Monthly Rentals in Anna Maria Island

(25 rentals)
booking message booking message

3 BR | 3 BA | Sleeps 7 | Quick View

13

Distance to beach: 1 miles to Manatee beach

$253

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 ...

View all property information

Property Type

Anna Maria Island Condo

"Anna Maria rental"

Excellent stay clean and close to the beaches affordable. I would definitely stay there again love it

See all reviews

Show less

2 BR | 2 BA | Sleeps 5 | Quick View

6

$264

avg/night

View Details

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 ...

View all property information

Property Type

Anna Maria Island House

"Spectacular!"

We could not have asked for a more perfect home away from home. Gail is an amazing host, the home is beautiful, pristine, and well stocked with everything we needed plus more. The location is perfect for ...

See all reviews

Show less

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 ...

View all property information

Property Type

Anna Maria Island House

"Awesome house and outdoor area"

Nice house with a fantastic outdoor area with a nice pool, sitting area, bar, and t.v.. Close to the beach and there were chairs, tents, beach toys, and a wagon. Walking distance to several restaurants ...

See all reviews

Show less

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 ...

View all property information

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.

See all reviews

Show less

4 BR | 4 BA | Sleeps 8 | Quick View

$1042

avg/night

View Details

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 ...

View all property information

Property Type

Anna Maria Island House

Show less

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 and ...

View all property information

Property Type

Anna Maria Island House

"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 ...

See all reviews

Show less

2 BR | 1 BA | Sleeps 2 | Quick View

$137

avg/night

View Details

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 ...

View all property information

Property Type

Anna Maria Island Cottage

Show less

Key Amenities

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

About this property

Welcome to Beach Paradise on Bradenton Beach. This Gulf condo is sure to provide you a memorable stay with family or friends while spending relaxing days on the beach or lounging by the pool. This family-friendly condo has a view of the Gulf and Inter-coastal waterway and is just steps to the beautiful ...

View all property information

Property Type

Anna Maria Island Condo

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

$377

avg/night

View Details

Key Amenities

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

About this property

Island Retreat is a charming Beach House situated in a monthly vacation rental district in a quiet, single-family neighborhood on Anna Maria Island! Only 4 blocks to the beautiful beaches of Anna Maria Island! This 2 Bedroom 2 Bathroom Beach House offers Stainless Steel appliances and Granite counter ...

View all property information

Property Type

Anna Maria Island House

Show less

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 ...

View all property information

Property Type

Anna Maria Island Condo

"Fabulous condo for a month on AMI"

A wonderful "home away from home". Very clean and beautifully furnished; updated, especially the kitchen. Comfortable beds. A community pool and grill, and a well stocked kitchen and beach shed. The neighbors ...

See all reviews

Show less

4 BR | 2.5 BA | Sleeps 8 | Quick View

5.0 rating on other travel sites

$634

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

The Gables is a charming 4 bedroom / 2.5 bathroom southern style home that features a private pool and is centrally located in the heart of Holmes Beach and within walking distance to the white sandy beaches. The furnishings and facilities are of the highest quality to make your vacation one to remember. ...

View all property information

Property Type

Anna Maria Island House

Show less

4 BR | 4 BA | Sleeps 8 | Quick View

Owner special: Book now for the months of June or July 2023 and recieve a 10% discount on the nightly rate!

$840

avg/night

View Details

Key Amenities

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

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. ...

View all property information

Property Type

Anna Maria Island House

Show less

3 BR | 2.5 BA | Sleeps 6 | Quick View

4.7 rating on other travel sites

$862

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Sea Le Vie at Bradenton Beach Club offers panoramic views of the Gulf of Mexico and beautiful beaches from the living room, master suite or private screened balcony. This beach front condo is part of the Bradenton Beach Club that provides the very best in vacation accommodations. Amenities at the BBC ...

View all property information

Property Type

Anna Maria Island Condo

Show less

3 BR | 2 BA | Sleeps 4 | Quick View

5

Distance to beach: 4 miles to Anna Maria

$107

avg/night

View Details

Key Amenities

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

About this property

This ground floor fully furnished three bedroom fully two bath condo has just been totally renovated and recently redecorated. The condo features a comfortable coastal style that has been decorated and furnished by the owners. The condo is located on Overture Circle Bradenton just off 75th Street in ...

View all property information

Property Type

Anna Maria Island Condo

"A lovely place for a perfect vacation!"

I booked this condo for my children and their spouses to stay over Christmas, and it was even better than the listing information portrays. The space is decorated beautifully, and has everything you would ...

See all reviews

Show less

Key Amenities

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

About this property

Beautiful 4 bedroom, 2.5 bathroom home with direct access to Anna Maria Canal and private heated pool overlooking the water. Take a kayak ride right off your private dock area or cast a fishing pole and catch dinner. This home has lots of space and is ready for you to come enjoy all of what the island ...

View all property information

Property Type

Anna Maria Island House

"Very nice"

We met with the owner and he was very helpful in showing us around the property.The house was very clean and was everything we had expected. Brian and Marie

See all reviews

Show less

3 BR | 2.5 BA | Sleeps 6 | Quick View

4.9 rating on other travel sites

$584

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

A beacon of outstanding design, Anna Maria Island's newest landmark, The Lighthouse, is centrally located in Holmes Beach and only a short walk to the white sandy beaches. Standing tall, featuring 3 bedrooms / 2.5 bathrooms, a heated pool and a rooftop viewing deck with stunning 360 degree views. This ...

View all property information

Property Type

Anna Maria Island House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Beach Haven is a completely updated 2 bedroom 2 bathroom gulf to bay condo located in the Gulf Watch Community. Gulf Watch is a beautifully maintained complex boasting a sparkling heated pool to be enjoyed year-round. This condo is located in Bradenton Beach and only a few steps away from the beach yet ...

View all property information

Property Type

Anna Maria Island Condo

"Cozy and easily beach accessible"

Nice size townhouse for my husband and I. Very good location. Nice decor. Well equipped kitchen. Little inconvenient access to the grill, it is located on ground floor, near the pool. Would consider renting ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

3

Distance to beach: 0.5 miles to Manatee Beach

$169

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 ...

View all property information

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 ...

See all reviews

Show less

2 BR | 1 BA | Sleeps 4 | Quick View

8

$146

avg/night

View Details

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 ...

View all property information

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 ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to Paradise!When you come to Anna Maria Island for vacation, make this charming and inviting two-bedroom condo your home away from home! You're sure to love the relaxed island attitude with amenities like a heated pool, private screened lanai, and easy access to the beach, dining, and shopping. ...

View all property information

Property Type

Anna Maria Island Condo

"Stunning Accommodation"

We arrived, looking forward to a three day trip to the island. We were delighted to find this beautiful apartment was situated in a lovely quiet area but close to the free trolley bus stop and Publix supermarket. ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

5

$188

avg/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. ...

View all property information

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. ...

See all reviews

Show less

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, ...

View all property information

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.

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Savour a hibiscus-pink sunrise and gentle salt breezes from your Anna Maria Island balcony. Take your breakfast on the screened-in lanai and dine above tropical treetops, with views of the turquoise swimming pool. The morning is serene, with soft rhythms of surf in the distance. Sip your coffee or fresh ...

View all property information

Property Type

Anna Maria Island Condo

"Wonderful Winter Getaway!"

AMI is our go to getaway! This was our 10+ visit to AMI. This condo was all we needed! Well furnished and close to the beach! The pool and hot tub were an added bonus!

See all reviews

Show less

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 ...

View all property information

Property Type

Anna Maria Island Apartment

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

1

$210

avg/night

View Details

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 ...

View all property information

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.

See all reviews

Show less

Map
Expand map Close map
Anna Maria Island Vacation Rentals