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 Safety Harbor
4.96 out of 5 average rating, 156 reviewsHarbor Oasis with Hot Tub
30 Jul – 6 Aug
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
4.77 out of 5 average rating, 129 reviewsPink Gulfside Cottage, Steps to Beach, Pets OK
16–23 Nov
Cottage in Holmes Beach
4.91 out of 5 average rating, 44 reviewsKiwi Cottage *Heated Pool+Spa+ walk to the Beach!
21–28 Sep
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 63 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
11–18 Feb
Cottage in Indian Rocks Beach
4.82 out of 5 average rating, 62 reviewsTurtle Nest Cottage
12–19 Sep
Cottage in Bradenton
4.95 out of 5 average rating, 82 reviewsCoastal Cottage w/ Pool & Hot Tub
21–28 Aug
Cottage in Largo
4.95 out of 5 average rating, 58 reviewsHidden Oasis #1, just a few minutes to the beaches
12–19 Jul
Pet-friendly cottage rentals
Cottage in Siesta Key
4.89 out of 5 average rating, 141 reviewsSiesta Key Cozy Cottage across from the beach!
28 Oct – 4 Nov
Cottage in Tampa
4.99 out of 5 average rating, 139 reviewsBay Lake Cottage
21–28 Aug
Cottage in Sarasota
4.97 out of 5 average rating, 128 reviewsTropical Oasis SRQ.
13–20 Sep
Cottage in Gulfport
4.96 out of 5 average rating, 134 reviewsThe Pelicans Roost / Gulfport
12–19 Aug
Cottage in Dunedin
4.99 out of 5 average rating, 268 reviewsWalk to Downtown & Waterfront - Barefoot Parrot 2
29 Jul – 5 Aug
Cottage in Gulfport
4.99 out of 5 average rating, 256 reviewsGulfport Art District - One Block From Beach!
1–8 Oct
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
Cottage in Tampa
4.97 out of 5 average rating, 264 reviewsHistoric Heights Hideaway *LOW FEES*
22–29 Mar
Private cottage rentals
Cottage in Sarasota
4.83 out of 5 average rating, 150 reviewsCharming Beach Cottage
15–22 Jul
Cottage in Madeira Beach
4.8 out of 5 average rating, 162 reviews20% OFF Quaint Madeira Beach Cottage w Heated Pool
28 Dec – 4 Jan
Cottage in Treasure Island
4.91 out of 5 average rating, 114 reviewsHistoric Holly House on Treasure Island
19–26 Sep
Cottage in Indian Shores
4.86 out of 5 average rating, 161 reviews*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*
13–20 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”
4–11 Mar
Cottage in Holmes Beach
5.0 out of 5 average rating, 25 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
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- Rentals with outdoor seating Anna Maria Island
- Rentals with a firepit Anna Maria Island
- Fitness-friendly rentals Anna Maria Island
- Family-friendly rentals Anna Maria Island
- Rentals with a sauna Anna Maria Island
- Rentals with an EV charger Anna Maria Island
- Rentals with pools Anna Maria Island
- Rentals with a washing machine and dryer Anna Maria Island
- Villa rentals Anna Maria Island
- Rentals with a fireplace Anna Maria Island
- Pet-friendly rentals Anna Maria Island
- House rentals Anna Maria Island
- Family-friendly rentals Anna Maria Island
- Flat rentals Anna Maria Island
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- Monthly Rentals Anna Maria Island
- Rentals with a hot tub Anna Maria Island
- Rentals with beach access Anna Maria Island
- Rentals with a patio Anna Maria Island
- Apartment rentals Anna Maria Island
- Waterfront rentals Anna Maria Island
- Rentals with a kayak Anna Maria Island
- Rentals with lake access Anna Maria Island
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- Beach apartment rentals Anna Maria Island
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