Anna Maria Island Vacation Rentals

(115 rentals)
Lime Cottage Pool Beach House.... Ahh.... This is it!!!

$209

per night

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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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Vitamin Sea

5 BR | 5 BA | Sleeps 12 | Quick View

1

$499

per night

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

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: Summer Holidays are coming soon - book now! Free beach equipment rental included with 6 night stay.

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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Tiffany Place Condo

2 BR | 2 BA | Sleeps 4 | Quick View

$100

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Private Pool

About this property

This gorgeous open concept, two bedroom, two bath, family room, dining area and kitchen was decorated by one of Florida’s top decorators for luxury and comfort and has all the amenities and style for discriminating tastes. We used beautiful materials like tumbled marble, Florida tile, brushed nickel ...

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Property Type

Anna Maria Island Condo

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Surf Side Beach House

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

6605 Gulf Drive, Holmes Beach - FL - 34217 5 bedroom, 4.5 bathroom with 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 5 bedroom 4.5 bathroom home . With 11 foot ceilings ...

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Property Type

Anna Maria Island House

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Conch Out Beach House

4 BR | 3 BA | Sleeps 10 | Quick View

$329

per night

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

$375

per night

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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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Dolphin Cottage - 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 ...

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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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Casita Marina - 11101

3 BR | 2.5 BA | Sleeps 8 | Quick View

$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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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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Crosswind Cottages

3 BR | 2.5 BA | Sleeps 8 | Quick View

$149

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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 House

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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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Gulf View Beach House is READY for YOU!

$142

per night

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Key Amenities

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

About this property

This beach house is directly across from the beach with beach views from the kitchen, dining room, living room and the small porch! It is in great shape and is much prettier inside than outside!

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Property Type

Anna Maria Island House

"Loved this cottage!"
Reviewed January 13, 2020

This location is wonderful. Trolley handy, across from the beach and the path for walking or riding your bike.

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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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Paradise Found

6 BR | 6 BA | Sleeps 12 | Quick View

1

$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

"Awesome vacation house."
Reviewed November 2, 2019

Great house for vacation. 6 bedrooms and bathrooms. Nice pool and hot tub. Already had friends interested.

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

$271

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

"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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Sandcastle 4

3 BR | 2 BA | Sleeps 6 | Quick View

$194

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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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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307 65th Street

5 BR | 4 BA | Sleeps 10 | Quick View

2

$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

"Just Like Home!!!"
Reviewed December 22, 2019

This property is everything you see…we had a huge family (10) have an opportunity to stay at this beautiful property. Once you opened the door to walk in you immediately knew it wasn’t like other beach ...

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Good Time and Tan Lines

3 BR | 3 BA | Sleeps 6 | Quick View

$299

per night

View Details

Key Amenities

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

About this property

Don't miss the opportunity to one of the first to stay in this Stunning 3 bedroom 3 bathroom with bonus den area that has been completely renovated from bottom to top. This property is a new hidden gem of Holmes Beach.   The open concept floor plan is warm and inviting making you feel at home ...

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Property Type

Anna Maria Island Townhome

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

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

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 250 feet to About a 50 second walk

$185

per night

View Details

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. If you deserve the best and would like to enjoy the best at introductory rates, read on! You can literally watch the sunrise and sunset ...

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Property Type

Anna Maria Island Townhome

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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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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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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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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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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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Ocean View

6 BR | 5 BA | Sleeps 12 | Quick View

$449

per night

View Details

Key Amenities

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

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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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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Sandy Shores Condo

2 BR | 2 BA | Sleeps 4 | Quick View

$179

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

5608 Gulf Dr 201 Sun PlazaThis newly renovated 2 bed 2 bath condo is only steps to the white sand beaches of Anna Maria island. Granite counter tops, stainless steal appliances this condo has everything you could ask for in a relaxing beach escape. W With large sun drenched pool, lite tennis ...

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Property Type

Anna Maria Island Condo

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Manna-Tee Beach House

3 BR | 3 BA | Sleeps 8 | Quick View

$153

per night

View Details

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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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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'Searenity' Stand Alone Home steps from beach!

$93

per night

View Details

Key Amenities

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

About this property

Searenity is a charming ground-level stand alone cottage that is beautifully decorated and has two large bedrooms to sleep four. There is a full bathroom with a soaking tub and shower. It’s a newly renovated unit with granite counters, Italian tile floors, screened in lanai, air and water purification, ...

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Property Type

Anna Maria Island House

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

$307

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

"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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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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Stunning Luxury Beachfront House W/Pool &Spa

4 BR | 4.5 BA | Sleeps 8 | Quick View

Owner special: Cancellation 18 Apr-25 Apr 2020 now available price reduced from $5900 to $4900

$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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Beautiful super private tropical garden home with waterfall pool

$257

per night

View Details

Key Amenities

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

About this property

NOTE - Our home is ONLY available for FULL WEEK RENTALS, or longer.From mid-December through August our home is ONLY available from SATURDAY to SATURDAY. During the off season in the fall we can make exceptions to this policy.PRIVATE ISLAND PARADISE - Completely remodeled in 2019, this custom ...

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Property Type

Anna Maria Island House

"PARADISE FOUND"
Reviewed February 18, 2020

While we very impressed with the pictures of the house that were posted on the website, little did we know how fabulous this house was going to be! It had everything you could possibly think of from a totally ...

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Runaway Bay 201

2 BR | 2 BA | Sleeps 6 | Quick View

$133

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

OVERVIEW 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 ...

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Property Type

Anna Maria Island Apartment

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Bare Feet Retreat

3 BR | 3 BA | Sleeps 6 | Quick View

$299

per night

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Key Amenities

  • Full Kitchen

About this property

Stunning beach front resort with gated covered parking.

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Property Type

Anna Maria Island House

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A Hart of the Gulf

3 BR | 2 BA | Sleeps 6 | Quick View

$92

per night

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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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Resting Beach Place

2 BR | 2 BA | Sleeps 6 | Quick View

$199

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Don't miss out on the opportunity to stay steps away from one of the best beaches in Florida. This complex includes Tennis Court, Gazebo, Community Pool, Shuffle Board Court, Sauna, Pool Baths, Private ground level storage room, under building assigned parking, elevator, and garbage shoot. and laundry ...

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Property Type

Anna Maria Island Condo

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Escape the Madness

2 BR | 2 BA | Sleeps 6 | Quick View

2

$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

"Just what we needed!"
Reviewed November 4, 2019

Howard, your place is fantastic! Great location on Bean Point, and the house was well equipped with everything we wanted for the beach, in the kitchen, and even towels and linens- perfect! Thank you for ...

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Gulf Sound - A

2 BR | 1 BA | Sleeps 6 | Quick View

$143

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

OverviewGulf Sound is a gulf side, ground level tri-plex located on 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 six people. The unit has been updated and is comfortably furnished. It's quiet, yet close to ...

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Property Type

Anna Maria Island House

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Sea Horse

3 BR | 3 BA | Sleeps 8 | Quick View

$204

per night

View Details

Key Amenities

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

About this property

Make your way to Anna Maria Island and experience a one-of-a-kind paradise when you stay in this beautiful, stylish, recently renovated three-bedroom, three bath home with a private heated pool and bonus cottage complete with game room. Not only will you have easy access to dining, the beach is only a ...

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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!