Cottage rentals near Anna Maria Island

4.96 out of 5 average rating, 106 reviews

A fenced-in outdoor area features a swimming pool surrounded by a red brick patio. Sun loungers are positioned beside the pool, and a pool house is visible in the background, complemented by lush greenery and large trees draped with moss.

Cottage in Palmetto

1930s Cottage + Pool 12 miles to Beach

Located in the heart of historic Palmetto FL, you will find this adorable cottage. This home has 2 bedrooms & 1 bath in the main home with a pull out sofa, as well as, a pool house with a full bath & daybed. You will love the southern charm of this home while relaxing by the pool or having morning coffee on the front porch. There are many restaurants & shops w/in walking distance as well as local parks & preserves. If you love the beach, this home is just a short drive to FL's beautiful beaches.

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.

4.94 out of 5 average rating, 145 reviews

Waterfront Escape•PingPong•Relax & Recharge•Pool

Your peaceful waterfront escape awaits. This cozy 2BR/2BA cottage offers two living areas. The bright Florida room overlooks the canal. It includes areas for a game of ping pong, a life‑size Jenga set, watching tv, having a bite at the table, and a sleeper sofa. Enjoy morning coffee at the dock watching the fish jump or grab your pole. Relax by the sunny pool or practice on the putting green ⛳. Fast WiFi, a dedicated workspace, beach gear, and a full kitchen make winter stays easy and relaxing.

4.97 out of 5 average rating, 354 reviews

The exterior of a coastal cottage is shown, featuring a gravel driveway and tropical landscaping with palm trees. Two wicker chairs are positioned under a covered porch, inviting relaxation. Large windows allow natural light to brighten the welcoming facade.

Cottage in Dunedin

Walk Downtown and to Waterfront, Mins to Beaches

Steps to Main Street ! Experience modern coastal luxury in this stylish, spacious upstairs 2-bedroom cottage. Professionally designed and fully stocked. Steps from Main Street Dunedin, short stroll to gorgeous sunsets at the waterfront, quick drive to award winning beaches--Honeymoon Island & Clearwater Beach. Walk to restaurants, shops, & breweries. Pet-friendly w/ 2 king beds, a sleeper sectional, & lovely treetop views. Treat yourself today. Book your escape at the Barefoot Parrot Cottages.

4.8 out of 5 average rating, 261 reviews

Cottage in Madeira Beach

2 bed/1 bath Hummingbird Beach Cottage (4 beds)

This is a 1951 beach bungalow with all the updates, including a walk-in shower, on-demand hot water, and stainless steel appliances. Comfortable, clean, and cozy. Two queen beds and two full sofa sleepers! The beach is just a short walk across Gulf Blvd and views of million-dollar homes, piers, and sunsets to die for! Great shell collecting. Fantastic location with lots to walk to. Groceries, Dollar store, bars, restaurants, and coffee are all walkable. Just under two miles to John's Pass.

A sandy path leads from a grassy area to the shoreline, flanked by light vegetation. The vibrant blue sky is dotted with clouds, while the gentle waves of the ocean are visible in the distance.

4.76 out of 5 average rating, 117 reviews

#5 Beach Front Cottage w view- Indian Rocks Beach

LOCATION, location! Closest beach cottage to the water at Indian Rocks beach, view of the water from your porch & easy access to grass for pets. Perfect couples getaway. Enjoy some of Florida’s best beaches. Minimalistic living. *Kitchen recently updated* Shared gazebo & picnic table next door. Shared Washer & dryer takes quarters. Walking distance to local restaurants and bars. Minutes away from Clearwater beach, tourist attractions and mini golf. Property located next 2 public access.

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.

4.96 out of 5 average rating, 169 reviews

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes IRB! Welcome to Mango, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem radiating a whimsical, small-town charm that evokes nostalgic memories of carefree childhood summers by the shore. Just ✌🏽 blocks away, the Gulf of Mexico beckons, offering pristine fluffy sand and unforgettable sunsets. As the sister cottage of Coco, Mango invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

A private pool is surrounded by a paved area, featuring two lounge chairs positioned near the water. Green foliage adds a natural touch, while a white fence encloses the space, creating a secluded atmosphere. The clear blue water reflects the sky, inviting relaxation.

4.93 out of 5 average rating, 137 reviews

Private Heated Pool Casita Near Downtown & Beaches

Built in 1925, Our Casaita Verde 2 Bedroom, 1 Bath home still retains its vintage charm but with modern touches. Enjoy watching the 55 inch flat screen TV with HD cable and stay in touch with the world with WI-FI internet. Lounge by the private pool or take in the beautiful evenings on the deck with your favorite beverage. Pet Friendly! Conveniently located near Downtown Sarasota on Bahia Vista with easy drive to Lido Key, our World Famous Siesta Key or I-75 for longer adventures.

An open-concept kitchen and dining area features modern fixtures and wooden accents. A large island bar is surrounded by high-backed chairs, with a dining table visible in the background. Light blue walls and stylish light fixtures create a bright atmosphere.

4.98 out of 5 average rating, 160 reviews

New Beach Retreat– Hammock, PAC-MAN, Steps 2 Sand!

Sandy Feet Cottage is a newly remodeled beach retreat just 2 minutes from Indian Rocks Beach. Enjoy an open layout, new furnishings, a spa-style bath, and a private yard with fire pit, hammock, and patio. Walk to dining, bars, and shops—your stylish Gulf Coast escape! ***NEW AIRBNB PRICING UPDATE*** Starting mid-October 2025, Airbnb will display all-in pricing—including a 15.5% Airbnb service fee (charged directly by Airbnb to the host), plus cleaning and pet fees if applicable!

4.89 out of 5 average rating, 204 reviews

A cozy dining area is framed by large windows, offering a direct view of the beach and ocean. Two light-colored chairs surround a round wooden table. Outside, lounge chairs are positioned on the sand, with stunning sunset colors reflecting on the water.

Cottage in Indian Shores

*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*

Step out the door and into the sand! Ground floor DIRECT beachfront one- bedroom/one-bath cottage nestled in the sand directly on the Gulf of Mexico with awesome amenities for the perfect Gulf Beach getaway! Enjoy a cozy bedroom, living/dining area, fully-equipped kitchen, beachfront patio and private beach area with lounge chairs. Conveniently located near a trolley stop for easy access to local restaurants, shops, and attractions. Book now for an unforgettable beach vacation!l

4.85 out of 5 average rating, 144 reviews

A sandy pathway leads through beach grass and wildflowers, with palm trees framing the scene. The azure ocean and clear blue sky serve as a backdrop, inviting guests to enjoy the nearby beach.

Cottage in Clearwater

Mermaid Cottage

Located in a three unit 'Olde Florida Style Complex' and just 45 steps to Clearwater Beach! The Mermaid Cottage is located on the 1st floor at the back of the complex. This Florida style unit is adorned wood floors and charming island decor. Open to an outdoor patio with furniture. The cottage has two bedrooms, two full baths and an outdoor shower! Living room has a queen pull-out bed. The patio area is completely fenced for private use. Nice, park like charcoal grill.

A mobile home with a welcoming front porch is surrounded by lush greenery and colorful flowering plants. The structure features a light exterior, complemented by a decorative element above the porch. A carport for vehicle parking is visible, alongside a well-maintained pathway.

4.97 out of 5 average rating, 122 reviews

Coastal Style 2BR cottage near Anna Maria Island

Relax with the whole family at this peaceful place to stay. Located in a mobile home/RV park 6.5 miles from Anna Maria Island, which offers some of the most beautiful beaches on the gulf coast. Centrally located between St. Petersburg and Siesta Key. This kid friendly community offers many amenities such as Pickle ball, swimming pool, shuffle board, horseshoes and gym on site. Stay a few days or a few months! Snow birds are welcome! Only 3.3 miles to Sarasota Airport.

Cottage in Bradenton Beach

4.97 out of 5 average rating, 158 reviews

Darling Old Florida Beach Cottage Steps From Gulf!

Fully Renovated Coastal Gem! Welcome to Cottage By The Sea — a beautifully updated retreat just steps from the sugar-white sands and turquoise waters of the Gulf of Mexico on Anna Maria Island. Tucked away in the peaceful community of Bradenton Beach, this charming escape is one of the few remaining “Old Florida” cottages, lovingly restored with modern touches and cheerful, sun-filled décor. Leave your worries behind and unwind in your own slice of island paradise!

Popular amenities for cottage rentals near Anna Maria Island

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A serene outdoor space showcases a private heated pool and spa, surrounded by lush tropical landscaping. Paved with light-colored stones, the area features several lounge chairs positioned for relaxation under the bright sky. The backdrop includes a white wall and large windows of the house, enhancing natural light.

5 out of 5 average rating, 3 reviews

Yacht Rock Ranch

4.98 out of 5 average rating, 42 reviews

Beachy Keen Cottage A only steps to the Beach

4.91 out of 5 average rating, 105 reviews

A private hot tub is positioned on a wooden deck, outfitted with two black chairs and a small table. The cottage features a light blue exterior with a white door framed by two towels. A pergola with climbing plants is visible in the background.

Cottage in Safety Harbor

Heart of Safety Harbor | Hot Tub | Luxe Comfort

4.78 out of 5 average rating, 165 reviews

Cottage in Clearwater

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

4.99 out of 5 average rating, 69 reviews

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

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

4.91 out of 5 average rating, 70 reviews

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

Cozy Cottage 1 block from Beach

4.91 out of 5 average rating, 77 reviews

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

A shaded outdoor dining area features a glass table surrounded by decorative metal chairs. Lush greenery and colorful flowers adorn the space, with a wooden structure visible in the background. The garden offers a feeling of seclusion and connection to nature.

Cottage in St. Petersburg

4.56 out of 5 average rating, 36 reviews

Castle Keep Guest House

Pet-friendly cottage rentals

4.77 out of 5 average rating, 182 reviews

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

Cool Breeze Cottage by the Bay in South Tampa

4.96 out of 5 average rating, 167 reviews

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

The Pelicans Roost / Gulfport

Cottage in St. Petersburg

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.

4.95 out of 5 average rating, 131 reviews

Artsy guest house; near downtown w/ private patio

4.91 out of 5 average rating, 129 reviews

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

Little Manatee River Cottage

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.

4.9 out of 5 average rating, 321 reviews

Vintage Florida Beach Cottage B

4.86 out of 5 average rating, 379 reviews

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

Cozy up in a French Country nest NEAR EVERYTHING

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.

4.8 out of 5 average rating, 280 reviews

Cozy Cottage by the Bay

4.99 out of 5 average rating, 280 reviews

The cottage exterior features a light teal facade with white trim and multiple windows allowing natural light. A welcoming front porch includes a central entry door flanked by two large windows. The address is displayed prominently above the door. Lush greenery surrounds the base of the structure.

Cottage in Gulfport

Gulfport Art District - One Block From Beach!

Private cottage rentals

4.85 out of 5 average rating, 148 reviews

The single-family beach cottage features a light yellow exterior with red accents and three prominent windows. Surrounding the home, palm trees and landscaping provide a lush atmosphere. A paved area holds several designated parking spaces in front of the cottage, with a stone picnic table nearby.

Cottage in Madeira Beach

Family Friendly Beach Cottage in Madeira Beach, FL

4.95 out of 5 average rating, 142 reviews

A cozy living space features a well-equipped kitchenette with modern appliances, including a coffee maker and microwave. A dining table with two chairs is positioned beside expansive windows. A spacious bed occupies the corner, complemented by light-colored bedding and gentle lighting from ceiling fans.

Cottage in Largo

Walk to beach shops food drinks “The Sweet”

A cozy living area features a light grey sofa adorned with throw pillows, complemented by two round coffee tables. A floor lamp and a potted plant add warmth. Natural light floods the room through large windows, enhancing the welcoming atmosphere.

5 out of 5 average rating, 36 reviews

Hibiscus Villa by Beach Boutique Rentals

Cottage in Treasure Island

The living room features modern teal leather seating, including a spacious sofa and two armchairs, arranged to encourage conversation. Natural light filters in through two windows, adorned with patterned curtains. A door with clear glass inserts leads outside, enhancing the room's openness.

4.99 out of 5 average rating, 226 reviews

Island Time Stay: Sunrise

The exterior of a light blue house is framed by a manicured lawn featuring lush greenery and colorful plants. Two wooden chairs sit on the porch, providing a welcoming space to relax. Large windows allow natural light to fill the interior.

4.98 out of 5 average rating, 46 reviews

NEW* 3BR •Wi-Fi, Self Check-In, Great Comfort

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.

4.98 out of 5 average rating, 99 reviews

Cortez ~ Grouper Cottage. BRING YOUR BOAT!

A comfortable living area is depicted, featuring a light-colored sofa accompanied by two side lamps on small tables. A ceiling fan is visible, and a round piece of wall art echoes a coastal theme. Natural light filters in through the window with white blinds.

4.94 out of 5 average rating, 206 reviews

Kooky Coconut Cottage, Indian Rocks Beach

A modern cottage is set within a spacious, manicured lawn surrounded by trees. A circular driveway leads to the house, which features a dark metal roof and large windows. Lush greenery frames the property, emphasizing its serene outdoor environment.

4.96 out of 5 average rating, 54 reviews

Bee Keepers Cottage

Luxury cottage rentals

4.92 out of 5 average rating, 83 reviews

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

Location 3 Bed Cottage 1 block to SiestaKey beach

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.

4.5 out of 5 average rating, 10 reviews

3 Palms Beachfront Cottages - Beachfront

Cottage in St. Petersburg

Two chairs in green and blue are positioned on a sandy area overlooking calm waters. The image features a distant pier with a modern structure, framed by a clear blue sky, enhancing the serene coastal ambiance.

5 out of 5 average rating, 23 reviews

Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bike

4.8 out of 5 average rating, 5 reviews

A charming Gulf-side cottage is nestled among lush greenery, featuring a spacious porch with white railings. The exterior displays a light-colored facade, complemented by tropical palm trees and well-maintained landscaping along the brick pathway leading to the entrance.

Cottage in Longboat Key

2BR Gulf Side Cottage: Longboat Key

A serene backyard pool area is framed by lush palm trees, creating a tropical oasis. A semi-circular seating area under a Tiki umbrella provides a shaded spot next to the pool. Adjacent seating and a grill enhance this inviting outdoor space.

4.99 out of 5 average rating, 78 reviews

Poolside Oasis on Anna Maria Island!

Cottage in St. Pete Beach

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.

5 out of 5 average rating, 21 reviews

Pass-a-Grille Historic Cottage Duplex

A bright kitchen area features a long countertop with comfortable seating for four. Pendant lights illuminate the space, highlighting the blue and green decorative plates displayed on the wall. Natural light enters through the window, creating a welcoming ambiance.

4.79 out of 5 average rating, 38 reviews

Sailfish Gulf Suites #3, Modern Amenities, Steps t

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.