Vacation rentals in Anna Maria

A light and airy bedroom features a spacious bed with striped linens, complemented by a soft area rug. Large glass doors open to the outdoor plunge pool area, providing a view of the patio. A ceiling fan and a decorative wall piece enhance the inviting space.

4.96 out of 5 average rating, 180 reviews

Be an AMI

This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.

4.93 out of 5 average rating, 123 reviews

A view of the beach featuring three blue adirondack chairs positioned on the sandy shore. In the background, the ocean sparkles under the sunlight, with gentle waves lapping at the beach. A small palm plant and coastal vegetation add a natural touch to the scene.

Condo in Bradenton Beach

Beach Escape & Pool, steps to Beach & restaurants

One block from beautiful beach and waterfront dining. Newly renovated Villa #1 in quaint condo building close to everything Anna Maria Island has to offer. Pickleball court across the street. Pool literally out your back door. Perfect for a small family or a romantic getaway. 2 minute walk to beach, trendy Bridge Street shops, marina, waterfront restaurants, bars, boat tours, mini golf and more. Brand new appliances, well-appointed kitchen has everything you need. Beach supplies in condo.

4.98 out of 5 average rating, 117 reviews

Condo in Bradenton

KING Bed + AMI Beaches!

🎙️🦩Welcome to the Retro Flamingo! Your tropical getaway that combines style, fun, and the serene beauty of the Gulf Coast. This cozy, vibrant themed condo is the perfect destination for your next Beach vacation. Walking distance to Palma Sola Beach Causeway, where you can enjoy sun-bathing, horseback riding, jet skiing, and fishing! 5 mins or less from the Gulf of Mexico and powdery white sand beaches of Anna Maria Island! Kick back and relax in this retro “Old Florida” themed condo!

4.97 out of 5 average rating, 154 reviews

A landscaped path featuring stepping stones leads through a tropical garden. Lush greenery, including palm trees and shrubs, is surrounded by gravel and stone accents. A staircase leading to the upper level is visible in the background, enhancing the inviting outdoor space.

Apartment in Anna Maria

Beach Don't Kill My Vibe by Beach Boutique Rentals

*Features include* * Modern vacation rental directly on Pine Ave! * King bedroom with TV * Queen bedroom with TV * Bathroom with walk in shower * Small kitchenette with full-size refrigerator * Private deck with table and umbrella * Private back yard with putting green and outdoor seating * Off-street parking for one vehicle * Trolley stop across the street * Walkable to all shops and restaurants on Pine Avenue * Beach chairs, umbrella, and cart * Steps to the beach!

5 out of 5 average rating, 19 reviews

A private hot tub with bubbling water is situated under a covered patio, surrounded by tropical plants. A pathway lined with lush greenery leads further into the property, enhancing the serene setting for relaxation.

Tiny home in Bradenton

Romantic Luxe Tiny Home+ Hot Tub

Escape to a tropical paradise in this brand new luxury tiny home, nestled among palm trees. Relax in the private hot tub. Just 6 miles to Anna Maria. Ideal for a romantic getaway or a peaceful retreat. We are located in a quiet neighborhood with a 10PM noise ordinance. If you want a quiet relaxing getaway, our tiny home is perfect for you. A car is recommended in this area as there is limited public transportation. The best rental car rates can be found at TPA/SRQ airport.

A private heated pool oasis is surrounded by lush greenery and tropical plants. Comfortable lounge chairs are positioned around the circular pool, while a BBQ grill is set against a wooden fence, providing an ideal space for relaxation and gatherings.

4.99 out of 5 average rating, 115 reviews

1 block to Beach on Pine Ave! Private Pool Oasis

Sat-Sat rentals, usually... Our 3 bedroom, 2 bath townhouse, with a private heated-pool oasis, is on Pine Ave in the heart of Anna Maria - 1 ½ blocks from the best white sand beach on the island - 3 blocks in the other direction to the bay - from sunrise at the City Pier to Sunset on the Gulf of Mexico. Walk or ride a bike to all the quaint stores, shopping and restaurants (plus the local doughnut, taco shop and Northshore Cafe next door) without ever getting in your car!

Superhost

An aerial view captures the scenic stretch of white sandy beach merging with the turquoise Gulf waters. Nearby, a collection of homes is nestled among lush greenery, while the coastline extends toward the horizon under a clear blue sky, showcasing a serene vacation destination.

Condo in Anna Maria

4.88 out of 5 average rating, 33 reviews

Barefoot Mermaid 4, steps to the beach

Welcome to Barefoot Mermaid 4 a relaxed ground floor vacation rental located on the north end of gorgeous Anna Maria Island. The serene location of this property is just amazing. Located steps, less than 50 ft to white powder sand beaches of the Gulf of Mexico and less than a few flip flop steps to the restaurants and shops on Pine Ave and the free island trolley service. Barefoot Mermaid 4 is the Southwest unit of 4 units located within The Gulf Queen Apartments.

Cottage in Bradenton Beach

A wooden boardwalk extends along the beach, lined with colorful Adirondack chairs in shades of blue and green. Thatched umbrellas provide shade over small patio tables, with the turquoise waters of the Gulf visible in the background under a partly cloudy sky.

4.99 out of 5 average rating, 173 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.

4.98 out of 5 average rating, 106 reviews

Townhouse in Anna Maria

CHARMING HOUSE W/HEATED POOL,STEPS TO BEACH UNIT B

Location! North end of Anna Maria Island . This charming two story duplex- each unit has two bedrooms , one bathroom. Rent one unit or both. Perfect for a group of extended family and friends. Steps to the Bean Point Beach . Includes beach chairs, umbrellas and all you need for a perfect day at the beach! Heated pool , private seating, grilling areas, bicycles and much more available. MAX Occupancy 4 people including children of any age.

An open concept living area is showcased, featuring a central kitchen island with a granite countertop and dual sinks. Sunlight floods through multiple glass doors, enhancing the spaciousness, while a cozy seating area is positioned around a fireplace, visible at the far end.

4.94 out of 5 average rating, 106 reviews

The Peachy Beach House, steps to the gulf

Hurricane season cancellation possible. Saturday-Saturday for check-in and out. Two bedroom, 2 full bathroom, new heated private pool Steps from semi-private gulf beach, this 3 story on a quiet street in N. HB Well-stocked kitchen, 2 TVs, large master which is more like resort suite with new tempurpedic king bed Gulf views from bedrooms. You’ll find: crib, high chair, beach chairs, wagon, canopy, beach toys and towels!

4.96 out of 5 average rating, 239 reviews

Cottage in Anna Maria

Turtle Cottage - Anna Maria Island

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. Spectacular sunrises are just a short walk away at the Rod and Reel Pier, and the sunsets at Bean Point Beach are second to none, just a few blocks away. This great getaway sleeps up to 4.

5 out of 5 average rating, 31 reviews

A wooden pier extends over the calm waters, featuring a rustic sign that reads 'Rod & Reel Pier' above. A blue bicycle rests at the side, while a few beach umbrellas and chairs are set up along the shore, providing a peaceful seaside atmosphere.

Guesthouse in Anna Maria

The Boathouse

Would you like to feel like you are sleeping in a tree house with all the luxuries and comfort of a high end hotel? Then welcome to our brand new guest house, which accommodates a maximum of two guests and is a completely private tropical oasis. Standing on the edge of Lake LaVista, surrounded by tropical palms where you have use of the private and beautiful pool which we heat during the winter months.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Bungalows

Intimate homes. inviting architecture

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Anna Maria vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Anna Maria

An inviting outdoor area features a modern swimming pool surrounded by lush green grass and palm trees. A mini-golf course is visible, along with a covered seating area with dining furniture, providing ample space for relaxation and entertainment.

5 out of 5 average rating, 3 reviews

Beach! Spa, PuttPutt, Beach Gear, Pool Table&More

CoryRating, 5 stars2 months ago

We had an amazing stay at this beautiful Florida home! Absolutely loved our time here! The property was spotless, spacious, and had all the amenities you could ask for. The outdoor space was perfect, with a private pool/hot tub and landscaping that made it feel like a personal oasis. The location was perfect—close to the beach, great restaurants, and local attractions, but still peaceful and quiet at night. The host was super responsive and friendly, making sure everything went smoothly. We would absolutely stay here again and recommend it to anyone looking for a relaxing and fun Florida escape!

A bright dining area features a rustic table surrounded by woven chairs. Natural light pours in through large windows, offering views of the outdoor space and water. A stylish chandelier hangs above the table, and a cozy seating area is visible in the background.

5 out of 5 average rating, 8 reviews

Bayfront Beach access with Heated Pool!

DarciRating, 5 stars1 month ago

3 couples Spent 9 days of pure relaxation in this charming beach home with the best homey beach vibes and decor. The home is bright and Sunny with a private backyard that looks straight through the garage port to the beautiful ocean waters right from the pool when the garage door is open. The whole front of the house has a beautiful view. Great for sitting out on the deck and people watching . We could even see dolphins out there swimming from the house. All kinds of thoughtful personal touches and amenities were taken into consideration when thinking of guests and their vacation needs. We wouldn’t hesitate to rent this house again in the future. We felt right at home.

A spacious living area features a large sectional sofa, a wicker coffee table, and warm wooden ceilings. Natural light floods the room through multiple windows and doors. A cozy armchair and vibrant area rug complement the inviting layout, creating a relaxed atmosphere for gatherings.

4.79 out of 5 average rating, 215 reviews

Charming Beach house amongst huge Banyon Trees

KaleyRating, 5 stars5 days ago

My husband and I had a wonderful stay at Kim’s Airbnb! Great location, close to the beach, and lots of restaurants around. We plan on coming back!

A heated saltwater pool and spa are surrounded by lush greenery and palm trees. Lounge chairs and an outdoor dining area with umbrellas are positioned on the pool deck, providing shaded spaces for relaxation. White fencing offers privacy in this tranquil outdoor setting.

5 out of 5 average rating, 15 reviews

Pineapple Paradise! 1 block to Beach access!

TonyRating, 5 stars8 months ago

Amanda was the ideal host, lighting quick responses and so helpful. The place was just as described in the listing and very clean. The pool was so nice and relaxing. We are already thinking about our next stay at Pineapple Paradise!

An aerial view showcases the duplex surrounded by lush greenery and residential homes, with the beach visible in the distance. The coastline features gentle waves under a clear blue sky, while the quaint neighborhood is highlighted by a mix of tropical landscaping and well-maintained gardens.

4.89 out of 5 average rating, 18 reviews

1BR | Enclosed Yard | Deck | AC | W/D

HaydenRating, 5 stars8 months ago

10/10!! Beautiful, clean, and just steps from the beach!! I will definitely be returning. Thank you so much for making my vacation easy, cozy, and one to remember.

A private gazebo is situated on a well-manicured lawn, providing seating under a shaded roof. Two lounge chairs are positioned nearby, inviting relaxation in the sun. Surrounding greenery enhances the tranquil outdoor setting.

5 out of 5 average rating, 14 reviews

Shore's Nice - Private home across the street

JacquelineRating, 5 stars1 week ago

Location was perfect! We loved being steps away from the beach! The house was clean, nicely decorated and well equipped. It felt like a second home! Would definitely stay here again! We highly recommend this home!

Townhouse in Holmes Beach

5 out of 5 average rating, 15 reviews

Townhouse 200 Steps to the Beach

DarylAnnRating, 5 stars4 months ago

We were Barb’s first guests after the hurricanes and the townhouse was beautiful! She has provided lots of extras to make your stay as comfortable as possible. Her place is close to many great restaurants as well as the beach. Barb was very attentive to all of our needs and questions. We would highly recommend her townhouse to others, and we’re looking forward to staying here again in the future.