Anna Maria Island Vacation Rentals

(110 rentals)
Gone Coastal Too: Beautiful Family & Pet-Friendly Private Home

$171

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • 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 ...

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Property Type

Anna Maria Island House

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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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Salt Air East

2 BR | 2 BA | Sleeps 6 | Quick View

$199

per night

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Key Amenities

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

About this property

Relax and unwind in this gorgeous, newly renovated 2 bedroom, 2 bath home close to everything!Salt Air East villa, 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? ...

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Property Type

Anna Maria Island House

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The Salty Dog - North Shore

4 BR | 3 BA | Sleeps 8 | Quick View

$263

per night

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Key Amenities

  • Air Conditioning

About this property

Welcome to The Salty Dog. This luxury Key West style home has it all. Expansive bay views, private heated pool, extra large master suite with a double shower and Jacuzzi tub, fresh and modern decor, two large balconies, indoor sitting area off the pool, and 2 car garage. The home is walking distance to ...

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Property Type

Anna Maria Island House

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Paradise Found

6 BR | 6 BA | Sleeps 12 | Quick View

$349

per night

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About this property

401 42 nd Street - Holmes Beach - FL - 34217 This brand new 6 bedroom 6.5 bathroom - SLEEPS 14 Comfortably. 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. ...

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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

LAST MINUTE DEAL 7/14 - 7/26: Cancel 7/14-7/20 or 7/20-7/26 ONLY $1,850.00 (ALL INCLUSIVE)or 7/14-7/26 ONLY $3,400.00 Your Call

$214

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. 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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DEAL
Sea Breeze

3 BR | 2 BA | Sleeps 7 | Quick View

1

$143

per night

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Key Amenities

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

About this property

This 3 bed 2 bath island oasis will take you back to the days of old Florida charm but in a modern and well appointed setting. It is nestled away on a quiet street just a few minutes walk to the white sand beaches on the Gulf of Mexico. Located within walking distance to the award winning Beach Bistro ...

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Property Type

Anna Maria Island House

"Just like home!"
Reviewed February 7, 2019

This is a gorgeous house, and we would definitely rent it again. Beautifully decorated with beach colors. The owner has spared no expense with the quality of appliances or furnishings. Beds were very comfortable ...

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

$300

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

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Beach, Please! Lovely, tropical retreat less than 100 steps to the beach!

$140

per night

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Key Amenities

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

About this property

Beach Please AMI is a beautiful island duplex with two private getaways under the same roof! Perfect for traveling with friends or family so you can stay together but still have your own private space. This listing offers information on the entire rental BUT either half can be booked separately.Is ...

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Property Type

Anna Maria Island House

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Mermaid's Crossing

4 BR | 3 BA | Sleeps 10 | Quick View

1

$299

per night

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About this property

At 4 bedrooms and 3 full bathrooms, this is one of the most charming rentals on Anna Maria Island!! Located a few houses from the beach, it is only a two minute walk until white powdery sand is between your toes! Easy on the kids and even easier on you! Around the corner from restaurants, pubs & stores ...

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Property Type

Anna Maria Island House

"Yearly family vacation"
Reviewed May 20, 2019

Location was good with only a short walk to the beach and in a quiet location. House was clean and there was plenty of room for the group. Lots of pool and beach toys for us and the kids. The pool needed ...

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Turtle Cottage - Anna Maria Island

$220

per night

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Key Amenities

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

About this property

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. This great getaway sleeps up to 4.The space:The cottage has an ...

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Property Type

Anna Maria Island Cottage

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Late Summer, Fall Special - $2,500 All-In! No hidden fees.

4 BR | 3 BA | Sleeps 10 | Quick View

1
Owner special: Late Summer, Fall Special - $2,750 All-In! No hidden fees.

$299

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. We even have a baby changing station, and for sanitary reasons suggest guests bring or ...

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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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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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ALECASSANDRA VACATION VILLAS

11 BR | 10 BA | Sleeps 32 | Quick View

$229

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 - 6 Individual Villas - Sleeping for 32

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Property Type

Anna Maria Island Villa

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Emerald Bay

3 BR | 3 BA | Sleeps 6 | Quick View

$279

per night

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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

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4 BR w/ Heated Pool, Short Walk to Beautiful Gulf Beach

$225

per night

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Key Amenities

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

About this property

3 story single family home in a tropical setting with heated pool. Just a short walk to beautiful Gulf of Mexico beach. Professionally decorated, with large master suite and Roman tub, mini-master suite with private bath, bedrooms 3 & 4 have both queen beds and twin beds...Gulf beach access ...

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Property Type

Anna Maria Island House

"Great Family spot"
Reviewed February 17, 2019

Close to the beach, well equipped inside, and lots of toys for outside. Lots of room for everyone young and old!

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Beach Bliss

3 BR | 3 BA | Sleeps 6 | Quick View

$225

per night

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About this property

Incredible 3 Bed 3 Bath bungalow, Minutes From The Beach With Backyard OasisSpecial Rate does not include thanksgiving Christmas of New Years week This beautiful 3 bedroom 3 bathroom Bungalow is only minutes from the white sands beach of Anna Maria Island. Only a minute walk to the nearest free ...

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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

$270

per night

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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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Casita Marina - 11103

2 BR | 2 BA | Sleeps 6 | Quick View

1
LAST MINUTE DEAL 7/13 - 7/24: Cancel NOW All INCL 7/13-7/19 or 7/19-7/24 4 Day Min$1,100.00 or 7/13-7/24 for $2,000. Your call.

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

3 BR | 2.5 BA | Sleeps 8 | Quick View

3
Owner special: Open week July 20 to 27 at beach front house with beach views from 2nd & 3rd level balcony.

$214

per night

View Details

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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Ocean View

1 BR | 1 BA | Sleeps 1 | Quick View

$449

per night

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About this property

OCEAN VIEW is a brand new construction home that features 6 bedrooms and 5.5 bathrooms and a fantastic location-just a 1 minute stroll to the White sandy beaches at the 65 th st access! This lovely property offers a private heated pool with a spa, water slide and grotto. The backyard is an oasis with ...

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Property Type

Anna Maria Island House

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Seahorse Beach House

4 BR | 3 BA | Sleeps 8 | Quick View

$299

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

202 81 st Street - Holmes Beach - Fl 34217 This Beautiful 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 heated pool in your own backyard oasis. This house has every luxury you could ...

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Property Type

Anna Maria Island House

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Palm Haven

2 BR | 1 BA | Sleeps 6 | Quick View

$120

per night

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Key Amenities

  • Air Conditioning
  • Pet Friendly

About this property

This quaint 2 bedroom, 1 bath villa is just a short half block from the white sand beaches of Anna Maria Island. Quiet neighborhood on the beach side of Gulf Drive! Full kitchen, ground level, private back patio, BBQ, full size washer/dryer, WIFI, beach cart, beach chairs, cul du sac, sleeps 6 people.

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Property Type

Anna Maria Island Villa

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Sun Set Beach Bliss

2 BR | 2 BA | Sleeps 4 | Quick View

$171

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Pool

About this property

This beautiful 2 bed 2 bath Gulf front condo has everything you need to vacation for a weekend or a month! Beautiful beach views from the living room, bedroom and the private balcony. We have everything you need to relax and enjoy. Beautiful views. Check! Beach chairs and umbrella. Check! Bicycles. Check! ...

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Property Type

Anna Maria Island Condo

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Bay View Dream

4 BR | 3.5 BA | Sleeps 8 | Quick View

$300

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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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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Copacabana

3 BR | 2 BA | Sleeps 8 | Quick View

$233

per night

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Key Amenities

  • Air Conditioning

About this property

Copacabana is newly remodeled 3 bedroom, 2 bath private home that sits right on the canal in Anna Maria in a very quiet neighborhood. There is now a brand new kitchen for entertaining and new tile floors flow throughout and with a designer’s stylish touch, you will feel you have found your home ...

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Property Type

Anna Maria Island House

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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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Sea Glass Cottage

3 BR | 2 BA | Sleeps 6 | Quick View

Key Amenities

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

About this property

Adorable and completely updated 3 Bedroom 2 Bath home on Anna Maria Island! It's just 3 houses to the beach at Bean Point which is known as one of the most beautiful beaches in the US. Newly renovated and features a lovely private fenced yard and private heated pool. Amenities also include, Washer/Dryer, ...

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Property Type

Anna Maria Island House

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Coconut Breeze Estate

4 BR | 4 BA | Sleeps 12 | Quick View

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Coconut Breeze is a custom home on the north end of Anna Maria in the quiet residential area in the sought after City Of Anna Maria. Offering 4 bedrooms / 4 bathrooms. You will find that this home has everything you need for your perfect Anna Maria Island vacation! From the luxurious heated pool, gourmet ...

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Property Type

Anna Maria Island House

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Anna Maria Island Club Unit 22

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

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 ...

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Property Type

Anna Maria Island Condo

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Costa Lotta

3 BR | 3 BA | Sleeps 6 | Quick View

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Costa 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 distance ...

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Property Type

Anna Maria Island House

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Manna-Tee Beach House

3 BR | 2 BA | Sleeps 8 | Quick View

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

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 finishes ...

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Property Type

Anna Maria Island House

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Sandcastle 4

3 BR | 2 BA | Sleeps 6 | Quick View

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen

About this property

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 heart of ...

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Property Type

Anna Maria Island Condo

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Summer Breeze

4 BR | 3 BA | Sleeps 8 | Quick View

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Summer Breeze is a custom home nestled in the quiet residential area in the heart of Holmes Beach. Offering 4 bedrooms/3.5 bathrooms. There is also a Den where the kids can hang out with a TV and Queen Sleeper sofa. You will find that this home has everything you need for your perfect Anna Maria Island ...

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Property Type

Anna Maria Island House

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Bradenton Beach Club - Sleeps 6 with Private Beach Access

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

his beautiful condo sleeps up to six people with 2  bathrooms, washer/dryer, elevator from the covered garage area, large, screened balcony. The condo is part of the Bradenton Beach Club that provides the very best in vacation accommodations. Amenities at the BBC include two swimming pools (one ...

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Property Type

Anna Maria Island Condo

"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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245 Bradenton Beach Club

3 BR | 2 BA | Sleeps 6 | Quick View

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Bradenton 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 townhouse sleeps up to six people with 2 1/2 bathrooms, full laundry, elevator, garage and large, private, screened ...

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Property Type

Anna Maria Island Townhome

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Island Dream

3 BR | 2 BA | Sleeps 6 | Quick View

1

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Island Dream is a custom home nestled in the quiet residential area in the heart of Holmes Beach. Offering 3 bedrooms / 2 bathrooms. You will find that this home has everything you need for your perfect Anna Maria Island vacation! From the brand new (2018) luxurious heated pool and spa, gourmet kitchen, ...

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Property Type

Anna Maria Island House

"Summer Vacation"
Reviewed May 30, 2019

Highly recommend ! We were close to everything! And the home was so nice and spacious and enjoyed the pool and spa!!

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Walker Beach Cottage/Pet Friendly

$129

per night

View Details

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

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

$300

per night

View Details

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

"Great home with a beautiful yard on the Gulf of Mexico"
Reviewed November 6, 2018

We stayed here for a week and had a great stay. This is an “Old Florida” home, not a super renovated McMansion. The House was full of charm and very clean and comfortable. There are several sitting ...

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Dolphin Cottage - 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 ...

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Property Type

Anna Maria Island House

"Love the Dolphin Cottage!"
Reviewed April 23, 2019

This is where you want to stay at the beach for a quiet old Florida experience. A beautiful beach is less than a block away where you can enjoy shade under the old Australian pines. The cottage is clean, ...

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Casa Amiga

4 BR | 4 BA | Sleeps 10 | Quick View

$449

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

CASA AMIGOS is a brand new construction home that features 4 bedrooms and 4.5 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. Less than 5 minutes walk to Pine Ave where you can grab your morning coffee, take the ...

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Property Type

Anna Maria Island House

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A Hart of the Gulf

3 BR | 2 BA | Sleeps 8 | Quick View

$120

per night

View Details

Key Amenities

  • Air Conditioning

About this property

Quaint 3 bedroom, 2 bath private home in a quiet area of Holmes Beach only a short walk from the beach. A Hart of the Gulf is ground level and spacious with all the comforts of home included. Close to the free trolley, shops and restaurants. Accommodates up to 8 guests Amenities include: Linens, central ...

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Property Type

Anna Maria Island House

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Paradise Beach House

6 BR | 6 BA | Sleeps 14 | Quick View

$449

per night

View Details

Key Amenities

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

About this property

Stunning 6 bed 6.5 bath ~ Spectacular Pool & Spa ~ Walk to the beach and shops ***** IF YOU WOULD LIKE TO RENT FOR LESS THAN 7 DAYS PLEASE CONTACT US AT ***** Paradise Awaits Beach House ~ Be one of the first to enjoy this brand new 6 bedrooms, 6.5 bathrooms beach home that sleeps up to 14 and is ...

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Property Type

Anna Maria Island House

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Jacaranda

3 BR | 2 BA | Sleeps 8 | Quick View

$199

per night

View Details

Key Amenities

  • Air Conditioning
  • Pet Friendly
  • Private Pool

About this property

766 Jacaranda Road - Anna Maria- fl -34218 Unique 3 bedroom 2 baths with an upstairs bonus room close to the beautiful beaches if Bean Point and the Amazing Pine Ave.This beautiful 3 bedrooms 2 bathroom single family home is minutes from the white sands beach of Anna Maria Island. Only a short walk ...

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Property Type

Anna Maria Island House

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Island Escape

4 BR | 4 BA | Sleeps 8 | Quick View

$599

per night

View Details

Key Amenities

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

About this property

ISLAND ESCAPE is the most beautiful house you'll find on AMI ~ brand new and simply FABULOUS! The photos just can’t show exactly how special this home really is. Be one of the first to bring their family and enjoy this home that features upscale, professional décor without a detail missed. ...

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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

$150

per night

View Details

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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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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307 65th Street

5 BR | 4 BA | Sleeps 10 | Quick View

$399

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This stunning brand newly built and decorated 5 bedroom 4 bath home is just steps from the sparkling white sandy beaches of the Gulf of Mexico. Located in prime Holmes Beach you are with in walking distance to the award winning Beach Bistro and many other restaurants, live music , bars and more. The ...

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Property Type

Anna Maria Island House

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Oasis By The Beach

5 BR | 4 BA | Sleeps 12 | Quick View

1

$299

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This amazing rental is a favorite for all that stay. 5 bedroom, 4 bathroom beach home just a one minute walk to the famous Anna Maria Island beach. The beach stretches for miles in each directions. Feel the powdery sand between your toes and enjoy the warm Gulf waters. This home has all the style ...

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Property Type

Anna Maria Island House

"Lovely stay"
Reviewed May 6, 2019

Another family and ourselves rented the property. We found it very clean and equipped to a high standard. The pool and jacuzzi were great and well used especially by the kids. The management company were ...

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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!