Vacation Rentals & Beach Rentals in Anna Maria Island

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2,608 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. 1 hour 2 minutes

Price per night from

$130

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

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

“Beautiful condo, close to everything!” Everything was perfect in the condo which was new and updated! The 2 new full size beds in the 2nd bedroom were too hard. The pool was a nice size and stayed sunny most of the day. Shopping was close and the city beach also was close. We would drive down the road to our favorite stretch of the beach. I would definitely stay here again, very quiet location off the beaten path, but not far from it! Love the beach chairs, towels, cooler, umbrella, pool toys, and more provided!

Price per night from

$121

Gulf Beach Place - Just a few steps from the Beach

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful, friendly Beach Condo” Beautiful Condo right on the beach with awesome sunsets from the roof and a Dunkin Donuts within walking distance. While the teen/young adult slept in, I visited DD and walked the beach. The owner had a manual that provided lots of activities around the area and places to eat. We enjoyed our stay and would definitely visit again!

Responds fast! avg. 1 hour 49 minutes

Price per night from

$180

runaway bay 2 bedroom condo with wonderful access to restaurant, beach, shopping

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$172

Ocean View 3 bedroom, pool, North Shore Drive

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

“Amazing Oceanview Pool Home and Perfect Location On Anna Maria Island” Let me first say that Mark (the home owner) exceeded any and all expectations for our 15th wedding Anniversary! We booked last minute and when we wanted to stay an additional day Mark rescheduled planned maintenance in order to accommodate us. When we arrived there were fresh flowers, wine, cookies, music and a Anniversary Cake for us! The Beautiful ocean view pool home is in a perfect location on Anna Maria Island and equipped with everything you will need: floats for the pool, anything you would need to take to beach across the street, bikes to explore the island, a large kitchen stocked with everything you need to cook, very comfortable beds and spacious rooms, fresh orchids throughout the home, library of DVD's and books, and I could just keep going...make sure you take the bikes and explore - go to the Museum, to bean point, have fresh grouper sandwich at the Rod and Reel Pier, ride down to Two Scoops for an ice cream and take a walk on the City Pier, on Fridays at 12:30 you can pick up amazing fresh bread at Olive Oil Outpost with some other goodies, go have a custom snack at the Donut Experiment, A drink at the Sandbar Rest., Lunch or Dinner at the Waterfront is amazing, and more all a short bike ride away. All my wife and I can say is what a wonderful week and we will be back for sure!

Responds fast! avg. 7 minutes

Price per night from

$375

Dolphin Shores Beachfront directly on Gulf of Mexico

Holmes Beach condo

3 bedrooms / 2 bathrooms / sleeps 4

“This condo and beach are the the best of the best, great set up,awesome vacation spot!” This was our second year staying here and we absolutely love it! The beach is clean and not crowded at all even on a holiday weekend. The weather is excellent and so much to do on the island. We rented a paddle board for the week, which was delivered and picked up for us! So nice! This is a true vacation but also like being at home...less expensive than a hotel and you can cook meals for a lot less than going out all the time. It's nice to be able to do a load of laundry if you need to. It's nice to not have to bring towels, beach chairs and umbrella, it's already there! The view from the lanai is spectacular, we spent a lot of time out there, we ate our meals there,played cards, watched sunsets. Bedrooms are so comfortable ,bathrooms are spacious,TV in every room, books to read, just so convient and relaxing.

Responds fast! avg. 35 minutes

Price per night from

$221

Cozy Cabana West - Private Pool - Close to Beach

Holmes Beach villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 24 minutes

Price per night from

$195

Spacious house w/ private yard & great location near the beach - dogs ok!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 2 minutes

Price per night from

$166

AMI Bradenton Beach Ground Condo

Bradenton Beach condo

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$144

BAY FRONT HOUSE WITH PRIVATE DOCK

Bradenton Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 27 minutes

Price per night from

$201

Canalfront home w/ pool, dock & lanai - 2 blocks to the beach!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 2 minutes

Price per night from

$258

Island House - Funboard

Holmes Beach condo

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$94

Charming cottage less than a block from the beach! free trolley trolley nearby!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 2 minutes

Price per night from

$176

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

Ohana Hale North 2 Bedroom on Anna Maria

Holmes Beach house

2 bedrooms / 1 bathroom / sleeps 6

“Home is very comfortable and we really enjoyed our stay” Home is very comfortable. Loved the kitchen and owners could not be more accomadating.

Responds fast! avg. 1 hour 56 minutes

Price per night from

$178

Oceanfront dog-friendly home w/private pool & ocean view - right on the beach!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 48 minutes

Price per night from

$788

Steps to Beach, Gulf View, Footprints in the Sand

Bradenton Beach apartment

2 bedrooms / 1 bathroom / sleeps 4

“Footprints in the sand” We had a great time on Anna Maria Island. Footprints in the sand,its closeness to the beaches,restaurants and shops made it very convenient.The place was well stocked with all basic needs & amenities that were listed. Thanks (Note) 1. We were a little annoyed at times from the noise that came from upstairs tenant when their child would run and jump and bang their toys or something on the floor. 2. Bed sheet was clean but stained 3. Toilet leaks sometimes near base We thank you for the use of your place and I'm sure you will find things in good order. Thanks Carlos & Maria Diaz

Price per night from

$147

Dog-friendly cottage w/ private heated pool - minutes from beaches & more!

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 48 minutes

Price per night from

$565

Bright and cheery waterfront home with private pool and spa

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 2 minutes

Price per night from

$356

Beachfront Paradise w/ Private Beach, Dogs Stay Free, Beach in Backyard

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 32 minutes

Price per night from

$228

Waterfront and dog-friendly home with private pool, dock, views, and lanai!

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 2 minutes

Price per night from

$264

742 Jacaranda Rd

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$213

Coconuts Tahitian 205

Holmes Beach apartment

1 bedroom / 2 bathrooms / sleeps 4

“60th birthday” This rental was exactly what we were told and was a perfect location. Slept three perfectly. Beds were very comfy and anything you needed was available. Thinking of renting for month next year!

Price per night from

$149

'Seascape' PEACEFUL, Newly renovated, steps to beach & fishing dock on bay

Bradenton Beach condo

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 58 minutes

Price per night from

$194

250 feet from the beach

Bradenton Beach townhouse

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$123

Breezy canalfront home w/ pool & dock - 3 blocks to Bean Point Beach!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 2 minutes

Price per night from

$282

Ohana Hale Seaside 2 Bedroom

Anna Maria Island condo

2 bedrooms / 1 bathroom / sleeps 6

“Great Visit to AMI” I've stayed in two of Danny and Brenda's properties and both have been great. The properties are alway clean and in great condition. The location to the beach is perfect and the pool Is very nice. Looking forward to our next visit.

Responds fast! avg. 1 hour 56 minutes

Price per night from

$178

Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 2 minutes

Price per night from

$202

Dolphin Pointe

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 21 minutes

Price per night from

$295

On the Beach Paradise d

Holmes Beach cottage

2 bedrooms / 1 bathroom / sleeps 6

“Absolutely beautiful!” Everything was perfect. Enjoyed coffee on the beach every morning and beautiful sunsets every evening. Can't wait to go back next year!

Responds fast! avg. 2 hours 19 minutes

Price per night from

$206

Beautiful, well-maintained home w/private pool - walk to beach, dining, & more!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 2 minutes

Price per night from

$313

NEW LISTING! Great condo w/shared pool & access to beach, shopping & dining

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 11 minutes

Price per night from

$177

Charming house with private heated pool, patio, and grill - steps from beach

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 2 minutes

Price per night from

$257

Dog-friendly condo w/ beautiful upstairs deck and grill, steps from the beach

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 2 minutes

Price per night from

$185

Dog-friendly house with private pool, island views & nearby beach access!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 2 minutes

Price per night from

$188

AMI Island Living -Walk to Beach-Ground Level Unit

Bradenton Beach apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$172

Blue Bayou

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

“"Home from Home"” A very well appointed apartment in a great location that had everything you would wish for to enhance your vacation experience. A real home from home that is clean, well furnished and spacious. The owners have been great to deal with and nothing is too much trouble. I have already recommended this accommodation to friends who were similarly impressed and we will be staying here for the third time later this year.

Price per night from

$144

Ohana Hale South West Suite

Bradenton Beach house

2 bedrooms / 1 bathroom / sleeps 6

“Great place for a family Stay” We stayed for 5 days in June. Very clean and comfortble close to the beach and quiet. Excellent experience. We left some items there and they were even shipped to us promptly.

Responds fast! avg. 1 hour 56 minutes

Price per night from

$178

Viewing 38 of 2,608
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

Beachfront Paradise w/ Private Beach, Dogs Stay Free, Beach in Backyard
Wonderful place for relaxation

Incredible location with it's own private beach. Great laid back part of the island. Lots to do if you want to, or just relax and take in the natural beauty of the gulf. Accomodations for large family or group of friends. Plenty of parking. Comfortable beds and furniture. Clean house. Very nice owners and permit pets to be a part of the fun. Recommend to anyone looking for a vacation Anna Maria island. Short walk to the island public beaches too if that's what someone is looking for.see more
Dog-friendly duplex with two separate spaces, private pool, blocks to the beach!
Amazing layout with the a attached sections. Could separate those with different bedtimes!

Quick walk to the beach and a great area for entertaining downstairs. The kitchens were very well stocked with different types of equipment. The mosquitoes were a little bit of a bummer. … see more
Salt Air & Sea Oats- 809 North Bay Blvd, Anna Maria
Great place

Had a great week at AMI in the location. It was extremely spacious and accommodating. Just a few steps from the beach (although the beach wasn’t the best in the island) the house was great. Fran Maxon Real estate were great as well. … see more
Island House - Funboard
Florida Vacation

The Funboard location on Gulf Drive was perfect. Close to the beach and shopping. All walking distance. Will try and get same location for future trips to Florida. … see more
Dolphin Pointe
Great house!

The house was perfect; great open living room and kitchen and the pool was so fun. The location was great; close to the beach and lots of things to do. … see more
Cozy Cabana West - Private Pool - Close to Beach
Very well done with great location

Having stayed at this rental before it was always a great place to stay. It has since been updated and refreshed. Pool was great, location is a plus. … see more

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