5 average rating, 150 reviewsCharming Beach Cottage
Sep 30 – Oct 7
Cottage in Indian Shores
4.86 out of 5 average rating, 161 reviews*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*
Dec 25 – Jan 1
Cottage in Siesta Key
4.84 out of 5 average rating, 132 reviewsAdorable Cozy Silver Sands Cottage on Siesta Key!!
Aug 24 – 31
Cottage in Siesta Key
4.88 out of 5 average rating, 217 reviewsSiesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Dec 20 – 27
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