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Cottage rentals near Anna Maria Island

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Top-rated cottage rentals near Anna Maria Island

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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 St. Pete Beach

4.8 out of 5 average rating, 285 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

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 St. Pete 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.

A cozy living area is displayed, featuring a patterned sofa and a wooden coffee table with a small plant. A large television sits on a white dresser, while an air conditioning unit is installed above. The entrance door is visible, along with a wall clock and decorative wall art.

Cottage in Cortez

4.85 out of 5 average rating, 124 reviews

Ty's Canal Cottage

"Welcome to Ty's Cottage in Historic Cortez Fishing Village, which is one of Florida's last working fishing villages. Located within walking distance to well known Starfish, Swordfish, Tide Tables Restaurants and Tyler's Homemade ice cream. A short 1.3 mile walk to Anna Maria Island with gorgeous beaches. Short driving distance to beautiful golf courses such as IMG Academy Golf and Manatee County Golf Course. Local fishing charters for outstanding fishing. Outdoor sitting area on canal."

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, 153 reviews

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes! Welcome to #MangoIRB, 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, #MangoIRB invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

A welcoming entryway features a turquoise door and a decorative 'Welcome' sign. Two chairs with cushions are positioned at a small round table on a wooden deck, inviting relaxation. Nearby, flowers are displayed on a mail holder, completing the inviting exterior.

Cottage in Bradenton

4.91 out of 5 average rating, 360 reviews

Private King Bed Suite-Near AMI Beach-Walk D’Town.

Your relaxing vacation is here! Private Cottage with a huge deck. Wonderfully furnished with plush linens, beach towels/chairs. A great nights sleep with a king-size bed and pull-out couch which serves as 2nd bed. Private kitchen and bath. TV and fast WIFI. We are located in a historic and quiet neighborhood in DT Bradenton. There are 3 villas on our large corner property. Off street parking. Quiet times are between 10PM until 8:00AM. Please respect others. Walk to many great restaurants!

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, 128 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 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

4.87 out of 5 average rating, 134 reviews

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 charming coastal cottage features a light blue exterior and a welcoming front door. Lush palm trees and vibrant tropical plants surround the property. A stone pathway lined with decorative gravel leads up to the entrance, creating an inviting atmosphere.

Cottage in Bradenton Beach

4.97 out of 5 average rating, 145 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!

A bright living space is highlighted by light aqua walls. A black sofa with decorative pillows faces a small dining table with white chairs. Decorative wooden paddles are mounted on the wall, complementing the area. A stainless steel kitchenette with a commercial-style faucet is visible in the background.

Cottage in Bradenton Beach

4.9 out of 5 average rating, 184 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, 215 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.

Top guest favorite

A vibrant yellow cottage is surrounded by a sandy area with palm trees. Colorful adirondack chairs in pink, blue, and green are positioned on the white gravel. A covered outdoor seating area is visible to the side, enhancing the beachside environment.

Cottage in Bradenton Beach

4.98 out of 5 average rating, 191 reviews

Bradenton Beach Sunsets 2, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

Top guest favorite

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

4.97 out of 5 average rating, 324 reviews

Walk Downtown and Waterfront, Designer Getaway

Experience modern coastal luxury in this stylish, spacious upstairs 2-bedroom cottage. Steps from Main Street Dunedin. Walk to restaurants, shops, and breweries or take a short stroll to gorgeous sunsets. A quick drive to Honeymoon Island and Clearwater Beach, this pet-friendly retreat boasts two king beds, a sleeper sectional, and serene treetop views. Your sunny, coastal escape awaits—book your getaway at the Barefoot Parrot today!

Popular amenities for cottage rentals near Anna Maria Island

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

A spacious outdoor deck is shown, featuring a hot tub covered with a protective lid. Blue and white lounge chairs, along with bright cushions, are arranged for relaxation. The cottage's vibrant turquoise exterior is complemented by a cheerful yellow door and lush surrounding greenery.

Cottage in Safety Harbor

4.96 out of 5 average rating, 189 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

4.91 out of 5 average rating, 116 reviews

Sunny - Key West Vibe Cottage - Pool - Walkable

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, 60 reviews

Close to the Beach+ Private heated pool and spa!

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, 64 reviews

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

A private pool area is showcased, featuring a swim up table with a tiki-style umbrella at the center. Surrounding the pool are lush tropical plants and a wooden deck. Two lounge chairs sit nearby, adding to the inviting outdoor space.

Cottage in Holmes Beach

5 out of 5 average rating, 3 reviews

Beach Dream Cottage: Steps from the Beach with

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 Tampa

4.75 out of 5 average rating, 167 reviews

Good Vibes Cozy Cottage on Million $ Row

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, 159 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

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, 120 reviews

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.

Cottage in Indian Rocks Beach

4.9 out of 5 average rating, 303 reviews

Vintage Florida Beach Cottage B

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, 108 reviews

Casa Azul. 2 bed/2 bath on lake

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.

Cottage in Sarasota

4.8 out of 5 average rating, 259 reviews

Cozy Cottage by the Bay

Top guest favorite

Cottage in Gulfport

4.99 out of 5 average rating, 274 reviews

Gulfport Art District - One Block From Beach!

Private cottage rentals

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

4.85 out of 5 average rating, 137 reviews

Family Friendly Beach Cottage in Madeira Beach, FL

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

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.

Cottage in Holmes Beach

5 out of 5 average rating, 32 reviews

Hibiscus Villa by Beach Boutique Rentals

A serene sunset casts amber and golden hues across the ocean. Silhouetted against the vibrant sky, a figure walks along the beach, with gentle waves lapping at the shore. Tall grasses frame the foreground, adding a natural touch to the tranquil scene.

Cottage in Sarasota

4.83 out of 5 average rating, 127 reviews

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

Top guest favorite

A round dining table with a dark wood finish is accompanied by four white wooden chairs. The chairs feature a classic design, and the arrangement is set on a light marble floor, with kitchen cabinetry visible in the background.

Cottage in Madeira Beach

4.93 out of 5 average rating, 137 reviews

Flipper's @ Mad Beach Cottage

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, 24 reviews

Kamp Komfort Historic Family Beach House

A newly renovated kitchen and living area is seen, featuring modern appliances and white cabinetry. A comfortable gray sofa, accented with throw pillows, complements a small wooden table set for two. Natural light floods in through glass doors, which provide access to an outdoor space.

Cottage in Bradenton Beach

4.91 out of 5 average rating, 197 reviews

Ebb Tide @ Tides Inn

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, 198 reviews

*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*

Luxury cottage rentals

A charming duplex features a bright pink exterior with white awnings. A swing and patio chairs are located in the front yard, surrounded by potted plants. Bicycles are parked nearby, enhancing the inviting atmosphere of this beachside property.

Cottage in Clearwater

4.77 out of 5 average rating, 153 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

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

4.91 out of 5 average rating, 80 reviews

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.

Cottage in Indian Rocks Beach

4.5 out of 5 average rating, 10 reviews

3 Palms Beachfront Cottages - Beachfront

An aerial view captures the expansive stretch of Siesta Key Beach, highlighted by its soft, sandy shoreline and clear blue waters. Luxurious beachfront properties and lush greenery are visible along the coast, with a vibrant city skyline set against the horizon under an unobstructed blue sky.

Cottage in Sarasota

4.93 out of 5 average rating, 15 reviews

Siesta Key Cottages Crescent 3 Beach/Pool/Hot Tub

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

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, 92 reviews

Quaint Cottage,150 steps away from Crescent Beach!

Top guest favorite

A private heated pool is framed by lush tropical landscaping, presenting a serene setting. Multiple white lounge chairs surround the pool, complemented by a dining table. Nearby, vibrant greenery enhances the tranquil atmosphere under a clear blue sky.

Cottage in Anna Maria

4.96 out of 5 average rating, 24 reviews

Charming cottage w/heated pool in prime location.

A vibrant pool area is surrounded by tropical palm trees and colorful cottages. The clear, inviting pool is accompanied by a hot tub and a thatched-roof tiki bar, providing a relaxed atmosphere. Paved stones create an open layout, enhancing the inviting outdoor space.

Cottage in Indian Rocks Beach

4.92 out of 5 average rating, 38 reviews

Seaside Retreat Cottages #1

Quick stats about cottage rentals near Anna Maria Island

Total rentals
70 properties
Nightly prices starting at
ﺩ.ﺇ441 before taxes and fees
Total number of reviews
2.8K 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