Monthly Rentals in Anna Maria Island

(26 rentals)
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Anna Maria Island House
2 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1.5 bathrooms
11 reviews

$502

avg/night

$502
avg per night
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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Rentals by owner
  • WiFi

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 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

$188

avg/night

$188
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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 House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$500

avg/night

$500
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

*30 Day min rental @ $500/night rate + taxes and fees.Welcome to Pink Pearl – your perfect coastal escape! This stunningly renovated 4-bedroom, 3-bathroom oasis is ready to make your dream getaway a reality.Designed with both comfort and luxury in mind, this one-story home boasts a seamless ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
13 reviews

$363

avg/night

$363
avg per night
View Details

Key Amenities

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

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 Location and Spacious Condo"

We spent a wonderful month in this unit. You can see the beach from the front balcony as it's just across the street. It's very spacious with an open concept living room, kitchen and dining area. It ...

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Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$364

avg/night

$364
avg per night
View Details

Key Amenities

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

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

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Anna Maria Island House
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
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

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 Villa
4 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 4 bedrooms, 4 bathrooms
4 reviews

$229

avg/night

$229
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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

"Huge pool and awesome location"

We had a great time and our kids loved the pool! We rented bikes and used them everyday. We had a party of 12 and it was big enough for all. We would love to stay again!

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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

$175

avg/night

$175
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

- 7 min. walk to beach, beach chairs, umbrellas, towels, beach wagon provided- sleeps 4, 2 bedroom/2 bath, very private- On second floor with covered stairs. No elevator.- all linens provided, washer/dryer in unit- stores within short walk; Publix, Walgreens, CVS, Dollarama, Dunkin ...

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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 Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$220

avg/night

$220
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

30 day stays make this condo community wonderfully quiet and special. The view overlooks the big pool and the Bay. Bring your swimsuit, we are a short distance to AMI's famous white sand beaches, umbrella, beach canopy, cooler, beach towels, and chairs make for a perfect beach day and sunset and ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island Apartment
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
20 reviews

$204

avg/night

$204
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

This 1 BR, four-guest, condo strategically placed within short walks to the Beach (900ft, 275M), Marina (150ft, 46M), Historic Bridge Street (800ft, 245M), and Pier (1,056ft, 322M) will keep you CHEERFUL your entire stay! Coastal amenities: front screened lanai, heated pool, beach toy closet (including ...

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Property Type

Anna Maria Island Apartment

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Anna Maria Island House
5 BR | 6.5 BA | Sleeps 8 | Quick View
Sleeps 8, 5 bedrooms, 6.5 bathrooms
4.8 rating on other travel sites

$1104

avg/night

$1,104
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Anna Maria Beach House offers a 5 bedroom and 6.5 bathroom, pet-friendly property, making it a perfect vacation retreat for your whole family. Situated close to the beach, shops, and restaurants, this property is an ideal choice. Just a brief stroll away from the beach, the house boasts a pool and hot ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
5 BR | 5.5 BA | Sleeps 8 | Quick View
Sleeps 8, 5 bedrooms, 5.5 bathrooms
1 review

$1221

avg/night

$1,221
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Come stay at From Dusk 'Til Dune! This home is a recently built beach residence offering rooftop water views just one block away from the Gulf of Mexico beaches. This 5 bedroom, 5.5 bathroom, pet-friendly vacation haven is brimming with amenities. Its stunning backyard features a private pool, hot ...

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Property Type

Anna Maria Island House

Featured review

"Serenity on the Water"

The condo was only surpassed by the view, which included a nightly explosion of sunset glory over the sound. If one wanted to be closer to the sun from the beach, the club directly on the gulf was only ...

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Anna Maria Island House
9 BR | 8.5 BA | Sleeps 8 | Quick View
Sleeps 8, 9 bedrooms, 8.5 bathrooms
2 reviews

$1593

avg/night

$1,593
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Compass Rose, a captivating residence offering deluxe amenities including a lazy-river-style pool with a hot tub, a game room, an elevator and a rooftop deck boasting amazing views of the Gulf of Mexico. This 9 bedroom, 8.5 bathroom, pet-friendly abode is an ideal beach retreat suitable for multiple families ...

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Property Type

Anna Maria Island House

Featured review

"Great location"

Very clean and comfortable. Easy walk to everything you need and want to do. I would stay there again and highly recommend.

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Anna Maria Island Condo
2 BR | 1 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 1 bathroom

$229

avg/night

$229
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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 House
9 BR | 8.5 BA | Sleeps 8 | Quick View
Sleeps 8, 9 bedrooms, 8.5 bathrooms

$1659

avg/night

$1,659
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Get ready to be swept off your feet by the charm and luxury of Winding Waves, your dream vacation spot right on the beautiful Anna Maria Island. This dazzling nine-bedroom, eight-and-a-half bathroom beachfront home is all about fun in the sun and upscale relaxation!Splash and Play Outdoors: Dive ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 6.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 6.5 bathrooms

$799

avg/night

$799
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS MADE AFTER April 29, 2024! All Drivers must be over the age of 21. Drivers must provide valid US Driver's License and US Vehicle InsuranceSurfer's Dream boasts 4 bedrooms, 6 full bathrooms, and 1 half bath, and is also pet-friendly! This ...

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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
1 review

$379

avg/night

$379
avg per night
View Details

Key Amenities

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

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

Featured review

"Awesome House"

WOW! I can not say enough about the wonderful stay we had. The house was beautiful and stocked with everything a family would need and the location is perfect. Short walk to beach and Pine St. restaurants ...

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Anna Maria Island House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

$799

avg/night

$799
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

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
9 BR | 10 BA | Sleeps 18 | Quick View
Sleeps 18, 9 bedrooms, 10 bathrooms

$2343

avg/night

$2,343
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Gather your family and friends and head to Swanky Bubbles! Swanky Bubbles can accommodate 18 people! This exquisite 9-bedroom, 11-bathroom, pet-friendly with an elevator residence is ideally situated. Just steps away from the beach and within walking distance of shopping and restaurants, you'll have ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
8 BR | 8.5 BA | Sleeps 18 | Quick View
Sleeps 18, 8 bedrooms, 8.5 bathrooms
4.8 rating on other travel sites

$1487

avg/night

$1,487
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to “On the Rocks”! This professionally designed nautical themed home hosts 8 bedrooms and 8.5 bathrooms, plenty of space for large families or friends. This property has an elevator and is also pet-friendly. Bring your boat and fishing gear because On the Rocks is a waterfront home ...

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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

$333

avg/night

$333
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to "Come Sail A Bay"! Bring your boat and gear because this newly renovated, 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 ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
8 BR | 6.5 BA | Sleeps 18 | Quick View
Sleeps 18, 8 bedrooms, 6.5 bathrooms
1 review

$2508

avg/night

$2,508
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Paradise Beach lives up to its name! Nestled directly on the pristine soft white sands of Bradenton Beach, this remarkable property boasts 8 bedrooms, 6.5 bathrooms, and is pet-friendly. Complete with an elevator, it comfortably accommodates up to 18 guests. Bring your family and friends along to experience ...

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Property Type

Anna Maria Island House

Featured review

"Margaritaville Themed Paradise with 2 King Beds & Incredible Lanai!"

Truly an amazing resort and we loved staying in Sunset Seacret! Our family enjoyed every minute! We looked hard to find a beautiful, safe, clean, beachy condo with 2 king beds, as we were vacationing with ...

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Anna Maria Island Apartment
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$127

avg/night

$127
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

2 bedroom 2 bath 1000 square feet condo with a beachfront view of the Gulf of Mexico on the quiet, peaceful Anna Maria Island. Walking distance to many restaurants and bars. 30 minutes away from the Sarasota/Bradenton airport. Free trolley to go anywhere on the island.

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Property Type

Anna Maria Island Apartment

Featured review

"Queens Gate rentals-Neptune"

We had a great time. Kathy and Peter were amazing hosts who took care of our every need. We will be back again.

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Anna Maria Island Apartment
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$214

avg/night

$214
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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 Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$165

avg/night

$165
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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 House
2 BR | 2.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2.5 bathrooms

$543

avg/night

$543
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 Vacation Rentals