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Cottage vacation rentals in Anna Maria

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Top-rated cottage rentals in Anna Maria

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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 Pass-a-Grille Beach

4.8 out of 5 average rating, 283 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Welcome to your beach getaway! This cheerful, sun-soaked cottage is steps from the sand—or your next ice cream or seaside meal at a nearby restaurant. Perfect for couples or solo travelers, a comfy queen bed, a breezy living room, and a kitchen and dining area. Sip your morning drink on the upstairs porch as salty breezes drift by, or fire up the BBQ on the downstairs patio. Two bikes are yours to cruise the island like a local—Everything you need for a relaxing, joy-filled beach escape is here

The charming cottage exterior is framed by lush greenery and a well-kept lawn. A welcoming front porch features a blue door, flanked by plants and decorative details. An American flag is displayed, adding a touch of local character. Ample sunlight highlights the inviting atmosphere.

Cottage in Palmetto

4.96 out of 5 average rating, 100 reviews

Historic 1930s Palmetto Cottage

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.

Top guest favorite

A cozy living area showcases a modular blue sofa, adorned with soft pillows and a warm throw. A light wooden coffee table rests in the center, complemented by decorative items. Natural light enters through a window, creating a bright and welcoming atmosphere.

Cottage in Dunedin

4.99 out of 5 average rating, 332 reviews

Walk to Downtown and Waterfront - Private Yard

Bright and beachy with stylish modern décor and an open floor plan. Concrete construction, a private yard, and a gas grill makes this cottage feel like your personal oasis. Steps from Main Street Dunedin and a short walk to the water. Enjoy gorgeous sunsets and easy access to restaurants, breweries, shops, and live music. A quick drive to award-winning beaches like Honeymoon Island and Clearwater Beach. The perfect getaway in delightful Dunedin—come be our guest at the Barefoot Parrot Cottages.

Top guest favorite

The image captures the tranquil waterway with gentle ripples reflecting the sky. In the background, a charming beach cottage is framed by palm trees and boats docked nearby, creating a serene waterfront scene.

Cottage in Pass-a-Grille Beach

4.97 out of 5 average rating, 154 reviews

Pass-a-Grille Historic Cottage Unit 2

PASS-A-GRILLE HISTORIC COTTAGE UNIT 2 A fully renovated historic beach cottage located in beautiful Pass a Grille, Florida. Steps from the Gulf of Mexico and Boca Ciega Bay. This is a duplex; Unit 2 - 2 bedroom/1 bath. Household linens, towels, cookware & dishes provided. Appliances include; dishwasher, washer/dryer, flat screen TVs and wi-fi. Vintage-style tiled bathroom and shower. High end window shades on all windows. Front and back patio area w/ BBQ grill. Private parking for 2 vehicles.

Top guest favorite

A vibrant tropical mural featuring large flowers adds a pop of color to the room, while a cozy seating area includes a sofa adorned with decorative pillows. A small dining table with tropical-patterned chairs provides a space for meals. The outdoor area showcases a lit pool, creating a serene evening ambiance.

Cottage in Indian Rocks Beach

4.99 out of 5 average rating, 180 reviews

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes! Welcome to #CocoPalmsIRB, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem that radiates a whimsical, small-town charm, evoking nostalgic memories of carefree childhood summers by the shore. The Gulf of Mexico beckons just two blocks away, offering pristine fluffy sands and unforgettable sunsets. As the sister cottage of Mango, #CocoPalmsIRB invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect getaway awaits!

A sandy path leads through lush greenery towards the beach, framed by overhanging branches. The ocean is visible in the distance, with light reflecting off the water. Shadows create a peaceful atmosphere as the sun casts a warm glow.

Cottage in Indian Shores

4.96 out of 5 average rating, 160 reviews

Beautiful Beachfront Cottage on the Water

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

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.

Cottage in Sarasota

4.94 out of 5 average rating, 127 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.

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

4.88 out of 5 average rating, 195 reviews

*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

A cozy living area is highlighted by a black sofa adorned with colorful pillows. Two decorative paddles are mounted on a light blue wall. A white dining table is paired with chairs, while a stainless steel kitchenette is visible in the background, featuring a sink and countertop.

Cottage in Bradenton Beach

4.9 out of 5 average rating, 183 reviews

Ohana Gulfside C Historic 1 Bed - 250 ft. to Beach

COMPLETELY REMODELED! Aloha and welcome to our bit of old Florida. Ohana Hale Gulfside is 250 feet to the white sand beaches and turquoise water. Come join us for your vacation in the sun. The ideal bungalow for a couple or small family. This one bedroom, one bath with kitchenette is made for your best vacation memories. This unit is only one block to the beach and one block to the Bridge Street shopping district and the pier! This unit is one-pet friendly.

Top guest favorite

Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.

Cottage in Tampa

4.97 out of 5 average rating, 212 reviews

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake.Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Pet fee $50.

A charming cottage is surrounded by vibrant palm trees and native tropical plants. The front entrance features a welcoming white door, with large windows allowing natural light to fill the space. A brick pathway leads to the entrance, creating an inviting pathway to the home.

Cottage in Bradenton Beach

4.97 out of 5 average rating, 143 reviews

Darling Old Florida Beach Cottage Steps From Gulf!

Completely Remodeled! Welcome to Cottage By The Sea, a newly remodeled charming retreat just steps from the pristine Gulf of Mexico beaches on Anna Maria Island, nestled in the serene area of Bradenton Beach. This delightful getaway blends the nostalgic charm of one of the only "Old Florida" cottages left, with modern updates, featuring bright and sunny décor. It's time to leave your worries behind and embrace the tranquility of paradise!

Top guest favorite

A row of brightly colored Adirondack chairs is positioned on the sandy beach, facing the tranquil ocean. The hues include yellow, orange, green, blue, pink, and purple. A clear blue sky with soft clouds complements the serene shoreline.

Cottage in Nokomis

4.98 out of 5 average rating, 161 reviews

Staycation Sanctuary

Our property is clean and welcoming. You can enjoy a relaxing, warm and peaceful getaway from the rest of the world just steps to the beach. This is the perfect "Old Florida-style" location to experience the comfort and hospitality you so deserve! Grab your bathing suit/flip flops and enjoy tranquillity of beach life, sunsets and lazy days of fishing and bird/dolphin/manatee watching and gathering sea shells-- all only 2 blocks away!

Vacation rentals for every style

Get the amount of space that is right for you

Bungalows

Intimate homes. inviting architecture

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Popular amenities for Anna Maria cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

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

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, 47 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, 188 reviews

Harbor Oasis | Hot Tub | Private | Lush Backyard

A well-lit swimming pool reflects soft turquoise hues at night, surrounded by a spacious patio. The exterior of the single-level ranch home is accented with ambient lighting, while seating areas and an umbrella provide a welcoming outdoor space.

Cottage in Holmes Beach

5 out of 5 average rating, 3 reviews

Yacht Rock Ranch

The outdoor pool area features a clear water pool surrounded by lounge chairs and vibrant umbrellas. A bright blue building is visible in the background, complemented by colorful accents along the poolside. Lush greenery adds to the relaxed atmosphere.

Cottage in Dunedin

4.9 out of 5 average rating, 115 reviews

Sunny - Key West Vibe Cottage - Pool - Walkable

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 Beach

4.77 out of 5 average rating, 158 reviews

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

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 Crystal Beach

4.84 out of 5 average rating, 91 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, 62 reviews

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

Pet-friendly cottage rentals

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 Bayshore Beautiful

4.75 out of 5 average rating, 167 reviews

Good Vibes Cozy Cottage on Million $ Row

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, 19 reviews

Palm Villa by Beach Boutique Rentals

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

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

4.92 out of 5 average rating, 119 reviews

Little Manatee River Cottage

An aerial view highlights the river house set amid lush greenery, featuring a large wooden deck and fenced yard. The property is bordered by the Braden River, with its tranquil waters reflecting the surrounding trees and homes.

Cottage in Bradenton

4.95 out of 5 average rating, 37 reviews

2/2 Charming Riverfront Cottage w Deck & Kayaks

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, 303 reviews

Vintage Florida Beach Cottage B

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, 366 reviews

Cozy up in a French Country nest NEAR EVERYTHING

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

Private cottage rentals

An open-concept kitchen and dining area features a modern white island with seating for four. The kitchen includes stainless steel appliances and a washer and dryer. Natural light brightens the space, complementing the dining table set for four and a decorative centerpiece.

Cottage in Bradenton

4.93 out of 5 average rating, 14 reviews

Cottage 10mi from the beach 1mi from downtown.

A cozy living area features a colorful mermaid-themed couch against a backdrop of textured wooden wall planks. A mounted television sits above a decorative fireplace. Soft lighting from a ceiling fan enhances the open and welcoming atmosphere, accompanied by natural light from the front door and nearby window.

Cottage in Bradenton

4.87 out of 5 average rating, 99 reviews

The Magical Mermaid Cottage

The living room features a spacious sectional sofa and a central round coffee table. A ceiling fan is present above, and natural light enters through large windows adorned with patterned curtains. A desk and chairs provide workspace, while art and decor enhance the inviting ambiance.

Cottage in Sarasota

4.92 out of 5 average rating, 39 reviews

Historic Cocoanut Art Cottage

A serene beach scene features soft waves gently rolling onto the sandy shore, framed by tall coastal grasses. In the distance, a jetty is visible, extending into the calm waters of the Gulf of Mexico under a clear blue sky.

Cottage in Pass-a-Grille Beach

4.94 out of 5 average rating, 16 reviews

Beach Cottage- Pass a Grille- Steps to beach

A bright living area features a comfortable seating arrangement with a light-colored sofa and armchair, complemented by decorative pillows. A coffee table sits centrally, and a television is mounted on a white console. Natural light flows in through large windows, with views of the outdoor patio visible.

Cottage in Holmes Beach

4.97 out of 5 average rating, 31 reviews

Sailfish Gulf Suites #2, Beachfront, Steps to the

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

4.96 out of 5 average rating, 23 reviews

Kamp Komfort Historic Family Beach House

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.

Cottage in Bradenton

4.98 out of 5 average rating, 93 reviews

Cortez ~ Grouper Cottage. BRING YOUR BOAT!

A porch area features two wooden Adirondack chairs positioned on a wooden surface. A colorful area rug lies beneath them, and large windows provide a view into the interior. Lush greenery is visible in the background, creating a serene environment.

Cottage in Bradenton

4.89 out of 5 average rating, 9 reviews

Charming downtown cottage

Quick stats about cottage rentals in Anna Maria

Total rentals
10 properties
Nightly prices starting at
G$39,447 GYD before taxes and fees
Total number of reviews
680 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool

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