Cottage vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Anna Maria cottage rentals
Cottage rentals with a pool
Cottage in Madeira Beach
4.8 out of 5 average rating, 162 reviews20% OFF Quaint Madeira Beach Cottage w Heated Pool
Dec 13 – 20
Cottage in Sarasota
4.83 out of 5 average rating, 108 reviewsWalk to Beach & St. Armands/Private cottage &grill
Aug 16 – 23
Cottage in Siesta Key
4.88 out of 5 average rating, 215 reviewsSiesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Oct 2 – 9
Cottage in Sarasota
4.84 out of 5 average rating, 154 reviewsHeated Pool! Beach! Drift Inn Unit B Siesta Key!
Apr 14 – 21
Cottage in Siesta Key
4.84 out of 5 average rating, 132 reviewsAdorable Cozy Silver Sands Cottage on Siesta Key!!
Oct 13 – 20
Cottage in Siesta Key
4.81 out of 5 average rating, 260 reviewsSunspot Cottage 2BR/2B Getaway w/ private beach
Dec 2 – 9
Cottage in Madeira Beach
4.83 out of 5 average rating, 114 reviewsFamily Friendly Beach Cottage in Madeira Beach, FL
Apr 15 – 22
Cottage in Holmes Beach
4.75 out of 5 average rating, 8 reviewsBlu Idyll Getaway by Beach Boutique Rentals
Oct 10 – 17
Cottage rentals with a hot tub
Cottage in Safety Harbor
4.96 out of 5 average rating, 156 reviewsHarbor Oasis with Hot Tub
Jun 5 – 12
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 293 reviewsPrivate Heated pool/spa home!
Feb 23 – Mar 2
Cottage in Clearwater
4.76 out of 5 average rating, 165 reviewsTiki Cottage Sleeps 6, Pets OK, Steps to Beach
Nov 27 – Dec 4
Cottage in Holmes Beach
4.91 out of 5 average rating, 45 reviewsKiwi Cottage *Heated Pool+Spa+ walk to the Beach!
Mar 15 – 22
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 63 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
Nov 15 – 22
Cottage in Bradenton
4.95 out of 5 average rating, 82 reviewsCoastal Cottage w/ Pool & Hot Tub
Oct 28 – Nov 4
Cottage in Largo
4.95 out of 5 average rating, 58 reviewsHidden Oasis #1, just a few minutes to the beaches
Sep 23 – 30
Cottage in Treasure Island
5.0 out of 5 average rating, 28 reviewsCasa Sunset by Agua Salá
Sep 9 – 16
Pet-friendly cottage rentals
Cottage in Treasure Island
4.93 out of 5 average rating, 102 reviewsTreasure Island Beach Cottage
Nov 18 – 25
Cottage in Dunedin
4.96 out of 5 average rating, 303 reviewsWalk to Downtown & Waterfront- Barefoot Parrot 1
Sep 16 – 23
Cottage in Indian Rocks Beach
4.89 out of 5 average rating, 241 reviewsVintage Florida Beach Cottage B
Nov 20 – 27
Cottage in Sarasota
4.97 out of 5 average rating, 128 reviewsTropical Oasis SRQ.
Sep 19 – 26
Cottage in Bradenton Beach
4.86 out of 5 average rating, 123 reviewsAMI Beach Shack
Dec 2 – 9
Cottage in Siesta Key
4.89 out of 5 average rating, 143 reviewsSiesta Key Cozy Cottage across from the beach!
Oct 28 – Nov 4
Cottage in Tampa
4.97 out of 5 average rating, 265 reviewsHistoric Heights Hideaway *LOW FEES*
Aug 1 – 8
Cottage in Saint Pete Beach
4.86 out of 5 average rating, 155 reviewsSunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes
Dec 9 – 16
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
G$39,703 GYD before taxes and fees
Destinations to explore
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- Rentals with a hot tub Anna Maria
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