Airbnb your place

Cottage rentals near Anna Maria Island

Find and book unique cottages on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for cottage rentals near Anna Maria Island

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Cottage rentals with a hot tub

Top guest favorite
A spacious outdoor deck is shown, featuring a hot tub covered with a protective lid. Blue and white lounge chairs, along with bright cushions, are arranged for relaxation. The cottage's vibrant turquoise exterior is complemented by a cheerful yellow door and lush surrounding greenery.
Cottage in Safety Harbor
4.96 out of 5 average rating, 180 reviews

Harbor Oasis with Hot Tub

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, 55 reviews

Close to the Beach+ Private heated pool and spa!

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, 55 reviews

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

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 Palm Harbor
4.83 out of 5 average rating, 90 reviews

Happy Camper Cottage | Cozy Oasis with Hot Tub

Guest favorite
A vibrant outdoor area features a sparkling hot tub surrounded by lush greenery. Comfortable seating arrangements and a dining table create an inviting space for relaxation. A charming yellow cottage stands in the background, complemented by various tropical plants and trees.
Cottage in Largo
4.96 out of 5 average rating, 94 reviews

Hidden Oasis #1, hot tub near the beach

Guest favorite
A well-equipped kitchen features white cabinetry and a wooden countertop. Essential appliances include a retro-style refrigerator, a microwave, and a coffee maker. Decorative elements include open shelving with dishware and a vintage-style wall poster, providing a functional yet charming atmosphere.
Cottage in Siesta Key
4.92 out of 5 average rating, 62 reviews

Cozy Cottage 1 block from Beach

Top guest favorite
A spacious living area features a light-colored tiled floor and is illuminated by natural light coming through large windows. Comfortable seating options include a colorful sectional sofa, lounge chairs, and a dining table with high-backed chairs. Decorative accents and art pieces add character to the room.
Cottage in Sarasota
4.99 out of 5 average rating, 87 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, 76 reviews

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

Show all

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
4.77 out of 5 average rating, 158 reviews

Good Vibes Cozy Cottage on Million $ Row

Guest favorite
A serene sunset over the Little Manatee River is captured, with vibrant hues of orange and pink reflecting on the water surface. The dark outline of trees defines the horizon, creating a peaceful natural backdrop.
Cottage in Ruskin
4.91 out of 5 average rating, 117 reviews

Little Manatee River Cottage

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, 289 reviews

Vintage Florida Beach Cottage B

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, 205 reviews

Adorable Dog-Friendly Cottage in Quaint Dunedin

Guest favorite
A charming cottage exterior is highlighted by vibrant blue accents on the door and window frames. Lush palm trees surround the property, and a pathway of red bricks leads to the entrance. Gravel landscaping complements the home, enhancing its welcoming appearance.
Cottage in Indian Rocks Beach
4.7 out of 5 average rating, 210 reviews

Beachy Paradise

Top guest favorite
The vintage cottage is shown with a sunny yellow exterior, surrounded by lush greenery and shady oak trees. A stone pathway leads to the screened front porch, featuring vibrant flowers and plants along the edges, providing a welcoming entrance to the home.
Cottage in Sarasota
5 out of 5 average rating, 36 reviews

Cozy Cottage near Siesta Key Beach

Top guest favorite
A sparkling pool reflects sunlight, set against a backdrop of lush greenery. Two blue chairs are positioned near a small table on grass, offering a serene view of the adjacent canal. A decorative fence surrounds the backyard, enhancing the outdoor space's privacy.
Cottage in Bradenton
4.96 out of 5 average rating, 111 reviews

Waterfront*3bd 2ba*Pool* PingPong Table*relaxing

Top guest favorite
A spacious outdoor area features comfortable lounge chairs and a patio, surrounded by greenery. The deck extends toward the water, with a view of the canal. A covered seating area and plants add to the inviting atmosphere, while overcast skies hint at a serene ambiance.
Cottage in Lutz
4.97 out of 5 average rating, 103 reviews

Serene Waterfront Cottage with Tranquil Setting

Show all

Private cottage rentals

Superhost
A view of a sandy beach stretches toward calm blue waters under a clear sky. A wooden walkway leads from the beach access point, framed by green grass and beach plants. An umbrella and two figures are visible in the distance on the shore.
Cottage in Redington Shores
4.74 out of 5 average rating, 324 reviews

Below -Deck Studio Gulf Side 40 steps to the beach

Guest favorite
A wooden boardwalk leads to a rustic restaurant with a tin roof, surrounded by palm trees. Visitors stroll along the boardwalk, enjoying the view of the water. Coastal scenery and bright blue skies add to the inviting atmosphere of this popular dining location.
Cottage in Madeira Beach
4.84 out of 5 average rating, 129 reviews

Family Friendly Beach Cottage in Madeira Beach, FL

Superhost
Aerial view of a coastal neighborhood reveals a mix of colorful buildings surrounded by lush greenery. The shimmering water of the bay is visible in the distance, while palm trees dot the landscape. Streets are lined with vehicles, suggesting a vibrant community.
Cottage in Bradenton Beach
4.82 out of 5 average rating, 104 reviews

Charming Stand Alone Cottage! Walk 2 Beach/Bridge

Superhost
The image captures a sandy beach at sunset, with several silhouettes of people gathered along the shore. Tall palm trees frame the scene, and rays of sunlight break through scattered clouds over the water, creating a serene coastal atmosphere.
Cottage in Tarpon Springs
4.84 out of 5 average rating, 106 reviews

Palm Cottage * King Bed * Tropical Yard

Guest favorite
A kitchen counter displays a dual coffee pot and coffee pod machine beside a sleek microwave. Natural light filters in through a window, illuminating a wooden tray containing coffee mugs. Decorative items and basic kitchen supplies are arranged neatly in the background.
Cottage in Riverview
4.93 out of 5 average rating, 84 reviews

Alafia River Cottage

Top guest favorite
A view into a well-lit kitchen area is provided, showcasing modern appliances and minimalist decor. Rich, dark flooring contrasts with light walls, while a framed artwork of a cow and palm trees adds character to the space. A fireplace integrates traditional elements.
Cottage in Dunedin
5 out of 5 average rating, 221 reviews

Downtown Dunedin Historic Orange Blossom Cottage 2

Top guest favorite
The charming exterior of the cottage features a bright yellow door framed by flowering window boxes. A spacious front porch with screening provides a welcoming entryway, while a pathway leads to a well-maintained lawn bordered by a white picket fence.
Cottage in Oldsmar
4.96 out of 5 average rating, 297 reviews

Louisa's Cottage

Top guest favorite
A screened-in porch features a cozy seating area with a blue wicker sofa and decorative pillows. A circular table with intricate detailing is surrounded by several chairs. Natural light floods the space through large windows, enhancing the vibrant color palette of the furnishings.
Cottage in Bradenton
4.97 out of 5 average rating, 119 reviews

Coastal Style 2BR cottage near Anna Maria Island

Show all

Luxury cottage rentals

Top guest favorite
Cottage in Clearwater
4.96 out of 5 average rating, 74 reviews

Amazing! Coastal Home+ 10 Mins to Dunedin & Beach

Superhost
A shared beachfront patio offers comfortable seating and chaise lounges positioned under swaying palm trees. The open view reveals the sandy beach and tranquil ocean, with the vibrant blue sky adding to the inviting coastal atmosphere.
Cottage in Indian Rocks Beach
4.5 out of 5 average rating, 10 reviews

3 Palms Beachfront Cottages - Beachfront

Guest favorite
Cottage in Clearwater
4.91 out of 5 average rating, 57 reviews

Seashell Cottage

Superhost
Cottage in Siesta Key
5 out of 5 average rating, 3 reviews

4 Bdrm (2 unit Cottage) walk to Siesta Beach

Superhost
A wall-mounted artwork depicting a calm sea is displayed above a bedside table. The gentle waves are rendered in soft blues and whites. A sleek lamp with a gold finish sits beside a neatly made bed with white linens, contributing to a serene atmosphere.
Cottage in Sarasota
4.94 out of 5 average rating, 34 reviews

The All Hands On Deck Cottage at Casa Limonada

Superhost
Cottage in Holmes Beach
4.78 out of 5 average rating, 36 reviews

Sailfish Gulf Suites #3, Modern Amenities, Steps t

A serene view of the shoreline is captured, featuring tropical foliage and a sandy area leading to calm waters. A shaded patio with thatched roofing provides seating for relaxation, surrounded by low vegetation and wildflowers. The sky above is bright, suggesting a pleasant day.
Cottage in Siesta Key
5 out of 5 average rating, 9 reviews

Charming Beach Cottage with pool

Top guest favorite
Cottage in Anna Maria
4.94 out of 5 average rating, 16 reviews

Charming cottage w/heated pool in prime location.

Show all

Quick stats about cottage rentals near Anna Maria Island

  • Total rentals

    80 properties

  • Nightly prices starting at

    R2,162 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