Luxury Vacation Rentals in Anna Maria Island

(68 rentals)
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Anna Maria Island House
5 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 5 bedrooms, 4 bathrooms
1 review

$730

avg/night

$730
avg per night
View Details

Key Amenities

  • Pool
  • WiFi

About this property

Mia Bella Mia Bella has been completely restored and updated, creating one of the most unique and spacious residential properties on Anna Maria Island. The property is located on a deep water canal with over 80 feet of private patio running alongside mature mangroves. A new heated swimming pool is ...

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Property Type

Anna Maria Island House

Featured review

"Delight in Anna Maria Island"

Salty Mermaid Vacation Rental in Anna Maria Island- Even before arriving to Mia Bella, the communication with both Bella and David was incredible. They both go above and beyond to make you feel comfortable ...

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Anna Maria Island House
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3.5 bathrooms
2 reviews

$1268

avg/night

$1,268
avg per night
View Details

Key Amenities

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

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

Featured review

"Best Place On Anna Maria"

Hosts are fabulous! very responsive and caring! House is amazing! our friends and family were blown away by how much attention to detail they put in to the furnishings and the home itself! A true paradise!

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Anna Maria Island House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$744

avg/night

$744
avg per night
View Details

Key Amenities

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

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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Anna Maria Island Villa
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
3 reviews
owner special
Owner special: 10% your next vacation! Contact us for details!

$727

avg/night

$727
avg per night
Owner special:
10% your next vacation! Contact us for details!

View Details

Key Amenities

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

About this property

Welcome to Calico: Your Island Retreat on Anna Maria Island! Walk to Manatee Public Beach, Grocery Stores, Restaurants, Shopping & More! Private Heated Pool, Tiki Hut and Lanai! Game Room with Ping Pong, Basketball, Arcade and Extra Fridge! Fully stocked kitchen for all your favorite home-cooked ...

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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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Anna Maria Island House
5 BR | 4.5 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4.5 bathrooms
5 reviews

$799

avg/night

$799
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

This luxurious property offers a perfect blend of indoor and outdoor living, with spacious accommodations for large groups or families, all while staying steps from the pristine white sand beaches and centrally located on Anna Maria Island! As you step through the front door, you enter a bright and ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
2 reviews

$852

avg/night

$852
avg per night
View Details

Key Amenities

  • Pool
  • WiFi

About this property

Welcome to "Luana Breeze" located at 208 68th Street, Holmes Beach. Find ease and relaxation the moment you arrive, this property is about 100 steps to the Gulf of Mexico and one of the best beaches on the West Coast of Florida. This ground level beach house offers 4 bedrooms, 3 bathrooms ...

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Property Type

Anna Maria Island House

Featured review

"A True Retreat"

This is a true retreat any time of the year. The backyard and pool area is well designed and an oh so private area that includes a hot tub, a pool, ping pong table, mini golf and hammocks for relaxing. ...

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Anna Maria Island House
4 BR | 5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 5 bathrooms

$1147

avg/night

$1,147
avg per night
View Details

Key Amenities

  • Pool
  • WiFi

About this property

Welcome to “Salty Sunsets” on beautiful Anna Maria Island. This luxurious property is located north of Pine Ave with easy access to Bean Point. This Anna Maria Island vacation rental home offers all the goodies to make sure your vacation does not skip a beat. This beautiful property offers ...

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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
1 review

Distance to beach: 0.1 miles to Tampa Bay

$1018

avg/night

$1,018
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Views, views, views! Experience all the best of the North end of Anna Maria from this waterfront home with pool and mini golf. *Features include* * Ultimate Bay front vacation home * Private heated pool and full Putt-putt course * Paddleboards, kayak * Gas grill and outdoor dining * Huge ...

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Property Type

Anna Maria Island House

Featured review

"Sandtrap house with Beach Boutique"

Beautiful home, fantastic location and incredible service. Everything was perfect. Live the area, restaurants, biking, atmosphere and people. Super friendly. We will be back using Beach Boutique again!

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Anna Maria Island House
6 BR | 4.5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4.5 bathrooms
4.8 rating on other travel sites

$872

avg/night

$872
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Prime Location! VERY CLOSE TO BEACH!!! Luxurious ground level home located at 124 50th Street, Holmes Beach, in the „Golden Triangle" of Anna Maria Island, FL, only few steps to the beach. 6 Bedrooms, 4,5 Bathrooms. Accommodates up to 12 people. Beds: 2 Kings, 2 Queen, 4 Twins, 1 Queen Sleeper ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3.5 bathrooms

Distance to beach: 0.1 miles to Bean Point

$859

avg/night

$859
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Views, views, views! Experience the peace and beauty of the North end of Anna Maria from this sprawling home named for its spectacular porches and outdoor space. *Features include* * Ultimate vacation home with elevator^ (currently out of service due to hurricanes, please inquire) * Private heated ...

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Property Type

Anna Maria Island House

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

$732

avg/night

$732
avg per night
View Details

Key Amenities

  • Pool
  • WiFi

About this property

Welcome to “Oceans Blue” on beautiful Anna Maria Island. Enjoy Luxury Living all on one floor. There are no stairs to climb at this ground level home. Peace, tranquility and the ultimate in privacy are yours at this completely renovated beach house with brand new private pool and spa and ...

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Property Type

Anna Maria Island House

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Anna Maria Island House | On the beach
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 0.1 miles to 30 seconds to your left

$768

avg/night

$768
avg per night
View Details

Key Amenities

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

About this property

This newly redesigned elevated 3 Bedroom, 2 Bathroom home is beautifully appointed throughout, with state of the art quartzite counter tops, stainless steel appliances and driftwood style hardwood floors and ceilings. Relax on the covered porch with direct views of the Gulf of Mexico and it's stunningly ...

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Property Type

Anna Maria Island House

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Anna Maria Island Condo
7 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 5 bathrooms
5.0 rating on other travel sites

$1507

avg/night

$1,507
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to AMI Beach Lagoon, your dream vacation on Anna Maria Island! In our lakefront luxury resort (12,500 sqft) we offer three separate ground level apartments with a large outdoor area that can be rented together or separately. Enjoy the privacy of your own entrance, fully equipped kitchen and ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
2 reviews

$719

avg/night

$719
avg per night
View Details

Key Amenities

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

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

Featured review

"Great Property"

This house is in a great location, three blocks to the beach, restaurants, and three blocks to the pier, and many other amenities. It is beautiful, spacious and has everything you need to make your stay ...

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Anna Maria Island House
5 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 2 bathrooms
2 reviews

$904

avg/night

$904
avg per night
View Details

Key Amenities

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

About this property

One of the highest rated vacation homes on Anna Maria Island with more than 150 five-star ratings from Airbnb/VRBO! Stay at the home of a NY Times best-selling food writer! Big 5-bedroom house, pet friendly, lots of space and charm, great location (5-min walk to beach) with private lagoon-style heated ...

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Property Type

Anna Maria Island House

Featured review

"Hidden paradise"

We were attending a beach wedding and made a vacation out if it. I connected with the owner Kath immediately. She was generous, attentive, available and without a doubt the best host we have ever met. ...

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Anna Maria Island House | On the beach
5 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 5 bedrooms, 5 bathrooms
1 review

Distance to beach: 0.1 miles to Bayside Beach

$925

avg/night

$925
avg per night
View Details

Key Amenities

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

About this property

Just updated 2021, with state of the art finishes! 5 BR + 2 King Sleep Sofas, 1.5 Chaise Lounger, 5 BA Duplex can sleep many with direct views of Skyway Bridge and Tampa Bay in front and at canal end in back with frequent visits from Manatees!! Email owner about our other property that sleeps 6 for smaller ...

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Property Type

Anna Maria Island House

Featured review

"Family holiday"

Fabulous location and spotlessly clean family villa with every conceivable convenience to hand. Fitted our purposes exactly and the addition of the kayaks, boat and bikes/golf cart if you wanted them was ...

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Anna Maria Island House
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3.5 bathrooms
1 review

$700

avg/night

$700
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Ground Floor Luxury Home with Heated Pool/Spa, very close to Beach Welcome to the AMI Beach Home on beautiful Anna Maria Island ! Visit AMI Beach Home, a marvelous custom-built ground floor vacation rental home just a few steps from the white sandy beaches of Anna Maria Island on 201 69th Street. ...

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Property Type

Anna Maria Island House

Featured review

"Awesome stay!"

Great location, accessible for grandparents with limited mobility, open space for large family to hang out in the open concept kitchen and living room area. Very quick walk to the beach

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Anna Maria Island House
6 BR | 5.5 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 5.5 bathrooms
14 reviews

$1258

avg/night

$1,258
avg per night
View Details

Key Amenities

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

About this property

ASK US ABOUT MULTI WEEK DISCOUNTS!! Featuring 6 bedrooms 5.5 baths (sleeps 14) and a fantastic location - just a 1 minute walk to the white sands of the 65th St Beach Access! This vacation home offers a huge heated pool with spa, rock water slide and grotto waterfall. Covered outdoor entertaining ...

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Property Type

Anna Maria Island House

Featured review

"Perfect!"

This place was perfect for our family! The 4 bedrooms with King size beds and en suite baths made it so convenient for each couple. The bunk beds were perfect for the kids. The children (and adults) loved ...

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

$752

avg/night

$752
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool

About this property

Anna Maria Island Beach Palace offers incredible views in every direction because it’s situated in the best location on the entire island! The island is only 150 yards wide where this 3-story condo is located. The Gulf of Mexico is merely 75 yards to the west, and Florida’s Intracoastal Waterway ...

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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

$1739

avg/night

$1,739
avg per night
View Details

Key Amenities

  • Pet friendly
  • WiFi

About this property

Mintfish is a tropical hideaway that blends high-end decor with natural beauty. This 4 bedroom, 4 bath ground-level luxury vacation home has recently been remodeled to combine natural and sustainable materials with decadent living. The single-floor layout makes the home easily accessible to people of ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

$1127

avg/night

$1,127
avg per night
View Details

Key Amenities

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

About this property

6605 Gulf Drive Holmes Beach, FL 34217 VRC19-00290 Right across the street from the beach and the Beach Bistro! Gulf Views available from this beautiful home. This custom 4 bed 4.5 bath home was built with no expense spared! Custom kitchen with gas stove, wine bar, roof top deck with sweeping views ...

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Property Type

Anna Maria Island House

Featured review

"Ideal family vacation home!"

The property was great, and worked really well with our family-which includes a 4 year old and a 9 month old, so having the bedrooms in different areas and private baths, made everything much easier. Centrally ...

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Anna Maria Island House
8 BR | 5 BA | Sleeps 18 | Quick View
Sleeps 18, 8 bedrooms, 5 bathrooms
3 reviews

$1189

avg/night

$1,189
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Looking for a relaxing island retreat just steps from the soft white sand and turquoise waters in Bradenton Beach on Anna Maria Island? Look no further for your perfect vacation home for the whole family. Island Oasis is a custom-built spacious 8 bedroom/5 bathroom was professionally furnished to provide ...

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Property Type

Anna Maria Island House

Featured review

"Nice"

Very clean nice home enjoyed it...would consider renting again..thank you...talked with the owner and manager next door Great people

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Anna Maria Island House
6 BR | 4.5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4.5 bathrooms

$1217

avg/night

$1,217
avg per night
View Details

Key Amenities

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

About this property

Big Luxury 6 bdrm, Pool, Spa, Bikes, Kayak, Reviews, Beach! Come enjoy a large family and friends gathering at this spacious luxury home just a few minutes stroll to the beach. One of the larger homes on the island, with 6 bedrooms and 4.5 bathrooms and 3400 sq. ft, this home has plenty of room for ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3 bathrooms

$828

avg/night

$828
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

C-View is the perfect island getaway for your family vacation. Conveniently located within walking distance to Anna Maria's picturesque white sand beaches, Pine Avenue's restaurants and shops, and access to the free trolley. Be sure to bring your kayaks and paddle boards so you can take advantage ...

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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

$842

avg/night

$842
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 Insurance Surfer'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
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

$779

avg/night

$779
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
4 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2.5 bathrooms
4.9 rating on other travel sites

$859

avg/night

$859
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 5, 2023! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle Insurance Located just steps away from the sugary, soft sand and clear ocean water, Salty ...

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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

$2145

avg/night

$2,145
avg per night
View Details

Key Amenities

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

About this property

Private Beachfront Home - one block from Pine Avenue and the City Pier. Watch dolphins and manatees swim by from your back deck. Bike or take the golf cart (included) to explore the island and boutique shops and restaurants. Ground floor has a beachfront king bedroom with en-suite bathroom, second king ...

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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

$1208

avg/night

$1,208
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
5 BR | 3.5 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 3.5 bathrooms
21 reviews

Distance to beach: 0.2 miles to bradenton beach

$702

avg/night

$702
avg per night
View Details

Key Amenities

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

About this property

You will fall in love with this peaceful retreat. This home comes with a 6 person golf cart. You will love zooming around the island on the golf carts, window shopping at all of the gorgeous real estate. This unit is within walking distance to the beach, you will love being able to walk back and forth ...

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Property Type

Anna Maria Island House

Featured review

"Wonderful first experience to AMI"

This rental is everything you could dream of. A short walk to the beach and all the extras you could ever need. The golf carts were our favorite for evening strolls along the island. Taylar really thought ...

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

$1510

avg/night

$1,510
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 | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
3 reviews

$852

avg/night

$852
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

VRC If Guest needs to shorten their stay or change to a different property, the normal cancellation policy applies. No changes are permitted during the stay. This stunningly built and decorated 4 bedroom + Bunk Den 4 bath home is just steps from the sparkling white sandy beaches of the Gulf of Mexico ...

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Property Type

Anna Maria Island House

Featured review

"Pleasantly surprised"

We rented this house for a family vacation. This house is everything you see & more. We found it to be perfectly located from beach/stores/restaurants in a quite neighborhood. The house was perfectly ...

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

$773

avg/night

$773
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

The View at the Bradenton Beach Club offers panoramic views of the Gulf of Mexico and beautiful beaches from the living room, primary suite or private screened balcony. The condo is part of the Bradenton Beach Club that provides the very best in vacation accommodations. Amenities at the BBC include two ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island House
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3.5 bathrooms

$882

avg/night

$882
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS MADE AFTER 1/24/24 WITH A CHECK-IN DATE BETWEEN ! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle Insurance Coastal Serenity has a rooftop deck, private pool and spa, and an EV Charger! ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
5 BR | 6 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 6 bathrooms
1 review

$904

avg/night

$904
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

A 6-person electric golf cart is included with any new reservation for this property! You must be 21 years old and show proof of US driver's license and vehicle insurance. You'll fall in love with this incredible bay front 5 bedroom/6 full bathrooms home with a separate suite, having 2 full-size ...

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Property Type

Anna Maria Island House

Featured review

"Great getaway !"

A time much needed . We so enjoyed our stay at 2311 ave.c that we hope to return every year . We just felt like we were at home .

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Anna Maria Island House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

$1257

avg/night

$1,257
avg per night
View Details

Key Amenities

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

About this property

128 49th St Holmes Beach VRC You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that time, or for reservations made on or less ...

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Property Type

Anna Maria Island House

Featured review

"Great Thanksgiving Vacation!"

We spent Thanksgiving week at Sunset and Sand and it delivered on all our expectations. The home is clean, beautifully decorated and functional. The kids absolutely loved the heated pool and Spa and Its ...

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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

$1097

avg/night

$1,097
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
9 BR | 8.5 BA | Sleeps 8 | Quick View
Sleeps 8, 9 bedrooms, 8.5 bathrooms
2 reviews

$1477

avg/night

$1,477
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 House
4 BR | 6.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 6.5 bathrooms
1 review

$866

avg/night

$866
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 WITH A CHECK-IN DATE AFTER SEPTEMBER 5, 2023! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle Insurance This gorgeous, custom-built, professionally designed, private home is a 4 bedroom/6.5 ...

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Property Type

Anna Maria Island House

Featured review

"Better than i expected."

Wonderful house. Very clean and well stocked. The pool was clean and big. Very close to a very nice beach. Would stay here again.

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Anna Maria Island House
4 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2.5 bathrooms

$1242

avg/night

$1,242
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Discover Serendipity: Your Pet-Friendly Beachfront Haven on Anna Maria Island Beachfront Bliss Awaits You Indulge in the enchantment of beachfront bliss at Serendipity, an exceptional 4-bedroom home perfectly positioned on the coveted North End of Anna Maria Island. This tranquil escape beckons you to ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms

$978

avg/night

$978
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Large 4 bedroom/2 bathroom Ocean view home with screened porches in the front and back. Elevator to the main level. Beach is right across the street. Bikes, Paddle Boards and a golf cart included. We are pet friendly! Pre-approved pet's , a signed pet agreement and pet fee paid in full will be needed. ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
1 review

$787

avg/night

$787
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 23, 2023! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle Insurance With the feel of a five-star luxury resort and the privacy of a secluded island ...

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Property Type

Anna Maria Island House

Featured review

"Very nice home"

Home was very nice. The whole backyard is like paradise. Overall great experience. Pool was not refreshing but probably expected this time of year in Florida. The hot tub flows over into pool when ...

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Anna Maria Island Townhome
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms
1 review

$743

avg/night

$743
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

202 69 th Street - Holmes Beach - FL 34217 VRC Book with confidence: You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that ...

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Property Type

Anna Maria Island Townhome

Featured review

"Lovely stay"

Another family and ourselves rented the property. We found it very clean and equipped to a high standard. The pool and jacuzzi were great and well used especially by the kids. The management company were ...

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Anna Maria Island House
2 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 2 bedrooms, 4 bathrooms

$2058

avg/night

$2,058
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

LimeFish is a luxurious newly remodeled 3 bedroom (1 king-sized, 1 queen-sized, and a bunk room)/3 bathroom single level home right on the sands of Anna Maria Island. Additional sleeping accommodations can be added with the sleeper sofa in the living room. It is a perfect destination for a trip with family ...

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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

$1402

avg/night

$1,402
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
5 BR | 5 BA | Sleeps 8 | Quick View
Sleeps 8, 5 bedrooms, 5 bathrooms

$912

avg/night

$912
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Bring your family and guests to this 2-unit house! About 40 steps to the beach entrance of Anna Maria white, sandy beach, this home combined boasts 5 bedrooms, a sleeper sofa and 5 bathrooms. Bean Point Unit A boasts 3 bedrooms/3 bathrooms, while Unit B has 2 bedrooms/2 bathrooms. Both units feature well-equipped ...

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Property Type

Anna Maria Island House

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Anna Maria Island Condo
2 BR | 2.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2.5 bathrooms

$705

avg/night

$705
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Very few beachfront vacation homes will get you as close to the sand as Hidden Cove #1— a beautiful 2-bedroom condominium with exquisite views and unlimited access to the aquamarine Gulf of Mexico. Located within a charming coastal community that also offers a crystal-clear swimming pool, your family ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island House
4 BR | 5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 5 bathrooms

$2247

avg/night

$2,247
avg per night
View Details

Key Amenities

  • WiFi

About this property

Luxurious - 4 bedroom 4.5 bath Beach Front Home with a Beach Front Pool and Spa/Gourmet Kitchen, high-end finishes, and one-of-a-kind features. Walk to the Rod-n-Reel Pier or take one of our bikes to explore Pine Avenue. Our bikes are complementary as are the paddle board and kayak. 4 King size bedrooms. ...

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Property Type

Anna Maria Island House

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

$1202

avg/night

$1,202
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beachfront, North End, large 2 bedroom with expansive views of the dolphins frolicking in the azure waters of the North End of Anna Maria Island. BBQ grill, bikes, paddle boards, and kayaks are all included. Your backyard is a beautiful view of Egmont Key & the Skyway Bridge and your front yard is ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
5 BR | 4.5 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4.5 bathrooms

$1037

avg/night

$1,037
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Get ready to pack your bags because you'll be escaping to a tranquil oasis nestled within a lush tropical backyard, where a shimmering pool and soothing spa await your relaxation. Discover the serene charm of A Bean Point Paradise, a retreat boasting 5 bedrooms and 4.5 bathrooms with parking for ...

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Property Type

Anna Maria Island House

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