Anna Maria Island Vacation Rentals

(257 rentals)
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2 BR | 1 BA | Sleeps 4 | Quick View

$257

avg/night

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Key Amenities

  • Air conditioning

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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2 BR | 2 BA | Sleeps 6 | Quick View

$517

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

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4 BR | 2 BA | Sleeps 6 | Quick View

1

$262

avg/night

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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 #234”Welcome to Bradenton Beach Club #246! Here is a great opportunity to enjoy an updated condo featuring 3 bedrooms and 2 full baths. Bradenton beach ...

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Property Type

Anna Maria Island Apartment

"Beautiful Riverfront"

This house was beautiful lovely layout with 3 bedrooms and 2 bathrooms. Just steps away from the manatee river! Can’t wait to come back

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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

$225

avg/night

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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 | 2 BA | Sleeps 6 | Quick View

1

$304

avg/night

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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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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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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

$349

avg/night

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About this property

*VRC - CITY OF HOLMES BEACH VACATION RENTAL ORDINANCE REQUIRES 7-NIGHT MINIMUM STAYS. THIS PROPERTY REQUIRES A SATURDAY-TO-SATURDAY ARRIVAL/DEPARTURE**The Master Bathroom features a brand new Walk-In Shower!**There is a brand new Stackable Washer/Dryer for guest use!*Need a getaway? We have ...

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Property Type

Anna Maria Island Apartment

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Key Amenities

  • Kid friendly
  • Kitchen

About this property

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

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Property Type

Anna Maria Island House

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2 BR | 2 BA | Sleeps 6 | Quick View

1

$452

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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1 BR | 1 BA | Sleeps 3 | Quick View

1

$205

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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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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4 BR | 4 BA | Sleeps 8 | Quick View

$1266

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Gulf Beach Front 3 bedroom/3 bathroom home and separate 1/1 cottage Sunset's from your back deck and morning shell searches out your back door. All bedrooms are King Bed en-suite. Located on the North End of Anna Maria Island. Gas BBQ on the lower deck. TV are located in all bedrooms. Plenty of space ...

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Property Type

Anna Maria Island House

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2 BR | 1 BA | Sleeps 4 | Quick View

$257

avg/night

View Details

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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4 BR | 4 BA | Sleeps 12 | Quick View

4.8 rating on other travel sites

$775

avg/night

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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 | 2.5 BA | Sleeps 8 | Quick View

$1251

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

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

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Property Type

Anna Maria Island House

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5 BR | 5 BA | Sleeps 14 | Quick View

Distance to beach: 0.1 miles to Bayside Beach

$870

avg/night

View Details

Key Amenities

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

About this property

Just updated 2020, 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

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4 BR | 4 BA | Sleeps 8 | Quick View

$632

avg/night

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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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$183

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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4 BR | 3 BA | Sleeps 8 | Quick View

$669

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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2 BR | 2 BA | Sleeps 4 | Quick View

$305

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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$247

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Pool

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

"Recommend for a quiet stay in a very homey environment. Very Satisfied."

We gave this 5 stars but my husband wanted to do 4 1/2. The reason he was disappointed that the dock and pier are set up for fishing, but the staff knew nothing about it. Also, seems like it would be smart ...

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4 BR | 3 BA | Sleeps 8 | Quick View

2

$619

avg/night

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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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3 BR | 2 BA | Sleeps 8 | Quick View

$484

avg/night

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Key Amenities

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

About this property

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 cottages located directly on the beach.This is the place to put down your iPhones, and reset ...

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Property Type

Anna Maria Island House

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4 BR | 3 BA | Sleeps 8 | Quick View

$548

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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2 BR | 2 BA | Sleeps 4 | Quick View

3

Distance to beach: 100 yards to Manatee Beach

$314

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Anna Maria Island Condo

"Excellent"

Accommodations were excellent . The condo was very clean and orderly ! The kitchen is fully stocked for any cooking needs .The location was the best . Steps away from a free trolly that takes ...

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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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$449

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool

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 of Holmes Beach, FL. This stunning property can accommodate up to 6 guests and features a community heated pool, outdoor shower, and a fully equipped kitchen.The spacious ...

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Property Type

Anna Maria Island Condo

"Relaxing and fun"

What an amazingly spacious, comfortable and fun place to stay in Anna Maria Island Fla. Steps from Gulf and beach with beautiful sunsets from the place. Amenities galore making many options for daily activities ...

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$822

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

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

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Property Type

Anna Maria Island House

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3 BR | 3 BA | Sleeps 6 | Quick View

owner special
Owner special: Reduced pricing for August and September! Monthly rental at a fraction of the price!

$250

avg/night

View Details

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 | 1 BA | Sleeps 6 | Quick View

$341

avg/night

View Details

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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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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Key Amenities

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

About this property

We have developed a comprehensive Safety / Cleaning / Sanitation Plan and work with an amazing team to ensure the home & pool are sparkling clean for all of our guests. Our home goes through rigorous cleaning per CDC guidelines using only EPA approved detergent and highest MERV 13 A/C filters changed ...

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Property Type

Anna Maria Island House

"Great house"

We had a remarkable time at this house. The location, pool and house exceeded our expectations. We'll come back.

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Key Amenities

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

About this property

April 27 - May 4, 2024 Deal - now $2,099/wk plus fees and taxesMany new items not shown in photos;- New exterior Polywood dining table - New interior dining table set - New screened lanai conversation set - New coffee table set in living roomOUTSIDE HIGHLIGHTS: Soft Sandy Backyard Beach ...

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Property Type

Anna Maria Island House

"Such a perfect place for our entire family"

We loved our time at Sirena Cove. There were so many amenities and room for all of our adult children, their spouses and our grandchildren all under the age of four. The pool was great fun and we enjoyed ...

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Key Amenities

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

About this property

Beach Front/Heated Pool/Hot Tub/ 4 bedroom plus den North End of Anna Maria Island. Professionally decorated and finished with all King Beds and En-Suite Bathrooms. Chef's Kitchen with a 48inch gas range. Wine Cooler on two levels and a private covered porch to enjoy the sunsets on the upper levels. ...

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Property Type

Anna Maria Island House

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4 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 0.0 miles to Gulf Beach & Tampa Bay Beach

$797

avg/night

View Details

Key Amenities

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

About this property

Newly renovated! Read our description carefully as we have upgraded and added many amenities!Minimum Stays Required Based on Dates - Inquire DirectlySIRENIA BEACH HOUSE ~ Pick your beach! Sirenia Beach House is located between 2 beaches on a quiet cul de sac with fabulous views of the waterfront. ...

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Property Type

Anna Maria Island House

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3 BR | 2 BA | Sleeps 8 | Quick View

$598

avg/night

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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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2 BR | 2 BA | Sleeps 6 | Quick View

4
last minute deal
LAST MINUTE DEAL 5/9 - 6/20: July 6th forward open at discounted rates!!

$207

avg/night

View Details

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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DEAL

1 BR | 1 BA | Sleeps 4 | Quick View

$241

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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3 BR | 3 BA | Sleeps 8 | Quick View

3

$498

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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3 BR | 3 BA | Sleeps 6 | Quick View

$417

avg/night

View Details

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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4 BR | 5 BA | Sleeps 8 | Quick View

$1072

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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3 BR | 2 BA | Sleeps 8 | Quick View

1

$456

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

$1045

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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2 BR | 2.5 BA | Sleeps 4 | Quick View

$543

avg/night

View Details

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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3 BR | 2 BA | Sleeps 6 | Quick View

2

$287

avg/night

View Details

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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5 BR | 4 BA | Sleeps 8 | Quick View

$598

avg/night

View Details

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
  • 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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Anna Maria Island Vacation Rentals

Anna Maria Island Weather

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

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 257 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 $410.

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 123 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 23 oceanfront rentals in Anna Maria Island available on FloridaRentals.com. Use our filters to search and book yours today!