Anna Maria (Anna Maria Island, Florida) Vacation Rentals

(28 rentals)
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Anna Maria Island House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 3 Bathrooms
3 reviews

$522

avg/night

$522
avg per night
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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

Featured review

"Amazing house!!"

This house was great we have been coming to the island for about 10 years! This was the best house and so close to the beach!! We will be back

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Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 3 Bathrooms

$553

avg/night

$553
avg per night
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About this property

Welcome to West O’ Gulf, one of our brand-new luxury rentals at Salty Mermaid Vacation Rentals. If you are ready for a relaxing stay on beautiful Anna Maria Island, then this unit is for you! This exceptional custom-built 4 Bedroom 3 bathroom beach house makes it easy to perfect the art of vacationing. ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

$300

avg/night

$300
avg per night
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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 ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2 Bathrooms
1 review

$485

avg/night

$485
avg per night
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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

Featured review

"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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Anna Maria Island House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2 Bathrooms

$632

avg/night

$632
avg per night
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Key Amenities

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

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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Anna Maria Island House

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Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 3 Bathrooms
2 reviews

$598

avg/night

$598
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

Featured review

"Great Property"

This house is in a great location, three blocks to the beach, restaurants, and three blocks to the pier, and many other amenities. It is beautiful, spacious and has everything you need to make your stay ...

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Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 3 Bathrooms

$572

avg/night

$572
avg per night
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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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Anna Maria Island House

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Anna Maria Island House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
2 reviews

$415

avg/night

$415
avg per night
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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

Featured review

"Just right"

The property is centrally located on the island which makes it very convenient. It has everything you need, and was very clean. We would definitely rent it again.

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Anna Maria Island House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
2 reviews

$465

avg/night

$465
avg per night
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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

Featured review

"Great Place to stay!"

We stayed 6 nights and had a great time. The property was clean and had everything we needed. The Florida Rental staff checked on us after we arrived to make sure everything was good. Very caring staff. ...

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Anna Maria Island Apartment
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms

$260

avg/night

$260
avg per night
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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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Anna Maria Island House
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 3.5 Bathrooms
2 reviews

$1081

avg/night

$1,081
avg per night
View Details

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

Featured review

"Best Place On Anna Maria"

Hosts are fabulous! very responsive and caring! House is amazing! our friends and family were blown away by how much attention to detail they put in to the furnishings and the home itself! A true paradise!

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Anna Maria Island House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 3 Bathrooms

$425

avg/night

$425
avg per night
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About this property

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 vacation on AMI.Find ease and relaxation the moment you arrive, this charming multi-level home is nestled among ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 4 Bathrooms
1 review

Distance to beach: 0.1 miles to Tampa Bay

$785

avg/night

$785
avg per night
View Details

Key Amenities

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

About this property

Views, views, views! Experience all the best of the North end of Anna Maria from this waterfront home with pool, spa and mini golf.*Features include** Ultimate Bay front vacation home * Private heated pool and full Putt-putt course * Paddleboards, kayak * Standalone Hot Tub * Gas grill ...

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Property Type

Anna Maria Island House

Featured review

"Sandtrap house with Beach Boutique"

Beautiful home, fantastic location and incredible service. Everything was perfect. Live the area, restaurants, biking, atmosphere and people. Super friendly. We will be back using Beach Boutique again!

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Anna Maria Island House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
11 reviews

$325

avg/night

$325
avg per night
View Details

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 ...

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Property Type

Anna Maria Island House

Featured review

"Great spot!"

Ideally located, immaculate and 100% outfitted for a perfect vacation! We loved the decor and outdoor shower! Hope to be repeat visitors.

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Anna Maria Island House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 3 Bathrooms
1 review

$523

avg/night

$523
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 23, 2023! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle InsuranceWith the feel of a five-star luxury resort and the privacy of a secluded island ...

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Property Type

Anna Maria Island House

Featured review

"Very nice home"

Home was very nice. The whole backyard is like paradise. Overall great experience.Pool was not refreshing but probably expected this time of year in Florida. The hot tub flows over into pool when ...

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Anna Maria Island House
4 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 4 Bedrooms, 4 Bathrooms
4.6 rating on other travel sites

$593

avg/night

$593
avg per night
View Details

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, and an EV Charger. Upon entry in ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 3 Bathrooms

$472

avg/night

$472
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Colorful and inviting with a vibrant tropical style, Carefree Cottage is a perfectly-named oasis in Holmes Beach where all of your cares melt away the moment you walk through the front door. Located on a quiet residential street that offers plenty of peace and privacy yet keeps you close to the beaches ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms

$280

avg/night

$280
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Drive through the gated driveway with a manatee on it and you'll enter Manatee Retreat. This duplex is a private getaway on a canal! Unit B is separated by a fence so you have your own private retreat. This 2 bedroom/2 bathroom has a large living room with plenty of seating for you and your guests. ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 Bedrooms, 3 Bathrooms
4.7 rating on other travel sites

$602

avg/night

$602
avg per night
View Details

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 ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 4 Bathrooms

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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Anna Maria Island House
5 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 5 Bedrooms, 5 Bathrooms
4 reviews

$959

avg/night

$959
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • 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

Featured review

"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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Anna Maria Island House
4 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 4 Bedrooms, 3 Bathrooms
1 review

$535

avg/night

$535
avg per night
View Details

Key Amenities

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

About this property

Many new items not shown in photos;- New Kitchen Cabinetry coming soon! - New exterior Polywood dining table - New interior dining table set - New screened lanai conversation set - New coffee table set in living roomOUTSIDE HIGHLIGHTS: Soft Sandy Backyard Beach Area Tons of New Outdoor ...

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Property Type

Anna Maria Island House

Featured review

"Such a perfect place for our entire family"

We loved our time at Sirena Cove. There were so many amenities and room for all of our adult children, their spouses and our grandchildren all under the age of four. The pool was great fun and we enjoyed ...

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Anna Maria Island Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms
4.9 rating on other travel sites

$384

avg/night

$384
avg per 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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Anna Maria Island Condo
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 Bedroom, 1 Bathroom
4.9 rating on other travel sites

$312

avg/night

$312
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Resort-Style Ground Floor Suite, Prime Location, Lakefront, Heated Pool & SpaIn 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 ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island Condo
7 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 Bedrooms, 5 Bathrooms
5.0 rating on other travel sites

$1254

avg/night

$1,254
avg per 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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Anna Maria Island House
4 BR | 4.5 BA | Sleeps 10 | Quick View
Sleeps 10, 4 Bedrooms, 4.5 Bathrooms
4.9 rating on other travel sites

$746

avg/night

$746
avg per night
View Details

Key Amenities

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

About this property

144 Crescent Dr. Anna Maria, FL 34216 You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that time, or for reservations made ...

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Property Type

Anna Maria Island House

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Anna Maria Island Apartment | On the beach
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 1 Bathroom
4 reviews

Distance to beach: 0.3 miles to Anna Maria Bay Front part

$331

avg/night

$331
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

This stunning waterfront condominium is a true gem, featuring 2 bedrooms and 1 bathroom on the ground floor and over 822 square feet, accommodating up to 4 people. The location is unbeatable, situated at the end of Pine Avenue and boasting breathtaking views of the surrounding area. From your private ...

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Property Type

Anna Maria Island Apartment

Featured review

"Beautiful Property"

This property is located in a beautiful area! Very quiet and comfortable. Nice and clean…I highly recommend this property to anyone! You won’t regret it .

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Anna Maria Island Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms
4.9 rating on other travel sites

$411

avg/night

$411
avg per 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 luxury resort (12,500 sqft) located right on Vista Lake 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 ...

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Property Type

Anna Maria Island Condo

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Anna Maria (Anna Maria Island, Florida) Vacation Rentals