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Cottage vacation rentals in Anna Maria

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Anna Maria cottage rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Cottage rentals with a hot tub

Top guest favorite
Cottage in Safety Harbor
4.96 out of 5 average rating, 191 reviews

Harbor Oasis | Hot Tub | Private | Lush Backyard

Top guest favorite
A coastal-style duplex is framed by lush tropical landscaping, featuring palm trees and colorful flowering plants. The exterior showcases light-hued siding, a spacious front porch with railings, and two garage spaces below. A clear blue sky enhances the inviting atmosphere of the property.
Cottage in Holmes Beach
4.94 out of 5 average rating, 63 reviews

Close to the Beach+ Private heated pool and spa!

Guest favorite
A charming coastal cottage is depicted, featuring a welcoming front porch with rocking chairs and vibrant seating. Lush plants in decorative pots frame the entrance. The exterior is painted in soft grey tones, complemented by white shutters and a serene pathway leading to the door.
Cottage in Crystal Beach
4.85 out of 5 average rating, 97 reviews

Happy Camper Cottage | Cozy Oasis with Hot Tub

Top guest favorite
A bright and airy seating area features a hanging chair and a cozy sofa, adorned with colorful cushions. Natural light floods in through large windows, complemented by light-toned wooden flooring and a textured pink area rug that adds warmth to the space.
Cottage in Largo
4.98 out of 5 average rating, 66 reviews

Family FUN~Pool, GameRoom+Bikes, Near Beach/Trail

Guest favorite
A serene courtyard is surrounded by lush palm trees, creating a tranquil setting. A stone pathway leads to a Buddha statue nestled among greenery, providing a peaceful focal point. Shadows cast by the trees enhance the calm atmosphere of the space.
Cottage in Largo
4.94 out of 5 average rating, 102 reviews

Hidden Oasis #1, just a few mins to the beach

Guest favorite
A bright studio space features a spacious king-size bed and a cozy sofa in soft blue tones. Natural light filters through window treatments, highlighting white walls and wooden beams that add warmth. A mirror and wall decor complement the relaxing atmosphere, while a TV is mounted nearby.
Cottage in Siesta Key
4.91 out of 5 average rating, 67 reviews

Cozy Cottage 1 block from Beach

Top guest favorite
An open living area features tiled flooring and soft lighting, with comfortable seating arrangements including a sofa and armchairs. A dining area is visible, showcasing a wooden table with chairs. Decorative touches such as artwork and a side cabinet enhance the space's charm.
Cottage in Sarasota
4.99 out of 5 average rating, 96 reviews

Quaint Cottage,150 steps away from Crescent Beach!

Superhost
A private backyard space features a hot tub with a bubbling water feature, surrounded by a paved patio. A dining table with chairs is positioned nearby, catering to outdoor meals and relaxation. Lush greenery and landscaping enhance the tranquil environment.
Cottage in Bradenton
4.91 out of 5 average rating, 77 reviews

Sandy Cottage w/ Hot Tub, 20 min to Beach + Garden

Pet-friendly cottage rentals

Guest favorite
A comfortable seating area features two light-colored sofas with throw pillows, arranged around a rustic wooden coffee table. A decorative screen provides partial division from other spaces, and a textured rug is laid beneath the furniture, enhancing the warm ambiance of the room.
Cottage in Bayshore Beautiful
4.76 out of 5 average rating, 169 reviews

Good Vibes Cozy Cottage on Million $ Row

Top guest favorite
A cozy living room features a tan sofa positioned across from a purple armchair. A round coffee table is centered on a light-colored rug. Colorful artwork adorns the wall, while a floor lamp provides warm lighting. The space is brightened by natural light through a window.
Cottage in Euclid Place - St. Paul
4.95 out of 5 average rating, 124 reviews

Artsy guest house; near downtown w/ private patio

Guest favorite
An aerial view highlights the river house set amid lush greenery, featuring a large wooden deck and fenced yard. The property is bordered by the Braden River, with its tranquil waters reflecting the surrounding trees and homes.
Cottage in Bradenton
4.95 out of 5 average rating, 43 reviews

2/2 Charming Riverfront Cottage w Deck & Kayaks

Top guest favorite
A single-story cottage features a pink exterior with large windows allowing natural light. A landscaped garden with decorative stones is visible in the front. White chairs are placed near the entrance, and ample parking spaces are provided in the driveway.
Cottage in Indian Rocks Beach
4.9 out of 5 average rating, 305 reviews

Vintage Florida Beach Cottage B

Guest favorite
Cottage in Dunedin
4.95 out of 5 average rating, 212 reviews

Perfect Location Cottage in Delightful Dunedin

Top guest favorite
A cozy interior space features a neutral color palette with a striped bedspread. A serving tray holds two white cups beside a small dish of candy. Natural light fills the room, highlighting a kitchenette in the background, complemented by white cabinetry and a subtle decor.
Cottage in Dunedin
4.85 out of 5 average rating, 368 reviews

Cozy up in a French Country nest NEAR EVERYTHING

Top guest favorite
Cottage in Gulfport
4.99 out of 5 average rating, 278 reviews

Gulfport Art District - One Block From Beach!

Superhost
A spacious living area features a large sectional sofa in a neutral tone, accented by coastal-themed artwork on the walls. Light wood flooring complements the room, which includes a dining table and two bar stools, allowing for casual seating options. Bright natural light floods the space.
Cottage in Indian Rocks Beach
4.91 out of 5 average rating, 128 reviews

ALL NEW! Coral Sands II ~Coastal Modern 2/2 IRB

Private cottage rentals

Top guest favorite
An open-concept kitchen and dining area features a modern white island with seating for four. The kitchen includes stainless steel appliances and a washer and dryer. Natural light brightens the space, complementing the dining table set for four and a decorative centerpiece.
Cottage in Bradenton
4.94 out of 5 average rating, 18 reviews

Cottage 10mi from the beach 1mi from downtown.

Guest favorite
A cozy living area features a colorful mermaid-themed couch against a backdrop of textured wooden wall planks. A mounted television sits above a decorative fireplace. Soft lighting from a ceiling fan enhances the open and welcoming atmosphere, accompanied by natural light from the front door and nearby window.
Cottage in Bradenton
4.87 out of 5 average rating, 99 reviews

The Magical Mermaid Cottage

Guest favorite
A screened lanai is presented with light-colored wicker furniture, featuring green striped cushions. A small coffee table is positioned between the two seating areas, and a bicycle can be seen tucked in the corner, complementing the lush garden views visible through the screens.
Cottage in Indian Beach-Sapphire Shores
4.79 out of 5 average rating, 63 reviews

Walk to Bay light filled private Cottage King bed

Guest favorite
The exterior of a brightly colored cottage features a pale blue facade with navy blue shutters and a welcoming front porch. A U.S. flag is displayed on the porch, while lush greenery surrounds the home. A driveway provides access to an open carport.
Cottage in Palmetto
4.91 out of 5 average rating, 44 reviews

Aqua Breeze Cottage - Winter retreat 2 bd, 2 ba

Guest favorite
A bright and airy living space is shown, featuring a contemporary sofa facing a soft beige wall and natural wood accents. A stylish dining area with rattan chairs is visible in the foreground, adorned with dishes and a decorative centerpiece. Large windows allow ample natural light.
Cottage in Bradenton
4.98 out of 5 average rating, 42 reviews

NEW 3BR Home w/ grill | Near AMI, IMG & Beach,WiFi

Top guest favorite
A family beach house is showcased, featuring a main structure with a covered porch and large windows. Adjacent is a smaller cottage. Both buildings have a light-colored exterior and are surrounded by soft sandy ground and palm trees, highlighting the beachfront location.
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 27 reviews

Kamp Komfort Historic Family Beach House

Guest favorite
A porch area features two wooden Adirondack chairs positioned on a wooden surface. A colorful area rug lies beneath them, and large windows provide a view into the interior. Lush greenery is visible in the background, creating a serene environment.
Cottage in Wares Creek
4.89 out of 5 average rating, 9 reviews

Charming downtown cottage

Top guest favorite
An enclosed sitting area features a comfortable daybed adorned with colorful throw pillows against light wooden paneling. A small blue table accompanies the seating, with large windows allowing natural light to illuminate the space while offering views of the surrounding greenery.
Cottage in Osprey
4.97 out of 5 average rating, 65 reviews

Mattie’s Cottage by the Bay

Quick stats about cottage rentals in Anna Maria

  • Total rentals

    10 properties

  • Nightly prices starting at

    G$39,739 GYD before taxes and fees

  • Total number of reviews

    680 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

Destinations to explore

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