Anna Maria (Anna Maria Island, Florida) Vacation Rentals

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

$627

avg/night

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Key Amenities

  • Air conditioning
  • 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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4 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 0.0 miles to Gulf Beach & Tampa Bay Beach

$856

avg/night

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Key Amenities

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

About this property

Just renovated! Read our description carefully as we have upgraded and added many amenities that are not shown yet in our professional photos!new metal roof new exterior paint - white! lighting, garage doors, etc.. new composite decking on all stairs and balconies lanai - newly refinished dock new ...

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Property Type

Anna Maria Island House

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3 BR | 2 BA | Sleeps 8 | Quick View

$710

avg/night

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About this property

Welcome to “Willow Cottage” a charming sunny cottage just steps to the white sandy beaches on the north end of Anna Maria Island. Come bury your feet in the sand or lounge by your private pool. This pristine ground floor island cottage has all the luxuries and charm you’ll come to expect ...

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Property Type

Anna Maria Island House

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2 BR | 2 BA | Sleeps 6 | Quick View

$470

avg/night

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Key Amenities

  • Air conditioning
  • 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

$314

avg/night

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Key Amenities

  • Air conditioning

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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4 BR | 3 BA | Sleeps 8 | Quick View

$1280

avg/night

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About this property

"Emma's Cottage" is located on the north end of Anna Maria Island in the City of Anna Maria. It is offered exclusively through Salty Mermaid Vacation Rentals. Rich history and beautiful antiques await you. Built in 1912, one of four Gulf front Anna Maria homesteads known as the "Painted ...

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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

OUTSIDE HIGHLIGHTS: Soft Sandy Backyard Beach Area Tons of New Outdoor Sun Loungers New Pool Terrace Resurfaced and Newly Tiled Heated Pool New Outdoor Conversation Set New Hot Tub Outdoor Shower Hammock Refurbished the Outdoor Bar w/Granite and Stone New Outdoor Bar Stools Added Patio Sliders ...

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Property Type

Anna Maria Island House

"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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3 BR | 2 BA | Sleeps 8 | Quick View

$603

avg/night

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Key Amenities

  • Air conditioning

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

$726

avg/night

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Key Amenities

  • Air conditioning

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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2 BR | 2 BA | Sleeps 6 | Quick View

1

$433

avg/night

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Key Amenities

  • Air conditioning

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 7 | Quick View

10
Owner special: Reduced rates for July 9 - 16th!!

Distance to beach: 1 miles to Manatee beach

$267

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

"Villa Sea Shell"

Very nice stay at well kept 3 bdrm home with pool. Only complaint was grill old and didn't ignite...very dangerous to start.

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3 BR | 3 BA | Sleeps 8 | Quick View

2

$764

avg/night

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Key Amenities

  • Air conditioning
  • 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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4 BR | 2 BA | Sleeps 8 | Quick View

$648

avg/night

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Key Amenities

  • Air conditioning

About this property

Location, Location, Location…these three words say it all when describing Magnolia Gardens. This Anna Maria Island Home is just a few blocks from the white sandy beaches of the Gulf of Mexico and steps from the shops and resturaunts on Pine Ave.Magnolia Gardens offers 4 Bedrooms, 2 Bathrooms, ...

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Property Type

Anna Maria Island House

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3 BR | 2 BA | Sleeps 8 | Quick View

$570

avg/night

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Key Amenities

  • Air conditioning
  • 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

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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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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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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

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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2 BR | 2 BA | Sleeps 6 | Quick View

8

$270

avg/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 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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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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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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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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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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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