Anna Maria Island Vacation Rentals

(117 rentals)
Manna-Tee Beach House

3 BR | 3 BA | Sleeps 8 | Quick View

$153

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Overview If you are ready to put your "heels in the sand", look no further. Manna-Tee Beach House is the perfect vacation spot for relaxation on Anna Maria Island. This beautiful 3 bedroom, 2.5 bath home located on Holmes Beach on Anna Maria Island has all the amenities for you. Top-of-the-line ...

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Property Type

Anna Maria Island House

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Sandcastle 4

3 BR | 2 BA | Sleeps 6 | Quick View

$204

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

OVERVIEW Sandcastle is a beautiful beach front property offering all of the conveniences you would want in an island stay. You will find the furnishings & facilities very accommodating to make your vacation one to remember. This condo is a quaint 3 bedroom 2 bath beach front condo located in the ...

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Property Type

Anna Maria Island Apartment

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January special!

2 BR | 2 BA | Sleeps 4 | Quick View

$214

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Special January Rates offered for this beautiful two bed-room, two bath condominium located at "GulfView" Condominium on Bradenton Beach. Sleeps 4 comfortably. Direct gulf front views with a gulf front heated swimming pool. Located in the heart of Bradenton Beach within walking distance ...

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Property Type

Anna Maria Island Condo

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Southern Comfort

3 BR | 3 BA | Sleeps 6 | Quick View

$153

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Southern Comfort is a private, single family home centrally located in Holmes Beach. This gorgeous 3 bedroom 2.5 bath vacation rental offers a private heated pool, front and rear balconies, gas BBQ grill, tropical landscaping, one car garage and much more! Just a brief 4 minute stroll to the pristine ...

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Property Type

Anna Maria Island House

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Casita Marina - 11101

3 BR | 2.5 BA | Sleeps 8 | Quick View

$214

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

This classic home located on the North End of Anna Maria Island is the perfect home for your tropical beach vacation. The beautiful Anna Maria beach is across the street about 100 steps away! The home is a legal duplex. This is the larger unit and has three bedrooms and 3.5 bathrooms. The kitchen has ...

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Property Type

Anna Maria Island House

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ALECASSANDRA VACATION VILLAS, Your Family Reunion Accommodation

$257

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Ideal Location - Family Reunion Accommodation 1 Property - 2 - Buildings - 5 Individual Villas - Sleeping for 30The Alecassandra Vacation Villas is a small 10 bedroom vacation resort that is family owned by Nick and Vicki Zec and named after our children Alec & Cassandra. When renting entire ...

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Property Type

Anna Maria Island Villa

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Absolute Anna Maria

2 BR | 2 BA | Sleeps 6 | Quick View

$171

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Private Pool
  • Rentals by Owner

About this property

Surrounded by water with the Gulf of Mexico to the west, the Intra-Coastal Waterway to the east, Tampa Bay to the north and Sarasota Bay to the south. We have the best location on Anna Maria Island where the island is only 150 yards wide. Our complex stretches from the Gulf to the Intra-Coastal Waterway. ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island Club Unit 22

$179

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

This amazing beach front 2 bedroom / 2 bathroom condo is perfect for an island vacation. This unit features a fully equipped kitchen, elevator, washer & dryer, cable TV / wifi, shaded assigned parking and a shared heated pool & spa. But, it doesn't stop there, this unit has stunning views of the ...

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Property Type

Anna Maria Island Apartment

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Villa Del Mar

4 BR | 4 BA | Sleeps 10 | Quick View

$504

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Cool and calming tiled floors, modern furnishings, and updated appliances give this vacation home an air of Tommy Bahama feel. We know how exhausting and stressful traveling can be so don’t feel an ounce of guilt if the second thing you do is plop down on the living room’s couch and switch ...

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Property Type

Anna Maria Island House

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BEACH FRONT HOUSE with TIKI HUT ....SHADY PINES yard is 1 step to beach.

$307

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Rentals by Owner

About this property

The best of both worlds all in one family friendly spot! SUN and SHADE. Best lot on the Island according to frequent visitors. We do not accept pets. Shady Pines is a very comfortable tastefully decorated, 2 BR, 1-1/2 bath, beach house right on the beautiful Gulf of Mexico. Our guests say it feels ...

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Property Type

Anna Maria Island House

"Paradise Beach House"
Reviewed November 15, 2018

We have spent very nice week at Shady Pines Beach House. Every morning we had a breakfast outside in front of the house and watched the sea of Mexico Gulf. The atmosphere of the house gives to everybody ...

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LaPlage Unit 2

4 BR | 3 BA | Sleeps 8 | Quick View

$507

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Pool
  • Private Pool

About this property

L’Plage 2, located at 6402 Gulf Drive is Island luxury at its finest! It is among the few and one of the largest four bedroom condos available on the Island. The L’Plage condominium complex will exceed all your expectations. Nestled in the sugar sand, this ultra-luxurious beachfront property ...

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Property Type

Anna Maria Island House

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Dans Florida Condos - 1 bedroom 1 bath (Private Beach Access) Runaway Bay

$214

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool
  • Rentals by Owner

About this property

This non-smoking unit is over 900 sq ft with a screened in terrace complete with a quiet, peaceful view of the lagoon that flows through the center of the complex (see the pictures). Conveniently located close to Sarasota Airport (20 minutes) and the Tampa Airport (55 minutes). Also, close to major Florida ...

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Property Type

Anna Maria Island Condo

"Heated Pool!!!"
Reviewed May 13, 2019

Loved this unit and the excellent communication I had when booking with Dan's Florida Condos. The place had everything we needed, including beach towels & beach chairs. The heated salt water pool was awesome ...

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Walker Beach Cottage

2 BR | 2 BA | Sleeps 4 | Quick View

1

$129

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Rentals by Owner

About this property

My wood-frame beach cottage was built in 1936, and was originally part of 6-8 cottages and a lodge house. It is the only surviving cottage, many having been taken by hurricanes. (Forward of the cottage’s beach, a street and an entire city block of the old subdivision are submerged beneath the ...

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Property Type

Anna Maria Island Cottage

"Just what the Doctor ordered"
Reviewed October 7, 2019

This was the best vacation I have had in a few years. It was so easy to schedule - Libby the cottage manager was excellent and so accommodating. The cottage was charming, very clean, and well equipped ...

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Relax at The Ulmer House...Right on the Beach...Gulf Views Everywhere!

$307

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Rentals by Owner

About this property

As you drive up to The Ulmer House, the landscape is natural, graceful and compliments the house in an authentic way. It feels like a compound from the street looking through the mature trees that surround a very large property and shield it from the view of the public. There is a very private and spacious ...

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Property Type

Anna Maria Island House

"wonderful home in a beautiful location!"
Reviewed July 23, 2019

This home was beautiful and had everything we needed for a wonderful week at the beach. The shaded lot and views of the beach from the house were outstanding!

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Anna Maria Island Condo~Close to the beach, shops & restaurants, heated pool!

$100

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Welcome to Paradise!When you come to Anna Maria Island for vacation, make this charming and inviting two-bedroom condo your home away from home! You're sure to love the relaxed island attitude with amenities like a heated pool, private screened lanai, and easy access to the beach, dining, and shopping. ...

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Property Type

Anna Maria Island Condo

"Stunning Accommodation"
Reviewed November 18, 2019

We arrived, looking forward to a three day trip to the island. We were delighted to find this beautiful apartment was situated in a lovely quiet area but close to the free trolley bus stop and Publix supermarket. ...

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Real Gulf-Front Beach House - One Step to the Beach!

$307

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • 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 - with the best of both worlds - the sun and the shade.Beach and ...

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Property Type

Anna Maria Island House

"Simply the best!"
Reviewed December 29, 2019

We stayed at this lovely beach house over Christmas and it was everything we could ask for and more. You are ON THE BEACH with this fabulous location. The owners had a very well stocked home from beach ...

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Dans Florida Condos - 2bedroom 2 bath (Private Beach Access) Runaway Bay

$243

per night

View Details

Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

--Don't see the exact dates you are looking for? Check out the additional availabilty in my 1br 1 bath unit (40 steps away from this unit) /5597This updated 2 bedroom 2 bath condo is located at Bradenton Beach on Anna Maria Island, directly off Gulf Drive. Runaway Bay is a lovely vacation resort on ...

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Property Type

Anna Maria Island Condo

"Great location"
Reviewed May 13, 2019

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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Casita Marina - 11103

2 BR | 2 BA | Sleeps 6 | Quick View

1

$164

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

This classic home located on the North End of Anna Maria Island is the perfect home for your tropical beach vacation. The beautiful Anna Maria beach is across the street about 100 steps away! The home is a legal duplex (11101+11102 Gulf Drive). This unit has two bedrooms and two bathrooms. The Kitchen ...

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Property Type

Anna Maria Island Condo

"This is a Charming Beach Cottage"
Reviewed February 28, 2019

This duplex has been completely renovated inside with a nice kitchen and bathrooms. It is a perfect location in the quiet northern end of AMI. It is within walking distance to restaurants and the beach ...

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Gone Coastal 3 Beautiful Family and Pet Friendly Home

$243

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

Welcome to Gone Coastal 3! This quaint three bedroom, two bathrooms plus a half bath vacation home is located just a short walk from Anna Maria Island’s sugar white sands and crystal clear waters! Beach towels, six beach chairs, and a beach wagon are provided to ensure your days spent in the sun ...

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Property Type

Anna Maria Island House

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Fantastic Beach View - Convenience & Comfort at Beach House for Family Fun.

$214

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • 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 8 guests and is 150 feet from the ...

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Property Type

Anna Maria Island House

"Review of an Excellent Rental"
Reviewed April 19, 2019

The house is in a great location and is well equipped. Beach is only a few minutes away. The free trolley, which serves the entire island, is about a 5 minute walk.Supermarket and drug stores are nearby. ...

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New Listing! Penthouse Condo in One Particular Harbour Near Anna Maria Island

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: Need to fill a vacancy: Special 6 nights for the price of 5. March 9 thru March 15, 2020 - only.

Distance to beach: 2 miles to Manatee Beach

$129

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Rentals by Owner

About this property

2 BR / 2 BA Penthouse Sleeps 6 - 1.6 Miles from Anna Maria Island Beaches Fall in love with the amenities of the property and convenience to Anna Maria Island Beaches in this brand new 2 bed/2 bath penthouse condo! Enjoy coffee and a beautiful sunrise on the large sectional sleeper sofa with a relaxing ...

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Property Type

Anna Maria Island Condo

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Gone Coastal: Beautiful Family & Pet-Friendly Home with a Heated Salt Water Pool

$171

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Centrally located in Holmes Beach, this elevated two bedroom/two bath half duplex has its own private heated salt water pool and outdoor bbq area! It also has an outside shower for showering off after your trips to the beach. Inside it has a split plan with a king sized bedroom and a second bedroom with ...

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Property Type

Anna Maria Island House

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Sea Salt

3 BR | 3 BA | Sleeps 6 | Quick View

$153

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Sea Salt is a beautiful recently updated home home nestled in the heart of Holmes Beach-just a short 5 minute walk to the world renowned beaches of Anna Maria Island. This 3 bedroom 2.5 bath home offers everything you need for an unforgettable vacation. Enjoy the private heated pool with sand area, covered ...

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Property Type

Anna Maria Island House

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December and January Special $375/night plus fees and taxes- 5-night minimum

$375

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

PRIVATE HEATED SALTWATER POOL + PRIVATE ELEVATOR + STEPS TO GULF BEACH! SLEEPS 10 - FULLY EQUIPPED - ULTRA-CLEAN! WALKING DISTANCE TO SHOPS, RESTAURANTS, AND NIGHT SPOTS!This is a fully-equipped vacation rental:All bed and bath linen are provided. There are extra bath towels for each guest, and ...

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Property Type

Anna Maria Island Townhome

"Great home away from home!"
Reviewed October 6, 2018

My friends and I came to Anna Maria Island to get some much needed rest and relaxation, and this rental was the perfect place. The location is awesome, as it is walking distance from the beach. But who ...

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240 Bradenton Beach Club

3 BR | 2 BA | Sleeps 6 | Quick View

1

$133

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

OverviewBradenton Beach Club is a beautiful Gulf to Bay property that is 1/2 a block away from the beautiful beaches offering you all of the convinces you would want in an island stay. This beautiful condo sleeps up to six people with 2 bathrooms, washer/dryer, elevator from the covered garage area, ...

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Property Type

Anna Maria Island Apartment

"Again an Amazing Vacation!"
Reviewed July 9, 2018

We have stayed in this condo for the past three years and LOVE it! The condo is fully stocked and the owners are wonderful to deal with. Did I mention it comes with a locker for all your beach stuff right ...

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Sea Life Retreat on Anna Maria Island at Runaway Bay

Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Pool
  • Private Pool

About this property

Enjoy Anna Maria Island from this fresh and casual 2 bedroom, 2 bath poolside condo in Runaway Bay!Just steps from the beach and the bay, Runaway Bay has it all – a heated, salt water pool (the largest on the island!), tennis, bocce ball and shuffleboard courts, a work out room, clubhouse and ...

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Property Type

Anna Maria Island Condo

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Heated Pool...North End of Anna Maria!

2 BR | 1 BA | Sleeps 4 | Quick View

11

Distance to beach: 500 feet to Bean Point

$164

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Rentals by Owner

About this property

Two story duplex. Each unit is two bedrooms, one bathroom. Rent one or both.Shared heated pool, short walk to the beach and everything you need for your perfect Anna Maria Vacation.***Availability calendar does not distinguish between upstairs and downstairs units.

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Property Type

Anna Maria Island House

"Great place for a quiet vacation"
Reviewed June 20, 2019

This is a great place to vacation in Anna Maria, in a quiet well maintained neighborhood. We are looking forward to our next visit in 2020. This will be our eighth time staying at this property. Just ...

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Lime Cottage Pool Beach House.... Ahh.... This is it!!!

$209

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

We are now filling in spring summer and fall weeks. For an accurate quote please inquire with your dates and the number of guests.Many of our multiple repeat past guests really like A Lime Cottage based on their social media posts. For 360 degree virtual views of the property or a neighborhood video, ...

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Property Type

Anna Maria Island House

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Stunning Luxury Beachfront House W/Pool &Spa

$643

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Private Pool
  • Rentals by Owner

About this property

An outstanding luxury beach house furnished as our home to a very high standard. With a stunning beach coastal theme. It is located on the north end of Anna Maria island The house has 4 bedrooms and 4 bathrooms it was constructed in 2011 has been designed to accommodate a single family group. Please ...

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Property Type

Anna Maria Island House

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Beach Vacation at Angelinos Sea Lodge on Anna Maria Island

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 100 feet to Beach onsite

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Rentals by Owner

About this property

Angelinos Sea Lodge offers four unique vacation rentals right on the beach of Florida Gulf Coast, Anna Maria Island, Holmes Beach. Hidden in a quiet residential street, these beachfront cottages are quaint, charming, and just a few steps to the white sand and blue sea. All beach cottages have direct ocean ...

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Property Type

Anna Maria Island Cottage

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Osprey Roost - Pet-friendly and very close to beach!

$228

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Rentals by Owner

About this property

It is always summer on Anna Maria Island!We have one of the most pristine, un-crowded beaches you will ever visit. Enjoy a champagne breakfast, Duffy's burgers for lunch, or cocktails at sunset! In addition, there are many other fabulous things to do here - Busch Gardens, Universal Studios and Disney ...

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Property Type

Anna Maria Island House

"Ideal home away from home"
Reviewed April 15, 2019

We can't stop talking about how much we miss "our" Osprey Roost. The car rarely leaves the driveway, as everything we need and want is within walking distance. The gulf is a very short walk, as are the ...

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Vitamin Sea

5 BR | 5 BA | Sleeps 12 | Quick View

1

$499

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

VITAMIN SEA is a brand new construction 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 is an oasis ...

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Property Type

Anna Maria Island House

"Rain or Shine"
Reviewed June 1, 2018

Having a steamy hot tub, a pretty cool pool deck and pool during a tropical depression made everything alright. Staying here over Memorial weekend was just what we needed. Each room had it's own restroom, ...

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Starfish Isle

4 BR | 3 BA | Sleeps 10 | Quick View

$249

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

At 4 bedrooms and 3 full bathrooms, this is one of the best rentals on Anna Maria Island. A few short blocks to the beach, and around the corner to restaurants, pubs & stores. Featuring a heated pool to relax in after your busy day, Starfish Isle is a luxurious and welcome retreat in the perfect location ...

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Property Type

Anna Maria Island House

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SunSet Azul

2 BR | 1 BA | Sleeps 4 | Quick View

1

$146

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

OVERVIEWSunset Azul is a fully updated 2 bedroom 1 bath gulf side ground level villa on the southern end of Holmes Beach. This unit has been updated and is comfortably furnished. It's quiet, yet close to shopping, restaurants and trolley stops. Best of all, this unit is only a few short steps to the ...

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Property Type

Anna Maria Island Apartment

"Great stay at Sunset Vista as usual!"
Reviewed October 15, 2019

Went with my family 1st week of October. This is our second time staying at Sunset Vistas and we love it! We had wonderful weather and our room and view were great! We saw dolphins every morning. They maintain ...

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Sunset & Sand

4 BR | 3 BA | Sleeps 8 | Quick View

1

$299

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Brand New 4 Bedroom 3 Bathroom, Pool & SPA Garage & Bikes. Minutes from beach This brand new 4 bedroom 3 bathroom home ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the salt water heated pool in your own backyard ...

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Property Type

Anna Maria Island House

"Great Thanksgiving Vacation!"
Reviewed November 26, 2018

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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Conch Out Beach House

4 BR | 3 BA | Sleeps 10 | Quick View

$329

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

At 4 bedrooms and 3 full bathrooms, this is one of the best rentals on Anna Maria Island. Straight down the road 1 block to the beach, and around the corner to restaurants, pubs & stores. Featuring a huge heated pool to relax in after your busy day, Conch Out Beach House is a luxurious and welcome ...

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Property Type

Anna Maria Island House

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Peaceful retreat Mint Clean New! Dock Bikes (nearby), Grill Big Lanai WiFi Cable

$93

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront

About this property

This may be the nicest one bedroom vacation rental on Anna Maria Island!! You've looked at the rest now book the best. Book directly thru this site, in order to secure the dates you want and, at our current great rates. Read on to see what sets us apart from the rest!Our new 1 bedroom vacation rental ...

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Property Type

Anna Maria Island Condo

"SPECTACULAR"
Reviewed September 25, 2019

I really cannot say enough about this accommodation as it totally exceeded my expectations. Mark has thought of absolutely everything right down to the tiny little Florida inspired decor! You only need ...

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Turtle's Bay

3 BR | 3 BA | Sleeps 6 | Quick View

1

$279

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

This brand new 3 bedroom 3.5 bathroom + den . This home is ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the salt water heated pool in your own backyard oasis. This house has every luxury you could want, Flat screen TV’s, ...

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Property Type

Anna Maria Island House

"Beautiful Property"
Reviewed September 23, 2018

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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Costa Lotta

3 BR | 4 BA | Sleeps 8 | Quick View

$314

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

OverviewCosta Lotta is "home away from home”. All the amenities you will need in this 2100 sq. ft. home. Costa Lotta is the perfect vacation spot for relaxation on Anna Maria Island! Just 200 steps and you are on a gorgeous, white sandy beach looking at the spectacular Gulf of Mexico! Walking ...

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Property Type

Anna Maria Island House

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A Shore Thing

3 BR | 2 BA | Sleeps 8 | Quick View

$215

per night

View Details

Key Amenities

  • Air Conditioning
  • Pet Friendly

About this property

This beach house is “A Shore Thing” for creating fantastic vacation memories. This newly furnished ground level home is decorated in coastal living motif and has no stairs to climb. The open floor plan is ideal for one or two families to have a fantastic vacation. The living room, Florida ...

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Property Type

Anna Maria Island House

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Ground Floor Two Bedroom Condo Steps to Gulf of Mexico and Bay

2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 75 feet to Anna Maria

$139

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

This ground level walk out two bedroom two bath condo has just been totally renovated and recently redecorated. The condo features a comfortal coastal style that has been decorated by the owner. The condo sits midway between the Bay of Sarasota and the Gulf of Mexico. Runaway Bay offers many amenities ...

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Property Type

Anna Maria Island Condo

"Above and beyond expectations"
Reviewed January 13, 2020

I can’t say enough about unit 176. It was decorated beautifully. Fully stocked with everything you could possibly need. The beds and linens were like staying at the four seasons. I highly recommend unit ...

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Sand Dollar Villa

2 BR | 2 BA | Sleeps 6 | Quick View

$83

per night

View Details

Key Amenities

  • Air Conditioning
  • Pet Friendly

About this property

This 2 bedroom, 2 bath villa is in the heart of Anna Maria Island. It is located 300 feet to the beach in a residential neighborhood, west of Gulf Drive, which is the beach side of the main road. Decorated with simplicity, yet fully equipped this ground level villa is conveniently located in the center ...

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Property Type

Anna Maria Island Villa

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BRAND NEW! ‘Primo Flamingo' 3bed/2 full bath Deluxe renewed home, Fishing dock!

$185

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Rentals by Owner

About this property

Our newest 3 bedroom/2 full bathroom is one of the most deluxe vacation rentals available on Anna Maria Island and located in most sought after and narrow part of island. This is our biggest and best property! If you deserve the best and would like to enjoy the best at introductory rates, read on! You ...

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Property Type

Anna Maria Island Townhome

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OCEAN 72

2 BR | 2 BA | Sleeps 6 | Quick View

$149

per night

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About this property

Relax and unwind in this gorgeous, newly renovated 2 bedroom, 2 bath home close to everything!OCEAN 72, located only a short walk to the powdery white sandy beach of the Gulf of Mexico and ½ a mile from historic Pine Avenue on Anna Maria Island.Not in the mood for the beach? No Problem! ...

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Property Type

Anna Maria Island House

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Angel Sea

6 BR | 3 BA | Sleeps 12 | Quick View

$299

per night

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About this property

This ideally located 6 Bedroom 3.5 Bathroom is an amazing place to escape and unwind. It is the perfect place to get away with friends or family, offering a large open floor plan and multiple outdoor sitting area. This little piece of paradise is centrally located to everything you could desire, it ...

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Property Type

Anna Maria Island House

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Sunset Landings 1

2 BR | 2.5 BA | Sleeps 4 | Quick View

$98

per night

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Key Amenities

  • Air Conditioning
  • Pet Friendly

About this property

Watch the gorgeous Anna Maria Island sunsets from the comfort of your own balcony! This lovely 2 bedroom and 2.5 bathroom condo located on Bradenton Beach is just across the street from the pristine white sandy beaches of the Gulf of Mexico. With magnificent views of the Gulf waters, a fantastic location ...

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Property Type

Anna Maria Island Townhome

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Kickback Cabana

3 BR | 2 BA | Sleeps 6 | Quick View

$229

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

This large single-family home located in Holmes Beach on Anna Maria Island is the perfect spot to spend your next beach vacation. With 2 king bedrooms and a large 3rd bedroom with a queen bed and a single bunk bed, there is plenty of space for everyone. This home has just been completely repainted and ...

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Property Type

Anna Maria Island House

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Peacock Place - Pet-friendly and very close to beach!

$271

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Rentals by Owner

About this property

It is always summer on Anna Maria Island!We have one of the most pristine, un-crowded beaches you will ever visit. Enjoy a champagne breakfast, Duffy's burgers for lunch, or cocktails at sunset! In addition, there are many other fabulous things to do here - Busch Gardens, Universal Studios and Disney ...

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Property Type

Anna Maria Island House

"Family visit"
Reviewed July 3, 2019

Peacock Place is a great place for family reunions. Plenty of space. Close to the beach. We loved it.

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Bay View Dream

4 BR | 3.5 BA | Sleeps 10 | Quick View

$243

per night

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Key Amenities

  • Air Conditioning

About this property

Ah, Bay View Dream! This lovely 4 bedroom, 3.5 bath home is located in the heart of Historic Anna Maria City. It sits right on an expansive waterway leading into Tampa Bay and has been lavishly decorated with all the creature comforts and more. Stunning water views from living room, dining room, kitchen ...

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Property Type

Anna Maria Island House

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Shell Cove 4

2 BR | 1 BA | Sleeps 4 | Quick View

$155

per night

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Key Amenities

  • Air Conditioning

About this property

Shell Cove Condominium #4, is a direct Gulf front condo located at 2310 Gulf Drive in Bradenton Beach. Completely renovated in 2016 with high end features. Relax on the sugar sand beaches and cool off in the emerald green waters. This complex is conveniently located within walking distance to shopping ...

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Property Type

Anna Maria Island Condo

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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°

Choose a vacation rental on the little island that has it all

A mere 20 minutes from Bradenton, laid-back Anna Maria Island awaits. What feels like “old” Gulf Coast Florida with strict business regulations, little to no car traffic, and a peaceful way of life. That’s right, you won’t find any chain restaurants or high-rise, view-blocking buildings here. And oh, the beaches! A seven-mile strip of beautiful white-sand beaches line the barrier island of Anna Maria Island between the turquoise Gulf of Mexico and peninsular Florida. It won’t be difficult to unwind here.

Anna Maria Island has amazing beachfront with available accommodations for you. When staying in one of our Anna Maria Island vacation rentals instead of hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Use the filters to narrow down your choices and choose the rental that calls to you, just like Anna Maria Island does.

Climate

You come to Florida for warmth and guaranteed clear skies. You’ll find all that and more in Anna Maria Island. The average year-round temperature in Anna Maria Island is a comfortable 75 degrees making it an ideal destination to visit during any month. You won’t see too much shifting of temps and precipitation here, though try to avoid hurricane season in the fall. Otherwise, you can’t go wrong whenever you visit.

Getting around

Hop around the island on the Anna Maria Trolley, as it runs north to south from the pier all the way to Coquina Beach. It stops every few blocks for riders to get on and off. Since parking is rare throughout the city, the trolley is a fan favorite. The best part? This scenic, air-conditioned ride is completely FREE!

Top activities and attractions

Your family won’t run low on things to do in Anna Maria Island. You’re visiting for the beaches, of course, and the best public one is known as Bean Point, located at the north end of the island. From here, you can walk around the entire island without leaving the sand. At the southern end of the area you’ll find Bradenton Beach which is another highly-rated, soft-sand place to spread your blanket and enjoy the sun. Of course a seaside city excels at water sports, too. Try your hand at parasailing, snorkeling, jet-ski, water ski, and many more activities on the turquoise blue waves.

Once you’re through with the surf, walk along the Anna Maria City Pier. Over 100 yrs old, the Pier offers up some great views of Tampa Bay and the Sunshine Skyway bridge at the northern end of the island. Visitors can see an array of birds and marine life, including dolphins and manatee. For more scenic and historic walking, check out Coquina Baywalk. This pleasant park is fun to explore. Winding boardwalks and trails along the water's edge, hidden in the mangroves.

The local museums and art galleries are popular attractions as well and great alternatives to outdoor activities. Spend an afternoon at the Anna Maria Island Historical Museum and Park. Visitors to the museum and park can learn about the island’s history, take part in a scavenger hunt, and tour the cottage that fell into the bay.

Shopping and dining

You’ll want to shop the day away on Pine Avenue, known as “the greenest little main street in America”. It’s lined with boutiques all the way up to the City Pier. Holmes Beach is also a populars shopping center ideal for grabbing that perfect souvenir.

Nestled alongside the storefronts are award-winning dining options. For those with a sweet tooth, The Donut Experiment serves up custom creations daily including a Fruity Pebbles inspired masterpiece. Yum! Fresh seafood abounds, like at the popular Waterfront Restaurant and upscale Blue Marlin Grill. For a taste of Europe, and German hops, visit Old Hamburg Schnitzelhaus serving up sausage, beer, and pretzels - each more delicious than the last.

Events

Although we discussed how the year-round flawless weather makes AMI an ideal choice no matter the month, time your trip to coincide with some popular area events to maximize fun. Heritage Day in February features the wares and skills of local artists and crafters, and attendees can take part in activities, enjoy lively music and participate in old-fashioned games for kids. Later in spring, the Bridge Street Merchants host the Blues, Brews & BBQ event to showcase the area’s top musical talents. Outdoor Market Sundays take place November through April with crafts and local produce for sale.

Anna Maria Island beach rentals on FloridaRentals.com

Booking Anna Maria Island rentals on FloridaRentals.com can save you up to 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!