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, 163 reviewsQuaint Madeira Beach Cottage with Heated Pool
Aug 27 – Sep 3
Cottage in Siesta Key
4.84 out of 5 average rating, 133 reviewsAdorable Cozy Silver Sands Cottage on Siesta Key!!
Aug 17 – 24
Cottage in Siesta Key
4.88 out of 5 average rating, 217 reviewsSiesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Oct 31 – Nov 7
Cottage in Sarasota
4.66 out of 5 average rating, 122 reviewsHeated Pool! Beach! Drift Inn Unit A Siesta Key!
Oct 30 – Nov 6
Cottage in Sarasota
4.83 out of 5 average rating, 108 reviewsWalk to Beach & St. Armands/Private cottage &grill
Nov 23 – 30
Cottage in Siesta Key
4.81 out of 5 average rating, 260 reviewsSunspot Cottage 2BR/2B Getaway w/ private beach
Jul 3 – 10
Cottage in Madeira Beach
4.83 out of 5 average rating, 114 reviewsFamily Friendly Beach Cottage in Madeira Beach, FL
Sep 15 – 22
Cottage in Holmes Beach
4.75 out of 5 average rating, 8 reviewsBlu Idyll Getaway by Beach Boutique Rentals
Aug 4 – 11
Cottage rentals with a hot tub
Cottage in Safety Harbor
4.96 out of 5 average rating, 158 reviewsHarbor Oasis with Hot Tub
Oct 15 – 22
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 295 reviewsPrivate Heated pool/spa home!
Nov 28 – Dec 5
Cottage in Clearwater
4.77 out of 5 average rating, 167 reviewsTiki Cottage Sleeps 6, Pets OK, Steps to Beach
Dec 17 – 24
Cottage in Holmes Beach
4.91 out of 5 average rating, 45 reviewsKiwi Cottage *Heated Pool+Spa+ walk to the Beach!
Sep 28 – Oct 5
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 65 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
Dec 26 – Jan 2
Cottage in Palmetto
5.0 out of 5 average rating, 21 reviewsPalmetto Isles w/ Hot Tub
Jul 22 – 29
Cottage in Indian Rocks Beach
4.82 out of 5 average rating, 62 reviewsTurtle Nest Cottage
Nov 2 – 9
Cottage in Largo
5.0 out of 5 average rating, 19 reviewsFamily FUN~Pool, GameRoom+Bikes, Near Beach/Trail
Jun 11 – 18
Pet-friendly cottage rentals
Cottage in Gulfport
4.96 out of 5 average rating, 136 reviewsThe Pelicans Roost / Gulfport
Sep 5 – 12
Cottage in Tampa
4.97 out of 5 average rating, 271 reviewsHistoric Heights Hideaway *LOW FEES*
Oct 30 – Nov 6
Cottage in Indian Rocks Beach
4.99 out of 5 average rating, 156 reviewsCottage w/ Private Patio | 3 Min Walk to the Beach
Nov 9 – 16
Cottage in Sarasota
4.97 out of 5 average rating, 128 reviewsTropical Oasis SRQ.
May 28 – Jun 4
Cottage in Dunedin
4.96 out of 5 average rating, 307 reviewsWalk to Downtown & Waterfront- Barefoot Parrot 1
Nov 7 – 14
Cottage in Saint Pete Beach
4.86 out of 5 average rating, 155 reviewsSunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes
Mar 5 – 12
Cottage in Bradenton Beach
4.86 out of 5 average rating, 123 reviewsAMI Beach Shack
Apr 4 – 11
Cottage in St. Petersburg
4.96 out of 5 average rating, 127 reviewsHomey Cottage Close To It All
Nov 1 – 8
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
R3,530 ZAR before taxes and fees
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