Anna Maria Island Vacation Rentals

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

$500

avg/night

$500
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

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

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Property Type

Anna Maria Island House

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

$373

avg/night

$373
avg per night
View Details

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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Property Type

Anna Maria Island Condo

Featured review

"Perfect family condo!"

This amazingly clean, updated, and spacious condo was the perfect home base for our group of four adults and two kids. It was the ideal mix of private and quiet for relaxing after a long day at the private ...

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Anna Maria Island House
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

$988

avg/night

$988
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 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
2 reviews

$735

avg/night

$735
avg per night
View Details

Key Amenities

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

About this property

*New photos are coming soon!*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 ...

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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
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$659

avg/night

$659
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

North End Escape is a 2,300 sq. ft. Custom Built 3 bedroom 2 ½ bathroom Home featuring a 400 sq. ft. Rooftop Covered Gazebo; 750 sq. ft. of Covered Outdoor Living Area with Travertine flooring and a Heated Pool.This spacious home has wide plank hardwood flooring throughout; open concept living ...

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Anna Maria Island House

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

$489

avg/night

$489
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Need a GREAT AMI GETAWAY? Just steps from the bayfront park in the City of Anna Maria is a charming island beach house called “La Cocolia” lovingly translated as the "little crab". This property is ready to host you and your family as you enjoy this newly renovated and decorated ...

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Property Type

Anna Maria Island House

Featured review

"Just right"

The property is centrally located on the island which makes it very convenient. It has everything you need, and was very clean. We would definitely rent it again.

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

$762

avg/night

$762
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 completely restored after hurricanes Helene and Milton. This ...

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

$321

avg/night

$321
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

*This home is being rebuilt after the Major Hurricanes of 2024, new photos coming soon!*Welcome to Sea'Esta on gorgeous Anna Maria Island! Sea'Esta is a ground level Home that offers all the luxuries and comfort you will come to expect from staying at one of our vacation rentals on Anna ...

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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

$1236

avg/night

$1,236
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 Apartment
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom

$364

avg/night

$364
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • 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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Property Type

Anna Maria Island Apartment

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Anna Maria Island House
1 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 2 bathrooms

$276

avg/night

$276
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • 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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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

$1196

avg/night

$1,196
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • 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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Property Type

Anna Maria Island House

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

$360

avg/night

$360
avg per night
View Details

Key Amenities

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

About this property

This affordable & convenient 3 story home is one house off Holmes Beach. It has fantastic 2nd & 3rd level balcony beach views with no obstruction over the one story house in front of mine with no trees. The 3 bedroom 2.5 bath villa with 2 car garage accommodates 6 guests and is 150 feet from the ...

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Property Type

Anna Maria Island House

Featured review

"Great Vacation Spot. Great Owner. Awesome Location"

What an awesome place. Lots of rooms to stretch out. The 2 car garage and big drive way were nice for ease of parking and to securely store things. The large shared pool is wonderful and perfect temp. ...

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

$437

avg/night

$437
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Less than a minute's walk to the beach!Watch the sunset from the house!PARKING FOR ALL...Bring your boat or RV...Invite guests... There's room for everyone!Shell House is a two-story, 3-bed, 2-bath, multi-level fun-house on a large shady lot in a quiet residential neighborhood ...

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Property Type

Anna Maria Island House

Featured review

"Great Two Weeks in Holmes Beach"

I lived in Holmes Beach for many years. It was always my favorite place to be. When I needed to move I promised myself I would rent and come as often as I could. SunPlaza West has always been my go to ...

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Anna Maria Island Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
3 reviews

$319

avg/night

$319
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Vacations can be exciting and so overwhelming. Don’t worry, we’re here to help. Pack your bags and get ready to enjoy our beautiful island. 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 ...

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Property Type

Anna Maria Island Condo

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

$404

avg/night

$404
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Need a getaway? We have the perfect spot for you. Welcome to "Sun & Surf", a direct gulf front condominium on beautiful Anna Maria Island. This 2-bedroom, 2-bathroom condominium offers all the charm and comforts you will come to expect from a Salty Mermaid Vacation Rental. This unit has ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island Condo
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms
2 reviews

$286

avg/night

$286
avg per night
View Details

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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Property Type

Anna Maria Island Condo

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

$779

avg/night

$779
avg per night
View Details

Key Amenities

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

About this property

To Book Directly please visit: /its-miller-time If you are looking for something other than a 7 night stay, please give our office a call and we will do our very best to accommodate you! Beach Retreats Reservations Team: This custom 4 bed 4.5 bath home was built with no expense spared! Custom kitchen ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 3.5 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3.5 bathrooms

$716

avg/night

$716
avg per night
View Details

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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Property Type

Anna Maria Island House

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Anna Maria Island House
6 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4 bathrooms
3 reviews

$994

avg/night

$994
avg per night
View Details

Key Amenities

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

About this property

110 11th Street South - Bradenton Beach - FL 34217Book 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 ...

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Property Type

Anna Maria Island House

Featured review

"Anna Maria week long get away"

The home was lovely. The pool and whirl pool were fabulous. Strong recommendations: TV by pool never worked. Multiple lightbulbs in lamps, etc. need to be replaced. Two blow dryers need to be replaced. ...

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

$702

avg/night

$702
avg per night
View Details

Key Amenities

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

About this property

New pictures coming by early February!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 ...

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Property Type

Anna Maria Island House

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

$237

avg/night

$237
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Relax in the modern 3BR 2.5Bath condo in the majestic beachfront neighborhood in Bradenton Beach, FL. Soak up the sun by the two community swimming pools, or walk down to the sandy beach and experience the beautiful Gulf Coast.The picturesque location will leave you speechless!The Space HURRICANE ...

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Property Type

Anna Maria Island Condo

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

$533

avg/night

$533
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • 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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Property Type

Anna Maria Island House

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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Anna Maria Island House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
4.8 rating on other travel sites

$473

avg/night

$473
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

312 A 61st Street Holmes Beach, FL 34217 VRC Welcome!Welcome to this luxury Key West style home by the sea! It is your place in the sun to make memories and unwind! Get ready to make memories at Crosswinds Cottage!Your home away from homeThis home has been professionally decorated and ...

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Property Type

Anna Maria Island House

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

$551

avg/night

$551
avg per night
View Details

Key Amenities

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

About this property

New pictures coming by early February!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 ...

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Property Type

Anna Maria Island House

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

$361

avg/night

$361
avg per night
View Details

Key Amenities

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

About this property

This affordable & convenient 3 story home is one house off Holmes Beach. It has fantastic 2nd & 3rd level balcony beach views with no obstruction over the one story house in front of mine with no trees. The 3 bedroom 2.5 bath villa with 2 car garage accommodates 6 guests and is 150 feet from the ...

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Property Type

Anna Maria Island House

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Anna Maria Island Apartment
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 bedroom, 1 bathroom
1 review

$289

avg/night

$289
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • 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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Property Type

Anna Maria Island Apartment

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

$540

avg/night

$540
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

*This home is being rebuilt after the Major Hurricanes of 2024, 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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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
3 reviews

$644

avg/night

$644
avg per night
View Details

Key Amenities

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

About this property

New pictures coming by early February!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 ...

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Property Type

Anna Maria Island House

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

$842

avg/night

$842
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 Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 0.5 miles to Manatee Beach

$190

avg/night

$190
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

2 bed/2bath condo on second floor, fits up to four guests, close to the gulf beach. Turnkey furnished and spruced by the owner. Shops and restaurants are close by. Trolley stop for free rides on the island is around the corner. Come and enjoy!Just remodeled and equipped with more than everything ...

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Property Type

Anna Maria Island Condo

Featured review

"Fabulous stay on Anna Maria Island"

This condo was the PERFECT place for our family of three to enjoy Anna Maria Island! It was clean, cozy, and had everything we needed! Carla was a wonderful host who was very accommodating and gracious ...

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Anna Maria Island House
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

$865

avg/night

$865
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 Apartment
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$538

avg/night

$538
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

This 3 bedroom condo sits close to the Gulf Beaches at Gulf Place Condominium. Sit on the lanai and drink your coffee looking out onto the Gulf.

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Property Type

Anna Maria Island Apartment

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Anna Maria Island Cottage
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
54 reviews

$252

avg/night

$252
avg per night
View Details

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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Property Type

Anna Maria Island Cottage

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

$804

avg/night

$804
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
5 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 5 bathrooms
4 reviews

$1091

avg/night

$1,091
avg per night
View Details

Key Amenities

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

About this property

146 Crescent Dr, Anna Maria FL 34216 VITAMIN SEA is a home that features 5 bedrooms and 5 bathrooms and a fantastic location-just a 10 minute stroll to the White sandy beaches of BEAN POINT on the coveted north end of Anna Maria. This lovely property offers a private heated pool with a spa, The backyard ...

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Property Type

Anna Maria Island House

Featured review

"Paradise"

Vitamin Sea exceeded all expectations for our week's vacation for our family of 12. Location was perfect for daily visits to both sides of the island. House is stunning and fully equipped for swimming, ...

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Anna Maria Island House
4 BR | 2 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 2 bathrooms
2 reviews

$495

avg/night

$495
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • 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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Property Type

Anna Maria Island House

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

$340

avg/night

$340
avg per night
View Details

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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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

$596

avg/night

$596
avg per night
View Details

Key Amenities

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

About this property

Escape to this Anna Maria Island vacation rental “Katmandu” just 0.15 miles or 300 steps to the wonderful white sandy beaches of the Gulf of Mexico. This property is west of Gulf Drive, with no busy roads for beach access. This property suffered minimal damage from Hurricanes Helene and Milton ...

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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

  • Air conditioning
  • Pet friendly
  • 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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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 4.5 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4.5 bathrooms
4.9 rating on other travel sites

$905

avg/night

$905
avg per night
View Details

Key Amenities

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

About this property

144 Crescent Dr. Anna Maria, FL 34216 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 ...

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Property Type

Anna Maria Island House

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

$365

avg/night

$365
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to "Barefoot Mermaid 2" 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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Property Type

Anna Maria Island Apartment

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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

$1040

avg/night

$1,040
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
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$605

avg/night

$605
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Moon Shadow South's location can't be beat with views of Passage Key in Tampa Bay from the Primary Ensuite. You are just steps away to the bay beach access located directly across the street; walking distance to the Rod and Reel Pier, Bay Front Park and the popular white sandy beach of Bean ...

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Property Type

Anna Maria Island House

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Anna Maria Island Townhome
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms
1 review

$579

avg/night

$579
avg per night
View Details

Key Amenities

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

About this property

306 Clark drive (B) Holmes Beach, FL 34217 VRC Dog Friendly! Beautiful open concept home. 3 king bedrooms with en suites and a den with 2 single bunk beds make this property perfect for multi-generational or multi-family vacations. This home is ideally located just down the street from the white sand ...

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Property Type

Anna Maria Island Townhome

Featured review

"Beautiful Property"

Visiting Anna Maria Island was amazing!! The weather was beautiful and the home was beautiful too!! I would definitely come back to visit this area.

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

$254

avg/night

$254
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Ideal Location - Family Vacation Accommodation 2 Individual Villas, 4 Bedroom 4 Baths Sleeping for 8-12 Guests Pricing is for one villaDuring January February & March you can only rent 1 villa. During June & July you must rent both villas. Pricing on our site here is for only 1 villa.The ...

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Property Type

Anna Maria Island Villa

Featured review

"Huge pool and awesome location"

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

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Anna Maria Island Apartment
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 bedroom, 1 bathroom
2 reviews

$289

avg/night

$289
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • 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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Property Type

Anna Maria Island Apartment

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

$634

avg/night

$634
avg per night
View Details

Key Amenities

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

About this property

New pictures coming by early February!Discover island paradise at “Magnolia” located on Magnolia Ave., a *premier residential street* just south of Pine Ave. in Anna Maria. Magnolia is just 2 blocks from the gorgeous, white sandy beaches of Anna Maria Island, 1 ½ blocks from the ...

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Property Type

Anna Maria Island House

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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
6 reviews

Key Amenities

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

About this property

Click on calendar for available 2024 dates. Book now before they are gone! CALL FOR UNBELIEVABLE SAVINGS. ONLY PHONE CALLS GET DISCOUNTS.TWO WEEK MINIMUM STAY. No exceptions. No Pets. Sorry.20 STEPS TO THE SAND - GREAT VIEW Last minute deals don’t last long, we price to rent. We are ...

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Property Type

Anna Maria Island Condo

Featured review

"Ok"

️ love this area one of my favorite places to stay AnnaMaria island.. love it .. can’t wait to go o back

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

$581

avg/night

$581
avg per night
View Details

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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Property Type

Anna Maria Island House

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Anna Maria Island Vacation Rentals

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°

Enjoy the Perfect Anna Maria Island Getaway


Looking for a gorgeous and relaxing Anna Maria Island vacation rental without leaving the Florida coast? Anna Maria Island is the perfect vacation spot for you. Anna Maria Island is located on Florida’s western shore, just a few miles south of St. Petersburg.

This small, quaint island is separated from mainland Florida by the waters of Palma Sola Bay and Anna Maria Sound. However, the coast is connected to the island by way of U.S. Highways 64 and 684, making it easy to travel between the two. Despite its size, Anna Maria Island is packed with activities to enjoy and many gorgeous rental homes.

With FloridaRentals.com, you can live like a local while on your vacation by enjoying authentic architecture from the inside out within Anna Maria Island’s residential neighborhoods.

Hotel stays can be enjoyable, but there’s nothing quite like a high-quality rental home while on vacation. Not only will your trip feel more immersive within Anna Maria Island’s unique energy, but you will also be able to truly relax while on your trip.

There is no worrying about sharing a wall with strangers or lacking privacy. Additionally, you’ll be able to relax in a private backyard with some much-needed peace and quiet. Many Anna Maria rentals with FloridaRentals.com even feature unique amenities like pools, hot tubs, entertainment centers, walkable beach access, and much more.

Anna Maria Island Travel Tips


If you’re planning a trip to Anna Maria Island, you should keep a few key details in mind. The first is which airport you plan on flying into. Anna Maria Island is reachable by car from many of Florida’s largest cities, including St. Petersburg, Clearwater, Tampa, and Sarasota. However, depending on where you live, traveling to Anna Maria Island by plane might be easier.

There is no airport on the island, so you will have to fly into a nearby city and rent a car or take public transport from there. The closest commercial airport to Anna Maria Island is the Sarasota Bradenton International Airport, which is about 16 miles south of the island.

The St. Pete-Clearwater International Airport can also connect to Anna Maria Island via I-275 across Tampa Bay. This option is less convenient as this airport is about 45 miles north of the island. However, by flying into St. Pete–Clearwater, you could bundle multiple popular Florida destinations into one trip by taking the “long way.”

Another detail to keep in mind is the climate. Though many Florida cities experience warm weather throughout the year, the best time to enjoy the outdoors with warm yet pleasant temperatures on Anna Maria Island is mid-spring or fall. During these times of the year, average temperatures are between 80 and 85 degrees Fahrenheit, and chances of precipitation are low.


Best Eats on Anna Maria Island


There are many incredible restaurants and bars on Anna Maria Island, many featuring beachfront views. Rod and Reel Pier is a great example. Located on the northernmost tip of Anna Maria Island with a full menu of seafood and cocktails.

City Pier Grill and Bait, located on the end of Anna Maria Pier, is another great local spot for a meal with family, drinks with friends, or a romantic date. The delicious globally-inspired seafood dishes are complemented by the gorgeous view of Tampa Bay, which is especially breathtaking at sunset.

As you travel farther south down the island, there are many more eateries to explore during your visit to Anna Maria Island. Scott’s Deli is a great choice for fresh and delicious sandwiches if you’re looking to grab something quick to take for a picnic lunch on the beach.

Nearby are Duffy’s Tavern and Freckled Fin Irish Pub, two local bars that serve their own unique menus of American favorites and ice-cold drinks. If you’re looking for a more upscale after-dinner drinks experience, The Doctor’s Office is a hip cocktail bar in central Anna Maria with plenty of imaginative cocktails and light bites to enjoy. And yes, the building used to be a real doctor’s office!


Things to Do Near Anna Maria Island Vacation Rentals


Despite its small size, there is a huge variety of beaches to explore near Anna Maria Island rentals. Manatee Public Beach, located on the southwestern side of the island, is a popular destination for white sand, warm waters, and plenty of fun in the sun.

As you travel even farther south to the neighborhood of Bradenton Beach on Anna Maria Island, you’ll find spots like Coquina Beach, which wraps around the southern tip of the island. For prime beach access on the island’s northernmost tip, Bean Point Beach and Bayfront Park are two of the most popular. Many of the island’s beaches have a variety of amenities, such as playgrounds, volleyball nets, picnic tables, and concession stands.

The many Anna Maria Island piers are a special way to experience the beauty of the area from the water (without getting wet!). Some of these include Rod and Reel Pier, the Anna Maria City Pier, and Bridge Street Pier. Visitors can find local art and culture, gift shops, restaurants, and stunning views at any of the island’s piers.

Aside from taking a stroll along a pier, there are many other ways to experience the shimmering waters of Tampa Bay or the Gulf of Mexico. One popular activity for vacationers is to rent a boat or kayak from one of the many vendors along the island’s shores.

One of Anna Maria Island’s most popular rental shops is Beach Bums. At Beach Bums, you can rent kayaks and paddle boards for the whole family or even book a special kayak tour led by an experienced local. Need a break from the water? You can also rent bicycles or golf carts to explore Anna Maria Island by land!

Experience Bliss on Anna Maria Island


Adventure is waiting for you on Anna Maria Island. Make the most out of your adventure by vacationing at a luxurious private home, courtesy of FloridaRentals.com.


FAQ

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

There are 226 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 $127 per night with an average price per night of $477.

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 141 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 18 oceanfront rentals in Anna Maria Island available on FloridaRentals.com. Use our filters to search and book yours today!