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Vacation Rentals & Beach Rentals in Anna Maria Island

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2,041 beach rentals

ISLAND TOWNHOUSE - 200 Steps to the BEACH

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 4

“Even better than you can imagine!” We are so thrilled to have discovered this gem. Barb really has thought of everything you need for a perfect vacation - short or long stay. Quaint boutique shops, excellent dining - one of the best "Lobstah" dinners ever, and a beautiful beach with all the comforts of home - literally right around the corner.

Responds fast! avg. 42 minutes

Price per night from

$180

Anna Maria The Pink Flamingo

Holmes Beach cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 38 minutes

Price per night from

$218

2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!

Bradenton Beach cottage

3 bedrooms / 2 bathrooms / sleeps 8

“Perfect Beach House” We loved the quaint little duplex. The house was clean and ready for us when we arrived. Tim was a dream to work with. The A/C one of the units went out while we were there, and he had someone there first thing to take care of it. We will definitely be looking to rent from Tim again in the future.

Price per night from

$119

Spectacular Beach House With GulfView Only Steps to a Pristine Beach

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$687

Affordable Anna Maria Vacation - close to everything

Holmes Beach house

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 29 minutes

Price per night from

$92

Chic on the Beach Unit B

Holmes Beach villa

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$355

Direct Beachfront 2 BR Condo on Florida’S Beautiful Gulf Coast!

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

“A trip to paradise.” From the breathtaking views of both the Gulf and the Bay to the wonderful, eclectic furnishings, this condo is everything one could hope for. It has great amenities for entertaining friends and every convenience you will need. The heated pool overlooks the Gulf and allows direct access to the beach and the elevator provides ease in getting up to the condo. This vacation was the most enjoyable I've ever experienced.

Responds fast! avg. 3 hours 53 minutes

Price per night from

$384

BAY FRONT HOUSE WITH PRIVATE DOCK

Bradenton Beach house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 13 minutes

Price per night from

$287

"Sea Story" A two bedroom cottage minutes walking to beach.

Bradenton Beach cottage

2 bedrooms / 1 bathroom / sleeps 4

“Lovely cottage with great location” Our time at Sea Stories was memorable. We enjoyed the location for the beach and the restaurants. The cottage was adorable with everything we needed. Wendy was so helpful in solving a problem we had with sleeping arrangements for three girls. We will come back to Anna Maria Island with Sea Stories in mind. Thank you Wendy for all your help!

Price per night from

$327

AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$172

Great Townhouse Very Close to the Beach, Shops, and Restaurants

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

“Famous Holiday” Everything was so perfekt ... WE CAME back next Year THE HOUSE BEAUTIFUL AND CLEAN.. THE Area perfekt

Price per night from

$263

Endless vacation in beautiful house with heated swimming pool

Bradenton Beach house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$264

Family Reunion Villa on Anna Maria Island, Florida

Bradenton Beach villa

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$458

Lifestyle on the island

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$144

Anthony Beach Cottages Gulfview Condo

Bradenton Beach house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$258

Dream Lover Boat & Breakfast on Anna Maria Island

Bradenton Beach yacht

2 bedrooms / 2 bathrooms / sleeps 4

“Celebrate Birthdays & 24th Anniversary” We had a wonderful time on the Dream Lover this weekend. It was a special way to celebrate our birthdays and 24th Wedding Anniversary. We spent early mornings up on deck. The breakfasts were amazing! Love the area - so easy to walk to many restaurants, stores, and the beach. Kay and Jonathan are a wonderful couple wit such a positive and healthy outlook on life. They are a joy to spend time with. Oh and Skipper too!!! I was a wonderful weekend. Sue & Jim Hughes

Price per night from

$304

Gorgeous views,spectacular home!

Anna Maria house

5 bedrooms / 3 bathrooms / sleeps 12

“Majestic Views” Our family loved our visit to Anna Maria. The house is gorgeous and spacious. My kids enjoyed the pool and eating outside. We hope to return in the near future.

Responds fast! avg. 2 hours 9 minutes

Price per night from

$573

The Villas 2B

Holmes Beach house

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 41 minutes

Price per night from

$187

Beautiful 3 bed/2 bath Condo with an amazing view of the Gulf of Mexico with a p

Bradenton Beach apartment

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 59 minutes

Price per night from

$215

Anna Maria Island Retreat

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$149

If this isn't your view, you need to change your latitude ! Toes in the sand bea

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 59 minutes

Price per night from

$224

Runaway Bay unit 192 bay view 2bed/2Bath - Bradenton Beach - Anna Maria Island

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 4 minutes

Price per night from

$188

Enjoy a Romantic Vacation in a Special Condo right on Bradenton Beach for the pe

Holmes Beach apartment

1 bedroom / 2 bathrooms / sleeps 2

Responds fast! avg. 59 minutes

Price per night from

$194

Beach Dreams "DreamBoat Villa"

Bradenton Beach apartment

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$338

The Anna Maria Island Beach Retreat

Holmes Beach apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$92

Sandy Pointe #205

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$134

Beachfront view, toes in the sand and gulf. Simply paradise, book now your beach

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 59 minutes

Price per night from

$224

Anna Maria Island Beach View 209

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$297

Anna Maria Island--Two Month Min.--Gorgeous!

Holmes Beach apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$103

GULF COAST DESTINATION

Bradenton Beach condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 6 minutes

Price per night from

$144

Anna Maria Island Beach View 207

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$226

Steps to beach and bay on beautiful Anna Maria Island

Bradenton Beach apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$61

It's my Dream - private heated pool, 2 minute walk to the beach! Pet friendly

Holmes Beach apartment

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 14 minutes

Price per night from

$242

Beach Dreams "Tangerine Dreams Villa "

Bradenton Beach cottage

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$229

The Anna Maria Island Beach Castaway 2

Holmes Beach apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$142

Anna Maria Island, 2 Bed, 2 Bath Condo in quiet setting near to Beaches

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

“Great Value Stay in Paradise aMI!” This is a lovely spacious condo, nicely furnished, with decent wifi, aircon and all mod cons. The condos in the Sandy Point complex all share a pool and we found this to be very clean, nicely warm and never too crowded. Although it's on the quieter side of the island we liked the location - it's a five minute walk from Publix, even less to the free Island Trolley Bus, and less than 10 minutes to the beach for those amazing sunsets :-) The equipment cupboard allowing us to borrow beach chairs, swimming noodles, buckets and spades etc was much appreciated. Having looked around at other rentals we found this condo to be very keenly priced. Andrew and Jo were very pleasant and easy to deal with and we will definitely stay again some day.

Price per night from

$133

3902 GULF DRIVE 2

Holmes Beach apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 41 minutes

Price per night from

$221

Coastal Paradise! 5 mi to beaches! Heated Pool! Sleep up to 14

Bradenton Beach house

4 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 6 minutes

Price per night from

$984

Viewing 38 of 2,041
rentals in Anna Maria Island

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About Anna Maria Island

Just south of Tampa Bay on the turquoise Gulf of Mexico, sits a quaint Barrier Island located on Florida's West Coast. Lined by a seven-mile strip of beautiful white-sand beaches, Anna Maria Island is a cozy paradise that has long been considered one of the state's hidden gems. Here, "Old Florida" charm abounds and visitors can get a feel for Florida, the way it used to be.

With seven miles of uninterrupted beach, Anna Maria Island offers plenty of opportunities to enjoy fun in the sun and explore. The island shares its beach life with local wildlife. Turtles visit from May - November every year (nest tours are offered in the summer) and year round visitors shouldn't be surprised to see manatees, dolphins, rays and exotic fish beyond the waves.

In addition to its picturesque beaches, Anna Maria Island is home to many award-winning dining options, including bistros, cafes and restaurants (there are no chain restaurants to be found). The island has been recognized nationally for its locally sourced food, unique menu items and on-the-water locations offering top views. Diners can expect gourmet dining options offering cuisine from England, France, Germany, Italy, Asia and Spain, as well as "Floribbean" dishes and seafood delicacies straight from the nearby sea. Top seafood choices include: grouper, red snapper, mullet and blue crab. Visitors are even invited to bring their catch into some of the area's top restaurants, like the Sandbar and Beachhouse.

For guests looking for fun off the sand as well, there are many art galleries, museums or aquariums in the area. And, the island is surrounded by nature parks and gorgeous naturally landscaped paths worth exploring.

Anna Maria Island also offers many top options for shopping at its many souvenir, jewelry, clothing and antique stores. Pine Avenue (known as the Greenest Little Main Street in America) is lined by great stylish boutiques and specialty shops and leads directly on to the 100 year old Anna Maria City Pier which offers picturesque views of the bay. Holmes Beach offers seven blocks of stores, small unique gift shops, adorable café's, art galleries and a grocery store. Additionally, stores on the newly restored Bridge Street in Bradenton Beach offers an unusual blend of arts and crafts unique to the island, reflecting its Bohemian roots.

Anna Maria Island also boasts a wide variety of accommodations ranging from historic bed and breakfasts, to beach-side cottages, cozy luxury homes, as well as condo rentals and spacious villas, which are all locally owned and operated and offer a unique experience. Tall sky-rise and commercial buildings do not exist on Anna Maria Island, with most accommodations measuring at less than three stories.

Additionally, the island is becoming a top choice for beach destination weddings. So much so that many are referring to the setting as the "Beach Wedding Capital of Florida". Forbes named Anna Maria Island the "#3 Prettiest City in the Country" in 2013 and was a "TripAdvisor Traveler's Choice Destination Winner 2013 and 2014" and #3 of the top 10 islands in the US to go to in 2014.

Information provided by: Bradenton Area Convention and Visitor's Bureau

Top Destination reviews

Sandy Pointe #205
Holmes Beach Vacation

Nice, clean condo. Great location near to beach, shopping, and restaurants. Loved the outside patio. … see more
RUNAWAY BAY #230 - 2 BED/2 BATH CONDO - STEPS TO BRADENTON BEACH ON ANNA MARIA
Excellent condo for family just steps away from pool and beach!!

Super clean condo with everything that you need for a great vacation! Chairs, umbrella and anything you would need for a beach day. Great view of pond and pool area. Owner checked in and super quick to respond if you have questions. Would definitely stay here again! … see more
3A Villa's on Anna Maria Island
Perfection

Villa 3A was absolutely perfect. The owner was very responsive from the time we booked and through out our stay. Very clean and was the perfect set up for everything we needed. There was a view of the Ocean out the bedroom window!! We will be back again to stay at 3A. … see more
Affordable Anna Maria Vacation - close to everything
Great place, Right Price

We stayed here for a last minute family vacation. The place was well equipped for us to just sit back, relax and do what we like to do. Centrally located and near the boat launch we were able to take advantage of bikes to get just about everywhere. The interior was comfortable and our favorite part was the spacious back yard area where we could leave paddle boards and fishing equipment. It truly was a great value for a week's stay. Budget minded renters will get a great deal here.see more
Sand Castle well appointed home steps from beaches
Great times

Absolutely loved the house. Spent most days out by the pool. Very private. Practically everything needed was supplied except groceries. I plan on coming back next year. I give this place 5 stars … see more
Anna Maria Island Beach Sands 203
Nice Place to Stay

Close to everything, condo was very nice, busy street to cross but easy if you take charge & many drivers will stop for you if you are more timid. Nice views of the gulf & bay as well. … see more

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