Cottage holiday rentals in Anna Maria
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Top-rated cottage rentals in Anna Maria
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
Cottage rentals with a hot tub
Cottage in Safety Harbor
4.96 out of 5 average rating, 156 reviewsHarbor Oasis with Hot Tub
5–12 Jun
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
21–28 Aug
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
Pet-friendly cottage rentals
Cottage in Treasure Island
4.93 out of 5 average rating, 102 reviewsTreasure Island Beach Cottage
18–25 Nov
Cottage in Dunedin
4.96 out of 5 average rating, 303 reviewsWalk to Downtown & Waterfront- Barefoot Parrot 1
16–23 Sep
Cottage in Indian Rocks Beach
4.89 out of 5 average rating, 241 reviewsVintage Florida Beach Cottage B
20–27 Nov
Cottage in Sarasota
4.97 out of 5 average rating, 128 reviewsTropical Oasis SRQ.
19–26 Sep
Cottage in Bradenton Beach
4.86 out of 5 average rating, 123 reviewsAMI Beach Shack
2–9 Dec
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 Tampa
4.97 out of 5 average rating, 265 reviewsHistoric Heights Hideaway *LOW FEES*
1–8 Aug
Cottage in Saint Pete Beach
4.86 out of 5 average rating, 155 reviewsSunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes
9–16 Dec
Private cottage rentals
Cottage in Largo
4.94 out of 5 average rating, 124 reviewsFall special 3rd night free! “The Sweet”
15–22 Oct
Cottage in Madeira Beach
4.8 out of 5 average rating, 162 reviews20% OFF Quaint Madeira Beach Cottage w Heated Pool
13–20 Dec
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 Gulfport
4.95 out of 5 average rating, 235 reviewsGulfport Cottage STEPS to Beach & Restaurants
23–30 Jun
Cottage in Sarasota
4.83 out of 5 average rating, 150 reviewsCharming Beach Cottage
16–23 Jul
Cottage in St. Petersburg
4.87 out of 5 average rating, 142 reviewsBeachy St. Pete Cottage Retreat!
10–17 May
Cottage in Holmes Beach
5.0 out of 5 average rating, 26 reviewsOleander Villa by Beach Boutique Rentals
9–16 Oct
Quick stats about cottage rentals in Anna Maria
Total rentals
10 properties
Popular amenities
Kitchen, Wifi and Pool
Wifi availability
10 properties include access to wifi
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
580 reviews
Nightly prices starting at
₹15,848 before taxes and fees
Destinations to explore
- Anna Maria Island Holiday rentals
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- Rentals with a hot tub Anna Maria
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- Family-friendly rentals Anna Maria
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- Rentals with pools Anna Maria
- Pet-friendly rentals Anna Maria
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- Monthly Rentals Anna Maria
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