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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"

Top guest favorite
Cottage in Safety Harbor
4.96 out of 5 average rating, 185 reviews

Harbor Oasis with Hot Tub

Top 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 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

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, 95 reviews

Hidden Oasis #1, hot tub near the beach

Superhost
An expansive outdoor pool is showcased, featuring clear blue water under a bright sky. Surrounding the pool, lounge chairs with shaded umbrellas are arranged for relaxation. A spacious clubhouse with large windows is visible in the background, enhancing the resort's inviting atmosphere.
Cottage in Sarasota

Sunny Landings *Florida*

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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, 156 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, 207 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
4.89 out of 5 average rating, 295 reviews

Vintage Florida Beach Cottage B

Top guest favorite
A compact living space features a cozy bed with colorful bedding and a small dining table with two chairs. A kitchenette with modern appliances and a light-filled window creates a welcoming atmosphere. The flooring is light-toned, adding to the room's spacious feel.
Cottage in Largo
4.95 out of 5 average rating, 135 reviews

Walk to beach shops food drinks “The Sweet”

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, 101 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, 214 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!

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Private cottage rentals

Guest favorite
A modern kitchen is featured with white cabinetry and a striking teal backsplash. Open wooden shelves display glassware and decorative items. A stainless steel oven and a light blue kettle enhance the contemporary aesthetic, while ample natural light brightens the space.
Cottage in Holmes Beach
5 out of 5 average rating, 18 reviews

Palm Villa by Beach Boutique Rentals

Top guest favorite
A welcoming entryway features white railing and brick steps leading to a patio area. Potted plants hang above, with palm trees lining the view of the street and nearby buildings. A clean, aesthetic walkway is visible, enhancing the outdoor space.
Cottage in St. Pete Beach
4.96 out of 5 average rating, 204 reviews

Pass-a-Grille Historic Cottage Unit 1

Superhost
Cottage in Sarasota
4.83 out of 5 average rating, 122 reviews

Walk to Beach & St. Armands/Private cottage &grill

Superhost
A sandy pathway winds through lush greenery, leading toward the calm Gulf waters. The sun bathes the scene in natural light, creating a serene atmosphere. Gentle waves are visible in the distance, along with a sky dotted with soft clouds.
Cottage in Indian Rocks Beach
4.91 out of 5 average rating, 100 reviews

Historic Florida Beach Cottage steps from the sand

Superhost
A sandy pathway bordered by lush greenery leads to the beach. Silhouettes of palm trees and wooden posts are visible against a vibrant sunset sky, casting warm hues of orange and yellow over the horizon.
Cottage in Siesta Key
4.87 out of 5 average rating, 260 reviews

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

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, 40 reviews

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

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, 13 reviews

Kamp Komfort Historic Family Beach House

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

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Luxury cottage rentals

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, 170 reviews

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

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

Seashell Cottage

Guest favorite
Cottage in Holmes Beach
4.93 out of 5 average rating, 56 reviews

Close to the Beach+ Private heated pool and spa!

Guest favorite
A large shared patio area is shown with several patio tables and chairs beneath beige umbrellas. Lush greenery frames the space, and the sparkling turquoise waters of the Gulf of Mexico are visible in the background, creating a serene spot for relaxation.
Cottage in Holmes Beach
5 out of 5 average rating, 14 reviews

Sailfish Gulf Suites #1, Beachfront, Steps to the

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

Guest favorite
An aerial view captures a tranquil coastal neighborhood, showcasing sandy beaches and a vibrant blue ocean in the background. Several palm trees and buildings are visible, with the property marked for easy identification. The landscape displays greenery and well-maintained pathways.
Cottage in Siesta Key
4.92 out of 5 average rating, 63 reviews

Cozy Cottage 1 block from Beach

Top guest favorite
A sandy path lined with tall green grasses leads to the tranquil beach, where the turquoise water meets the sky. Beachgoers can be seen enjoying the shoreline, with umbrellas and lounge chairs dotting the landscape.
Cottage in Sarasota
4.99 out of 5 average rating, 88 reviews

Quaint Cottage,150 steps away from Crescent Beach!

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Quick stats about cottage rentals near Anna Maria Island

  • Total rentals

    80 properties

  • Nightly prices starting at

    G$25,106 GYD 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