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Vacation rental beach houses in Anna Maria

Vacation rental beach houses in Anna Maria

Book beachfront vacation rental houses, cottages, and more on Airbnb

Top-rated houses in Anna Maria

Guests agree: these stays are highly rated for location, cleanliness, and more.

Anna Cabana B
SUPERHOST
Entire house · 4 guests · 1 bed · 1 bath

Anna Cabana BAnna Cabana B is the perfect getaway, it has it's own private pool, patio, private entrance and driveway. A queen bedroom and a sofa bed will accommodate four, or it is just perfect for a getaway for two! Fully updated kitchen allows you to whip up a fabulous meal or perhaps the outside gas grill will entice you to grill up some freshly caught fish. This property also features professional linen service. Landscaping and fence provide plenty of privacy. Unit is a duplex with Anna CabanaA

Charming house w/heated pool,steps to beach-Unit A
SUPERHOST
Entire house · 4 guests · 3 beds · 1 bath

Charming house w/heated pool,steps to beach-Unit ALocation! 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 who want their own place but still be right together as a group. Heated inground pool, 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.

Shell House - 100 steps to the Beach! Clean & Cozy
Entire house · 6 guests · 4 beds · 2 baths

Shell House - 100 steps to the Beach! Clean & CozyLess than a minute walk to the beach! Watch the sunset from the house! Shell House is a two-story, 3-bed, 2-bath, multi-level fun-house on a large shady lot in a quiet residential neighborhood. Only two blocks from popular shopping & dining you’ll never run out of things to do! Fully equipped kitchen with all you’ll need for island cooking and entertaining. Comfortable dining for 8. Beach chairs, umbrellas, a cooler & 2 beach carts w large inflated tires for easy rolling over sugar sand.

Vacation rentals for every style

Get the amount of space that is right for you

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Popular house amenities in Anna Maria

  • Pool
  • Pets allowed
  • Air conditioning
  • Kitchen
  • Wifi

Cottages in Anna Maria

SUPERHOST
  1. Entire cottage
  2. 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.

ﺩ.ﺇ742 per night
SUPERHOST
  1. Entire cottage
  2. Anna Maria
Adorable Pine Ave Cottage ❤️Walk to Beach and Bay!

An island place is located right in the heart of Anna Maria Island's historic Pine Avenue. Just a short stroll to both the Gulf of Mexico and the brand new Anna Maria City Pier! This old Florida style one bedroom cottage, with high beamed ceilings, wood floors and shabby chic décor throughout is ideal spot for a vacation getaway! We are DOG FRIENDLY! A fee of $155 is required in advance for each dog you are bringing. Please see House Rules.

ﺩ.ﺇ698 per night
SUPERHOST
  1. Entire cottage
  2. Bradenton Beach
The Anchor Cottage 2

Anchor Cottage 2 is an Old Florida lifestyle on an amazing island like no other. Cottage offers 2 bedrooms, 1 bath, full kitchen, washer/dryer and is located 100 yards from the Gulf of Mexico beaches.

ﺩ.ﺇ979 per night
  1. Entire cottage
  2. Anna Maria
The Barefoot Gypsy-Quaint remodeled beach cottage

The Barefoot Gypsy is an enchanted cottage tucked in the north end of Anna Maria Island in the City of Anna Maria, .Florida, mere steps to the white powder sands of Tampa Bay leading to Bean Point and the Gulf of Mexico. The Barefoot Gypsy will be a home to revisit through the years to feel the charm of a true beach cottage. I welcome you to the cottage and hope you will feel the warmth and charm I share with you. Welcome! "The Barefoot Gypsy"

ﺩ.ﺇ1,204 per night
  1. Entire cottage
  2. Bradenton Beach
50 Steps to Beach🏖. Hot Tub! 1bd modern cottage🏝

Luxury Beach Cottage w/ HOT TUB, Fire Pit & BBQ. 1 bed/2bath sleeps 4 This is your chance to enjoy a unique getaway on the nicest beach! Stay in our newly remodeled beach cottage. White sandy beach & turquoise water is literally 50 ft from the door. Everything you need for a delightful & relaxing day at the beach is included. Chairs, beach towels, umbrella, snorkels, masks & a cooler. Enjoy the convenience of this premium location across Gulf blvd to Beach.

ﺩ.ﺇ1,084 per night
  1. Entire cottage
  2. Bradenton
Starfish Cottage Walk to beach, 8+eateries & bars

Welcome to the Starfish Cottage in historic Cortez Fishing Village, one of Florida's last working fishing village. An easy 1.3 mile walk to beautiful Anna Maria Island and glorious Florida beaches. Cortez has world famous Tyler's ice cream & bars/restaurants, several with regular music. 1 BR has a queen bed & the other has a trundle bed with 2 twin beds that can connect to make a king. Real wood floors, screened in backporch with grill, covered deck with outside seating, & large fenced yard.

ﺩ.ﺇ389 per night
SUPERHOST
  1. Entire cottage
  2. Bradenton Beach
Beach Cottage with private garden

Experience staying in a historic Anna Maria Cottage! This beautiful two bedroom one bath cottage with enclosed garden is in the middle of Bradenton Beach, only one and a half blocks from the beach and one and a half blocks from the bay.

ﺩ.ﺇ731 per night
SUPERHOST
  1. Entire cottage
  2. Holmes Beach
Cozy Cottage by the Beach sleeps 6 - Seascape

Welcome to Holmes Beach Hideaway. Seascape is a newly updated and redecorated 2 Bedroom (Sleeps 6) beach cottage 1.5 blocks to the Gulf, just walk around the corner to a quiet almost private beach access. Access to 8 restaurants and shopping are directly behind the cottage. No need for a car! Free trolley pickup is one block away. Brand New Hurricane rated windows and doors installed June '18. *Please read the important notes under "The Space"

ﺩ.ﺇ674 per night
SUPERHOST
  1. Entire cottage
  2. Bradenton Beach
Tides Inn 2 on the Bay

Newly renovated mid century beach bungalow. Both the beach and bridge street are within a few minutes walk from this great location. Boat dock recently added for guests to enjoy. Please ask for details if bringing a boat.

ﺩ.ﺇ742 per night
SUPERHOST
  1. Entire cottage
  2. Holmes Beach
Luxurious Tropical Villa by the Beach~Pet friendly!

Island Garden Villas will amaze you with it's old Florida charm and lush tropical surroundings. Orchid Villa is a true island oasis! *Features include* * 2 Bedrooms and 2 full baths * King bed, Queen bed and Queen sleeper sofa * Botanical courtyard with beautiful fountain * Stunning tropical landscape * Secluded back patio with sectional outdoor sofa * Only steps away from the beach path * Beach supplies provided * Ground level * Dog and small pet friendly!

ﺩ.ﺇ735 per night
SUPERHOST
  1. Entire cottage
  2. Anna Maria
MorSea Cottage: A Beachside Oasis

Welcome to MorSea Cottage. This beautiful house is located on a quiet street on Anna Maria! There are 4 bedrooms 3 full baths and 2 half baths. The beach is just steps away!

ﺩ.ﺇ1,267 per night
  1. Entire cottage
  2. Bradenton Beach
Darling "Cottage" Just Steps From The Gulf!

Our charming "Cottage By The Sea" is situated just a few steps from the beautiful Gulf of Mexico beaches on Anna Maria Island in the quiet end of Bradenton Beach. The cottage is a delightful throwback to "Old Florida" and is updated with bright and sunny décor, two private bedrooms, 1 full bath, sleeper sofa, full kitchen appliances with utensils, a washer/dryer laundry area and lovely gardens w/ grill and patio seating. You can leave your worries behind - you are in paradise!

ﺩ.ﺇ882 per night

Pet-friendly houses

SUPERHOST
  1. Entire house
  2. Holmes Beach
Anna Maria Island Duplex w/ private pool (side B)

Anna Maria Island duplex located in the Holmes Beach area. The side being rented sleeps 10, has its own private pool, is 3 blocks from beach access, 1 block from the free trolley stop & 1 block to Holmes Beach town center's restaurants, shopping & bars.

ﺩ.ﺇ1,286 per night
  1. Entire house
  2. Anna Maria
Anna Maria beachfront house - The Magnolia Lady

Amazing, newly redone 1912 bungalow on beautiful Anna Maria Island beach. Sleeps 10! 4/4.5 - bathrooms in each room! Incredible sunsets from the porch, comfy decor with awesome amenities with coffee stations in each room, huge flat screens, streaming video, and gourmet kitchen items. Majestic vacation rental located in the best spots on the island, close to local shopping, the best eatery's and much more. Come stay in our home and enjoy it as your own you will not regret it and likely return!!

ﺩ.ﺇ1,983 per night
SUPERHOST
  1. Entire house
  2. Holmes Beach
Captain's Quarters at Spinnakers Vacation Cottages

My place is close to the beach, family-friendly activities, nightlife, and the free AMI trolley. You’ll love my place because of the high ceilings, the location, and the ambiance. It is located in the lush tropical paradise of Spinnakers Vacation Cottages. With a large living room, dining area and large master suite, it is perfect for couples, families (with kids), and furry friends (dogs, with a small pet fee). Spa maintains same temperature as pool. Captains Quarters also has Private patio!

ﺩ.ﺇ1,168 per night
SUPERHOST
  1. Entire house
  2. Holmes Beach
Ohana Hale North 1 Bedroom

Aloha and welcome to our Island Home. Ohana is Hawaiian for family and that is who you are when you stay with us. This one bedroom suite is idea for a couples getaway or small family vacation. Our retreat is nestled on Anna Maria Island, Florida and is a short 7 minute walk to the white sand beaches and turquoise waters.

ﺩ.ﺇ570 per night
SUPERHOST
  1. Entire house
  2. Holmes Beach
AMI Starfish

AMI Starfish is your ideal island getaway! Beautiful custom pool! With open living floor plan and beautifully appointed home for your stay! A short two block walk to the beautiful beach! Two covered deck areas plus a covered bar/lounge area just off the pool area. Two living areas for everyone to relax and enjoy. Fully stocked kitchen with breakfast bar and dining table that seats six. Enjoy the king size beds in all sleeping areas.

ﺩ.ﺇ1,260 per night
SUPERHOST
  1. Entire house
  2. Anna Maria
Paddle Board Canal, Walk to Beach, Heated Pool

This is a NEW listing, which means last minute availability at a quality house! We are the owners of Amie House on AMI and are so proud to have the pleasure of sharing this cute vintage canal cottage with you. Casa Canal is a quaint home ideally situated right on the canal, short 6 minute walk to the beach. Enjoy your morning coffee on the dock watching the birdlife. Fire up the grill for the fish you catch right from the dock.

ﺩ.ﺇ1,384 per night
SUPERHOST
  1. Entire house
  2. Anna Maria
AMI Retreat

My place is close to the beach, family-friendly activities, nightlife, and the free AMI trolley. You’ll love my place because of the high ceilings, the location, and the ambiance. My place is good for couples, families (with kids), and dogs (small pet fee) AMI Retreat has a beautiful private heated pool. Spa maintains same temperature as pool. Beautiful living room leads to the well equipped kitchen with granite and stainless appliances. Well appointed family home on the north end of island.

ﺩ.ﺇ1,466 per night
SUPERHOST
  1. Entire house
  2. Anna Maria
⭐️ Seaside Sanctuary ⭐️ fischervacationrentals

Welcome to paradise! ANNA MARIA ISLAND is the first of the barrier islands located along Florida's Gulf Coast. It is about 7 miles long and 1/2 a mile wide. It is known for beautiful beaches, breathtaking sunsets and a boat load of really nice people. The number one activity in the area is to DO NOTHING AND RELAX ON THE BEACH.

ﺩ.ﺇ888 per night
SUPERHOST
  1. Entire house
  2. Bradenton
Duplex with shared Boat ramp/AMI beaches<2miles

Casa Cortez’s prime location provides quick access to AMI/Sarasota Bay/Jewfish Key/Longboat Key Pass and the Gulf! Come enjoy the water, boating, diving, snorkeling, kayaking, fishing, shelling, sunsets, etc. Rent a boat/kayak/jet ski or bring your own for an amazing vacation. Casa Cortez is just minutes from many great restaurants, bars, grocery and souvenir shops all without the island congestion. Follow #casacortez106 on Facebook & Instagram!

ﺩ.ﺇ692 per night
  1. Entire house
  2. Bradenton Beach
Sugar Sunsets AMI -Unit B. Steps to the beach!

This is the 2nd/ lower level of an elevated duplex, with 1170 sq feet. Enjoy happy hour by the solar panel heated pool (shared with 1 unit), or the sunset on your screened front porch. Less than a 2 minute walk to the beautiful beach of Anna Maria Island, and the waters of the Gulf of Mexico. 1 minute walk to the trolley stop to explore the island without worrying about parking. Or you can enjoy the high speed wifi for remote work and school while poolside.

ﺩ.ﺇ1,028 per night
SUPERHOST
  1. Entire house
  2. Bradenton
Paradise Found Family & Friends Retreat

"Paradise Found Family & Friends Retreat" is a fully remodeled, quaint Home nestled in the heart of Cortez's Fishing Village. This is a great place to just relax and unwind in a quiet, peaceful oasis. You are a 3 minute drive to the pristine white sand beaches, on Anna Maria Island, just over the Cortez Bridge. Or a bike ride away from the fishing docks for fresh seafood! Paradise Found has a little bit to offer for everyone!

ﺩ.ﺇ819 per night
SUPERHOST
  1. Entire house
  2. Bradenton Beach
The Anna Maria Beach Cottage - East

Welcome to Anna Maria Beach cottage! Our spacious, shady cottage is two short blocks from white, powder-sugar sand and clear water. Perfect for four to six guests with two private entrances, 1000 square feet of living space and a large, relaxing, enclosed lanai for gathering or dining. Three bedrooms, two baths and full kitchen make you feel right at home as you relax in between adventures in the island paradise just outside your door!!

ﺩ.ﺇ643 per night

Houses with pools

SUPERHOST
  1. Entire house
  2. Holmes Beach
AMI New Luxury Home With Panoramic Ocean Views

Just steps to the beach! This incredible newly built home sets the highest standards of luxury living. It's the ideal retreat with its expansive views of the outdoors from the moment you enter. Open concept and large sliders throughout the home creates the perfect indoor-outdoor lifestyle. Spend the day lounging in the resort-style heated pool w/spa, then enjoy drinks at sunset on the rooftop deck with wet bar, firepit and breathtaking views of the Gulf of Mexico. You'll never want to leave!

ﺩ.ﺇ2,935 per night
SUPERHOST
  1. Entire house
  2. Holmes Beach
Spectacular home 700 feet from the beach!

Beautiful home less than 2 blocks from the beach! Well-appointed 3 bedroom home with modern decor in quiet beach community. Brand new furniture in all rooms, Smart TV, WiFi and free access to Netflix, washer/dryer, full kitchen. Large screened in lanai. We supply everything for your dream beach vacation including bikes to ride the island, beach towels, chairs, umbrellas, toys and games! Perfect house for families. Saturday to Saturday rental only, 7 day minimum.

ﺩ.ﺇ804 per night
SUPERHOST
  1. Entire house
  2. Anna Maria
5-Stars- Rare Availibility 2 & 4 Nights Aug 7-9...

* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. * There's no better way to unwind and forget all your troubles, than staying at Sunshine Cottage, located in the City of Anna Maria!

ﺩ.ﺇ1,598 per night
SUPERHOST
  1. Entire house
  2. Holmes Beach
TRUE BEACHFRONT HOME WITH HEATED POOL - IDYLLIC

CLEANLINESS HAS ALWAYS BEEN A TOP PRIORITY. WE WANT YOU TO KNOW THAT WE ARE DOING OUR PART TO HELP OUR GUESTS STAY SAFE BY CLEANING AND DISINFECTING FREQUENTLY TOUCHED SURFACES (LIGHT SWITCHES, DOORKNOBS, CABINET HANDLES, REMOTES, ETC.) BEFORE YOU CHECK IN.

ﺩ.ﺇ2,388 per night
SUPERHOST
  1. Entire house
  2. Anna Maria
AMI Boathouse

Welcome to AMI Boathouse! At AMI Boathouse you have so many amenities to enjoy. 3 Bedrooms, 2 bathrooms with 6 beds for all your sleeping needs. An exquisite new pool that sits just steps to a deep water canal. Bring your boat, kayak, paddle board to enjoy the new 55’ dock. Watch the birds, manatee from the dock. Over 1,000 square feet of covered outdoor patios gives you so many options to enjoy the views! A short 200 step walk to beautiful Tampa Bay waters. This home is designed to relax!

ﺩ.ﺇ1,759 per night
SUPERHOST
  1. Entire house
  2. Holmes Beach
Sea 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.

ﺩ.ﺇ841 per night
  1. Entire house
  2. Bradenton
“New”. Private Getaway/Heated Pool/Great Location!

“New”. Looking to get away from it all, this is your opportunity to stay in your own very private tropical bungalow with all the comforts of home. This incredible secluded getaway features a private fenced in yard and its own heated pool.

ﺩ.ﺇ592 per night
SUPERHOST
  1. Entire house
  2. Bradenton Beach
Exquisite Private Pool Elevator Beach/Bay views

TWO MASTER SUITES! 25 steps to the beach Modern home within walking distance to Beach, Bay, Historic Bridge Street, pier, restaurants, shops, ice cream, mini golf, fishing, water sports, this location has it all! You will absolutely love the convenience here! Enjoy our beautiful beaches, watch sunsets and sunrises from your balconies or enjoying the heated pool . We are the second house from the beach 50 yards and your toes are in the sand. Clean quiet street but close enough to walk anywhere.

ﺩ.ﺇ2,200 per night
SUPERHOST
  1. Entire house
  2. Holmes Beach
Private, Comfy, Close to the Beach w/ heated pool

You’ll love this updated classic Florida beach house. New to the rental market, on a quiet, short street and close to everything in Holmes Beach. It’s a perfect home base for you to enjoy the laid back, Old Florida lifestyle of Anna Maria Island. Sandy Palms is managed by the owners who live in FL and are always available if you should need anything during your stay.

ﺩ.ﺇ1,102 per night
  1. Entire house
  2. Bradenton
Canal Front Bradenton Home - 2 Miles to Beach

Make this newly renovated 3-bed, 2-bath Bradenton vacation rental house your home-away-from-home for your Sunshine State retreat. Up to 8 guests will be able to enjoy 1,907 square feet of well-appointed living space with upscale amenities such as a pool, screened-in porch, free wireless internet access, flat-screen Smart TVs and a garage. You’ll be within 2 miles of restaurants, a beautiful beach with incredible golf courses, water sports and other attractions right at your fingertips.

ﺩ.ﺇ1,249 per night
SUPERHOST
  1. Entire house
  2. Anna Maria
White Pearl-New Premier AMI Home with Sunset Views

White Pearl is a brand new elevated custom home (2019) on the North end of Anna Maria. With over 2,100 square feet under air, 800 square feet of balconies and 700 square feet of outdoor space around the pool, this expansive, yet comfortable home, is contemporary and boosts a coastal modern decor. Located on one of the most enviable spots on Anna Maria Island, our exclusive home is on North Shore Drive - directly across from the beach which allows for beach views from the observatory balcony.

ﺩ.ﺇ3,118 per night
SUPERHOST
  1. Entire house
  2. Holmes Beach
Luxury 3BR/3BA, Private Heated Pool, Beach

Renovated and professionally decorated single family home that sleeps 8. 3 bedrooms and 3 full bathrooms. Living room with pullout couch as well as games, books and movie library. Luxurious heated pool with waterfall and Tiki table in private tropical backyard. Large covered lanai with TV, mini-fridge, granite counter for food preparation and gas BBQ. Large size Washer/Dryer. 4 minute easy stroll to beach. Attached garage. Low traffic street. Tons of toys as well as pool and beach supplies.

ﺩ.ﺇ1,223 per night

All About Anna Maria Island

With its beautiful beaches and brilliant blue waters, this seven-mile barrier island offers a nostalgic idyll on the Gulf of Mexico. Over the years, residents have proudly resisted development, so Anna Maria’s vibe is decidedly low-key, with thatched-roof open-air bars and fresh fish restaurants dotting the waterfront. Here, where the island-wide speed limit is 35 miles per hour, the pace of life is literally slower. There are three small towns on the island — Bradenton Beach in the south, Holmes Beach in the middle, and the largest, Anna Maria, in the north — each with its own charms.

How do I get around Anna Maria Island?

Sarasota-Bradenton International Airport (SRQ) is the closest airport at 20 miles away. You can take a taxi or rent a car to carry you over one of the two bridges that connect Anna Maria Island to the mainland. Once you settle in, you may not use a car much. The island is extremely walkable, and operates a free trolley between 6 a.m. and 10 p.m. with 14 stops, including at the beaches. Many visitors also choose to rent bikes or golf carts.

When is the best time to book a Anna Maria Island vacation rental?

January through April and October through December are popular months to visit as they offer temperatures between 70 and 80 degrees Fahrenheit. April and May bring temperatures in the high 80s, and June through September can be quite hot, with temperatures in the 90s. If you opt for a sunny winter holiday, make sure to pack a layer for cooler evenings.

What are the top things to do in Anna Maria Island?

Coquina Beach

You won’t have trouble finding a spot for your towel on this serene beach with sand dunes and waving beach grass. Although more sedate than nearby Manatee Public Beach, which draws more crowds, Coquina Beach doesn’t scrimp on amenities. There are picnic tables, bathrooms, and a lifeguard, making it an ideal spot for families. Bring a picnic, or fuel up at the Coquina Beach Cafe, which serves breakfast, fish tacos, and — for the grown-ups — frozen drinks at its tiki bar.

Coquina Baywalk

Get acquainted with the island’s unique ecosystem on this short walk through Leffis Key Preserve on an elevated wooden walkway. You’ll see mangrove trees alongside thousands of native plant species. You’re also likely to spot local wildlife such as geckos, crabs, stingrays, and birds — including the remarkable frigatebird, famous for showboating males who inflate an enormous red pouch under their beaks when courting.

Bean Point Beach

If you’re yearning for that Robinson Crusoe feel, Bean Point Beach is your best bet. Located on the northern tip of the island, this gorgeous stretch of sand is where the island’s founding family, chose to build their estate in 1892. Their homestead is long gone, but the beauty that drew them to the land is very much present. Off the beaten path, this public beach has no parking lots or lifeguard. What it does have is scenic splendor, a calming sense of privacy, and unobstructed sunset views.

Anna Maria Island Historical Society Museum Complex

Home to a former icehouse converted to a museum and a restored cottage built in 1920, many visitors flock to this site to snap a quirky photo at the island’s former jail, built in 1927. Its wooden roof burned in 1940, and since then it’s been reborn as a kitschy photo op.

Nearby destinations