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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
4.93 out of 5 average rating, 46 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, 185 reviews

Harbor Oasis - Hot Tub - Private

Guest favorite
A shared hot tub is surrounded by palm trees and lush greenery. Sunlight filters through the leaves, creating a serene atmosphere. A small seating area with chairs is visible in the background, offering a spot for relaxation.
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 39 reviews

Beachy Keen Cottage A only steps to the Beach

Guest favorite
A hot tub is seen on a patio, surrounded by greenery and overlooking a serene river. Two individuals are comfortably seated, enjoying the bubbling water. Trees and shrubs frame the scene, contributing to a peaceful outdoor setting.
Cottage in Tampa
4.94 out of 5 average rating, 125 reviews

Hot tub, 2 floors riverfront, Bush Gardens, kajaks

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, 58 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 Palm Harbor
4.83 out of 5 average rating, 90 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, 58 reviews

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

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Pet-friendly cottage rentals

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, 297 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
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, 215 reviews

Beachy Paradise

Top guest favorite
Cottage in Gulfport
4.99 out of 5 average rating, 267 reviews

Gulfport Art District - One Block From Beach!

Guest favorite
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, 126 reviews

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

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Private cottage rentals

Guest favorite
Cottage in Holmes Beach
4.89 out of 5 average rating, 9 reviews

Anna Maria Cottage w/Golf Cart

Superhost
The cottage's exterior features a covered porch with two wicker chairs and a small table, providing a relaxed seating area. Large windows are adorned with shutters, allowing natural light to fill the interior. A sandy pathway leads to the beach, framed by tropical greenery.
Cottage in Indian Rocks Beach
4.88 out of 5 average rating, 101 reviews

Historic Florida Beach Cottage steps from the sand

Guest favorite
A bright bedroom features a spacious bed with neatly arranged white linens and decorative pillows. Two woven shades adorn the windows, allowing soft light to filter in. On either side of the bed, small tables with lamps complete the serene decor, complemented by a calming artwork above.
Cottage in Bradenton
4.98 out of 5 average rating, 41 reviews

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

Guest favorite
A bright and airy living room features a light-colored sofa and an accent chair, inviting relaxation. A wooden coffee table sits at the center of the room, complemented by a lamp on a side table. Soft light filters in through the two windows, enhancing the tranquil atmosphere.
Cottage in Sarasota
4.89 out of 5 average rating, 231 reviews

"Honeybee Hideaway" Cozy Cottage Near SIESTA KEY

Guest favorite
A sandy path leads to the beach, where three white lounge chairs are positioned facing the turquoise Gulf of Mexico. Lush greenery and dunes frame the view, and a clear blue sky complements the serene coastal setting.
Cottage in Holmes Beach
4.97 out of 5 average rating, 30 reviews

Sailfish Gulf Suites #2, Beachfront, Steps to the

Top guest favorite
A sandy pathway leads from the cottage towards the beach, framed by the serene glow of the sunset. Soft hues of orange and pink illuminate the sky, while the gentle waves can be seen in the background. The structure displays a quaint coastal charm.
Cottage in Indian Rocks Beach
5 out of 5 average rating, 15 reviews

Kamp Komfort Historic Family Beach House

Guest favorite
Cottage in Bradenton Beach
4.91 out of 5 average rating, 193 reviews

Ebb Tide @ Tides Inn

Guest favorite
A charming waterfront cottage is showcased, featuring an orange exterior and welcoming front porch. Surrounding palm trees provide greenery, while a picnic area with a stone table and umbrella sits on a well-maintained lawn. Additional cottages are visible in the background.
Cottage in Bradenton
4.98 out of 5 average rating, 87 reviews

Cortez ~ Grouper Cottage. BRING YOUR BOAT!

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Luxury cottage rentals

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

Wow! Coastal Home+ 10 Mins to Dunedin & Beach

Superhost
A beachfront cottage is surrounded by tropical palms, offering a vibrant blue facade. A covered pavilion sits nearby, providing shaded seating. Sun loungers are arranged on the sandy area, leading directly to the water, while a charming outdoor dining space is visible on the patio.
Cottage in Indian Rocks Beach
4.76 out of 5 average rating, 33 reviews

Yachtsman Gulf front on sand, Sleeps 6 Heated Pool

Superhost
A light-filled living area features a comfortable sofa and armchair, with a round coffee table at its center. Large sliding doors open to a beachfront patio, allowing for seamless access to outdoor views and seating. Neutral tones create a serene ambiance.
Cottage in Indian Rocks Beach
4.5 out of 5 average rating, 10 reviews

3 Palms Beachfront Cottages - Beachfront

Superhost
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 sandy pathway leads through tall grass, guiding towards the beach and ocean. A sunset fills the sky with soft pastel colors, while wooden benches can be seen in the distance, offering a place to relax and enjoy the view.
Cottage in St. Pete Beach
4.88 out of 5 average rating, 171 reviews

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

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

Guest favorite
Wide sandy beach stretches into the distance, dotted with colorful umbrellas. Gentle waves can be seen lapping at the shore under a clear blue sky, while blades of grass gently sway at the beach's edge, offering a serene coastal view.
Cottage in Clearwater
4.91 out of 5 average rating, 57 reviews

Seashell Cottage

Guest favorite
Cottage in Indian Rocks Beach
4.95 out of 5 average rating, 19 reviews

Sandy/Salty- Sleep 16 - 2 homes connected by yards

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Quick stats about cottage rentals near Anna Maria Island

  • Total rentals

    80 properties

  • Nightly prices starting at

    ﺩ.ﺇ441 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