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!
26 Mar – 2 Apr
Cottage in Clearwater
4.77 out of 5 average rating, 123 reviewsCorner Cottage Sleeps 5, Steps to Beach, Pets OK.
19–26 Oct
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 63 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
19–26 Nov
Cottage in Bradenton
4.95 out of 5 average rating, 82 reviewsCoastal Cottage w/ Pool & Hot Tub
28 Oct – 4 Nov
Cottage in Palm Harbor
4.84 out of 5 average rating, 49 reviewsHappy Camper Cottage | Cozy Oasis with Hot Tub
24–31 Jan
Cottage in Largo
4.95 out of 5 average rating, 58 reviewsHidden Oasis #1, just a few minutes to the beaches
7–14 Jan
Cottage in Odessa
5.0 out of 5 average rating, 15 reviewsBreathtaking Lakefront Glass Cottage
23–30 Aug
Pet-friendly cottage rentals
Cottage in Palm Harbor
4.78 out of 5 average rating, 167 reviewsCrystal Beach Cottage #1
17–24 Aug
Cottage in Myakka City
4.99 out of 5 average rating, 113 reviewsNEW! Peaceful Country Cottage near Lakewood Ranch
12–19 Mar
Cottage in Tampa
4.99 out of 5 average rating, 140 reviewsBay Lake Cottage
11–18 Dec
Cottage in Dunedin
4.96 out of 5 average rating, 303 reviewsWalk to Downtown & Waterfront- Barefoot Parrot 1
16–23 Sept
Cottage in Sarasota
4.97 out of 5 average rating, 128 reviewsTropical Oasis SRQ.
25 Aug – 1 Sept
Cottage in Tampa
4.97 out of 5 average rating, 265 reviewsHistoric Heights Hideaway *LOW FEES*
18–25 Nov
Cottage in Siesta Key
4.89 out of 5 average rating, 143 reviewsSiesta Key Cozy Cottage across from the beach!
15–22 Aug
Cottage in Saint Pete Beach
4.86 out of 5 average rating, 155 reviewsSunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes
31 Aug – 7 Sept
Private cottage rentals
Cottage in Sarasota
4.94 out of 5 average rating, 138 reviewsSea-esta Cottage-cheerful 2bd/1ba w/ free parking
18–25 Nov
Cottage in Bradenton Beach
4.9 out of 5 average rating, 170 reviewsOhana Gulfside C Historic 1 Bed - 250 ft. to Beach
21–28 Dec
Cottage in Largo
4.94 out of 5 average rating, 124 reviewsFall special 3rd night free! “The Sweet”
13–20 Mar
Cottage in Madeira Beach
4.8 out of 5 average rating, 163 reviews20% OFF Quaint Madeira Beach Cottage w Heated Pool
13–20 Dec
Cottage in Gulfport
4.95 out of 5 average rating, 235 reviewsGulfport Cottage STEPS to Beach & Restaurants
23–30 Jun
Cottage in Treasure Island
4.91 out of 5 average rating, 114 reviewsHistoric Holly House on Treasure Island
25 Sept – 2 Oct
Cottage in Sarasota
4.83 out of 5 average rating, 150 reviewsCharming Beach Cottage
9–16 Nov
Cottage in St. Petersburg
4.87 out of 5 average rating, 142 reviewsBeachy St. Pete Cottage Retreat!
10–17 May
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
£152 before taxes and fees
Destinations to explore
- Anna Maria Island Holiday rentals
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- Rentals with a hot tub Anna Maria
- Apartment rentals Anna Maria
- Family-friendly rentals Anna Maria
- House rentals Anna Maria
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- Luxury rentals Anna Maria
- Rentals with a washing machine and dryer Anna Maria
- Family-friendly rentals Anna Maria
- Wheelchair-accessible rentals Anna Maria
- Rentals with pools Anna Maria
- Pet-friendly rentals Anna Maria
- Flat rentals Anna Maria
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- Monthly Rentals Anna Maria
- Rentals with outdoor seating Anna Maria
- Beachfront rentals Anna Maria
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