Anna Maria (Anna Maria Island, Florida) Vacation Rentals

(32 rentals)
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3 BR | 3 BA | Sleeps 8 | Quick View

2

$551

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

*A Brand new Pool/Spa has been installed and is ready for guest use! New Pool pictures are at the end of the photo list*Come Relax and Unwind at the "North Shore" on gorgeous Anna Maria Island. This ground level, newly renovated and professionally decorated 3 bedroom, 3 bath beach house ...

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Property Type

Anna Maria Island House

"Gertie's East"

We stayed at Gertie's East and had a great vacation. Perfect duplex for 2. Very clean and cute. Very close to Publix and to the beach. Pool was very clean and a perfect size. Patio with a propane grill ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$527

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

WELCOME to “Island in the Sun” ...this newly renovated home on AMI offers charm, comfort, and luxury. Island in the Sun is located just one block south of Pine Ave and just a few flip flop steps away from the City Pier Bay Beach and the popular restaurant - The Waterfront. The City Pier Bay ...

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Property Type

Anna Maria Island House

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4 BR | 3 BA | Sleeps 8 | Quick View

$709

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

Welcome to “Pineapple Cottage” – a beautifully updated ground level beach cottage located in the heart of Anna Maria City and just 1 block from all the shops, restaurants and fun on Pine Avenue. This charming cottage has been professionally decorated and offers all the luxuries you will ...

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Property Type

Anna Maria Island House

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3 BR | 3 BA | Sleeps 6 | Quick View

$460

avg/night

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Key Amenities

  • Air conditioning

About this property

*New 2022 & 2023 bookings are 15% off, the quoted rates already reflect this discount. No promotion code needed*Welcome to "Beach Escape" on beautiful Anna Maria Island. Appropriately named, this Mediterranean-inspired beach house offers all the charm and luxury you expect from a memorable ...

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Property Type

Anna Maria Island House

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2 BR | 2 BA | Sleeps 4 | Quick View

$265

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

Come experience Unit 201 at Sun Plaza West on beautiful Anna Maria Island. This 2 bedroom 2 bathroom Condo is located in the heart of Holmes Beach within walking distance to restaurants, shopping and the Islands Free Trolley. Sun Plaza West complex offers a secure entry, an elevator, heated pool and an ...

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Property Type

Anna Maria Island Apartment

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4 BR | 2 BA | Sleeps 8 | Quick View

$601

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly

About this property

*3 Night Minimum stays are allowed during low season, please refer to the rate table for the specific date ranges* Magnolia Location, Location, Location! Magnolia is situated on a quiet residential street, 2 blocks from the gorgeous white sand beaches of the Gulf of Mexico and 2 blocks from ...

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Property Type

Anna Maria Island House

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2 BR | 2 BA | Sleeps 6 | Quick View

$317

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly

About this property

Welcome to Sea'Esta on gorgeous Anna Maria Island! Sea'Esta is a ground level Home that offers all the luxuries and comfort you will come to expect from staying at one of our vacation rentals on Anna Maria Island. This 2 Bed/2 Bath sweet and cozy beach home is located on North Shore Drive right on the ...

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Property Type

Anna Maria Island House

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3 BR | 2 BA | Sleeps 8 | Quick View

$655

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly

About this property

Welcome to Zen Gardens on beautiful AMI. BIG NEWS: a brand new, full sized pool and spa was installed and is ready for your use. Zen Gardens is located just north of Pine Ave - and 1 house from the beach - in the City of Anna Maria. This property offers a beachy bohemian vibe and has all you need for ...

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Property Type

Anna Maria Island House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Have the best of both worlds with the bay & the gulf beaches at this new 4 bed/3.5 bath luxury home. Enjoy the quiet, laid back way of life on the north end of the island being only steps to the gorgeous bayside beach with city park or a 5 minute walk to the world renowned Bean Point! You are also ...

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Property Type

Anna Maria Island House

"Paradise"

Everything about this rental was easy. Everyone was very responsive. Would totally use Florida Rentals again. Highly recommended!!

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4 BR | 3 BA | Sleeps 12 | Quick View

$867

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly

About this property

Welcome to Sunset Shore!Sunset Shore is situated on a secluded lake on the prestigious North Shore Drive on Anna Maria Island. This quiet residential street is only 1 block from the gorgeous white sand beaches of the Gulf of Mexico and 1 block away from many amazing shops and restaurants on Pine Ave. ...

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Property Type

Anna Maria Island House

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3 BR | 3 BA | Sleeps 7 | Quick View

13

Distance to beach: 1 miles to Manatee beach

$254

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Pool

About this property

High-end resort living, endless amenities and easy access to Anna Maria Island beaches and attractions make this 1,650-square-foot condo an unbeatable home base for your warm-weather retreat! Located in the One Particular Harbor, Margaritaville Resort complex on the Anna Maria Island Sound.Head south ...

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Property Type

Anna Maria Island Condo

"Anna Maria rental"

Excellent stay clean and close to the beaches affordable. I would definitely stay there again love it

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3 BR | 2 BA | Sleeps 8 | Quick View

1

$495

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

Treat yourself to “Crescent Palms” on the north end of Anna Maria Island. This ground level, newly renovated and professionally decorated 3 bedroom, 2 bath beach house offers comfort, luxury, and relaxation. Crescent Palms is located on a quiet street- north of Pine Ave and just a few flip ...

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Property Type

Anna Maria Island House

"Peaceful and relaxing family trip"

We were looking for a quiet spot for the family and hit the bullseye at Max and Denise's place on Northern Anna Maria island. Centrally located, 3 blocks either way, between the Gulf of Mexico or Tampa ...

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2 BR | 2 BA | Sleeps 6 | Quick View

1

$483

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly

About this property

Need a GREAT AMI GETAWAY? Just steps from the bayfront park in the City of Anna Maria is a charming island beach house called “La Cocolia” lovingly translated as the "little crab". This property is ready to host you and your family as you enjoy this newly renovated and decorated ...

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Property Type

Anna Maria Island House

"Spectacular"

We have rented many properties on Anna Maria Island and this one was my favorite! The home is wonderful with every amenity you can imagine and immaculate as far as cleanliness! It is completely updated ...

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3 BR | 2 BA | Sleeps 6 | Quick View

$502

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Private pool

About this property

Moon Shadow South's location can't be beat with views of Passage Key in Tampa Bay from the Primary Ensuite. You are just steps away to the bay beach access located directly across the street; walking distance to the Rod and Reel Pier, Bay Front Park and the popular white sandy beach of Bean Point. Enjoy ...

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Property Type

Anna Maria Island House

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2 BR | 2 BA | Sleeps 4 | Quick View

$283

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Pine Avenue HideAway is a secluded Beach Bungalow tucked away on Historic Pine Avenue on Anna Maria's North End. Conveniently located in the heart of it all, and just a short stroll to the beach, restaurants, boutiques, Anna Maria City Pier and a trolley stop to explore Anna Maria the islanders way!. ...

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Property Type

Anna Maria Island Bungalow

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3 BR | 2 BA | Sleeps 6 | Quick View

$367

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

Come enjoy the relaxed vibe and unique feel of this stunning Hawaii meets Anna Maria Island-themed Beach Cottage. Only 500 feet from the white sugar sand beaches with no streets to cross, and with a “free” trolley stop nearby – it is a convenient way to explore Anna Maria Island.Owned ...

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Property Type

Anna Maria Island Cottage

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4 BR | 3 BA | Sleeps 10 | Quick View

4.7 rating on other travel sites

$926

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

If you're looking for the perfect spot to drop anchor on Anna Maria Island— look no further than this spacious four-bedroom oasis. Located on the idyllic north end, Anchor Splash is a short stroll from the white sandy beaches and warm, aquamarine gulf waters. It's also within walking distance of ...

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Property Type

Anna Maria Island House

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4 BR | 4 BA | Sleeps 8 | Quick View

1

Distance to beach: 700 feet to Bayside or Gulf Side - Bean Point

$1174

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly

About this property

Located at the north end of Anna Maria Island, this 4 bedroom/3.5 bath home offers unique and well-appointed surroundings to make your trip memorable. Custom finishes, light fixtures, and furnishings were all handpicked to make this home truly one of a kind. The main level offers two guest suites, a ...

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Property Type

Anna Maria Island House

"Simply Paradise!!!"

From the moment we arrived at the house, we knew our experience would be exceptional. It was just stunning! Not only is it on the north end of the island but also the photos just don't do it justice. First ...

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2 BR | 2 BA | Sleeps 6 | Quick View

8

$281

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Rentals by owner

About this property

Escape the Madness to the serenity of Anna Maria's north end. This single family, two bedroom, 2 bathroom, ground level house is located on the far north end of Anna Maria Island near Bean Point. The property is only 250 feet from the sugar sand beaches where you can walk for hours or sit and enjoy ...

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Property Type

Anna Maria Island House

"Cottage by the Sea"

We visited Anna Maria in November with lifetime friends. The house was charming and comfortable. The kitchen was well-equipped and we cooked several dinners and ate outside under the beautiful palms and ...

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2 BR | 2 BA | Sleeps 6 | Quick View

4.7 rating on other travel sites

$517

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Bring your boat or jet skis to Pelican Point, an Anna Maria canal front home complete with a private boat dock with lift and a private screened, heated pool. This 2 bedroom 2 bathroom home is located on a quiet canal street and features a private dock where you can fish, view wildlife or simply just sit ...

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Property Type

Anna Maria Island House

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3 BR | 3 BA | Sleeps 8 | Quick View

4.9 rating on other travel sites

$933

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

With the feel of a five-star luxury resort and the privacy of a secluded island cabana, Coconut Cove is the perfect balance of sumptuous seaside escape and comfy family home. Tucked among the swaying palm trees on Anna Maria Island's coveted north end, you'll be a short walk away from the sandy beach ...

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Property Type

Anna Maria Island House

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4 BR | 4 BA | Sleeps 12 | Quick View

4.6 rating on other travel sites

$1024

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Come enjoy this 4 bedroom/4 bath duplex that can sleep up to 12 people with the add-on of the sleeper sofas. Blue Lagoon is located on North Shore which is just a few blocks from the renowned shopping and dining of Pine Avenue and features a large, shared heated pool. Upon entry in both units, you will ...

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Property Type

Anna Maria Island House

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4 BR | 4 BA | Sleeps 12 | Quick View

4.8 rating on other travel sites

$1035

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Looking for a relaxing retreat just steps to the soft white sand and turquoise waters? Coconut Breeze offers the perfect seascape for large family or friend gatherings. This custom home with coastal art touches delivers fun for everyone with its private heated pool, spacious four bedrooms with TV's in ...

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Property Type

Anna Maria Island House

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4 BR | 4 BA | Sleeps 8 | Quick View

4.9 rating on other travel sites

$809

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Make your way to Anna Maria Island and experience a one-of-a-kind paradise when you stay in this beautiful, stylish, recently renovated 4 bedroom/4 bath home with a private heated pool and bonus cottage complete with game room. Not only will you have easy access to dining, the beach is only a short distance ...

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Property Type

Anna Maria Island House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

146 Crescent Dr, Anna Maria FL 34216 VITAMIN SEA is a home that features 5 bedrooms and 5 bathrooms and a fantastic location-just a 10 minute stroll to the White sandy beaches of BEAN POINT on the coveted north end of Anna Maria. This lovely property offers a private heated pool with a spa, The backyard ...

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Property Type

Anna Maria Island House

"Paradise"

Vitamin Sea exceeded all expectations for our week's vacation for our family of 12. Location was perfect for daily visits to both sides of the island. House is stunning and fully equipped for swimming, ...

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4 BR | 4.5 BA | Sleeps 10 | Quick View

4.9 rating on other travel sites

$1324

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

144 Crescent Dr. Anna Maria, FL 34216 Book with confidence: Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive 70% of the ...

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Property Type

Anna Maria Island House

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4 BR | 4 BA | Sleeps 10 | Quick View

1

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

At A GlanceBe one of the very first to stay at this gorgeous new home! Just listed!Just a hop, skip and a jump From The Beach Gulf Views! Contactless entry Private Heated Pool Gas BBQ Grill 2 Car Garage Parking for 4 Fully Equipped Kitchen Just under 2000 Sq feet of completely remodeled ...

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Property Type

Anna Maria Island House

"Excellent place to stay!"

This house was incredible! Absolutely beautiful, well stocked, an amazing pool and outdoor setup, and so conveniently located! While it's not beach-front, it's just a house or two away from the beach entrance ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

It’s all about location on vacation, and Reef Romance does not disappoint! Sail away to this beautiful four-bedroom, four-and-a-half-bathroom custom-built home for a dose of luxury at the beach. Located on the prestigious north end of Anna Maria Island, you’re just a few houses away from the ...

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Property Type

Anna Maria Island House

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7 BR | 5 BA | Sleeps 14 | Quick View

5.0 rating on other travel sites

$1511

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to AMI Beach Lagoon, your dream vacation on Anna Maria Island!In our lakefront luxury resort (12,500 sqft) we offer three separate ground level apartments with a large outdoor area that can be rented together or separately. Enjoy the privacy of your own entrance, fully equipped kitchen and ...

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Property Type

Anna Maria Island Condo

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3 BR | 2 BA | Sleeps 6 | Quick View

4.8 rating on other travel sites

$640

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to the Pelican Suite of AMI Beach Lagoon on Anna Maria Island!In our lakefront luxury resort (12,500 sqft) we offer three separate ground level apartments with a large outdoor area that can be rented together or separately. Enjoy the privacy of your own entrance, fully equipped kitchen and ...

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Property Type

Anna Maria Island Condo

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1 BR | 1 BA | Sleeps 2 | Quick View

4.9 rating on other travel sites

$523

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

In our lakefront luxury resort (12,500 sqft) we offer three separate ground level apartments with a large outdoor area that can be rented together or separately. Enjoy the privacy of your own entrance, fully equipped kitchen and outside seating area or spend time as a group at the large, Mickey Mouse-shaped, ...

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Property Type

Anna Maria Island Condo

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3 BR | 2 BA | Sleeps 6 | Quick View

4.8 rating on other travel sites

$608

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to the Manatee Suite of AMI Beach Lagoon on Anna Maria Island!In our lakefront luxury resort (12,500 sqft) we offer three separate ground level apartments with a large outdoor area that can be rented together or separately. Enjoy the privacy of your own entrance, fully equipped kitchen and ...

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Property Type

Anna Maria Island Condo

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Anna Maria (Anna Maria Island, Florida) Vacation Rentals