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Anna Maria Island Vacation Rentals

(272 rentals)
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Buckeye Haven is situated in one of the most sought after communities on Anna Maria Island. Playa Encantada is a tropical beach front community with the white sandy beaches of Anna Maria Island! This popular destination is sure to please beach goers, as well as tennis and pickleball enthusiasts. The...

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$262
avg per night
Anna Maria Island Condo
Sleeps 8, 4 bedrooms, 2 bathrooms
12 reviews

Key Amenities

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

About this property

Beachfront Holidays are the gift everyone loves! Celebrate the season steps from the beach at Island Suites Unit 1. The island charms you with music, holiday lights, festive eats, shops, and holiday cheer - providing the perfect atmosphere for an unforgettable holiday together. Relax on our large screened...

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$457
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Shell Game has been transformed into a fun and stunning tropical retreat that offers 1,154 sq. ft. of spacious living area with a newly upgraded kitchen.Located in the sought after complex of Playa Encantada; Shell Game is a tropical beach front community on the white sandy beaches of Anna Maria...

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$254
avg per night
Anna Maria Island House
Sleeps 5, 2 bedrooms, 1 bathroom
15 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

The Holidays are here and we are excited to share them with you. Our space provides the perfect backdrop for escaping the hurried pace of the holidays and slowing things down. With the sandy beaches just steps away, spending your days soaking in the sunshine and hearing the crashing waves is just what...

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$350
avg per night
Anna Maria Island House
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

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

About this property

Welcome to Gone Coastal, where every detail was carefully crafted for an unforgettable stay.*Features include** Private saltwater pool * 2 bedrooms and 2 full bathrooms * Queen sleeper sofa - sleeps 6 total * Stainless appliances * Keurig coffee maker and regular drip coffee maker *...

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Featured review

"Perfect beach location with beautiful interior"

This duplex includes stunning beachy interior decorating, great location (quiet neighborhood with an easy walk to a white sands beach) with a bonus heated pool with outdoor shower, which was ideal after...

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$396
avg per night

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Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • WiFi

About this property

Your Own Oasis on Anna Maria Island awaits you and your family with this custom built island retreat. The large, central great room is a wonderful place to gather to share a meal or play a game, while the split bedroom configuration creates privacy. Hand scraped hardwood floors and 11' ceilings complete...

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$355
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

From the moment you step inside this hidden gem you are struck by the breathtaking views. Whether you are cooking in the kitchen, enjoying a meal in the dining room, sitting at the desk, or out on the screened lanai, you are captivated by the calming waters, beautiful yachts, and the many birds that call...

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$317
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 0.1 miles to Beach Access 45th St

Key Amenities

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

About this property

Address of Manatee Watch: 205 N Harbor Drive, Holmes Beach, FL 34217MANATEE WATCH - A marvelous waterfront 3 bedroom/ 2 bath home just a short walk away from an astonishing white sand beach. Heated pool, hot tub and a spacious dock with beautiful views of the canal. Many months each year you can watch...

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$475
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3.5 bathrooms
1 review

Distance to beach: 0.1 miles to Beach Access 45th St

Key Amenities

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

About this property

Address of Areca Cove: 206 N Harbor Drive, Holmes Beach, FL 34217ARECA COVE - A bright and wonderful 4 bedroom/ 3.5 bath home just a 3-minute walk away from an astonishing white sand beach. With a heated pool in tropical and private surroundings, a covered patio by the pool area and multiple balconies...

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Featured review

"Perfect home and wonderful hosts!"

Olaf and Marissa were wonderful hosts - welcoming and responsive. Their home was absolutely perfect for a family get together with mixed ages. They have everything you need for a beach stay and the space...

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$466
avg per night
Last Minute Deal
Anna Maria Island Condo
Sleeps 5, 2 bedrooms, 1 bathroom
1 review

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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Featured review

"Enjoyed it very much."

The unit was lovely. Well equipped and very clean. The pool area is very nice and a 1 minute walk to a beautiful beach.

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$239
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Amazing views from the living room and primary bedroom of this 2 bedroom/2.5 bathroom. Take a drink outside and sit on your private balcony and watch the incredible sunsets. This beautiful condo sits right on the beach in Holmes Beach. After a day on the beach, take a dip in the community pool or sit...

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$490
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Kai Blue is located in Holmes Beach, just steps from the beautiful AMI beaches. This 4 bedroom/2.5 bathroom with an elevator also has a private backyard with a pool. Kai Blue gives you the dreamy coastal vibe and it's close to restaurants, Island stores and right next to the free trolley stop.Pull...

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$481
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to "Gulf Breeze" – Your Island Retreat in Holmes BeachLooking for your perfect island escape? "Gulf Breeze" is a bright and breezy 2-bedroom, 2-bathroom second-floor condo (Unit 208) located in the quiet and friendly Cayman Cay community in Holmes Beach on Anna Maria...

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$245
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private 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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$921
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 1 bathroom
3 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Sunset Azul is a fully-updated 2 bedroom/1 bath gulf-side ground level villa on the southern end of Holmes Beach. It's quiet, yet close to shopping, restaurants and trolley stops. Best of all, this unit is only a few short steps to the white sandy beaches. This villa has a fully-equipped kitchen,...

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Featured review

"Beautiful place - Highly recommended!!"

This is a great condo!! Full kitchen, washer and dryer IN unit, comfortable bed and beautiful natural light throughout. Only a 2 minute walk to the Gulf beach, Walgreens and Public. 2 parking spots are...

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$312
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Please note that surrounding units may still be undergoing improvements. The shuffleboard, club house, and fitness center are currently unavailable until further notice. For updates, please contact SeaBreeze Vacation at .Come relax and enjoy this stunning 2 bedroom/2 bathroom, second level, recently...

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$265
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Please note that surrounding units may still be undergoing improvements. The shuffleboard, club house, and fitness center are currently unavailable until further notice. For updates, please contact SeaBreeze Vacation at .Run to the Sun is a 2 bedroom/2 bathroom updated condo located in the sought...

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Featured review

"Pure PLEASURE"

Such a wonderful location right across from the beach, unit was spacious, clean everything use need. Anna Maria is so special the sunsets are amazing, it's walkable for restaurants, shopping. I've been...

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$238
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Perfectly located 2 bedroom/2 bathroom condo is directly across the street from the gulf beaches. Pelican Cove is located in a small, private complex on a very unique part of the Island. It is one of the few condos with views of both the Gulf and the Bay. Pelican Cove is just 40 yards from one of the...

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Featured review

"Perfect"

Our stay at Pelican Cove 3 couldn't have been better. The condo was clean, steps away from the beach, and check in was a charm. We truly enjoyed our evening view of the beach and the sunsets from our balcony....

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$349
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Relax, unwind, and make the best beach memories in this beachy home! This home has a fully-equipped kitchen that will make preparing meals easy. Spend time grilling on the private patio after a day of fun on the beach.You are just a seashell's throw from the white sands of the Gulf of Mexico, it...

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$272
avg per night
Anna Maria Island Townhome
Sleeps 8, 3 bedrooms, 2.5 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Bradenton Beach Club is a beautiful Gulf to Bay property that is 1/2 a block away from the beautiful beaches offering you all of the conveniences you would want in an island stay. This beautiful townhouse sleeps up to eight people with 3 bedrooms/2.5 bathrooms, full laundry, elevator, garage, and large...

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Featured review

"Best week!"

My family and I travel every year for the 4th of July, this year we decided to visit Anna Maria Island. WE LOVED IT! Everything was great, the weather, the relaxed atmosphere, the water temperature and...

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$341
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private 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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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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$817
avg per night
New
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Please note that surrounding units may still be undergoing improvements. The shuffleboard, club house, and fitness center are currently unavailable until further notice. For updates, please contact SeaBreeze Vacation at .Bougie Bay, a beautiful renovated ground-floor condo located in the sought-after...

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$270
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Indulge in the ultimate beach escape to “Oceans Blue” located on the *premier corner* of Coconut & Los Cedros in Anna Maria. Oceans Blue is a very short walk (only 0.15 miles) to the gorgeous, white sandy beaches of Anna Maria Island, just north of Pine Ave. This *ultimate beach house*...

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$705
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Pelican Cove is a beautiful Gulf to Bay property with a prime location just steps to the beach, five-star restaurants, shops and more - it's the tropical vacation you've been dreaming of offering you all of the conveniences you would want in an island stay. This beautiful condo was completely...

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Featured review

"Great Island Location"

Clean, cute updated condo. Photos represent the property correctly. Great view of the bay, right on the water. Only a short walk across the street to the beach. Easy walk (5 blocks) to great shopping...

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$300
avg per night
Anna Maria Island House
Sleeps 8, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

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$434
avg per night
Anna Maria Island Townhome
Sleeps 9, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Escape to our Gulf-to-Bay townhome on Anna Maria Island for a truly unforgettable vacation. With its ideal location, luxurious amenities, and proximity to the beach, this property is a haven for beach lovers and those seeking a taste of island paradise. Relax, explore, and create cherished memories in...

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$407
avg per night
New
Anna Maria Island House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to “Anna Maria Beach House,” your perfect island retreat on beautiful Anna Maria Island.This inviting coastal getaway blends relaxed beach-town charm with bright, comfortable spaces, offering everything you need for an unforgettable stay on AMI.From the moment you arrive, you’ll...

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$522
avg per night
Anna Maria Island Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to Bradenton Beach Club #246 “The Sea Grape”! Here is a wonderful opportunity to enjoy an updated condominium featuring 3 bedrooms and 2 full baths. Bradenton Beach Club is a great Beach to Bay complex offering many amenities such as private beach access and a boardwalk that takes...

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Featured review

"Sea Grape Condo"

Condo was as advertised. Spacious and comfortable. Nice heated pool, not too busy. Easy walk to beach and nice beach chairs and cart to use. Indoor parking was nice to have. Hot tub was out of commission...

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$304
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

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$688
avg per night
Anna Maria Island House
Sleeps 8, 5 bedrooms, 5 bathrooms

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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$984
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Looking for the perfect beach destination? Well, it doesn't get better than this! This 2 bedroom/2 bath condo, recently updated, is centrally located on Holmes Beach and is only steps from the sparkling gulf waters and white sandy beaches. New floors, new furnishings and decor - this place is your...

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Featured review

"Tropical Sunset #1"

Location is where it's at! Close to everything, yet on a quiet street. We had a great time celebrating 5 years post cancer! Loved the Island and everyone on it. We didn't want to leave! Loved the way...

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$335
avg per night
New
Anna Maria Island House
Sleeps 6, 2 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Make a salty margarita as soon as you arrive at Salty Margarita, a beautifully renovated 2-bedroom, 3-bathroom single-family home just moments from the beach on stunning Anna Maria Island. Step inside through the sliding balcony doors and you'll be greeted by an open-concept living area that connects...

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$408
avg per night
Anna Maria Island Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Just a 2 minute walk across the street to the beautiful beaches of Anna Maria Island. This updated coastal beach condo is all you need for a stay in paradise, so slow down and enjoy the Beach life at 3 on Avenue Sea. Bradenton beach is centrally located just south of Anna Maria and Holmes Beach, just...

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$209
avg per night
Anna Maria Island House
Sleeps 12, 5 bedrooms, 6 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

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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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$769
avg per night
Anna Maria Island Bungalow
Sleeps 4, 1 bedroom, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • WiFi

About this property

The Magic Dolphin Unit A and B can be booked together for larger groups up to 8 people. Please call our office or use the link provided below to check availability on Unit B.Unit B: Visit Unit BWelcome to “The Magic Dolphin A” an elevated vacation rental located on the northern section...

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Featured review

"Magic Dolphin A"

We had a wonderful stay at Magic Dolphin A. The unit was very clean and well maintained, which made settling in easy and comfortable. The beds were especially cozy- we slept great throughout our trip.It...

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$318
avg per night
New
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Please note that surrounding units may still be undergoing improvements. The shuffleboard, club house, and fitness center are currently unavailable until further notice. For updates, please contact SeaBreeze Vacation at .Recently Renovated!Welcome to your perfect beach retreat! This beautifully...

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$273
avg per night
Anna Maria Island House
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come enjoy this 2 bedroom/2 bath duplex that can sleep up to 6 people with the add-on of the sleeper sofa. Blue Lagoon is located on North Shore which is just a few blocks from the renowned shopping and dining of Pine Avenue and features a large, shared heated pool, and an EV charger. Upon entry, you...

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Featured review

"Blue Lagoon South"

We stayed at Blue Lagoon South on AMI!!!! This place was amazing for my children and I. Very clean and cozy!!! Modern!

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$358
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Costa Lotta is "home away from home”. All the amenities you will need in this 2,100 sq.ft. home. Costa Lotta is the perfect vacation spot for relaxation on Anna Maria Island! Just 200 steps and you are on a gorgeous, white sandy beach looking at the spectacular Gulf of Mexico! Walking distance...

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$450
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

A picture is worth a thousand words, and you'll have plenty of photo-ops from your spacious, screened-in, second story balcony with unmatched up-close views of the ocean. Whether it's swimming in the shared heated pool or lying on the beautiful beach, there's no shortage of conveniences....

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$456
avg per night
Anna Maria Island Villa
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

For our beachgoer guests, the beach entrance to Anna Maria's sandy, white beaches are approximately 40 steps away. Bean Point Residence Unit B, the lower level of a two-unit home, offers 2 bedrooms and 2 bathrooms. Modern amenities include stainless steel appliances and up-to-date kitchen cabinets....

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$394
avg per night
Anna Maria Island Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Located on the tranquil beaches of Anna Maria Island, Sandy Turtle is mere steps away from the beach and offers picturesque views of the Gulf of Mexico. The only thing distancing the balcony from the sand is a large, heated, shared swimming pool. This condo is one of the few originals left on the island...

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$562
avg per night
Anna Maria Island Condo
Sleeps 4, 1 bedroom, 1 bathroom
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Please note that the condo complex is currently an active construction site. The shuffleboard and fitness center are currently unavailable until further notice. For updates on construction progress and amenity availability, please contact SeaBreeze Vacation at .35 Steps to the Beach at Runaway Bay...

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Featured review

"Great location, beautiful condo and excellent restaurants."

First time to Anna Maria Island and we really enjoyed it. We usually stay in Siesta Key but I think we found a new favorite area. The pool was very nice at this property and the beach is right across...

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$228
avg per night
Anna Maria Island Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Please note that surrounding units may still be undergoing improvements. The shuffleboard, club house, and fitness center are currently unavailable until further notice. For updates, please contact SeaBreeze Vacation at .35 Steps to the Sea at Runaway Bay 112 is a 1 bedroom/1 bath, ground floor condo...

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Featured review

"Fantastic vacation all around"

This was a very nice condo. Clean and well kept. Very close to the beach and to the pool. Location was everything we wanted. Walking distance to restaurants and the heart of town. Great food, great people....

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$226
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Located right across the street from the world-famous Anna Maria Island beaches, this two-bedroom condo is newly remodeled and updated and is less than 100 steps away from the warm turquoise gulf waters and sparkling white sand. Tropical Sunset #2 is one of only four units in the entire building and also...

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Featured review

"Amazing Location"

Perfect location, beach was less busy because we were far enough away from the public beach area. Plenty of space to set up and not be on top of other people. The condo itself is good and had everything...

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$326
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Please note that surrounding units may still be undergoing improvements. The shuffleboard, club house, and fitness center are currently unavailable until further notice. For updates, please contact SeaBreeze Vacation at .This beautiful second-level condo offers the perfect blend of comfort and coastal...

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Featured review

"Excellent beach vacation"

Such a pleasant stay, great location for walking to restaurants, shops, steps from the beach. We loved staying on the island it's been years since we've been and really appreciated all that it has to offer....

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$262
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Island Dream is your perfect coastal escape. This spacious 4-bedroom, 4-bathroom coastal retreat with a fully equipped kitchen and a stunning backyard perfect for outdoor entertaining. Ideally located near the beach, shops and restaurants, it offers the perfect blend of comfort, convenience and relaxation.Step...

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$522
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Aqua Blu is a newly remodeled 2 bedroom/2 bathroom gulf front condo that offers everything you will need for a carefree getaway including a heated community pool and spa. From the moment you walk in, you are welcomed by stunning gulf views. Your private balcony will be the perfect resting place both day...

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$435
avg per night
Anna Maria Island Apartment
Sleeps 3, 1 bedroom, 1 bathroom
2 reviews

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to “Barefoot Mermaid 3” a relaxed ground floor vacation rental located on the north end of gorgeous Anna Maria Island. The serene location of this property is just amazing. Located steps, less than 50 ft to white powder sand beaches of the Gulf of Mexico and less than a few flip flop...

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Featured review

"Lovely Accomodation"

We were so pleased with Barefoot Mermaid 3. Everything was so clean and well cared for. The kitchen was stocked with the things we might need. We were so close to all our favorites like The Sandbar, Mademoiselles...

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$279
avg per night
Anna Maria Island House
Sleeps 16, 7 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

View all property information

$1,039
avg per night
New
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

Welcome to Martinique Cheer, your cheerful beachside escape on beautiful Anna Maria Island! This rare higher-rise Holmes Beach condo offers incredible Gulf views and a prime location in a quiet, well-maintained complex. Just steps from the sand and a short stroll to the heart of Holmes Beach, you’ll...

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$241
avg per night
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Anna Maria Island Weather

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7423°  5211°
JANUARY
Ocean 6518°
7624°  5412°
FEBRUARY
Ocean 6518°
7926°  5714°
MARCH
Ocean 6820°
8328°  6116°
APRIL
Ocean 7423°
8831°  6719°
MAY
Ocean 7926°
9133°  7222°
JUNE
Ocean 8328°
9133°  7323°
JULY
Ocean 8529°
9233°  7423°
AUGUST
Ocean 8731°
9032°  7323°
SEPTEMBER
Ocean 8529°
8630°  6719°
OCTOBER
Ocean 8228°
8127°  6016°
NOVEMBER
Ocean 7624°
7624°  5412°
DECEMBER
Ocean 7021°

FAQ

How many vacation rentals are there in/around Anna Maria Island?

There are 272 Anna Maria Island vacation rentals available on FloridaRentals.com. From house rentals to condo rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Anna Maria Island?

There are vacation rentals available in Anna Maria Island for as low as $115 per night with an average price per night of $394.

Can I find a vacation rental in Anna Maria Island?

Yes, you can find vacation rentals in Anna Maria Island close to Holmes Beach, Coquina Beach, and Bradenton Beach. Don't forget to stop in to Bean Point or Manatee Public Beach.

Do any vacation rentals in Anna Maria Island have a pool?

Yes, there are 193 vacation rentals with a pool in Anna Maria Island on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Anna Maria Island vacation rentals on the ocean?

There are 22 oceanfront rentals in Anna Maria Island available on FloridaRentals.com. Use our filters to search and book yours today!