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Vacation Rentals & Beach Rentals in Anna Maria Island

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Vacation Rentals & Beach Rentals in Anna Maria Island

About Anna Maria Island

3,033 beach rentals

Dolphin Shores Beachfront directly on Gulf of Mexico

Holmes Beach condo

3 bedrooms / 2 bathrooms / sleeps 4

“The perfect rental for a memorable vacation on the beach...” Marilyn maintains high standards for her rental: meticulously well kept and clean, warm cozy atmosphere, well stocked modern kitchen and bathrooms, and large lanai. Location right on Holmes Beach means long walks on the white sand beach and beautiful sunsets. What I liked best was being able to walk to stores, restaurants, and the local library. Take it from someone who traveled extensively, Marilyn's beach front property is the perfect place for someone who wants a relaxing vacation in a beautiful area. There's also lots to see and do if you are willing to travel a few miles to the high end shopping areas and museums.

Responds fast! avg. 1 hour 15 minutes

Price per night from

$208

1 / 44

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!

Responds fast! avg. 3 hours 17 minutes

Price per night from

$129

1 / 14

Gulf Beach Place - September Special Rates

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

“Fantastic Vacation” Just came back from our family vacation with my sons, daughter, and grandchildren. It was just fantastic! The condo was very comfortable, spacious, and nicely kept. Perfectly equipped for vacationers (coffee maker, kitchenware, extra linens, air mattress, beach towels, etc) just a three minute walk to Publix Supermarket, Walgreens and many more shops). We enjoyed the sunset on the rooftop, the heated pool, and my favorite part about it was that the beach is literally right in your backyard!! Minutes away from renting jet skis, boating, fishing, parasailing, etc. You may be lucky enough (like we were) to see a family of manatees cruise in front of us at the shoreline. What a show! To make a long story short, nobody wanted to leave. Guess we are coming back!!!!!!

Responds fast! avg. 1 hour 27 minutes

Price per night from

$100

1 / 21

Midnightchannel

Anna Maria Island house

7 bedrooms / 5 bathrooms / sleeps 16

Price per night from

$497

1 / 48

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.

Price per night from

$125

1 / 17

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

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 43 minutes

Price per night from

$192

1 / 25

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 51 minutes

Price per night from

$125

1 / 18

Stay & Spoil yourself! Pool, Hot tub,Fish, Dock, Kayak* Steps to Gulfside beach!

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 8

“Fanta-bulous!” My third visit to Beach Nest and I never want to leave! Love my daily walks on the beach and falling asleep to the sounds of waves. Just discovered fishing and kayaking. I can do both at the same time off the dock in my backyard. Easy access to a free trolley that rumbles up and down the island makes exploring boutiques easy for my wife. The kids are addicted to Dips ice-cream after dinner. Thanks to the owners for making each visit more comfortable and enjoyable than the visit before!

Responds fast! avg. 2 hours 22 minutes

Price per night from

$355

1 / 23

private pool/spa beach gear

Holmes Beach townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$298

1 / 34

NEW LISTING! Oceanfront house with great views, easy beach access, and free WiFi

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 43 minutes

Price per night from

$202

1 / 34

Coconuts Beach Front 112 Upstairs

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 55 minutes

Price per night from

$199

1 / 14

Sea Breeze Retreat (Holmes Beach)

Holmes Beach townhouse

2 bedrooms / 2 bathrooms / sleeps 5

“Great beachside condo, bring your boat!” Cute condo within a short walking distance to a beautiful sandy beach. The location is great, there are restaurants and shops within walking distance. Anna Maria Pier and Rod & Reel Pier a short drive away. This condo is an end unit and has a very nice back yard and plenty of room to the side of the house for you to bring your boat. This area has a gate and is private. The condo is very comfortable with good internet and TV. The owner Tina is wonderful and is quick to answer your questions. We will be coming back.

Price per night from

$179

1 / 24

NEW LISTING! Breezy condo w/shared pool -minutes from beach & dining

Bradenton Beach house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 43 minutes

Price per night from

$68

1 / 37

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

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 43 minutes

Price per night from

$136

1 / 29

Holmes Beach Condo

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

“Ideal accomodation” I've been traveling from New York to anna Maria Island for nine years and anne's Holmes beach condo is tops. The perfect location.Right next to the perfect beach with great food and surrounded by fine dining and superb shopping. Anne was marvelous to deal with, very pleasant and her place is just what the doctor ordered. Clean, quiet, peacefull, and private. Also its just steps to the beach with a fantastic view from sun up to sunset !! Just like at home with everything we needed from the kitchen to the beach. Next year we will stay with anne!! And the weather was perfect this time of year. Benny & Marge Oliveri

Price per night from

$125

1 / 12

The beautiful Cove on Anna Maria Island

Holmes Beach apartment

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

$103

1 / 29

Coconuts Beach Front 105 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 55 minutes

Price per night from

$199

1 / 19

Gulf Beach Place, miles of whites sandy beach

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 48 minutes

Price per night from

$149

1 / 8

Coconuts Beach Front 107 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 55 minutes

Price per night from

$199

1 / 18

Coconuts Beach Front 109 Upstairs

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 55 minutes

Price per night from

$155

1 / 20

Condo In Paradise On Anna Maria Island

Bradenton Beach apartment

2 bedrooms / 1 bathroom / sleeps 4

“Fantastic” Our stay was wonderful, the condo was in great shape, everything was clean. Larry has a beach umbrella, chairs, a cooler, and other items to use at the beach, which was right across the street. We truly enjoyed our stay! Thank you!

Responds fast! avg. 2 hours 9 minutes

Price per night from

$149

1 / 17

742 Jacaranda Rd

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$186

1 / 30

CHARMING 2 Bed 2 Bath with Heated PRIVATE HEATED Pool SPA Sleeps 6 F

Holmes Beach townhouse

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$148

1 / 26

Stylish, cozy duplex with shared pool & easy beach access - free WiFi!

Holmes Beach house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 43 minutes

Price per night from

$122

1 / 35

NEW! Holmes Beach Home w/ Pool - Steps to Beach!

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 44 minutes

Price per night from

$257

1 / 29

Coconuts Beach Front 106 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 55 minutes

Price per night from

$199

1 / 17

Fully Remodeled Vacation Rental Anna Maria Island

Holmes Beach apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 31 minutes

Price per night from

$110

1 / 15

Luxury 3BR/3BA, Private Heated Pool, Beach

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 8

“Christmas at the Beach” It was a wonderful family vacation for two families going away for Christmas! There were 4 adults and 6 children! The pool was amazing and the house was perfect! Anna Maria Island is gorgeous and the house is in a perfect location for the beach, food and shopping! The owners were available for any needs that needed to be met! Awesome Owners!

Responds fast! avg. 1 hour 45 minutes

Price per night from

$204

1 / 34

Steps to Beach, Gulf View, Footprints in the Sand

Bradenton Beach apartment

2 bedrooms / 1 bathroom / sleeps 4

“Won't wait so long to visit paradise again!” My husband and I hadn't taken a vacation in years and decided to visit Florida and baseball Spring Training this March. Footprints in the Sand was the perfect home to our perfect destination. Mayra was great to work with, responded quickly to all inquiries and kept in touch each step of the way. The condo was clean and had everything you possibly could want on a trip to an island. Many restaurants/bars were within walking distance. You felt very safe on the island. The restaurants were all great but we particularly liked the Sandbar and BeachHouse as far as food quality and atmosphere to catch anna Maria's trademark beautiful sunsets. Attractions in Bradenton and Sarasota are also an easy drive away. Thanks, Mayra, we had a great time and hope to visit again in the future!

Responds fast! avg. 1 hour 41 minutes

Price per night from

$128

1 / 42

116 Maple Breeze

Anna Maria house

4 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$229

1 / 24

Coconuts Beach Front 110 Upstairs

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 55 minutes

Price per night from

$199

1 / 20

Light-filled home w/ screened balcony - one block to the beach, small dogs OK!

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 43 minutes

Price per night from

$122

1 / 24

Spacious and bright home w/ heated private pool, one block to white sand beach!

Holmes Beach house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 43 minutes

Price per night from

$299

1 / 44

Gorgeous views,spectacular home!

Anna Maria house

5 bedrooms / 3 bathrooms / sleeps 12

“Can't wait to go back” Our extended family had a great time staying in this house. The only downside was absolutely unrelated to the house itself, but it was unseasonably cold for Florida. Nothing that kept us from the beach and enjoying ourselves, but a bit colder than usual. As for the house, there was no downside. It is large and comfortable. The living area is large and the rooms are big as well (unlike other 5 bedroom properties we have stayed at in the past). The views from the decks are the best. Good pool area private and sheltered from the wind, heated as well. The location is ideal. We parked and only used the car once, walking and riding bikes everywhere. So much is within walking distance. I saw that a pool table was just added. We didn't have it and had a great time, but it's a wonderful addition.

Responds fast! avg. 3 hours 9 minutes

Price per night from

$397

1 / 46

Coconuts Tahitian 207

Holmes Beach apartment

1 bedroom / 2 bathrooms / sleeps 2

“Great beach location!” This is a wonderful location for a little beach cottage! Plenty of space, walking distance to not only the beach, but restaurants, the local trolly stops, the list goes on! Cleanliness of the cottage was a little disappointing. When we first arrived, most of the rugs still had dust and dirt on them and you could tell they had not been touched or swept. There was still hair in the sink and it had not been wiped down or cleaned. Other than that, the place was perfect for our little weekend beach getaway!

Responds fast! avg. 2 hours 55 minutes

Price per night from

$130

1 / 13

Gulf / Sunset Views!!! Apt. D,1BR is a Centrally Located, walk to all location!

Bradenton Beach villa

1 bedroom / 1 bathroom / sleeps 3

“Great” Conveniently located right across from the beach. Very clean and up to date. The most complete set of amenaties I've ever seen in a rental. It's like they stayed at the Ritz and made a list. From a rolling cart for transporting your stuff to the beach to kitchen utensils I didn't know what to do with. The owner here really knows what he or she is doing.

Responds fast! avg. 2 hours 54 minutes

Price per night from

$94

1 / 26

Ocean View 3 bedroom, pool, North Shore Drive

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

“Fantastic family holiday on anna Maria Island” I always say I'm going to write a review but never do. However, I didn't want to let the opportunity pass this time to rave a bit about this rental. We've stayed in plenty of places over the years but seldom come across one that is so well maintained and well stocked. The only issue we had was with the pool heater. We called about it Saturday afternoon and it was resolved the following morning ... on a Sunday! We stayed here comfortable with 4 adults, a toddler and a baby. There was plenty of room for everyone and having two full bathrooms was perfect. There was a wide selection of (3D) movies as well. The beach is a quick walk across a quite street and along a path. Though I took advantage of one of the bikes provided to do some shopping, it was certainly possible to walk it as well. There's a street with shops, ice cream store, homemade donuts shop, restaurants and a general store close-by with the pier at the end. We would definitely stay here again and recommend it to friends.

Responds fast! avg. 49 minutes

Price per night from

$107

1 / 123

Coconuts Beach Front 108 Ground floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

“Great” Great location! Beautiful view. The condo was was spacious enough for a small group. The beds were a little harder than I would like but the location of the condo and view were great.

Responds fast! avg. 3 hours 17 minutes

Price per night from

$198

1 / 19
Viewing 38 of 3,033

About Anna Maria Island

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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

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