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Anna Maria Island Vacation Rentals

(234 rentals)
Anna Maria Island Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Escape to paradise in this beautiful 3-bedroom, 2-bathroom vacation rental home located just steps away from the white sandy beaches.The spacious living area is perfect for relaxing after a day at the beach, with comfortable seating and a large flat-screen TV. The kitchen is fully equipped with everything ...

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Featured review

"Fabulous on beach condo"

This 3 bedroom, 2 bath condo in Holmes Beach was a fabulous place for our vacation of 6 retirees. From the spacious living area, open kitchen, sunny lanai, pool and good size bedrooms to being located ...

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$265
avg per night
Anna Maria Island Condo
Sleeps 4, 1 bedroom, 1 bathroom
9 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Smuggler’s Cove Resort is a family friendly timeshare property that offers studio and one-bedroom units. PLEASE INQUIRE AS TO AVAILABILITY OF UNIT TYPE, AS WE ARE UNABLE TO DELINEATE ON WEBSITE, THANKS! Each studio unit sleeps two with a queen-size bed and has a full kitchen. One-bedroom units ...

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Featured review

"Great place to stay"

We recently stayed in one of the bay side units for vacation. This place is the best of both worlds. We had a view of water from our balcony but the private beach for the ocean was right across the road. ...

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$188
avg per night
Anna Maria Island House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

*This home is being rebuilt after the Major Hurricanes of 2024, new photos coming soon!**3 Night Minimum stays are allowed during low season, please refer to the rate table for the specific date ranges*Welcome to Zen Gardens…the perfect beach cottage only 1 house from the gorgeous white ...

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$646
avg per night
Anna Maria Island Condo
Sleeps 7, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to "Lazy Manatee" at Bradenton Beach Club, where even the manatees envy the level of relaxation we offer! This spiffy condo boasts three bedrooms and two full baths, giving you more space than a hermit crab's dream home. New decor, furniture and paint!At Bradenton Beach Club, ...

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Featured review

"Amazing condo"

This spacious condo appears to have been very recently completely renovated and extremely nicely updated. The large space was perfect for our group and we could have easily and comfortably added a couple ...

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$220
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Come experience Unit 201 at Sun Plaza West on beautiful Anna Maria Island. This 2 bedroom 2 bathroom Condo is located in the heart of Holmes Beach within walking distance to restaurants, shopping and the Islands Free Trolley. Sun Plaza West complex offers a secure entry, an elevator, heated pool and an ...

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$288
avg per night

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Anna Maria Island House
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Create unforgettable memories at “Crescent Palms”. This *perfect island house* has been fully renovated after hurricanes Helene and Milton. Crescent Palms is centrally located, just north of Pine Avenue in Anna Maria. This home is steps away from the gorgeous white sandy beaches of Bayfront ...

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Featured review

"Peaceful and relaxing family trip"

We were looking for a quiet spot for the family and hit the bullseye at Max and Denise's place on Northern Anna Maria island. Centrally located, 3 blocks either way, between the Gulf of Mexico or Tampa ...

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$395
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

Welcome to Sun Plaza West 101! *Highlighted Amenities** Location! Gulf Front Resort Condo Community! * 2 Bedrooms / 2 Bathrooms * 1 King Bed & 2 Twin Beds (Or can make 1 King upon request) * Open Air Balcony off Master Bedroom * Screened Lanai with Patio Furniture * 3rd Balcony with view ...

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$206
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 “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 completely restored after hurricanes Helene and Milton. This ...

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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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$627
avg per night
Anna Maria Island Cottage
Sleeps 4, 1 bedroom, 1 bathroom
54 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Condo-cottage with Old Florida charm..... Welcome to paradise.....This updated cottage is within a small resort, just steps from a beautiful private gulf beach. Drive into the Tradewinds Resort, and you will find quaint, pastel colored cottages on both sides of you hidden behind lush tropical foliage. ...

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Featured review

"AMI’s the Best!"

Love Anna Marie Island, it’s food, shopping, beaches and wonderful places to stay! The family enjoyed staying at the Tradewinds, the location is great. The cottages fit our needs perfectly. We enjoyed ...

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$239
avg per night
Special Offer
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms

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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$342
avg per night
New
Anna Maria Island Villa
Sleeps 6, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Welcome to Seaside Inn, a CLEAN,, PRISTINE & OWNER OPERATED, single story, waterfront, 2/2 + bath en-suite that sleeps 6. Enjoy the island breeze on the private patio watching the sunrise or the dolphins swim by, spend time in the open concept, fully equipped kitchen with water views, the perfect ...

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$350
avg per night
Anna Maria Island House
Sleeps 10, 5 bedrooms, 4.5 bathrooms
5 reviews

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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$609
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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$248
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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$587
avg per night
Anna Maria Island House
Sleeps 14, 5 bedrooms, 5 bathrooms
1 review

Distance to beach: 0.1 miles to Bayside Beach

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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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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$838
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to West O’ Gulf. This property suffered minimal damage from hurricanes Helene and Milton and is better than ever! If you are ready for a relaxing stay on beautiful Anna Maria Island, then this is the beach house for you! This exceptional custom-built 4 Bedroom 3-bathroom house makes it easy ...

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$486
avg per night
New
Last Minute Deal
Anna Maria Island Condo
Sleeps 7, 3 bedrooms, 2 bathrooms
7 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to "Blue Skies" at Bradenton Beach Club!Discover your perfect getaway in this beautifully updated three-bedroom, two-bath condo, designed for families and friends looking to unwind in style. With coastal decor and modern furnishings, you’ll feel right at home from the moment ...

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Featured review

"Beach Lovers Condo"

This condo has everything you need for the perfect vacation and then some. The location is what I thought was the best part of staying here. A short walk and before you know it, your on a beautiful white ...

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$230
avg per night
Anna Maria Island House
Sleeps 9, 4 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to the “Blue Pearl”. This gorgeous beach house offers all the charm and comfort you will come to expect from staying at one of our vacation rentals on Anna Maria Island.Find ease and relaxation the moment you arrive …” Blue Pearl” is the perfect vacation rental ...

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Featured review

"Family vacation"

The house was great! Close proximity to the trolly, which made exploring the island very easy!The beach is just a few minute walk, and was so convenient. Everyone loved the pool and hot tub, even though ...

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$470
avg per night
Anna Maria Island Townhome
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

To Book Directly please visit: /island-nautilusIf you have further questions, please give our office a call and we will do our very best to accommodate you! Beach Retreats Reservations Team:This second floor newly renovated 3-bedroom 2-bathroom condominium is your perfect vacation destination ...

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$466
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 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. Property suffered minimal damage from the hurricanes and is better than ever. This Anna Maria Island vacation rental home offers all the goodies to ...

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$836
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 100 yards to Manatee Beach

Key Amenities

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

About this property

Welcome to our home away from home on the breathtaking Anna Maria Island in the charming town of Holmes Beach Florida. Anna Maria is a barrier island on the Gulf of Mexico with an old time feel.Its only 7 miles long by 3 miles wide.Our condo is on the beach roughly 200 yds from the Gulf.We ...

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Featured review

"In the league with the best…"

We can testify that, although there are some great gulf front places on AMI, this is among them. The interior was terrific – from the premium countertops, tiled floor, and tastefully decorated interior, ...

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$314
avg per night
Anna Maria Island House
Sleeps 8, 3 bedrooms, 3 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Discover island paradise at “North Shore” located on the *premier corner* of North Shore & Palmetto in Anna Maria, only 2 blocks from the gorgeous, white sandy beaches of Anna Maria Island and a few steps from very popular Slim’s Place restaurant and sports bar. This *ultimate beach ...

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Featured review

"Amazing house!!"

This house was great we have been coming to the island for about 10 years! This was the best house and so close to the beach!! We will be back

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$431
avg per night
Anna Maria Island House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Indulge in the ultimate beach escape to “Mary’s Place” located on Los Cedros, a *premier location* just north of Pine Avenue in the city of Anna Maria. Mary’s Place is a very short walk to the gorgeous, white sandy beaches of Anna Maria Island. This *ultimate beach house* has been ...

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$421
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3.5 bathrooms
2 reviews

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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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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$1,108
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

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

About this property

Beachfront paradise awaits you at the TripleTail.Located in a prime location - just one block from Pine Avenue and the City Pier, the 4 bed/4 bath bayfront home offers everything you need for the perfect vacation.On the ground floor, you’ll find a beachfront king bedroom, along with a ...

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$1,519
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

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

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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$785
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to “Coastal Breeze” on beautiful Anna Maria Island. This vibrant four-bedroom, three-bathroom island retreat is your perfect vacation escape on AMI. The backyard is a true highlight, featuring a private heated pool with spa, cozy and colorful seating areas, and a one-of-a-kind tiki ...

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$587
avg per night
Anna Maria Island House
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

WELCOME to “Island in the Sun” ...this newly renovated home on AMI offers charm, comfort, and luxury. No damage from hurricane Helene or Milton. This Anna Maria Island vacation rental is located just one block south of Pine Ave and just a few flip flop steps away from the City Pier Bay Beach ...

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Featured review

"Great Place to stay!"

We stayed 6 nights and had a great time. The property was clean and had everything we needed. The Florida Rental staff checked on us after we arrived to make sure everything was good. Very caring staff. ...

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$477
avg per night
Anna Maria Island Apartment
Sleeps 4, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to “Barefoot Mermaid 1” 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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$303
avg per night
New
Anna Maria Island House
Sleeps 14, 5 bedrooms, 4 bathrooms
2 reviews

Key Amenities

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

About this property

NEW MANAGEMENT...Welcome to Breathe Inn, your island escape where the sea breeze is plentiful and the relaxation comes naturally. This beautifully renovated 5-bedroom, 3.5-bath duplex invites you to exhale and settle into vacation mode. With two fully private units under one roof, it's the perfect ...

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$675
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

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

About this property

This stylish 3 bedroom, 2 and a half bath vacation home is located just a short walk from Anna Maria Island's sugar white beach. Gone Coastal 3 is amazingly updated and chic!*Features include** Super close to the beach * Heated private pool * Outdoor shower * Tiki Bar with games and ...

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$458
avg per night
New
Last Minute Deal
Anna Maria Island House
Sleeps 10, 4 bedrooms, 3.5 bathrooms
9 reviews

Key Amenities

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

About this property

Discover Your Perfect Beach Retreat at Bimini Breeze!Pack your bags (and some sunscreen) because you’re about to dive into an unforgettable getaway at Bimini Breeze! This stunning elevated home is just steps away from the pristine beaches of Anna Maria Island. With four bedrooms and three and ...

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Featured review

"Perfect location and amenities!"

This house is fabulous! So close to bridge st but yet it feels so private ! I am rebooking for next year ! It was so clean and plenty of room .

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$472
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
6 reviews

Key Amenities

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

About this property

Welcome to The Cheerful Pelican – Your Perfect Beach-to-Bay Getaway!Discover the ultimate escape in this charming 2-bedroom, 2-bathroom retreat, perfectly nestled between the stunning Gulf beaches and tranquil bay waters. The Cheerful Pelican offers the best of both worlds with sunrise views ...

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Featured review

"Cheerful Pelican was great!"

We stayed for 3 weeks, great location across from the beach, and walking distance to Bridge street. The layout of this condo has 2 patios, one in bedroom facing east watching sunrise, and the 2nd in living ...

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$225
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 6 bathrooms

Key Amenities

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

About this property

Welcome to Shangri-La, an idyllic vacation rental nestled on the exclusive tip of Anna Maria Island at Bean Point. This luxurious, fenced, and gated private property offers an escape from the everyday, inviting you to unwind and rejuvenate in a setting of unparalleled beauty and comfort. Available for ...

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$3,646
avg per night
Anna Maria Island Villa
Sleeps 12, 4 bedrooms, 4 bathrooms
4 reviews

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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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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$214
avg per night
Anna Maria Island House
Sleeps 8, 5 bedrooms, 5 bathrooms

Key Amenities

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

About this property

Welcome to paradise! This beachfront blends modernity with relaxation to give your group a heavenly experience. Located in a prime location on the North End of Anna Maria Island, Cloud 9 has everything that your group needs for a perfect vacation. Each of the 4 bedrooms is professionally decorated and ...

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$2,106
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to "Beach Escape" on beautiful Anna Maria Island. Appropriately named, this Mediterranean-inspired beach house offers all the charm and luxury you expect from a memorable vacation on AMI.Find ease and relaxation the moment you arrive, this charming multi-level home is nestled among ...

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Featured review

"Location location"

Our stay at Beach Escape was lovely. The location was close to perfect. However I did leave a few recommendations for the realty people. Support from the Salty Mermaid was top notch.

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$401
avg per night
Anna Maria Island House
Sleeps 4, 1 bedroom, 2 bathrooms

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 A.Unit A: Visit Unit AWelcome to “The Magic Dolphin B” an elevated vacation rental located on the northern section ...

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$224
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 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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$541
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

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

About this property

Escape to Your Exclusive Tropical Retreat! Indulge in the privacy of your own backyard oasis, complete with a sprawling pool and a dedicated Beach Volleyball Court. Open the back gate and find yourself steps away from the pristine Gulf Beaches. This ground-floor haven offers unparalleled convenience, ...

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$1,633
avg per night
Anna Maria Island House
Sleeps 4, 1 bedroom, 2 bathrooms

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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$221
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Create unforgettable memories at “Mia Bella” located on Hammock Road, just north of Pine Avenue, in a *premier deep water canal location* in Anna Maria. Mia Bella is a short walk to the gorgeous, white sandy beaches of Anna Maria Island. This *very spacious beach house* has been fully renovated ...

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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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$559
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Come experience Unit 204 at Sun Plaza West on beautiful Anna Maria Island. This 2-bedroom 2-bathroom Condo is in the heart of Holmes Beach within walking distance to restaurants, shopping, and the Islands Free Trolley. Sun Plaza West complex offers secure entry, an elevator, heated pool, and an On-Site ...

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$288
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

Key Amenities

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

About this property

Dreaming of an island vacation? This unit with its PRIVATE entrance is part of a 3 unit complex. These units only share pool and grilling area. Step outside your door and find our beautiful beaches; many local eateries; FREE rides on the Island trolley; unique boutique shopping or you can stay on site ...

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$218
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
24 reviews

Key Amenities

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

About this property

Located on 5th Avenue in Holmes Beach this unit is out of the way on a dead end street. Seaduction offers a heated pool, and every amenity to make your stay here a comfortable one. There are only 4 units in the complex so to pool is "semi private".This beautiful unit sleeps six with a king ...

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Featured review

"Wunderschöne Wohnung"

Wir haben eine Woche in der Wohnung auf Anna Maria Island verbracht. Es war traumhaft schön. Die Wohnung ist sehr gut ausgestattet: vom Eiswürfelspender bis zur Waschmaschine, vom Strandwegen mit Stühlen ...

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$201
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 5 bathrooms

Key Amenities

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

About this property

Luxury and the beach intersect at a point titled Serendipity Deux. This gorgeous 4 bedroom home offers all the allure of an extravagantly decorated space while giving you premium beach access and an ideal location. The Master Suite is located on the first level and comes outfitted with a king bed, tub ...

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$2,133
avg per night
Anna Maria Island House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

*This home is being rebuilt after the Major Hurricanes of 2025, new photos coming soon!*Welcome to Sunrise Vista on gorgeous Anna Maria Island. Pack up the family car and head to Anna Maria Island's perfectly located beach house. Find one of the last-remaining generations owned single-family ...

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$452
avg per night
Anna Maria Island Apartment
Sleeps 3, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to “Barefoot Mermaid 4” 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

"Perfect location."

Perfect 1-bedroom apartment, only a steps away from the beach! Perfect location within walking distance to everything on Pine Street.

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$248
avg per night
Anna Maria Island Condo
Sleeps 8, 4 bedrooms, 2 bathrooms
9 reviews

Key Amenities

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

About this property

Longing for an island vacation? This unit with its PRIVATE entrance is part of a 3 unit complex. These units only share pool and grilling area. Just steps outside your door you will find our beautiful beaches; many local eateries; FREE rides on the Island trolley; unique boutique shopping or you can stay ...

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$389
avg per night
Anna Maria Island House
Sleeps 6, 2 bedrooms, 1.5 bathrooms
11 reviews

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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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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$490
avg per night
Full map
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Anna Maria Island Weather

 | 

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 234 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 $107 per night with an average price per night of $333.

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 162 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 20 oceanfront rentals in Anna Maria Island available on FloridaRentals.com. Use our filters to search and book yours today!