Anna Maria Island Vacation Rentals

(258 rentals)
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3 BR | 2 BA | Sleeps 8 | Quick View

$576

avg/night

View Details

Key Amenities

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

About this property

Welcome to Zen Gardens on beautiful AMI. BIG NEWS: a brand new, full sized pool and spa was installed and is ready for your use. Zen Gardens is located just north of Pine Ave - and 1 house from the beach - in the City of Anna Maria. This property offers a beachy bohemian vibe and has all you need for ...

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Property Type

Anna Maria Island House

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4 BR | 3.5 BA | Sleeps 8 | Quick View

Distance to beach: 0.1 miles to Bean Point

$829

avg/night

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Key Amenities

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

About this property

Views, views, views! Experience the peace and beauty of the North end of Anna Maria from this sprawling luxury home named for its spectacular porches and outdoor space.*Features include** Ultimate luxury vacation home with elevator^ * Private heated pool and backyard oasis * Poolside lounge, ...

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Property Type

Anna Maria Island House

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3 BR | 2 BA | Sleeps 6 | Quick View

2

$276

avg/night

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About this property

Welcome to “Sand Dollar Villa”, one of our newest luxury properties at Salty Mermaid Vacation Rentals. This elevated condo offers all the luxury and comfort you will come to expect from staying at one of our vacation rentals on Anna Maria Island. Find ease, relaxation, and luxury the moment ...

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Property Type

Anna Maria Island Apartment

"Sand dollar"

Great location. Comfortable. Looks bed it. Great weather. Adequate furnishings Elevator to First condo was working and appreciated Will rent again if on market.

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Key Amenities

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

About this property

Have the best of both worlds with the bay & the gulf beaches at this new 4 bed/3.5 bath luxury home. Enjoy the quiet, laid back way of life on the north end of the island being only steps to the gorgeous bayside beach with city park or a 5 minute walk to the world renowned Bean Point! You are also ...

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Property Type

Anna Maria Island House

"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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2 BR | 2 BA | Sleeps 6 | Quick View

2
owner special
Owner special: Budget Friendly! July openings!!

$177

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

This spacious 2 bedroom condo is close to the beach and in the heart of it all. This stunning condo offers everything you want in a beach retreat. The unit has ample space your family. The open concept living area is perfect for entertaining, with a kitchen featuring all new appliances. You can also open ...

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Property Type

Anna Maria Island Condo

"Great vacation rental!"

My husband and I rented this condo, Sand & Surf, from Owner, Morgan Henderson, and we were completely pleased with the accommodations. Morgan was wonderful about replying immediately to any questions we ...

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2 BR | 1 BA | Sleeps 6 | Quick View

$322

avg/night

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Key Amenities

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

About this property

Haverkos on Holmes- The Haven Unit 2 is part of a ground-level duplex, located in a peaceful residential area of the City of Holmes Beach. So you can enjoy peace and quiet during your island vacation, while still being close to everything else that the city has to offer! Such as great local dining and ...

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Property Type

Anna Maria Island House

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3 BR | 2 BA | Sleeps 7 | Quick View

2
owner special
Owner special: Brand new to rental market! Open calendar!

$266

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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

"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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4 BR | 4 BA | Sleeps 8 | Quick View

Distance to beach: 0.1 miles to Tampa Bay

$859

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Anna Maria Island House

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2 BR | 2 BA | Sleeps 4 | Quick View

$220

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Oceanfront
  • Pet friendly
  • Pool
  • Private pool

About this property

Come experience Unit 204 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 ...

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Property Type

Anna Maria Island Condo

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3 BR | 3 BA | Sleeps 6 | Quick View

$393

avg/night

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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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Property Type

Anna Maria Island House

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2 BR | 2 BA | Sleeps 6 | Quick View

$280

avg/night

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About this property

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 Maria Island. This 2 Bed/2 Bath sweet and cozy beach home is located on North Shore Drive right ...

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Property Type

Anna Maria Island House

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1 BR | 1 BA | Sleeps 4 | Quick View

8
owner special
Owner special: Last minute June and Summer openings! Book direct on our website. New Bayfront 1 and 2br options!!

$169

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

Dans Florida Condos Sea Esta, located within Runaway Bay, a lovely private community on beautiful grounds with private beach access to the Gulf of Mexico.The highlight of our community is the largest heated salt water pool on the island! The condo grounds highlight tennis/pickleball courts, bocce ...

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Property Type

Anna Maria Island Apartment

"Wonderful condo, great location"

The location is great, right across street from beach. Trolly stop nearby to ride around the beach and get off at other stops for free. Places to eat within walking distance. Nice pool and tennis courts. ...

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Key Amenities

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

About this property

- 7 min. walk to beach, beach chairs, umbrellas, towels, beach wagon provided- sleeps 4, 2 bedroom/2 bath, very private and quiet- all linens provided, washer/dryer in unit- stores within short walk; Publix, Walgreens, CVS, Dollarama, Dunkin Donuts/ Baskin Robbins, beach stores, Ace Hardware, ...

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Property Type

Anna Maria Island Condo

"Hayward by the Sea"

The unit was very clean and the location was secluded and quiet while also being a short walk to the beach, Publix, shops and restaurants. There is also a garage to park 2 cars. The center of Anna Marie ...

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4 BR | 5 BA | Sleeps 8 | Quick View

$994

avg/night

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About this property

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

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Property Type

Anna Maria Island House

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4 BR | 3 BA | Sleeps 8 | Quick View

$608

avg/night

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About this property

Welcome to West O’ Gulf, one of our brand-new luxury rentals at Salty Mermaid Vacation Rentals. If you are ready for a relaxing stay on beautiful Anna Maria Island, then this unit is for you! This exceptional custom-built 4 Bedroom 3 bathroom beach house makes it easy to perfect the art of vacationing. ...

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Property Type

Anna Maria Island House

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4 BR | 2 BA | Sleeps 9 | Quick View

2

$434

avg/night

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About this property

Welcome to the “Blue Pearl” one of our newest properties at Salty Mermaid Vacation Rentals. BIG NEWS: a brand new, full sized pool and spa was installed this fall and is ready for your use. This gorgeous beach house offers all the charm and comfort you will come to expect from staying at one ...

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Property Type

Anna Maria Island House

"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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2 BR | 2.5 BA | Sleeps 4 | Quick View

$543

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront

About this property

The Beach House is a charming beach bungalow nestled among numerous Australian pines and sea grapes. A unique setting directly on the Gulf of Mexico shaded among the trees. Walk out the back door on your private path to a white sugar-sand beach. Best of both worlds, you have the shade and sunny beach. The ...

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Property Type

Anna Maria Island House

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2 BR | 2 BA | Sleeps 6 | Quick View

4
owner special
Owner special: Last minute June and Summer openings! Book direct on our website. New Bayfront 1 and 2br options!!

$198

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

Dans Florida Condos Sea Dream, located within Runaway Bay, a lovely private community on beautiful grounds with private beach access to the Gulf of Mexico.The highlight of our community is the largest heated salt water pool on the island! The condo grounds highlight tennis/pickleball courts, bocce ...

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Property Type

Anna Maria Island Apartment

"Great location"

This is the first time we stayed at Dans Florida Condos. The condos were right across the street from the private beach access, and I could not have asked for a cleaner unit. Pictures tell the whole story. ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

Absolutely beautiful monthly rental in highly sought after Holmes Beach on Anna Maria Island. If you are interested in dates blocked on the calendar, please message me. This 100% updated home has everything from a large heated pool, outdoor shower, lush mature landscaping, completely furnished inside ...

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Property Type

Anna Maria Island House

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2 BR | 2 BA | Sleeps 6 | Quick View

1

$423

avg/night

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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

"Spectacular"

We have rented many properties on Anna Maria Island and this one was my favorite! The home is wonderful with every amenity you can imagine and immaculate as far as cleanliness! It is completely updated ...

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Key Amenities

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

About this property

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

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Property Type

Anna Maria Island House

"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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2 BR | 2 BA | Sleeps 6 | Quick View

23
last minute deal
LAST MINUTE DEAL 6/4 - 7/16: July 13th - July 20th just opened up!

$202

avg/night

View Details

Key Amenities

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

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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Property Type

Anna Maria Island Condo

"5 star experience"

My family enjoyed this vacation rental for a glorious week. The place was so comfy and inviting. They really thought of everything when it came to the overall experience. The property offers a nice peaceful ...

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DEAL

3 BR | 2 BA | Sleeps 6 | Quick View

1

$290

avg/night

View Details

About this property

If you are travelling with another family or have a larger party than 6 people, we also offer the sister property to this unit at “BBC #246”Welcome to “Bradenton Beach Club #234” on beautiful Anna Maria Island!Need something close to the beach that offers a pool – ...

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Property Type

Anna Maria Island Apartment

"Great place"

We were happy staying at the sandpiper. The proximity to the beach is excellent. It is also easy to get to other areas. Having never been to Ana Maria Island before it was a great experience. Condo is clean ...

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5 BR | 4 BA | Sleeps 8 | Quick View

$576

avg/night

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About this property

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

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Property Type

Anna Maria Island House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

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

"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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2 BR | 2 BA | Sleeps 4 | Quick View

$290

avg/night

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About this property

Welcome to “Beachcomber” a cozy villa reminiscent of days past on Anna Maria. This charming villa is only 3 houses (300 Ft) TO DIRECT BEACH ACCESS in the City of Holmes Beach on Anna Maria Island!!! When arriving at “Beachcomber” you will get excited with how close you are ...

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Property Type

Anna Maria Island Villa

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4 BR | 3 BA | Sleeps 8 | Quick View

$526

avg/night

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About this property

*3 Night Minimum stays are allowed during low season, please refer to the rate table for the specific date ranges* Magnolia Location, Location, Location! Magnolia is situated on a quiet residential street, 2 blocks from the gorgeous white sand beaches of the Gulf of Mexico and 2 blocks from ...

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Property Type

Anna Maria Island House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool

About this property

Relax with the whole family at this peaceful place to stay.Endless Summer is two bedroom, two bath condo located on Anna Maria Island. Specifically, located in Runaway Bay on Bradenton Beach.We have beach wagon. umbrella, chairs and cooler for your use. This unit is ground level, no stairs!Endless ...

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Property Type

Anna Maria Island Condo

"Great Place, Perfect Location"

My husband and I recently stayed at this condo while visiting family and friends. This was the perfect condo and perfect location for us. Unfortunately, the pool was down for repairs of some sort but we ...

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4 BR | 3 BA | Sleeps 8 | Quick View

2

$585

avg/night

View Details

About this property

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

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Property Type

Anna Maria Island House

"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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6 BR | 4 BA | Sleeps 17 | Quick View

$978

avg/night

View Details

Key Amenities

  • Air conditioning
  • Private pool

About this property

Welcome to Coastal Cove, your ultimate Anna Maria Island vacation rental experience! Discover the luxurious charm of this 6-bedroom, 4.5-bathroom beach home located in the heart of Bradenton Beach. This stunning property features a private heated pool and spa, along with a rooftop deck offering breathtaking ...

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Property Type

Anna Maria Island House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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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Property Type

Anna Maria Island Condo

"Great stay!"

We really enjoyed our suite. Our balcony faced the bay and the ocean was just across the street. We loved having a full kitchen and living area to make our vacation feel more like home. Thank yo for a ...

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1 BR | 1 BA | Sleeps 3 | Quick View

1

$201

avg/night

View Details

Key Amenities

  • Air conditioning

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

"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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3 BR | 2 BA | Sleeps 6 | Quick View

5.0 rating on other travel sites

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

$702

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

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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4 BR | 4 BA | Sleeps 8 | Quick View

$602

avg/night

View Details

Key Amenities

  • Air conditioning
  • Private pool

About this property

*Under new owners, and new property management*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 located west of Gulf drive, with no busy roads to cross for beach access. ...

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Property Type

Anna Maria Island House

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Key Amenities

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

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

"Great stay!"

We loved our stay at this unit. It was very comfortable, convenient to the beach and loved the roof top seating area with a beautiful view of the beach.

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2 BR | 2 BA | Sleeps 4 | Quick View

$220

avg/night

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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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Property Type

Anna Maria Island Apartment

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Key Amenities

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

About this property

This beautiful property offers a perfect blend of indoor and outdoor living, with welcoming accommodations for a maximum of 6 guests, all just a short walk to the pristine white sand beaches and centrally located on Anna Maria Island!The decor is a perfect blend of coastal elegance and comfort, featuring ...

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Property Type

Anna Maria Island House

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3 BR | 2 BA | Sleeps 8 | Quick View

1

$440

avg/night

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About this property

Treat yourself to “Crescent Palms” on the north end of Anna Maria Island. This ground level, newly renovated and professionally decorated 3 bedroom, 2 bath beach house offers comfort, luxury, and relaxation. Crescent Palms is located on a quiet street- north of Pine Ave and just a few flip ...

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Property Type

Anna Maria Island House

"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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Key Amenities

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

About this property

Corner Unit, Not 1 But 2 Private Balconies, Minimum 7 Day Stay. Saturday to Saturday Rentals Available, On Site Management Company for all Service Needs, Private Pool, Tennis Court, BBQ Area, Underneath Parking, Minutes from Longboat Key, Sarasota, Siesta Key and Bradenton!! For Bookings and Availability, ...

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Property Type

Anna Maria Island Condo

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5 BR | 2 BA | Sleeps 10 | Quick View

2
last minute deal
LAST MINUTE DEAL 6/15 - 6/22: Last-minute cancellation - July 4th week! $575 night - 150+ five-star reviews

$510

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

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

"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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DEAL

3 BR | 1 BA | Sleeps 6 | Quick View

4

$400

avg/night

View Details

Key Amenities

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

About this property

It is almost always Summer on Anna Maria Island! Availability is updated frequently, so please check our calendar often. A good chunk of Summer 2024 is still available!Dolphin Cottage is a cozy, charming old-Florida home with 3 bedrooms and 1 full bathroom - perfect for a couple or family. It is very ...

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Property Type

Anna Maria Island House

"Quintessential delightful Beach Cottage"

Everything you dream of for a relaxing , invigorating holiday is found just as you step inside Dolphin Cottage. Calm yourself in the outside shower under the stars listening to the palm trees singing ...

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2 BR | 2 BA | Sleeps 6 | Quick View

1

$481

avg/night

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About this property

WELCOME to “Island in the Sun” ...this newly renovated home on AMI offers charm, comfort, and luxury. Island in the Sun is located just one block south of Pine Ave and just a few flip flop steps away from the City Pier Bay Beach and the popular restaurant - The Waterfront. The City Pier Bay ...

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Property Type

Anna Maria Island House

"Anna marie ️"

Wonderful house with new appliances comfortable king beds on a quiet street. With awesome pool and hot tub. Outdoor shower also, shade areas front and back super Nice. Close to restaurants pier and beach ...

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4 BR | 4 BA | Sleeps 12 | Quick View

4.8 rating on other travel sites

$734

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Welcome to our beautiful Italian Mediterranean home in Holmes Beach, Anna Maria Fl! Recently renovated, this home sleeps 12 comfortably 8 adults, 4 children with 5 Beds and 1 new gel bed sofa sleeper. It has a private enclosed heated pool area with an outdoor bar, and a luxury outdoor Pottery Barn Extended ...

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Property Type

Anna Maria Island House

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4 BR | 3 BA | Sleeps 8 | Quick View

2

$624

avg/night

View Details

Key Amenities

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

About this property

Welcome to “Pineapple Cottage” – a beautifully updated ground level beach cottage located in the heart of Anna Maria City and just 1 block from all the shops, restaurants and fun on Pine Avenue. This charming cottage has been professionally decorated and offers all the luxuries you will ...

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Property Type

Anna Maria Island House

"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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1 BR | 1 BA | Sleeps 4 | Quick View

$222

avg/night

View Details

Key Amenities

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

About this property

Part of the Haverkos on Holmes, The Haven Unit 1 is a 1 bed 1 bath, ground-level duplex that’s located in a peaceful residential area of Holmes Beach. Though still close enough to the restaurants and shopping so that you can experience what the island has to offer. This dog-friendly unit is a great ...

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Property Type

Anna Maria Island House

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1 BR | 1 BA | Sleeps 4 | Quick View

1

$201

avg/night

View Details

Key Amenities

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

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 Condo

"Perfect!"

Spent a long weekend for our anniversary. Perfect location, just a few steps to the beach, food and stores. Condo was clean and beautiful. We had an amazing time.

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3 BR | 3 BA | Sleeps 8 | Quick View

3

$476

avg/night

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About this property

*A Brand new Pool/Spa has been installed and is ready for guest use! New Pool pictures are at the end of the photo list*Come Relax and Unwind at the "North Shore" on gorgeous Anna Maria Island. This ground level, newly renovated and professionally decorated 3 bedroom, 3 bath beach house ...

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Property Type

Anna Maria Island House

"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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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Rentals by owner

About this property

Shady Palms is a cozy secluded beach cottage right on the beautiful Gulf of Mexico. Walk out the back door to a white, sugar-sand beach and the sparkling Gulf waters. Shady Palms is the most perfect spot you'll ever find on the beach - have the best of both worlds - the sun and the shade.Beach ...

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Property Type

Anna Maria Island House

"AMAZING!!!"

This house is the best rental we have ever stayed in! The scenery out back is incredibly relaxing.. trees, Adirondack chairs, the OCEAN!! It is so private, and also the best equipped kitchen I’ve ever ...

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2 BR | 1 BA | Sleeps 4 | Quick View

$241

avg/night

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Key Amenities

  • Air conditioning

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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

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

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Property Type

Anna Maria Island House

"Oceanview"

Beach house was so nice, clean and beautiful. We had plenty of room for our party of eleven. Very short walk to the beach. Loved the pool area. Would stay at Oceanview again. Weldon checked on us and made ...

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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 258 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 $387.

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 124 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 21 oceanfront rentals in Anna Maria Island available on FloridaRentals.com. Use our filters to search and book yours today!