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Cottage rentals near Anna Maria Island

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Popular amenities for cottage rentals near Anna Maria Island

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Cottage rentals with a hot tub

Superhost
A bright living area includes large windows with light filtering through sheer curtains. A comfortable leather sofa sits alongside a tufted storage ottoman. A dining table with four chairs is set with an orange table runner, enhancing the overall inviting atmosphere.
Cottage in Sarasota

Sun Outdoors Sarasota, FL "Jungle Bridge Retreat"

Guest favorite
The entryway features warm wooden floors and natural light streaming through large windows. A vibrant blue door adds a pop of color, while a stylish desk and lamp provide a functional workspace. A wooden cabinet with glass doors showcases decorative items and greenery.
Cottage in Palmetto
4.94 out of 5 average rating, 47 reviews

Charming Home w/ Hot Tub, 20 min to Beach + Garden

Top guest favorite
Cottage in Safety Harbor
4.96 out of 5 average rating, 186 reviews

Harbor Oasis | Hot Tub | Private | Lush Backyard

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
4.93 out of 5 average rating, 59 reviews

Close to the Beach+ Private heated pool and spa!

The exterior view of a charming blue cottage is presented, featuring white accents and shutters. Two light-colored lounge chairs are positioned on the paved front area. Lush greenery surrounds the property, enhancing the inviting beach house vibe.
Cottage in Clearwater
4.77 out of 5 average rating, 157 reviews

Corner Cottage Sleeps 5, Steps to Beach, Pets OK.

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, 61 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
4.95 out of 5 average rating, 98 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, 65 reviews

Cozy Cottage 1 block from Beach

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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 Tampa
4.75 out of 5 average rating, 166 reviews

Good Vibes Cozy Cottage on Million $ Row

Top guest favorite
A spacious backyard is featured, bordered by a wooden fence for privacy and lined with tropical plants and trees. A concrete patio area is included, which features a grill covered for protection. The lawn is open and well-maintained, providing a serene outdoor space.
Cottage in Gulfport
4.96 out of 5 average rating, 157 reviews

The Pelicans Roost / Gulfport

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 St. Petersburg
4.95 out of 5 average rating, 123 reviews

Artsy guest house; near downtown w/ private patio

Top guest favorite
A dining area is showcased with a white table set for four, featuring floral tableware and a decorative centerpiece. A large window allows natural light to illuminate the space, which is complemented by a cozy seating area in the background and a TV mounted on the wall.
Cottage in Dunedin
4.96 out of 5 average rating, 208 reviews

Adorable Dog-Friendly Cottage in Quaint Dunedin

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, 300 reviews

Vintage Florida Beach Cottage B

Superhost
A comfortable living area features a spacious gray sectional sofa adorned with decorative pillows. A light wooden coffee table sits in front, complemented by a soft area rug. Three colorful art pieces hang on the wall, while natural light enters from a nearby window covered with sheer curtains.
Cottage in Bradenton
4.85 out of 5 average rating, 104 reviews

Casa Azul. 2 bed/2 bath on lake

Superhost
The cottage features a welcoming exterior with a screened-in lanai, framed by decorative beams and charming window boxes. Lush greenery surrounds the property, and a large tree adds to the tranquil setting. A pathway leads to the front door, enhancing the inviting atmosphere.
Cottage in Sarasota
4.81 out of 5 average rating, 251 reviews

Cozy Cottage by the Bay

Top guest favorite
Cottage in Gulfport
4.99 out of 5 average rating, 270 reviews

Gulfport Art District - One Block From Beach!

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Private cottage rentals

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
5 out of 5 average rating, 10 reviews

Cottage 10mi from the beach 1mi from downtown.

Guest favorite
A bright living area features a light blue sectional sofa with accented pillows, alongside a cozy chaise. Sunlight filters through large windows adorned with wooden blinds, highlighting the warm earth-toned tile flooring. A woven side table and a decorative plant add a touch of natural charm.
Cottage in Holmes Beach
5 out of 5 average rating, 19 reviews

Palm Villa by Beach Boutique Rentals

Top 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
5 out of 5 average rating, 33 reviews

2/2 Charming Riverfront Cottage w Deck & Kayaks

Top guest favorite
A round dining table with a dark wood finish is accompanied by four white wooden chairs. The chairs feature a classic design, and the arrangement is set on a light marble floor, with kitchen cabinetry visible in the background.
Cottage in Madeira Beach
4.93 out of 5 average rating, 136 reviews

Flipper's @ Mad Beach Cottage

Top guest favorite
A charming beach house is positioned among gentle sand dunes and swaying palm trees. Soft evening light highlights the house's light-colored facade, with chairs visible on the porch. The backdrop features a mix of pastel hues in the sky, reflecting a serene coastal atmosphere.
Cottage in Indian Rocks Beach
4.95 out of 5 average rating, 42 reviews

Shady Nook Beachfront Cottage

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, 41 reviews

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

Guest favorite
A bright living area features a comfortable seating arrangement with a light-colored sofa and armchair, complemented by decorative pillows. A coffee table sits centrally, and a television is mounted on a white console. Natural light flows in through large windows, with views of the outdoor patio visible.
Cottage in Holmes Beach
4.97 out of 5 average rating, 31 reviews

Sailfish Gulf Suites #2, Beachfront, Steps to the

Guest favorite
An open-concept living area features exposed wooden beams and light hardwood flooring. A dining area with a table and chairs is positioned near a fully equipped kitchen. Glass double doors lead to a cozy sleeping space with a bed and large windows, allowing natural light to fill the room.
Cottage in Bradenton
4.98 out of 5 average rating, 89 reviews

Cortez ~ Grouper Cottage. BRING YOUR BOAT!

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Luxury cottage rentals

Superhost
A beachfront view reveals a secluded area with soft sand and lush tropical vegetation leading to a covered patio. Palm trees frame the scene, with the inviting exterior of the cottages visible in the background under a clear blue sky.
Cottage in Indian Rocks Beach
4.5 out of 5 average rating, 10 reviews

3 Palms Beachfront Cottages - Beachfront

Superhost
A charming cottage is showcased behind a white picket fence, surrounded by tropical landscaping featuring palm trees and green foliage. A gravel driveway leads towards the entrance, and a covered porch is visible, enhancing the welcoming appearance of the home.
Cottage in Siesta Key
4.92 out of 5 average rating, 78 reviews

Location 3 Bed Cottage 1 block to SiestaKey beach

Guest favorite
A wooden boardwalk leads directly to the beach, framed by sandy dunes and swaying grass. The clear blue sky meets the calm waters of the Gulf, creating an inviting scene for beachgoers. The soft beach sand stretches out, blending seamlessly into the horizon.
Cottage in St. Pete Beach
4.88 out of 5 average rating, 173 reviews

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike

Superhost
A modern living area is featured with a comfortable sectional sofa and a small dining table surrounded by yellow chairs. The fully equipped kitchen is visible in the background, matched with light cabinetry. Natural light enters through the window, enhancing the space.
Cottage in Bradenton Beach
4.82 out of 5 average rating, 104 reviews

Charming Stand Alone Cottage! Walk 2 Beach/Bridge

Superhost
The exterior of the cottage is shown, featuring a light-colored facade and a peaked roof. Lush greenery surrounds the front, including tall tropical plants. Large windows allow natural light to enter, while a blue accent decoration adds a touch of color.
Cottage in Clearwater
4.91 out of 5 average rating, 57 reviews

Seashell Cottage

Superhost
The exterior of a charming blue cottage features a welcoming porch with decorative trim and bright yellow shutters. Lush greenery surrounds the home, and palm trees contribute to the tropical ambiance. A spacious lawn leads up to the inviting entrance.
Cottage in Dunedin
4.82 out of 5 average rating, 57 reviews

Elegant Rustic Cottage w/Studio. Central Location

Superhost
A spacious bedroom features a large bed adorned with a blue throw and several pillows. Two framed art pieces are displayed above the headboard. Nightstands with lamps are placed on either side, while a door on the left leads to another room.
Cottage in Sarasota
4.94 out of 5 average rating, 35 reviews

The All Hands On Deck Cottage at Casa Limonada

Superhost
A dining table with a circular design is set on a wooden deck, accompanied by four woven chairs. The space overlooks the bay, with calm water visible beyond the railing and greenery in the background, creating a peaceful outdoor setting.
Cottage in Longboat Key

Family Time: 4BR Cottage with Bay Views

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Quick stats about cottage rentals near Anna Maria Island

  • Total rentals

    80 properties

  • Nightly prices starting at

    R2,128 ZAR before taxes and fees

  • Total number of reviews

    2.6K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with a pool

    40 properties have a pool

Destinations to explore