Anna Maria Island Vacation Rentals

(102 rentals)
Anna Maria Island Townhouse - Simply Beautiful!

$225

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

This townhouse is beautifully decorated and completely modern with everything you need for the perfect vacation in paradise! The townhouse is convenient to everything on the island - walk to the beach, supermarket, retail shops, and restaurants. Or catch the local trolley and cruise the island to a vast ...

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Property Type

Anna Maria Island Townhome

"Spacious, beautiful private view, nice location!"
Reviewed April 14, 2019

We stayed at this property and were very pleased! The rental was spacious for our large family and was nicely appointed. The location is great for catching the trolley, running to many restaurants and ...

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Walker Beach Cottage/Pet Friendly

$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

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SLEEPS 10 - PRIVATE HEATED SALTWATER POOL + ELEVATOR - 2 HOUSES FROM GULF BEACH!

4 BR | 3 BA | Sleeps 10 | Quick View

1
Owner special: Summer Special - $375/night plus fees and taxes, minimum 7 nights, Saturday to Saturday rental! F

$264

per night

View Details

Key Amenities

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

About this property

5-Star Beachhome 4 Bdrm, 3 Bath, Private Pool and Elevator - Anna Maria Island, Florida.Go to and take a 3D Virtual Tour throughout this magnificent home! Amazing! Just like being in the home!This is a fully-equipped vacation rental. Just bring your clothes and toiletries! Everything necessary ...

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

$157

per night

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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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Coconut Breeze Estate

4 BR | 4 BA | Sleeps 12 | Quick View

$436

per night

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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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Casita Marina - 11103

2 BR | 2 BA | Sleeps 6 | Quick View

1

$164

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 (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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Absolute Anna Maria

2 BR | 2 BA | Sleeps 6 | Quick View

$150

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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North End of Anna Maria Duplex with heated pool!

2 BR | 1 BA | Sleeps 4 | Quick View

3

Distance to beach: 500 feet to Bean Point

$179

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. Upstairs available: Downstairs ...

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Property Type

Anna Maria Island House

"Favorite place to stay on Anna Maria!"
Reviewed April 22, 2019

Wonderful accommodations have had us coming back for years. Everything you could want/need is provided, clean and cheery atmosphere, and a beautiful private pool. Plus only a short walk to the most beautiful ...

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Convenience & Comfort at Beach House for Family Fun.

$214

per night

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Key Amenities

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

About this property

This affordable & convenient 3 story home is one house off Holmes Beach. The 3 bedroom 2.5 bath villa with 2 car garage accommodates 8 guests and is 150 feet from the pristine white sandy beaches with easy access. It has a 16 x 36 ft heated pool shared with identical rental house next door. The unit ...

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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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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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Sandcastle 4

3 BR | 2 BA | Sleeps 6 | Quick View

$230

per night

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

$225

per night

View Details

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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Manna-Tee Beach House

3 BR | 2 BA | Sleeps 8 | Quick View

$199

per night

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

$100

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Sandy Point condo is situated in a private complex right in the heart of Holmes Beach and is conveniently located across the street from the island grocery store, shops and restaurants. Just 4 short blocks and you are within walking distance to the most picture-perfect sugar-sand beaches of Anna Maria ...

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Property Type

Anna Maria Island Condo

"Our 3rd time in this condo- loved it every time!"
Reviewed March 29, 2019

We have stayed in this condo three times now and have loved it every time. Nicely appointed, comfortable furniture, well equipped from kitchen to beach chairs & umbrellas. Perfect location- short walk to ...

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

$129

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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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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Anna Maria Paradise - Private Pool & Canal front home

$167

per night

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Key Amenities

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

About this property

Beautiful 4 bedroom, 2.5 bathroom home with direct access to Anna Maria Canal and private heated pool overlooking the water. Take a kayak ride right off your private dock area or cast a fishing pole and catch dinner. This home has lots of space and is ready for you to come enjoy all of what the island ...

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Property Type

Anna Maria Island House

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Almost Beach Apartments

2 BR | 1 BA | Sleeps 5 | Quick View

1

$90

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

We are a small, clean, 'Old Florida' business located directly across the street from the Gulf of Mexico.Our units are comfortable and priced to allow the average person a chance to spend quality vacation time on our beautiful wide sandy beaches of the Gulf of Mexico! We are located on the free trolley ...

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Property Type

Anna Maria Island Apartment

"Family Vacation 2019"
Reviewed April 5, 2019

Everything was just as expected and we enjoyed everyday! The beach is right out your doorstep, well it is the best part. We'd love to stay again!

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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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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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Jacaranda

3 BR | 2 BA | Sleeps 8 | Quick View

$199

per night

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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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Summer Breeze

4 BR | 3 BA | Sleeps 8 | Quick View

$257

per night

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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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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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Escape the Madness

2 BR | 2 BA | Sleeps 6 | Quick View

$175

per night

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Key Amenities

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

About this property

Escape the Madness to the serenity of Anna Maria's north end. This single family, two bedroom, 2 bathroom, ground level house is located on the far north end of Anna Maria Island near Bean Point. The property is only 250 feet from the sugar sand beaches where you can walk for hours or sit and enjoy ...

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Property Type

Anna Maria Island House

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Coconut Cove

6 BR | 4 BA | Sleeps 14 | Quick View

$399

per night

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Key Amenities

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

About this property

205 17th St N - Bradenton Beach - FL - 34217 6 bedroom, 5 bathroom with saltwater pool/spa, gulf views minutes from beach.Special rate does not include holiday periods and is only good for a 7 day rentalThere was no expensive spared building this stunning 6 bedroom 5 bathroom home . With 11 ...

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Property Type

Anna Maria Island House

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SunSet Villas A

2 BR | 1 BA | Sleeps 6 | Quick View

$121

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Sunset Villas is a 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 white sandy beaches. ...

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Property Type

Anna Maria Island Villa

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Caribbean Surf

3 BR | 2 BA | Sleeps 6 | Quick View

1

$169

per night

View Details

Key Amenities

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

About this property

This beach 3 bedrooms 2 bathroom home is only a short stroll to the beautiful white sand beaches and miles away from any care. Covered deck looking over the pool is a wonderful spot to sit and relax or enjoy a meal. As they say, location is everything and this property is close to it all. 2 blocks ...

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Property Type

Anna Maria Island House

"Great home on Anna Maria Island"
Reviewed January 28, 2019

Beautiful home has everything thing you need. Wonderful heated pool my grandson loved the pool. Just a few blocks from the beach. Definitely would stay here again.

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Mermaids Landing

6 BR | 5 BA | Sleeps 12 | Quick View

2

$449

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Relax and unwind in this brand new custom built and professionally decorated 6 bedroom 5 bath home located just steps from both the Gulf of Mexico and the bay. This coastal style property boast luxury views from each room and features smart tvs in all the bedrooms as well as the living room and the outdoor ...

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Property Type

Anna Maria Island House

"Amazing house, would visit again in a heartbeat!"
Reviewed December 12, 2018

We rented this house for 8 adults and 3 little kids for a long weekend in October 2018, and really loved every minute of our stay. We were looking for a house that was on the beach, but being four houses ...

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Gulf Sound - A

2 BR | 1 BA | Sleeps 4 | Quick View

$141

per night

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Key Amenities

  • Air Conditioning
  • Pool

About this property

Gulf Sound is a gulf side, ground level tri-plex located at 2814 Gulf Drive in the southern end of Holmes Beach. Unit A at Gulf Sound is the southern unit. It is a two bedroom, one bath that will sleep four people. The unit has been updated and is comfortably furnished. It's quiet, yet close to shopping, ...

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Property Type

Anna Maria Island House

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Crosswind Cottages

3 BR | 2 BA | Sleeps 6 | Quick View

$149

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

312 (B) 61st street - Holmes Beach - FL - 34217 Welcome to this luxury Key West style home by the sea! It is your place in the sun to make memories and unwind!Crosswinds Cottage is just a short five minute walk to Anna Maria Island's world renowned white sandy beaches where you will enjoy time with ...

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Property Type

Anna Maria Island Cottage

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Salt Air East

2 BR | 2 BA | Sleeps 6 | Quick View

$199

per night

View Details

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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Runaway Bay 201

2 BR | 2 BA | Sleeps 6 | Quick View

$114

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Runaway Bay condominium located on northern Bradenton Beach, is a comfortable two bedroom, two bath second level condo located in a very popular complex. Runaway Bay is a bayfront complex unit 201 is only a few steps away from the beautiful beaches offering you all of the conveniences you would want in ...

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Property Type

Anna Maria Island Condo

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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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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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Bermuda Bay 1467

3 BR | 2 BA | Sleeps 6 | Quick View

$141

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Bermuda Bay is a beautiful Gulf to Bay property that is located 1/2 block away from the beautiful beaches offering you all of the conveniences you would want in an island stay. The complex has a large heated pool and spa, from the pool you can stroll down the boardwalk to the bay where you can take in ...

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Property Type

Anna Maria Island House

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Summer Retreat

4 BR | 4 BA | Sleeps 12 | Quick View

$371

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Summer Retreat is an absolutely amazing, brand new (2017) custom luxury home nestled in the quiet residential area in the heart of Bradenton Beach. Offering 4 bedrooms/4.5 bathrooms. Each bedroom has a private bathroom. There is also a kids gaming room with Xbox and an arcade game. You will find that ...

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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

View Details

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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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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Island Dream

3 BR | 2 BA | Sleeps 6 | Quick View

$221

per night

View Details

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

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Paradise Found

6 BR | 6 BA | Sleeps 12 | Quick View

$349

per night

View Details

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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Casa Del Mar

4 BR | 2 BA | Sleeps 8 | Quick View

$204

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Casa Del Mar is a beautiful Key West style home featuring four bedrooms and two and a half baths. This property is located on the north end of Holmes Beach close to shopping, restaurants and trolley stops. Best of all, this unit is within walking distance to the white sandy beaches. Amenities also include ...

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Property Type

Anna Maria Island Villa

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Absolutely perfect

2 BR | 2 BA | Sleeps 4 | Quick View

2

Distance to beach: 0.5 miles to Manatee Beach

$100

per night

View Details

Key Amenities

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

About this property

Very contemporary condo (danish style), just refurnished and remodeled, and equipped with more than everything you need for a relaxing and unforgettable vacation in Paradise.The unit is inspiring and gives you a laid back feeling immediately after entering. A huge pool with lounges and sun umbrellas ...

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Property Type

Anna Maria Island Condo

"Fantastic stay!"
Reviewed July 22, 2018

The condo has everything you could possibly need. Carla and her husband were wonderful to work with, as was the local rental agency that managed the condo. We called for a minor issue - but they came ...

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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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Inn Real Life, A White House Vacation Property

1 BR | 1 BA | Sleeps 4 | Quick View

2

Distance to beach: 150 feet to Cortez Beach heading south to Coquina Beach

$114

per night

View Details

Key Amenities

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

About this property

For more information:Cute one-bedroom apartments half a block to Gulf of Mexico beaches. No extra cleaning fees. Short visits (two night minimum) welcome except for holidays (three night minimum) and January through March when snowbirds come for three months.A separate bedroom and full size ...

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Property Type

Anna Maria Island Apartment

"White House"
Reviewed January 2, 2019

Found the rooms to be well furnished and very clean. Friendly atmosphere and close to restaurants - quiet area...

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242 Bradenton Beach Club

3 BR | 2 BA | Sleeps 8 | Quick View

$136

per night

View Details

Key Amenities

  • Full Kitchen
  • Pool

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 conveniences you would want in an island stay. This beautiful condo sleeps up to eight people with 3 bedrooms, 2 bathrooms, washer/dryer, elevator from the covered/lighted ...

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Property Type

Anna Maria Island Condo

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Pool Party Cottages

4 BR | 4 BA | Sleeps 12 | Quick View

$219

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

The Pool Party Cottage North & South is a beautiful duplex featuring 4 bedrooms and 4 baths with a pool area that is unsurpassed! This property is located in the heart of Holmes Beach close to shopping, restaurants and trolley stops. Best of all, these units are within walking distance to the white ...

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Property Type

Anna Maria Island Cottage

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

$250

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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Sun Plaza West - 204

2 BR | 2 BA | Sleeps 4 | Quick View

$121

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Sun Plaza West 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 recently updated, quaint 2 bedroom 2 bath beach front condo located ...

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Property Type

Anna Maria Island Condo

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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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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!