Monthly Rentals in Anna Maria Island

(16 rentals)
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Anna Maria Island Villa
4 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 4 Bedrooms, 4 Bathrooms
3 reviews

$271

avg/night

$271
avg per night
View Details

Key Amenities

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

About this property

Ideal Location - Family Vacation Accommodation 2 Individual Villas, 4 Bedroom 4 Baths Sleeping for 8-12 Guests Pricing is for one villaDuring January February & March you can only rent 1 villa. During June & July you must rent both villas. Pricing on our site here is for only 1 villa.The ...

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Property Type

Anna Maria Island Villa

Featured review

"Great stay!"

We loved our stay at this unit. It was very comfortable, convenient to the beach and loved the roof top seating area with a beautiful view of the beach.

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Anna Maria Island House | On the beach
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2.5 Bathrooms
12 reviews

$324

avg/night

$324
avg per night
View Details

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 6 guests and is 150 feet from the ...

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Property Type

Anna Maria Island House

Featured review

"Great Vacation Spot. Great Owner. Awesome Location"

What an awesome place. Lots of rooms to stretch out. The 2 car garage and big drive way were nice for ease of parking and to securely store things. The large shared pool is wonderful and perfect temp. ...

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

$210

avg/night

$210
avg per night
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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 House | On the beach
2 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 1.5 Bathrooms
11 reviews

$495

avg/night

$495
avg per night
View Details

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 - have the best of both worlds - the sun and the shade.Beach ...

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Property Type

Anna Maria Island House

Featured review

"AMAZING!!!"

This house is the best rental we have ever stayed in! The scenery out back is incredibly relaxing.. trees, Adirondack chairs, the OCEAN!! It is so private, and also the best equipped kitchen I’ve ever ...

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Anna Maria Island House | On the beach
2 BR | 2.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2.5 Bathrooms

$566

avg/night

$566
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront

About this property

The Beach House is a charming beach bungalow nestled among numerous Australian pines and sea grapes. A unique setting directly on the Gulf of Mexico shaded among the trees. Walk out the back door on your private path to a white sugar-sand beach. Best of both worlds, you have the shade and sunny beach. The ...

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Property Type

Anna Maria Island House

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

$417

avg/night

$417
avg per night
View Details

Key Amenities

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

About this property

Absolutely beautiful monthly rental in highly sought after Holmes Beach on Anna Maria Island. If you are interested in dates blocked on the calendar, please message me. This 100% updated home has everything from a large heated pool, outdoor shower, lush mature landscaping, completely furnished inside ...

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Property Type

Anna Maria Island House

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

$133

avg/night

$133
avg per night
View Details

Key Amenities

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

About this property

- 7 min. walk to beach, beach chairs, umbrellas, towels, beach wagon provided- sleeps 4, 2 bedroom/2 bath, very private and quiet- all linens provided, washer/dryer in unit- stores within short walk; Publix, Walgreens, CVS, Dollarama, Dunkin Donuts/ Baskin Robbins, beach stores, Ace Hardware, ...

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Property Type

Anna Maria Island Condo

Featured review

"Great condo!"

We enjoyed our stay! The condo was clean, spacious & inviting! The location was wonderful. We will definitely stay again. The owner was very quick to reply to my emails.

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

$395

avg/night

$395
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to "Come Sail A Bay"! Bring your boat and gear because this charming single-level home boasts 3 bedrooms and 3 bathrooms, situated on the canal just a few homes away from the open bay! With a minimum stay of 30 nights, "Come Sail A Bay" offers stunning waterfront views the ...

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Property Type

Anna Maria Island House

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Anna Maria Island House | On the beach
6 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 6 Bedrooms, 4 Bathrooms

$500

avg/night

$500
avg per night
View Details

Key Amenities

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

About this property

This upper and lower unit duplex home is located steps from the Gulf of Mexico on historic Anna Maria Island. These Holmes Beach bungalows have a large heated pool and are rented in unison, perfect for friends and large families, as well. Both units are pet friendly. Only 1/2 mile from shops and restaurants ...

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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

$680

avg/night

$680
avg per night
View Details

Key Amenities

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

About this property

Breathtaking sunset views atop your own expansive and elevated deck await at this spacious single story home on gorgeous Anna Maria Island! This home features 4 large bedrooms, each with its own private en suite bathroom, a large kitchen, living room, additional sitting area plus two separate dining spaces. ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms

$419

avg/night

$419
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Take one step into this home and you will think you are dreaming! It's the epitome of coastal living because it's absolutely breathtaking! Bring your boat! Look straight out the sliders in the kitchen and you'll see an amazing crystal blue pool with a sun deck, artificial turf with a putting ...

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Property Type

Anna Maria Island House

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Anna Maria Island Villa
3 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 4 Bathrooms
3 reviews
last minute deal
LAST MINUTE DEAL 11/16 - 12/9: 15% your next vacation for the months of Nov. and Dec! Contact us for details!

$556

avg/night

$556
avg per night
Offer for: Nov 16 - Dec 9:
15% your next vacation for the months of Nov. and Dec! Contact us for details!

View Details

Key Amenities

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

About this property

Escape to your own tropical paradise at this stunning villa on Anna Maria Island! This beautiful property offers everything you need for the ultimate island getaway, including a private heated pool with a serene waterfall, a convenient elevator, a spacious lanai, and a charming Tiki hut for relaxing in ...

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Property Type

Anna Maria Island Villa

Featured review

"Beautiful house and Celine is an excellent host"

Beautiful house and Celine is an excellent host. We stayed here a week for a family vacation and really enjoyed our time. House had everything we needed and more. Very clean and super close to the beach. ...

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

$200

avg/night

$200
avg per night
View Details

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

Featured review

"Amazing view and great host"

Terry's home is in a perfect location, with a great view, comfortable beds, and within walking distance of so many great places. I'll definitely book with him again!

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Anna Maria Island Condo
2 BR | 1 BA | Sleeps 5 | Quick View
Sleeps 5, 2 Bedrooms, 1 Bathroom

$166

avg/night

$166
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Palm Cay unit 10 is a two bedroom , one bath condo just 50 steps from the pristine Gulf waters of Homes Beach. There is a shared pool centered in a courtyard surrounded by lush , tropical vegetation. There is a double sofa bed in the living room. The kitchen is fully equipped , including a coffee ...

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Property Type

Anna Maria Island Condo

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

$272

avg/night

$272
avg per night
View Details

Key Amenities

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

About this property

Welcome to paradise on beautiful Anna Maria Island! Sunbow Bay 209 is a newly furnished 2 bedroom 2 bath condo with new appliances and coastal decor overlooking a peaceful serene lagoon with kayak and canoe access directly to the intercoastal waterway.Enjoy stunning sunrises with a cup of coffee on ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
5 reviews

Distance to beach: 0.5 miles to Manatee Beach

$222

avg/night

$222
avg per 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

Featured review

"Fabulous stay on Anna Maria Island"

This condo was the PERFECT place for our family of three to enjoy Anna Maria Island! It was clean, cozy, and had everything we needed! Carla was a wonderful host who was very accommodating and gracious ...

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Anna Maria Island Vacation Rentals