Monthly Rentals in Anna Maria Island

(16 rentals)
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3 BR | 2 BA | Sleeps 6 | Quick View

1

$327

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly

About this property

Welcome to “Sand Dollar Villa”, one of our newest luxury properties at Salty Mermaid Vacation Rentals. This elevated condo offers all the luxury and comfort you will come to expect from staying at one of our vacation rentals on Anna Maria Island. Find ease, relaxation, and luxury the moment ...

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Property Type

Anna Maria Island Apartment

"Beautiful"

The place was very clean and close to the beach. We had no issues with check in or out. The property manager was helpful and made themselves accessible at any time. We had a great time and did not have ...

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Key Amenities

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

About this property

Shady Palms is a cozy secluded beach cottage right on the beautiful Gulf of Mexico. Walk out the back door to a white, sugar-sand beach and the sparkling Gulf waters. Shady Palms is the most perfect spot you'll ever find on the beach - with the best of both worlds - the sun and the shade.Beach and ...

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Property Type

Anna Maria Island House

"Excellent"

This was a perfect place for our family to stay. The memory of it is pure perfection. The host was phenomenal and the stay accommodations were very comfortable.

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3 BR | 3 BA | Sleeps 7 | Quick View

12
Owner special: December openings! Deeply discounted!!

Distance to beach: 1 miles to Manatee beach

$215

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

"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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4 BR | 4 BA | Sleeps 8 | Quick View

$1100

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Cool and calming tiled floors, modern furnishings, and updated appliances give this vacation home an air of Tommy Bahama feel. We know how exhausting and stressful traveling can be so don’t feel an ounce of guilt if the second thing you do is plop down on the living room’s couch and switch ...

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Property Type

Anna Maria Island House

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2 BR | 2 BA | Sleeps 4 | Quick View

1

$344

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Two bedroom, two bath condo for rent in the lovely Runaway Bay complex in Bradenton Beach, on beautiful Anna Maria Island, Florida! Live the relaxed lifestyle on Anna Maria. Enjoy morning walks and evening sunsets on the beach, just across the road. While away the afternoon by the big, beautiful pool ...

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Property Type

Anna Maria Island Condo

"Snowbird Retreat"

We enjoyed this unit very much! It has all the amenities we need! It is a very quiet spot and has a nice view of the pond.

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

Absolute Anna Maria on Anna Maria Island is a tropical paradise offering you seven miles of the most beautiful and peaceful powdery white sand beaches found anywhere in the world. Anna Maria Island is not a place where you go to the beach; Anna Maria Island is a place where you are at the beach. Completely ...

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Property Type

Anna Maria Island Condo

"Excellent Stay"

Love this property, loved the location and could not have had a better experience. Owner as great to work with and the communication was outstanding.

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2 BR | 1 BA | Sleeps 2 | Quick View

$138

avg/night

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Key Amenities

  • Air conditioning

About this property

Welcome to the “The Gathering Place” a cute cottage reminiscent of days past on Anna Maria. This charming ground floor cottage is only 4 houses (300 Ft) TO DIRECT BEACH ACCESS in the City of Holmes Beach on Anna Maria Island!!!Looking to get out of the snow and cold rain for the upcoming ...

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Property Type

Anna Maria Island Cottage

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

This affordable & convenient 3 story home is one house off Holmes Beach. It has fantastic 2nd & 3rd level balcony beach views with no obstruction over the one story house in front of mine with no trees. The 3 bedroom 2.5 bath villa with 2 car garage accommodates 8 guests and is 150 feet from the ...

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Property Type

Anna Maria Island House

"Location!"

The location was awesome, we were only one block from the beach! We kept our loaded wagon in the garage and were ready to go each morning. The house was roomy and bright; with 3 decks there was lots of ...

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2 BR | 2 BA | Sleeps 5 | Quick View

4

$251

avg/night

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Key Amenities

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

About this property

Ann's cottage is a cozy, original 1950’s, one story beach cottage in the Holmes Beach section of Anna Maria Island. It is a short walk- six houses to the beautiful sugar white sands and sparkling blue waters of the Gulf of Mexico. The homes sits in a quiet neighborhood, yet is only one street away ...

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Property Type

Anna Maria Island House

"Love it"

This cottage is amazing, has everything you need (even for kids). The location is great - the beach is 5 min walking, has nice restarants near by. We'd like to visit again.

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2 BR | 2 BA | Sleeps 4 | Quick View

3

Distance to beach: 0.5 miles to Manatee Beach

$198

avg/night

View Details

Key Amenities

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

About this property

2 bed/2bath condo on second floor, fits up to four guests, close to the gulf beach. Turnkey furnished and spruced by the owner. Shops and restaurants are close by. Trolley stop for free rides on the island is around the corner. Come and enjoy!Just remodeled and equipped with more than everything ...

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Property Type

Anna Maria Island Condo

"Amazing vacation"

Carla is an excellent hostess. It was my first time ever renting from someone and she answered my million questions and was very patient. Condo was wonderful and clean with everything you need in a great ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

A classic coastal condominium with easy beach access, this two-bedroom home in beautiful Holmes Beach features 1,000 square feet of immaculate, updated living space. Gulf Breeze is located within a lovely condo complex that features tons of exceptional extras— like a sparkling swimming pool, a barbecue ...

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Property Type

Anna Maria Island Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Looking for the perfect beach destination well, it doesn't get better than this! This 2 bedroom, 2 bath condo is centrally located on Holmes Beach and is only steps from the sparkling gulf waters and white sandy beaches. There is plenty of natural lighting with the large windows in the living room, a ...

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Property Type

Anna Maria Island Condo

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Key Amenities

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

About this property

This amazing 1 bedroom house is directly across from the beach and offers full beach views from your huge deck, the living room and kitchen. Heck, you can even see the beach from your bed! We offer a clean house will all of the amenities you need and more! All linens, towels, dishes, washer and dryer, ...

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Property Type

Anna Maria Island Cottage

"Perfect place"

This place is special. If you rent it,you will see what Im talking about....just rent it. You won't be sorry,I promise...Thanks Bruce for a wonderful stay. We will most definitely be back.

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2 BR | 2 BA | Sleeps 4 | Quick View

5

$194

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Rentals by owner

About this property

This is a two bedroom house on Anna Maria island, and faces the bay side. The water is literally 20 ft from your back door. Looking from your private dock to the north is the Manatee bridge, the Skyway bridge and a view of St Pete. Looking to the south you see the Cortez bridge and beyond to Sarasota. ...

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Property Type

Anna Maria Island House

"Manatee Cove"

Great location. Great view. Great everything! Can't wait to come back. Terry is great and we appreciate the work that went in to the clean up after Hurricane Ian so we could fall in love with this place. ...

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2 BR | 1 BA | Sleeps 4 | Quick View

8

$177

avg/night

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Key Amenities

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

About this property

A guest had this to say: "Songbird is a cute little purple house on a quiet side street on Anna Maria Island. I referred to the house as little, it is really quite spacious & comfortable. This is our 6th stay at Songbird & we are looking forward to our next stay. This trip we were on side ...

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Property Type

Anna Maria Island Cottage

"Cute, Comfy, Clean, and Convenient Beach Cottage"

Excellent Stay!!! This was our 3rd time visiting Anna Maria Island and our 1st time staying at Songbird Staying at Songbird was the BEST and most comfortable stay of all our visits! Joel is the perfect ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Enjoy beautiful Anna Maria Island relaxing in a spacious ground floor condo unit with 2 bedrooms and 2 baths overlooking the heated community pool. This quiet slice of paradise has a large screened lanai off the living room with a pool view. Enjoy the amazing white sand beach and gorgeous sunsets within ...

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Property Type

Anna Maria Island Apartment

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Anna Maria Island Vacation Rentals