Anna Maria Island Vacation Rentals

(125 rentals)
Villa Del Mar

4 BR | 4 BA | Sleeps 10 | Quick View

$504

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

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

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Property Type

Anna Maria Island House

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Beach Bliss

3 BR | 3 BA | Sleeps 6 | Quick View

$308

avg/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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Seahorse Beach House

4 BR | 3 BA | Sleeps 8 | Quick View

$393

avg/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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OCEAN 72

2 BR | 2 BA | Sleeps 6 | Quick View

1

$216

avg/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

"Vacay 2020"
Reviewed July 5, 2020

Enjoyed a lovely vacay staying on AMI. Every year it doesn’t disappoint, this year was no different!

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Island Nautilus

3 BR | 2 BA | Sleeps 8 | Quick View

$234

avg/night

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Key Amenities

  • Air Conditioning

About this property

This second floor newly renovated 3-bedroom 2-bathroom condominium is your perfect vacation destination complete with a shared heated pool, private elevator, gas grill and only a two minute walk from the white sandy beaches. Island Nautilus features a living room with 50” smart, flat screen TV, ...

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Property Type

Anna Maria Island Apartment

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Life's a Beach

2 BR | 1 BA | Sleeps 6 | Quick View

$173

avg/night

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Key Amenities

  • Air Conditioning
  • Pet Friendly

About this property

Life's a beach is a cozy, newly renovated 2 bedroom 1.5 bath home located in the heart of Holmes Beach. Being only a Short distance to the beach access means you can walk there with your morning coffee, or drink in hand to enjoy the spectacular evening sunsets! Life's a beach features a living room, dining ...

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Property Type

Anna Maria Island House

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CHARMING HOUSE W/ HEATED POOL, STEPS TO BEAN POINT BEACH, PINE AVE, AND SHOPPING

2 BR | 1 BA | Sleeps 4 | Quick View

7

Distance to beach: 0.2 miles to Bean Point Beach

$215

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Location, Location, Location! North end of Anna Maria Island . This charming two story duplex- each unit has two bedrooms , one bathroom. Rent one unit or both. Perfect for a group of extended family and friends who want their own place but still be right together as a group. Heated inground pool, steps ...

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Property Type

Anna Maria Island House

"Home away from home!"
Reviewed September 7, 2020

We could not have been more pleased with our rental. Not only was the place in the perfect location, just a 5 minute walk to the beach, it was super clean and nicely equipped with everything we needed ...

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Beautiful Anna Maria Island! THIS PLACE ROCKS!

$129

avg/night

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Key Amenities

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

About this property

This amazing 1 bedroom house is directly across from the beach and offers full beach views from your huge deck, the living room and kitchen. Heck, you can even see the beach from your bed! We offer a clean house will all of the amenities you need and more! All linens, towels, dishes, washer and dryer, ...

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Property Type

Anna Maria Island Cottage

"Amazing"
Reviewed July 21, 2020

I was in love with this place!! First it was so clean, the house is old but so well taken care off. I loved that I was in a house and not a condo. I was so close to the beach and the views are amazing. ...

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The Merry Mermaid on Beautiful Anna Maria Island is ready for you!

$100

avg/night

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Key Amenities

  • Air Conditioning

About this property

The Merry Mermaid is a complete 1 bedroom addition to the main house. The amenities are first rate with love and thoughtfulness put into the finishing touches of this charming property. The beach is only 100 feet away from your front door which also leads to your private patio! The patio has your private ...

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Property Type

Anna Maria Island House

"Best location❤️❤️❤️"
Reviewed February 10, 2020

If you are local and want a great weekend or week getaway, this is the place for you. Location, location, location. Beach access directly across the street! Best local restaurants within walking distance ...

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Blue Bay View

3 BR | 2 BA | Sleeps 8 | Quick View

$388

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront

About this property

Panoramic Views of Tampa Bay! Blue Bay View is a charming Waterfront home located at the prestigious North End of Anna Maria Island! Escape to your personal oasis where you wake up every morning to the sunrise over the Bay. Enjoy your coffee on your very own PRIVATE BEACH while watching dolphins playing ...

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Property Type

Anna Maria Island House

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Penthouse Condo in One Particular Harbour Near Anna Maria Island / Marina Access

2 BR | 2 BA | Sleeps 5 | Quick View

3

Distance to beach: 2 miles to Manatee Beach

$170

avg/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 5 comfortably - 1.6 Miles from Anna Maria Island BeachesFall 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! The adjoining marina is a great convenience for guests that want to bring ...

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Property Type

Anna Maria Island Condo

"Incredible condo,location and ammenities"
Reviewed August 31, 2020

We had previously rented from Robert and Andrea and loved the condo so much we rented again for 6 weeks! We have rented many places in the past but this condo is the best. It has been professionally decorated ...

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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

3

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

$204

avg/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! But before you do, watch our new 5 minute ...

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Property Type

Anna Maria Island Townhome

"Amazing place"
Reviewed September 3, 2020

Mark was an amazing host. Hands down the best vacation destination. Across the street from the beach, and the mariana. The house is beautiful, the city is great. I cant wait to come back. One of my favorite ...

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Casita Marina - 11103

2 BR | 2 BA | Sleeps 6 | Quick View

2

$183

avg/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

"Great Location"
Reviewed August 12, 2020

Pros: The pool and hot tub are lovely. You can walk to the beach in 5 minutes and then walk back to go to the bathroom or make yourself a sandwich without having to carry your full day of food and drink ...

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Starfish Isle

4 BR | 3 BA | Sleeps 10 | Quick View

$279

avg/night

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Key Amenities

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

About this property

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

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Property Type

Anna Maria Island House

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Casita Marina - 11101

3 BR | 2.5 BA | Sleeps 8 | Quick View

$253

avg/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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ALECASSANDRA VACATION VILLAS, Your Family Reunion Accommodation

$313

avg/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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2203 Ave C Bradenton Beach 5-Star Townhome on Anna Maria Island

$430

avg/night

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Key Amenities

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

About this property

WHAT PRIOR GUESTS HAVE SAID ABOUT HOW WE ARE HANDLING COVID-19 RELATED RESERVATIONS:Jen and Joe were extremely cooperative with us as we canceled our May 20 beach trip. We were devastated but felt we needed to cancel in light of the COVID-19 crisis. Thank you, Jen and Joe, and we hope to rent from ...

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Property Type

Anna Maria Island Townhome

"Best vacation ever!"
Reviewed September 4, 2020

My family enjoyed an unforgettable week at Jen and Joe's property. The house is even prettier than the photos and meticulously clean. Everything, and I do mean everything that you would require is included. ...

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

$238

avg/night

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Key Amenities

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

About this property

This affordable & convenient 3 story home is one house off Holmes Beach. It has fantastic 2nd & 3rd level balcony beach views with no obstruction over the one story house in front of mine with no trees. The 3 bedroom 2.5 bath villa with 2 car garage accommodates 8 guests and is 150 feet from the ...

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Property Type

Anna Maria Island House

"Great time in August"
Reviewed August 20, 2020

This is the 3rd time we have stayed here. As always we had a great time and no rain. House was very clean and no issues. The owner has a list of expectations which is great. The owner is available if you ...

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B100 step to the sugar sand gulf front view & pool

Key Amenities

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

About this property

You’ll love it because of the views, the kitchen, the comfy bed, the coziness & the beautiful pool/jacuzzi. My place is good for couples and families (with kids). I have two units together that can accommodate up to 10 people. Recently remodeled upgraded --- modern elegant Super super clean ...

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Property Type

Anna Maria Island House

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SMUGGLER'S COVE RESORT-Private Beach Access

$129

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Smuggler’s Cove Resort is a family friendly timeshare property that offers studio and one-bedroom units. Each studio unit sleeps two with a queen-size bed or queen Murphy bed plus a full kitchen. One-bedroom units sleep four and offer a king size bed in the bedroom and a queen sleeper sofa in the ...

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Property Type

Anna Maria Island Condo

"Outstanding value and meticulous facility"
Reviewed May 25, 2020

Smugglers cove was a tremendous value we have paid a lot more for vacation rentals and received a great deal less, will book again very soon! Everyone on the staff was very professional ,friendly and just ...

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'Searenity' Stand Alone Home steps from beach!

2 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 0.0 miles to Cortez about 50 second walk

$133

avg/night

View Details

Key Amenities

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

About this property

Rest assured that before you arrive, every surface has been sanitized. You will even see a "fully sanitized" sign hanging on door knob and band in bathroom! We also provide UV air purification that eliminates Virus, mold, as well as bacteria! So important in todays world! No need to pack your ...

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Property Type

Anna Maria Island House

"Worry free vacation"
Reviewed June 9, 2020

We have booked with Mark for the past few years. His properties are in the perfect location. Less than two minute walks to the beach and a perfect view of the bay. Walking distance to shops and restaurants. ...

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AMI Waterfront Bradenton Beach Condo w Pool!

$140

avg/night

View Details

Key Amenities

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

About this property

Featuring 2 bedrooms and 2 baths, this waterfront home base comfortably accommodates up to 6 guests. Pack the sunscreen and get ready for a memorable stay with family or friends at the Gulf condo. Look forward to spending relaxing days on the beach or lounging by the community pool. Get out on the water ...

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Property Type

Anna Maria Island Condo

"Excellent"
Reviewed August 24, 2020

My family stayed at Morgan’s condo and we greatly enjoyed it! It was beautifully decorated and had everything we needed. The kitchen was stocked with pretty much anything you need to cook. We enjoyed ...

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Beach Vacation at Angelinos Sea Lodge on Anna Maria Island

1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 100 feet to Beach onsite

$156

avg/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

"Paradise on the Beach!!"
Reviewed March 6, 2020

The hosts are kind and accommodating and share their beautiful property generously! The unit was equipped with all necessary items for an enjoyable stay. The comfortable bed provided a great sleep after ...

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

$340

avg/night

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Key Amenities

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

About this property

Shady Palms is a cozy secluded beach cottage right on the beautiful Gulf of Mexico. Walk out the back door to a white, sugar-sand beach and the sparkling Gulf waters. Shady Palms is the most perfect spot you'll ever find on the beach - with the best of both worlds - the sun and the shade.Beach and ...

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Property Type

Anna Maria Island House

"Beautiful!"
Reviewed June 26, 2020

Our family of four stayed for a week in June. Cindy was a pleasure to rent from. She was so helpful and hospitable and did everything to make us feel very welcome. The house and location were perfect. You ...

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Walker Beach Cottage

2 BR | 2 BA | Sleeps 4 | Quick View

3

$148

avg/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

"Paradise"
Reviewed August 27, 2020

This beach cottage is perfect. We have been coming here for the past 6 years. The location and privacy are awesome.Just a little walk between the sea oats to the wonderful white soft beach. The sunsets ...

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Stunning Luxury Beachfront House W/Pool &Spa

$749

avg/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

"Spotless Home, Perfect Vacation"
Reviewed August 20, 2020

We had one of the best family vacations thanks to this perfect rental. The home was in BEAUTIFUL condition and the location in AMI is perfect. It was very clean upon our arrival. I am picky and can truly ...

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Crosswind Cottages

3 BR | 2.5 BA | Sleeps 8 | Quick View

$272

avg/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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307 65th Street

5 BR | 4 BA | Sleeps 10 | Quick View

3

$539

avg/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

"Pleasantly surprised"
Reviewed August 11, 2020

We rented this house for a family vacation. This house is everything you see & more. We found it to be perfectly located from beach/stores/restaurants in a quite neighborhood. The house was perfectly ...

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Southern Comfort

3 BR | 2 BA | Sleeps 6 | Quick View

$244

avg/night

View Details

Key Amenities

  • Air Conditioning
  • 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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Mermaids Landing

6 BR | 5 BA | Sleeps 12 | Quick View

2

$604

avg/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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Tropical Sunset 1

3 BR | 2 BA | Sleeps 6 | Quick View

$179

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Pool

About this property

Looking for the perfect beach destination well, it doesn't get better than this! This 2 bedroom, 2 bath condo is centrally located on Holmes Beach and is only steps from the sparkling gulf waters and white sandy beaches. There is plenty of natural lighting with the large windows in the living room, a ...

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Property Type

Anna Maria Island Apartment

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Edge of Paradise at Margaritaville

3 BR | 3 BA | Sleeps 8 | Quick View

LAST MINUTE DEAL 9/17 - 9/30: 20% off your September Stay!! Send inquiry and I will give discount in quote!

Distance to beach: 1 miles to Manatee beach

$170

avg/night

View Details

About this property

High-end resort living, endless amenities and easy access to Anna Maria Island beaches and attractions make this 1,650-square-foot condo an unbeatable home base for your warm-weather retreat! Located in the One Particular Harbor, Margaritaville Resort complex on the Anna Maria Island Sound.Head south ...

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Property Type

Anna Maria Island Condo

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DEAL
Breezy Palms

2 BR | 2 BA | Sleeps 6 | Quick View

$196

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Pet Friendly

About this property

Why stay in a condominium or hotel when you can have your own private beach house with heated pool and spa? This 2 bedroom 2 bath completely remodeled private home is located on the north end of Holmes Beach, less than a 7min walk to the white sandy beaches, close to the sought after Pine Ave, restaurants ...

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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

$330

avg/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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Emerald Bay

3 BR | 3 BA | Sleeps 6 | Quick View

$323

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Pet Friendly
  • Private Pool

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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Manna-Tee Beach House

4 BR | 2 BA | Sleeps 8 | Quick View

$244

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Private Pool

About this property

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

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Property Type

Anna Maria Island House

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Sandcastle 4

3 BR | 2 BA | Sleeps 6 | Quick View

$304

avg/night

View Details

Key Amenities

  • Air Conditioning

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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Surf Side Beach House

5 BR | 4.5 BA | Sleeps 12 | Quick View

$591

avg/night

View Details

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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Pool Party South Cottage

2 BR | 2 BA | Sleeps 6 | Quick View

$141

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Pet Friendly

About this property

OVERVIEW The Pool Party South Cottage is a beautiful duplex featuring two bedrooms and two 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, this unit is with walking distance to the white sandy ...

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Property Type

Anna Maria Island House

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Dolphin Cottage Holmes Beach

3 BR | 1.5 BA | Sleeps 6 | Quick View

2

$292

avg/night

View Details

Key Amenities

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

About this property

Availability is updated frequently. Sadly, many of our beloved snowbird regulars have canceled for 2021 due to concerns about travel, disease and unrest. Please check our calendar often.Dolphin Cottage, our 'little house' on Anna Maria Island, is a cozy, charming old-Florida home with 3 bedrooms ...

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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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Lazy Pelican

2 BR | 2 BA | Sleeps 6 | Quick View

$208

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Private Pool

About this property

Looking for a great vacation location on beautiful Holme Beach, then look no further. This newly renovated light & bright private 2 bedroom, 2 bathroom home features a great floor plan complete with brand new heated pool with spa & sun-shelf, game room, full size washer / dryer, cable TV, WiFi ...

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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

$397

avg/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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Bare Feet Retreat

3 BR | 3 BA | Sleeps 6 | Quick View

$552

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

$162

avg/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

"Incredible Condo & Owner"
Reviewed September 16, 2020

My sister and I stayed at Dan’s condo for a few weeks.The condo location was very handy to all shops & grocery stores.The condo was excellent in enough space, amenities & relaxing view, the ...

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225 Bradenton Beach Club

3 BR | 2 BA | Sleeps 8 | Quick View

$228

avg/night

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Key Amenities

  • Air Conditioning
  • 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 convinces you would want in an island stay. This beautiful townhouse sleeps up to eight people with 2 1/2 bathrooms, full laundry, elevator, garage, and large private, screened ...

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Property Type

Anna Maria Island Villa

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Gone Coastal 3 Beautiful Family and Pet Friendly Home

$277

avg/night

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Key Amenities

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

About this property

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

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Property Type

Anna Maria Island House

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The Pink Chicken ! Updated Beach House 2 Blocks to Beach w/ Private Pool!

$241

avg/night

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Key Amenities

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

About this property

Please note we offer SEVERAL GORGEOUS VACATION RENTALS on Anna Maria Island. Listed below is one of our options. Contact us or visit our website at beachboutiquerentals . com to see all the homes ranging from 1-4 bedrooms throughout the island.Welcome to the Pink Chicken! A beautifully updated and ...

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Property Type

Anna Maria Island House

"Perfect location"
Reviewed October 9, 2019

Julie was great to work with and responded very promptly to questions. The property was exactly as presented. The property was clean and inviting. Everyone in our party loved it. Additional information ...

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Shell House- Seconds to the beach! Clean, cozy, & spacious

$281

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

Less than a minute walk to the beach!Watch the sunset from the house!Shell House is a two-story, 3-bed, 2-bath, multi-level fun-house on a large shady lot in a quiet residential neighborhood only two blocks from popular shopping & dining.Two king beds and one queen in the three bedrooms ...

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Property Type

Anna Maria Island House

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Casa Amiga

4 BR | 4 BA | Sleeps 10 | Quick View

$589

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Fall Special - Work from the Sunshine state! Pay for 3 weeks, get the 4th week FREE!! call for info 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 ...

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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

$222

avg/night

View Details

Key Amenities

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

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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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!