Anna Maria (Anna Maria Island, Florida) Vacation Rentals

(24 rentals)
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4 BR | 3 BA | Sleeps 8 | Quick View

$533

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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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

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3 BR | 2 BA | Sleeps 8 | Quick View

$455

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

*3 Night Minimum stays are allowed during low season, please refer to the rate table for the specific date ranges*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 ...

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Property Type

Anna Maria Island House

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3 BR | 2 BA | Sleeps 8 | Quick View

$619

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly

About this property

Upgrades are coming to Shore Beats Work! During Fall 2022 the Kitchen, Bathrooms and Floors will all be remodeled! New photos will come once work is completed in the Fall.Shore Beats Work … yes, the name says it ALL! Welcome to this elevated sweet and cozy beach home located on North Shore ...

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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

*3 Night Minimum stays are allowed during low season, please refer to the rate table for the specific date ranges*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 ...

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Property Type

Anna Maria Island House

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4 BR | 2 BA | Sleeps 8 | Quick View

$542

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*MagnoliaLocation, 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

$270

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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2 BR | 2 BA | Sleeps 6 | Quick View

$410

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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2 BR | 2 BA | Sleeps 6 | Quick View

1

$387

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 | 3 BA | Sleeps 8 | Quick View

2

$542

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

*3 Night Minimum stays are allowed during low season, please refer to the rate table for the specific date ranges*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 offers ...

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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

$294

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 | 3 BA | Sleeps 7 | Quick View

12

Distance to beach: 1 miles to Manatee beach

$215

avg/night

View Details

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

"We Loved Our Stay"

We absolutely loved our stay! And Morgan was fantastic and was quick to respond and help us with any issues. We will be back!

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3 BR | 3 BA | Sleeps 6 | Quick View

$469

avg/night

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Key Amenities

  • Air conditioning

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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4 BR | 2.5 BA | Sleeps 10 | Quick View

4.7 rating on other travel sites

$557

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 12 | Quick View

4.6 rating on other travel sites

$628

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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2 BR | 2 BA | Sleeps 6 | Quick View

8

$266

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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4 BR | 4 BA | Sleeps 8 | Quick View

4.9 rating on other travel sites

$651

avg/night

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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 Four-bedroom, Four 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 ...

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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

"Second time around"

This was the second time in 2 years that our family of 10 stayed for one week at Vitamin Sea. Things started out kind of rough with Emma not remembering that we were coming - so the house was not cleaned, ...

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4 BR | 4 BA | Sleeps 12 | Quick View

4.8 rating on other travel sites

$833

avg/night

View Details

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 | 4.5 BA | Sleeps 10 | Quick View

4.8 rating on other travel sites

$788

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 made up until 14 days prior to arrival result in a refund of 85% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 30 days prior to arrival in order to receive 85% ...

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Property Type

Anna Maria Island House

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2 BR | 2 BA | Sleeps 6 | Quick View

4.7 rating on other travel sites

$329

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 and outdoor hot tub. This 2 bedroom 2 bathroom home is located on a quiet canal street and features a private dock where you can fish, view wildlife ...

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Property Type

Anna Maria Island House

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3 BR | 3 BA | Sleeps 8 | Quick View

5.0 rating on other travel sites

$670

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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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

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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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Anna Maria (Anna Maria Island, Florida) Vacation Rentals