Bungalow rentals near Anna Maria Island

A pool area is surrounded by vibrant tropical landscaping, featuring lounge chairs arranged around a circular pool. Soft lighting illuminates the scene, enhancing the greenery. In the background, a pink float adds a playful touch to the inviting ambiance of the outdoor space.

4.93 out of 5 average rating, 177 reviews

Neptune's Nest | Amazing Htd Pool | Steps to Beach

An original early 1900 Indian Rocks Beach bungalow, updated with all the comforts of home. Grill on your private patio or relax in the pool area in our tropically landscaped grounds. Cross Gulf Boulevard to 8th Ave beach access to the beautiful turquoise waters and white sandy beaches of the Gulf of Mexico. Enjoy swimming, shelling and fishing as you live the island life. Splash Harbour water park, shops and restaurants are within walking distance. Come for an unforgettable stay! City tax#1479

4.92 out of 5 average rating, 384 reviews

Pool & fenced-in yard in downtown edge bungalow

MESSAGE ME FOR DAYS U DONT C. This 2 bed-2 bath house is an original Florida bungalow with wood floors & natural light in quiet neighborhood on downtown core edge. Spacious, private fenced-in backyard with pool, covered grill and eating area. Minutes away from Siesta and Lido beaches, the Legacy Trail, Bay and Payne parks, dining, live music, bars, theatres, comedy, opera, performance venues, comedy club, antiquing, kayak launches, tennis and basketball courts, farmer's market, shopping & more.

The exterior of a mid-century modern house showcases a vibrant blue facade with large windows. A covered porch is accessible, providing shade. Lush greenery and palm trees frame the property, with a gravel pathway leading to the entrance. A spacious yard is visible, enhancing the inviting atmosphere.

4.89 out of 5 average rating, 198 reviews

Beach Bungalow 1 Block to Sand w/Private Pool

CLEAN - CUTE Mid-Century Modern w/New Pool & New A/C in Cozy Quiet Neighborhood 1 Block (2 min. walk) to Beach, and Walking Distance to Restaurants, Bars and Shops. Water Activities & Sand are at your fingertips, so come enjoy what the “Old Florida” town of Indian Rocks Beach has to offer. Fully Furnished 3 Bedroom 2 Bath House with all linens, towels, cookware and utensils. Walk-In Double shower. Patio Furniture/Gas Grill. Smart TV & WiFi. BeachWagon/Chairs/Umbrella/Towels/Cooler. (BTR#2185)

4.9 out of 5 average rating, 111 reviews

Bungalow in Palmetto

Island Home 5 min to Park, 25 min to Beach, Pool

Soak up the relaxing Florida weather from this inviting 1969 home on Snead Island! Whether it's the oceanside air, or the beachy design of this impeccably clean vacation rental, guests find themselves relaxing as soon as they arrive. Our light-filled interior includes a fully equipped kitchen and all the comforts of home. Spend time by the pool & hot tub, then head to the shores of lovely Anna Maria Island 14 miles away for a beach picnic just in time for sunset! Message me about multiple pets

4.97 out of 5 average rating, 200 reviews

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

DIRECT BEACHFRONT BUNGALOW "MARLIN'S HIDEAWAY." Rare free standing direct beach front house! with private sandy beach backyard! NOT a condo - No crowded elevators, hallways, lobby area, NO faraway parking spaces FEATURES: Great room plan, Sleeps 6, 2 BR + sleeper sofa, all SMART TVs, high speed Wi-Fi. Kitchen is fully equipped. Bathroom is tub/shower with seat. Approx 850 sq ft. Private, fenced deck - PETS ok. BARRETT BEACH BUNGALOWS is a boutique resort ONLY 4 bungalows share heated pool

Bungalow in Bradenton Beach

A tranquil outdoor space features a wooden dining table surrounded by eight chairs set on a tiled patio. A small, curved swimming pool is framed by lush tropical plants, and umbrellas provide shaded areas. The vibrant greenery creates a serene atmosphere.

Bougie Bungalow at the Beach

This newly renovated, completely private, comfortable Anna Maria Island bungalow is super clean & very comfortable. It has an open, split floor plan, 2 king bedrooms, each with private baths, separate dining and Florida room & is only 3 houses from the amazing white sand beach, the bay & Pier. Only 1 block over is Historic Bridge Street with cool restaurants, mini golf, quaint shops & bars with live music. Once here, you never need to drive -everything is within a block walking distance!

4.91 out of 5 average rating, 127 reviews

The exterior of the bungalow showcases a single-story structure with a welcoming entrance. The driveway extends alongside a lush green lawn, while tropical landscaping, including palm trees and bushes, frames the home, creating a relaxed and inviting atmosphere.

4.93 out of 5 average rating, 123 reviews

Cheerful 3BR Home•Walk Downtown•Close to Lido Key

Relax Near the Bay-Ideal for Families & Professionals Welcome to Bayview Bungalow-your stylish Sarasota retreat just steps from the bay! This 3-BR, 2-bath home is perfect for families and professionals. Enjoy: •A fully stocked kitchen •Free driveway parking •Fenced yard with BBQ •Beach gear & supplies included Walk across the street to Bay Park, grab coffee at a nearby café, or catch a show at Van Wezel Performing Arts Center. Minutes from Lido Key, St. Armands, and downtown hotspots.

A spacious, screened-in lanai surrounds a shimmering pool, complemented by comfortable seating and a dining area. Light filters through the enclosure, highlighting the pink exterior walls of the home. Toys and colorful items are visible at the poolside, adding a playful touch.

4.84 out of 5 average rating, 187 reviews

Pink Flamingo: 4 Beds/3 Baths Screened Pool Oasis

This wonderful pool home is located in the heart of Sarasota and just minutes away from the world-famous Siesta Key Beach! This fantastic vacation home offers 4 relaxing bedrooms and 3 full baths - there is also a Queen-size pull out sofa in the living room. A real bonus is having two master suites! The first offers a King-size bed with an adjoining bathroom featuring a walk-in shower plus his & her sinks. The second master is appointed with a Queen-sized bed and adjoining bathroom.

4.84 out of 5 average rating, 207 reviews

Bungalow in Anna Maria

Bay Breeze Cottages #3

Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.

A serene beach scene captures gentle waves lapping against the shore. The tranquil ocean extends towards a clear blue sky, creating a calm and peaceful atmosphere. Soft sand covers the foreground, while the horizon showcases a seamless blend of sea and sky.

4.92 out of 5 average rating, 306 reviews

Beach Bungalow -Step in to the Sand! Indian Shores

If you are looking for a 5 star vacation this is your place! Floor to celing everything is brand new! Step on to the white sandy beach from our front porch. We have totally refreshed our private 2 Bed, 1 Bath, slice of paradise and it will melt your stress away. This Charming Bungalow is perfect for any vacation. Indian Shores is centrally located between St. Pete Beach and Clearwater Beach. Pinellas County is full of shops, restaurants, and activities. Book with us now!

Bungalow in Redington Beach

Single Family Home One Level ~ Walk to the Beach!

The Beachhouse has been completely renovated since Hurricane Helene; including all new electrical, new mini-split AC in every room, brand new cabinets and appliances in the kitchen and new fixtures in the bathrooms. This 3 bedroom, 2 bath Beach Bungalow is the perfect home for your vacation to the Beach! Relax or entertain, have a cookout in the private fenced in backyard, make a fire in the fire pit. Walk to the beach we have chairs, umbrellas, toys & a cart!

4.93 out of 5 average rating, 269 reviews

An aerial view showcases a cluster of charming two-story homes nestled near the beach. The golden hues of the sunset reflect off the water, while the sandy shore and gentle waves create a serene coastal atmosphere.

5.0 out of 5 average rating, 251 reviews

Quiet Beachfront Bungalow on Florida’s Gulf Coast

Welcome to The Sunset Beach Bungalow! This top-floor luxury water-front home located in Indian Shores, FL has been completely remodeled. Our serene getaway is situated on the Gulfs Coast. The large deck looks out over the water, providing a calming sanctuary to which you can retreat any time of day or night. Our home is over 1000 sq. ft and is newly furnished with plenty of room to relax during your stay. Our beach is private so there aren’t large crowds!

Popular amenities for bungalow rentals near Anna Maria Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Beachfront bungalow rentals

Bungalow in Clearwater Beach

A living area is displayed, featuring a gray sofa with colorful cushions and a coffee table. A dining table with chairs is positioned nearby, and artwork adorns the walls. Sunlight enters through a window, illuminating the beige tiled flooring.

Villa 4 -1 BR, 2 min walk to beach,

4.89 out of 5 average rating, 262 reviews

Bungalow in Bradenton Beach

A bright living area features light walls and soft furnishings. A cozy sofa faces a modern television displaying a beach scene. A circular mirror adds depth, while a wooden table and chair provide a comfortable workspace. Natural light fills the space through sheer curtains.

Barefoot Boho- Breezy Bungalow on the Beach!

4.98 out of 5 average rating, 46 reviews

Bungalow in Redington Beach

Redington Beach Bungalow steps to Private Beach

4.95 out of 5 average rating, 22 reviews

4.92 out of 5 average rating, 97 reviews

Heated Pool, Hot Tub/Spa, Sleep Number Beds, Beach

Bungalow in Davis Islands

The exterior of the bungalow features a charming blue brick facade, complemented by white trim and shutters. A red electric buggy is parked in the foreground, while cozy yellow chairs are positioned on the porch behind a white railing, surrounded by well-maintained greenery.

Davis Island Bungalow

4.99 out of 5 average rating, 79 reviews

4.43 out of 5 average rating, 7 reviews

Bungalow in Sunset Beach

Unit 14 I Renovated 2 BR Beach Bungalow

4.81 out of 5 average rating, 69 reviews

Completely renovated Beachfront Bungalow

A sandy path leads through tall grass toward the beach, flanked by wooden walkways. Nearby signs indicate beach access, and buildings are visible on either side. The bright blue sky is dotted with a few white clouds.

4.74 out of 5 average rating, 42 reviews

Sea La Vie Cottage by the Beach - Unit B

Private bungalow rentals

4.96 out of 5 average rating, 160 reviews

The charming bungalow is presented with a yellow exterior and contrasting blue shutters. A welcoming front porch features a light fixture, while steps lead to the entrance. Lush greenery and neatly arranged plants enhance the front yard, contributing to the inviting appearance of the home.

Bungalow in Bradenton

Sugar Sand Cottage -beach 8 miles away

A modern kitchen features white cabinetry and black appliances, including a spacious black refrigerator and oven. A window provides natural light over a wooden countertop, accentuated by decorative items. The patterned floor tiles add contrast to the overall design, creating a functional cooking space.

4.99 out of 5 average rating, 122 reviews

Luxury - Pet Friendly, Farmhouse Bungalow DT Tampa

A kidney-shaped deep-water pool is framed by a modern patio featuring light-colored pavers. Lounging chairs positioned on the side invite relaxation. Surrounding tropical landscaping includes palm trees and lush greenery, enhancing the tranquil outdoor setting that is privately fenced.

4.93 out of 5 average rating, 101 reviews

Tropical 3bd bungalow with pool! Walk to Bayshore!

4.82 out of 5 average rating, 223 reviews

A spacious living area features a leather sofa and loveseat centered around a decorative stone fireplace. A wall-mounted television is positioned opposite the seating, and a round mirror hangs above a vintage-style coffee table. Natural light filters in through the windows, enhancing the room's welcoming ambiance.

Bungalow in Clearwater

Sweet Craftsman home, free bikes, near beach & DT

Bungalow in Historic Kenwood

3 BR Garden Bungalow in Historic Kenwood

4.98 out of 5 average rating, 138 reviews

A well-lit bedroom features a spacious bed with a floral-patterned quilt. Natural light filters through two windows, illuminating the neutral-toned walls. A wooden dresser and a bedside table with a lamp complement the serene atmosphere. A comfortable chair is placed in one corner of the room.

4.87 out of 5 average rating, 143 reviews

Cute home! Near D’town Sarasota/Beaches

4.92 out of 5 average rating, 130 reviews

Bungalow in Clearwater

Permaculture Homestead

4.98 out of 5 average rating, 123 reviews

Luxury Stay • Hot Tub & Heated Pool • Fenced Yard!

Other bungalow holiday rentals

The charming exterior features a blue wooden house with a welcoming front porch. Two bright yellow chairs sit invitingly on the porch. Lush greenery surrounds the home, and a white picket fence adds to the inviting atmosphere. A decorative plant is positioned beside the door.

4.94 out of 5 average rating, 142 reviews

•La Casa De Belen• Bungalow in Ybor City!

Bungalow in Treasure Island

A serene beach scene features soft sand meeting calm, turquoise waters under a clear blue sky. Gentle waves create a subtle shoreline, inviting relaxation and tranquility.

YOUR VACATION HOME

4.91 out of 5 average rating, 128 reviews

Bungalow in Tampa Heights

A spacious dining area features a large wooden table surrounded by six dark upholstered chairs. Light reflects off a large mirror, while a stylish chandelier hangs above. In the background, a cozy living room is partially visible with ample natural light filtering through the windows.

Prime Location: Stylish 2BR w/ Cozy Outdoor Dining

4.98 out of 5 average rating, 140 reviews

A spacious backyard is shown, featuring a vibrant green lawn and shaded areas created by large umbrellas. Comfortable lounge chairs are positioned under the shade, while potted plants add a touch of greenery. A covered seating area can be seen in the background.

4.98 out of 5 average rating, 104 reviews

Welcome to The Plaza Tampa

Bungalow in St. Petersburg

The exterior of the cottage features bright blue siding and a welcoming yellow front door, framed by lush green grass and palm trees. A charming white picket fence encloses the yard, providing a serene outdoor space. Light filters down from a clear blue sky.

Crescent lake Mins to Downtown Hot Tub

4.96 out of 5 average rating, 102 reviews

4.8 out of 5 average rating, 41 reviews

Bungalow in Holmes Beach

Steps to Beach |Heated Pool+Spa|Direct Pool access

4.98 out of 5 average rating, 57 reviews

A charming beach cottage entrance showcases a covered porch with white railings and steps leading up to the door. Lush tropical plants frame the path, while blue siding reflects a coastal vibe under a clear blue sky.

Bungalow in Holmes Beach

LAZY PALM COTTAGE, HEATED POOL, STEPS TO THE BEACH

5.0 out of 5 average rating, 11 reviews

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay

Other great holiday rentals near Anna Maria Island

4.98 out of 5 average rating, 125 reviews

Home in Bradenton Beach

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

Cottage in Bradenton Beach

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.

Bradenton Beach Sunsets 2, Anna Maria Island, FL

4.98 out of 5 average rating, 257 reviews

5.0 out of 5 average rating, 108 reviews

Home in Anna Maria

Bean Pt. Bungalow - Half duplex w/private pool

Apartment in Holmes Beach

#terraceLIFE | 2 Blocks to Beach | Heated Pool

4.88 out of 5 average rating, 112 reviews

Apartment in Holmes Beach

Steps to the beach! Condo with pool at The Terrace

4.96 out of 5 average rating, 111 reviews

Townhouse in Holmes Beach

An aerial view captures the coastal neighborhood, showcasing a collection of charming homes with grey rooftops. The vibrant blue ocean and sandy beach are visible in the background, while lush palm trees surround the area, contributing to the serene island atmosphere.

Steps from Beach! Heated Pool & Spacious Lanai!

4.98 out of 5 average rating, 172 reviews

4.96 out of 5 average rating, 282 reviews

A private outdoor space featuring a heated pool and spa, surrounded by palm trees and lounge chairs. The vibrant blue cottage is visible in the background, complemented by carefully arranged landscaping. A pathway of stepping stones leads toward the entrance of the cottage.

Cottage in Anna Maria

Turtle Cottage - Anna Maria Island