Cottage holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for cottage rentals in Anna Maria Island
Cottage rentals with a hot tub
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 293 reviewsPrivate Heated pool/spa home!
23 Feb – 2 Mar
Cottage in Clearwater
4.76 out of 5 average rating, 165 reviewsTiki Cottage Sleeps 6, Pets OK, Steps to Beach
27 Nov – 4 Dec
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 63 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
15–22 Nov
Cottage in Bradenton
4.95 out of 5 average rating, 82 reviewsCoastal Cottage w/ Pool & Hot Tub
28 Oct – 4 Nov
Cottage in Largo
4.95 out of 5 average rating, 58 reviewsHidden Oasis #1, just a few minutes to the beaches
23–30 Sep
Cottage in Treasure Island
5.0 out of 5 average rating, 28 reviewsCasa Sunset by Agua Salá
9–16 Sep
Cottage in Largo
5.0 out of 5 average rating, 18 reviewsFamily FUN~Pool, GameRoom+Bikes, Near Beach/Trail
14–21 Jun
Cottage in Sarasota
4.96 out of 5 average rating, 23 reviewsCharming Coastal Oasis 2 Bed/2 Bath Cottage
29 Sep – 6 Oct
Pet-friendly cottage rentals
Cottage in Siesta Key
4.89 out of 5 average rating, 143 reviewsSiesta Key Cozy Cottage across from the beach!
28 Oct – 4 Nov
Cottage in Indian Rocks Beach
4.89 out of 5 average rating, 241 reviewsVintage Florida Beach Cottage B
20–27 Nov
Cottage in Dunedin
4.96 out of 5 average rating, 303 reviewsWalk to Downtown & Waterfront- Barefoot Parrot 1
16–23 Sep
Cottage in Sarasota
4.97 out of 5 average rating, 128 reviewsTropical Oasis SRQ.
19–26 Sep
Cottage in Gulfport
4.96 out of 5 average rating, 135 reviewsThe Pelicans Roost / Gulfport
12–19 Aug
Cottage in Gulfport
4.99 out of 5 average rating, 257 reviewsGulfport Art District - One Block From Beach!
1–8 Oct
Cottage in Tampa
4.99 out of 5 average rating, 140 reviewsBay Lake Cottage
11–18 Dec
Cottage in Indian Rocks Beach
4.99 out of 5 average rating, 155 reviewsCottage w/ Private Patio | 3 Min Walk to the Beach
28 Jul – 4 Aug
Private cottage rentals
Cottage in Sarasota
4.83 out of 5 average rating, 150 reviewsCharming Beach Cottage
16–23 Jul
Cottage in Sarasota
4.92 out of 5 average rating, 152 reviewsCasa El Sueño - 8 min to Siesta Key - Intracoastal
20–27 May
Cottage in Bradenton Beach
4.9 out of 5 average rating, 170 reviewsOhana Gulfside C Historic 1 Bed - 250 ft. to Beach
30 Mar – 6 Apr
Cottage in Indian Shores
4.86 out of 5 average rating, 161 reviews*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*
15–22 Aug
Cottage in Madeira Beach
4.96 out of 5 average rating, 134 reviewsBEACHFRONT FAIRWINDS Cottage Lower
31 Oct – 7 Nov
Cottage in Largo
4.94 out of 5 average rating, 124 reviewsFall special 3rd night free! “The Sweet”
15–22 Oct
Cottage in Holmes Beach
5.0 out of 5 average rating, 26 reviewsOleander Villa by Beach Boutique Rentals
9–16 Oct
Cottage in Cortez
4.82 out of 5 average rating, 94 reviewsTy's Canal Cottage
8–15 Jan
Destinations to explore
- St Petersburg Holiday rentals
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- Rentals with a firepit Anna Maria Island
- Rentals with a kayak Anna Maria Island
- House rentals Anna Maria Island
- Wheelchair-accessible rentals Anna Maria Island
- Rentals with a fireplace Anna Maria Island
- Beach house rentals Anna Maria Island
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- Rentals with an EV charger Anna Maria Island
- Monthly Rentals Anna Maria Island
- Rentals with a hot tub Anna Maria Island
- Rentals with lake access Anna Maria Island
- Townhouse rentals Anna Maria Island
- Apartment rentals Anna Maria Island
- Rentals with a sauna Anna Maria Island
- Pet-friendly rentals Anna Maria Island
- Flat rentals Anna Maria Island
- Beach apartment rentals Anna Maria Island
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- Rentals with a patio Anna Maria Island
- Rentals with pools Anna Maria Island
- Family-friendly rentals Anna Maria Island
- Villa rentals Anna Maria Island
- Rentals with a washing machine and dryer Anna Maria Island
- Family-friendly rentals Anna Maria Island
- Rentals with beach access Anna Maria Island
- Rentals with outdoor seating Anna Maria Island
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