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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

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, 48 reviews

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

Top guest favorite
Cottage in Indian Rocks Beach
4.98 out of 5 average rating, 42 reviews

Beachy Keen Cottage A only steps to the Beach

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, 65 reviews

Close to the Beach+ Private heated pool and spa!

Superhost
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
4.78 out of 5 average rating, 161 reviews

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

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 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, 68 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!

Guest favorite
An aerial view captures the expansive Siesta Key coastline, showcasing a stretch of sandy beach meeting calm blue waters. Nearby buildings and lush greenery punctuate the landscape, highlighting the serene environment just minutes away from the cottages.
Cottage in Sarasota
4.78 out of 5 average rating, 142 reviews

Siesta Key Cottages Crescent 1B Beach/Pool/Hot Tub

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
4.76 out of 5 average rating, 172 reviews

Good Vibes Cozy Cottage on Million $ Row

Superhost
A serene beach scene shows soft, white sand stretching along the shoreline, meeting gentle turquoise waves under a clear blue sky. A few people are visible enjoying the beach, with vibrant green vegetation and distant structures lining the coast.
Cottage in St. Pete Beach
4.8 out of 5 average rating, 289 reviews

Sunny PaG Island rental w/bikes-just steps2beach

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, 125 reviews

Artsy guest house; near downtown w/ private patio

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, 309 reviews

Vintage Florida Beach Cottage B

Superhost
A modern kitchen features a blend of grey and white cabinetry, with a stainless steel dishwasher and sink. Countertops are adorned with kitchen essentials. A coffee maker and kettle are visible, along with stylish lighting fixtures above the island, creating a functional and inviting space.
Cottage in Bradenton
4.83 out of 5 average rating, 113 reviews

Casa Azul. 2 bed/2 bath on lake

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, 372 reviews

Cozy up in a French Country nest NEAR EVERYTHING

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, 218 reviews

Beachy Paradise

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, 129 reviews

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

Private cottage rentals

Superhost
The living area features a high, wooden ceiling with a decorative octagonal window, allowing natural light to fill the space. Comfortable seating includes a blue sofa and a floral-patterned chair, positioned near large windows that frame views of the outdoor patio.
Cottage in Indian Rocks Beach
4.78 out of 5 average rating, 36 reviews

Yachtsman Gulf front on sand, Sleeps 6 Heated Pool

Top 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, 20 reviews

Palm Villa by Beach Boutique Rentals

Guest favorite
A wooden deck extends from the cottage, featuring a sturdy chair positioned for relaxation. The light blue exterior of the house contrasts with the greenery surrounding the space. Steps lead up to the deck, enhancing accessibility to the entrance.
Cottage in Bradenton
4.87 out of 5 average rating, 70 reviews

Cozy Cottage

Guest favorite
A cozy living area is highlighted by a sleek white media console and a mounted television. Natural light floods in through glass sliding doors, revealing views of the marina. A neutral-colored sofa is paired with a glass coffee table, enhancing the serene ambiance.
Cottage in Madeira Beach
4.8 out of 5 average rating, 112 reviews

Water Front Super Chic 2BD/ 1 bath - Cottage Wi-Fi

Guest favorite
A comfortably furnished living area features a neutral sofa adorned with patterned pillows. Two geometric wooden tables are positioned in front, with a single armchair nearby. Light wood ceilings enhance the bright atmosphere, while decorative artwork is displayed on the wall.
Cottage in Holmes Beach
4.97 out of 5 average rating, 38 reviews

Sailfish Gulf Suites #4, Garden Views, Steps from

Guest favorite
Cottage in Bradenton
4.98 out of 5 average rating, 42 reviews

*Fall Special* NEW 3BR | Near AMI, IMG & Beach

Guest favorite
A circular pool is surrounded by a landscaped area featuring vibrant plants and red stones. Lounge chairs offer seating nearby, while a shaded umbrella provides relief from the sun. Inflatable rings float in the clear water, and a view of the canal can be seen in the background.
Cottage in Bradenton
4.94 out of 5 average rating, 134 reviews

Waterfront+Pool+Putting Green+Beach Gear! 2BR/2BA

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
4.97 out of 5 average rating, 29 reviews

Kamp Komfort Historic Family Beach House

Luxury cottage rentals

Guest favorite
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, 83 reviews

Location 3 Bed Cottage 1 block to SiestaKey beach

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

Guest favorite
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
4.92 out of 5 average rating, 60 reviews

Seashell Cottage

Top guest favorite
An inviting heated saltwater pool is softly lit in the evening, surrounded by sun loungers. The vibrant mural features a large tropical flower. A close-up shows a decorative pillow with the word 'SUNSET.' The living area offers a cozy seating arrangement with colorful cushions and a decorative coffee table.
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 160 reviews

Luxury Beach Bungalow | Walk to Dining & Sunset

Guest favorite
A serene waterfront view captures the calm water reflecting the blue sky and scattered clouds. Palm trees line the shore, adding greenery to the scene, while wooden posts stand in the water, hinting at nearby docks and boats.
Cottage in St. Pete Beach
5 out of 5 average rating, 21 reviews

Pass-a-Grille Historic Cottage Duplex

Guest favorite
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, 36 reviews

The All Hands On Deck Cottage at Casa Limonada

Superhost
A charming cottage is set amidst lush greenery, featuring a pathway made of red bricks leading to the entrance. Tropical plants and palm trees provide a serene backdrop, while natural light brightens the white exterior of the home, contributing to a welcoming appearance.
Cottage in Longboat Key
5 out of 5 average rating, 3 reviews

Bayside Bliss: 1BR Cottage on Longboat Key

Guest favorite
The outdoor area features a large heated saltwater pool surrounded by a spacious patio. A tiki bar with seating is visible, along with two red lounge chairs. Lush palm trees add greenery to the setting, creating a relaxed and inviting atmosphere.
Cottage in Indian Rocks Beach
4.95 out of 5 average rating, 41 reviews

Seaside Retreat Cottages #3

Quick stats about cottage rentals near Anna Maria Island

  • Total rentals

    60 properties

  • Nightly prices starting at

    € 95 before taxes and fees

  • Total number of reviews

    3.1K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    30 properties have a pool

Destinations to explore