Popular Cottages in Anna Maria Island

Cottage for 5 people, with pool and hot tub, with pets in Anna Maria Island
Cottage for 5 people, with pool and hot tub, with pets
2 bedrooms200yd to the beach
5.0
(20 reviews)
from $571 / night
Cottage for 2 people, with ocean view in Anna Maria Island
Cottage for 2 people, with ocean view
1 bedroom30yd to the beach
5.0
(20 reviews)
from $232 / night
Cottage for 6 people, with yard and pool in Anna Maria Island
Cottage for 6 people, with yard and pool
3 bedrooms90yd to the beach
4.6
(20 reviews)
from $237 / night
Cottage for 2 people, with yard in Anna Maria Island
Cottage for 2 people, with yard
1 bedroom100yd to the beach
3.3
(17 reviews)
from $132 / nightFREE cancellation
Cottage for 4 people, with pets in Anna Maria Island
Cottage for 4 people, with pets
2 bedrooms60yd to the beach
4.5
(20 reviews)
from $202 / night
Cottage for 6 people in Anna Maria Island
Cottage for 6 people
2 bedrooms350yd to the beach
5.0
(20 reviews)
from $188 / night
Cottage for 2 people, with pool in Anna Maria Island
Cottage for 2 people, with pool
1 bedroom200yd to the beach
4.7
(17 reviews)
from $163 / night
Cottage for 4 people, with pool in Anna Maria Island
Cottage for 4 people, with pool
1 bedroom150yd to the beach
4.8
(20 reviews)
from $219 / night
Cottage for 5 people, with ocean view and balcony in Anna Maria Island
Cottage for 5 people, with ocean view and balcony
1 bedroom20yd to the beach
4.8
(20 reviews)
from $467 / night
Cottage for 5 people, with balcony and ocean view in Anna Maria Island
Cottage for 5 people, with balcony and ocean view
2 bedrooms60yd to the beach
4.8
(20 reviews)
from $208 / night
Cottage for 5 people, with yard in Anna Maria Island
Cottage for 5 people, with yard
2 bedrooms100yd to the beach
3.8
(15 reviews)
from $131 / nightFREE cancellation
Cottage for 4 people, with pool in Anna Maria Island
Cottage for 4 people, with pool
2 bedrooms100yd to the beach
4.8
(21 reviews)
from $217 / night
Cottage for 4 people, with yard, with pets in Anna Maria Island
Cottage for 4 people, with yard, with pets
2 bedrooms400yd to the beach
5.0
(20 reviews)
from $309 / night
Cottage for 2 people in Anna Maria Island
Cottage for 2 people
1 bedroom150yd to the beach
4.8
(40 reviews)
from $207 / night
Cottage for 6 people, with pool in Anna Maria Island
Cottage for 6 people, with pool
2 bedrooms100yd to the beach
4.7
(22 reviews)
from $195 / night
Cottage for 4 people in Anna Maria Island
Cottage for 4 people
1 bedroom300yd to the beach
4.6
(19 reviews)
from $192 / night
Cottage for 4 people in Anna Maria Island
Cottage for 4 people
1 bedroom200yd to the beach
4.6
(20 reviews)
from $218 / night
Cottage for 6 people in Anna Maria Island
Cottage for 6 people
2 bedrooms0.6mi to the beach
4.8
(20 reviews)
from $221 / night
Cottage for 8 people, with yard and pool in Anna Maria Island
Cottage for 8 people, with yard and pool
4 bedrooms150yd to the beach
4.9
(20 reviews)
from $676 / night
Cottage for 4 people, with yard in Anna Maria Island
Cottage for 4 people, with yard
2 bedrooms150yd to the beach
4.9
(20 reviews)
from $396 / night
Cottage for 4 people, with ocean view in Anna Maria Island
Cottage for 4 people, with ocean view
1 bedroom30yd to the beach
5.0
(20 reviews)
from $226 / night
Cottage for 4 people in Anna Maria Island
Cottage for 4 people
1 bedroom50yd to the beach
4.6
(20 reviews)
from $197 / night
Cottage for 5 people, with ocean view in Anna Maria Island
Cottage for 5 people, with ocean view
2 bedrooms100yd to the beach
4.3
(20 reviews)
from $323 / night
Cottage for 6 people, with balcony in Anna Maria Island
Cottage for 6 people, with balcony
2 bedrooms200yd to the beach
5.0
(17 reviews)
from $201 / night
Cottage for 6 people, with pool in Anna Maria Island
Cottage for 6 people, with pool
3 bedrooms90yd to the beach
4.7
(20 reviews)
from $397 / night
Cottage for 4 people in Anna Maria Island
Cottage for 4 people
1 bedroom350yd to the beach
5.0
(20 reviews)
from $267 / night
Cottage for 4 people, with pool, with pets in Anna Maria Island
Cottage for 4 people, with pool, with pets
1 bedroom250yd to the beach
4.9
(15 reviews)
from $286 / night
Cottage for 5 people, with pool, with pets in Anna Maria Island
Cottage for 5 people, with pool, with pets
2 bedrooms150yd to the beach
5.0
(12 reviews)
from $277 / night

Find Cottages in Anna Maria Island

Highlights in Anna Maria Island

  • Gulf of Mexico adventure
  • Florida beach cottage
  • Romantic couples getaway
  • winter sun getaway
  • Paradise island retreat

Best Cottages in Anna Maria Island

Guests agree: these stays are highly rated for location, cleanliness, and more.
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Holmes Beach, Anna Maria Island
Cottage • 441 ft² • 1 Bedroom
5.0
(20 reviews)
Our five unit property was featured in the January/February 2020 issue of Southern Living, and we are honored and thrilled! Welcome to our Cottage! If you are looking for a simple, quiet, stress-free place to enjoy the beach, this is it. It's not a fancy condo-- no long hallways, distant parking, elevators, or crowds-- and there are no streets to cross to reach the beach. The Cottage is a duplex, and this listing is for the larger side. VRBO #327896 will show you the smaller side. The two sides share a screened porch facing the beach. The cottage was constructed in 1916 or so, as a caretake...
from $226 / night
more...
Bradenton Beach, Anna Maria Island
Cottage • 5 Guests • 2 Bedrooms
3.8
(15 reviews)
Welcome to Cottage Haven! This charming cottage located in Bradenton Beach is a very short walk to the beautiful white sand beaches. Featuring its own private backyard you can sit back and unwind on one of the loungers as you enjoy a home-cooked meal from the propane grill. The ground level home is nicely decorated and exudes a sunny, quaint “Old Florida” atmosphere. The cottage offers a fully equipped kitchen and full sized washer/dryer. There are two queen bedrooms with televisions and 2 full baths, 1 with shower/tub combo and 1 with a walk-in shower.A day bed which sleeps 2 is nestled in...
from $131 / night
more...
Bradenton Beach, Anna Maria Island
Cottage • 2 Guests • 1 Bedroom
3.3
(17 reviews)
Welcome to Cottage Lighthouse! An addendum to our cancellation policy: If the governor of Florida issues a Florida travel ban you will receive a refund. Additionally, every reservation is offered two different trip insurance policies. One:) cancel for thirty different reasons and receive a full refund (cost 7% of the gross rental amount). Two:) cancel for any reason, no questions asked and receive a 60% refund (cost 10.8% of the gross booking amount).This beautiful and charming holiday home located in Bradenton Beach is a short walk to the beautiful white sands of the Gulf of Mexico. This q...
from $132 / night

Beach Houses in Anna Maria Island

Stunning cottages located on the island of Anna Maria

Escape to a breezy, Gulf of Mexico paradise island location where lanky palms sway in the warm sunshine and turquoise ocean sparkles next to immaculate white beach sand. Combine this with a quintessentially charming beach town vibe, sorbet shades of wood build architecture and miles of beach cruiser biking and you have the perfect oceanside oasis to escape to! This sliver of 7 mile long, 8 city block wide, barrier island beach destination is located on Florida’s stunning Gulf Coast within easy driving distance from Tampa. This idyllic, upmarket island destination with miles of soft sand beaches and breathtaking views is a place you will never want to leave!

Perfect paradise island destination for everyone

These immaculate, breezy, fully equipped, comfortable, spacious, beautifully decorated cottages are perfectly situated close to some of the most stunning beaches you will ever see and have everything you need for the perfect paradise island stay. Anna Maria island is an ideal destination for newlyweds! Many of these cottages are perfect for a romantic Gulf of Mexico getaway for two while others have plenty of space for a family of up to 6. Sparkling private pools are available at many of these lovely beach cottages as well as stunning outdoor terraces with ocean views for relaxing with an ice cold beverage or for enjoying a sunset meal.

Travelers and activities

Anna Maria island for beach lovers

Travel no further than Florida’s Gulf Coast for an authentic, tropical Eden, island experience. With year round sunshine and 7 miles of breathtaking beaches and wonderful local amenities in an upmarket setting, where there are no chain restaurants or highrises, there are plenty of reasons to put Anna Maria Island on your bucket list of fabulous destinations. Your cottage is just a short hop from a pale sand beach and an endless expanse of aquamarine ocean. The water is warm and inviting for swimming and you can spend languid days here truly unwinding and getting away from it all!

Anna Maria Island for water sport enthusiasts

Watersport lovers are in for days of fun with the incredible variety of options for enjoying being in the water. There are several, conveniently situated rental companies on the island that specialize in water sport equipment rentals of all types. Try an hourly jet ski rental for a wild aquatic thrill! There are miles of ocean for parasailing, kayaking, swimming or surfing. Surfers will find the best location for surfing on the island at White Avenue beach access in the town of Anna Maria. Join a local dive charter for a deep sea dive adventure exploring a famous offshore wreck or try snorkeling or spearfishing. Book a charter boat cruise and watch dolphins leap and frolic at sunset!

Did you know, locals lovingly refer to Anna Maria Island as “AMI” or “The Island”

Top 7 travel tips in Anna Maria Island

1.Explore the island by bike

Anna Maria Island has several high quality bike rental shops dotted around the island where you will find your perfect vacation bike for glorious, leisurely biking. Most of the rentals are located on or near the beachfront for easy access and the island is a haven for cyclists with its impeccable cycling infrastructure. If you decide to stop off for a delectable meal en route you will find convenient, free bike racks all over the place to stow your bike safely. You can ride the entire length of the island via the wide bike paths along the main central avenue, perfect for beach hopping! Cycle to southernmost Coquina Beach to see dolphins playing in the water!

2. Have a Kayaking Adventure

Head 10 miles west across the strait to the mainland via Manatee Avenue the spectacular 600 acre Robinson Preserve is waiting to be discovered. Kayak Rentals are available from nearby Surferbus to make the most of this salt marsh aquatic oasis. There are beautiful, pristine kayak and canoe waterways as well as sublime picnic spots and gorgeous, lush, primal mangrove forests to enjoy with a 53 foot observation tower located in the center of the Preserve for a magnificent panoramic view of the entire Tampa Bay. Pack a picnic and head to this secluded, peaceful waterpark for a day of kayaking to remember!

3. Take a trip to Tampa

Head off early from your paradise island and drive to Tampa for the day. This sleek, coastal city situated on the sweeping arc of Tampa Bay with it’s glittering skyscrapers and impressive waterfront is a playground for museums and theme park attractions, shopping, restaurants and nightlife. The Tampa Museum of Art, Tampa Bay History Center and the Glazers Children’s Museum are top rated attractions and world class museum venues that will enthrall the whole family with awe inspiring exhibits. Families will love a trip to Busch Gardens larger than life theme park that features thrilling roller coasters and adventure rides and spectacular ice skating shows. Tampa Zoo is ranked amongst the top 25 zoos in the USA!

4. Shop and dine on historic Bridge Street

Spend a lazy, few hours meandering about on this picturesque, historical street. This is Anna Maria Island’s most iconic destination for shopping, dining and entertainment. Hop on board the free, all day trolley a stone’s throw from your island cottage rental and hop off in this gorgeous part of town. Browse and buy beautifully unique, local, handmade artisan items and explore novelty shops selling high end gifts, art and beachwear. Florida palm trees, sea breeze, sorbet colors and aquamarine ocean combine here for the ultimate island beach vibe. Enjoy fresh oysters, surf and turf, live music and incredible seafood when you start to get hungry!

5. Island hop to Longboat Key and Lido Key

Make the most of your time in this paradise location and island hop to Longboat Key located South of Anna Maria Island. Head south via Gulf drive over Longboat Pass Bridge. Lido Key is south of Longboat Key via John Ringling Parkway. The beaches on these two barrier islands are stunning and you will never want to leave the shimmering soft sand and warm aqua waters of this Gulf of Mexico coastal resort. The sunsets over the Gulf of Mexico are spectacular from here. North Lido beach is a fantastic location for bird watching due to the numbers of birds that nest here.

6. Play golf at the fabled Longboat Key Resort Golf Course

Longboat Key golf course has been highly rated and commended over time as one of the finest places to play golf in the USA. This Gulf Coast golfing oasis is the winner of prestigious Golf Digest awards. This beautiful course features an unparalleled view of Sarasota Bay and you could not find a more perfect oceanside setting than this to play your favorite game. There are big greens, verdant natural areas and stunning water features on this magnificent 45 hole, exciting championship golf course.

7. Visit Perico Preserve

This idyllic spot located just 2.7 miles to the west in Bradenton is a scenic, serene marshland nature preserve with a selection of trails and plenty of opportunity for birdwatching. The beautiful walking trail loops around ponds and tidal areas where you can view incredible native plants, see fish and get close to a wide range of stunning native birds such as ospreys, herons, ducks, eagles and pelicans. This magnificently transformed 175 acre former farmland has been regenerated and now boasts coastal wetlands and scrub hills that provide vital breeding ground for gorgeous native birds to flourish.

FAQs: Cottages in Anna Maria Island

Which types of facilities can you expect to find at the cottages on Anna Maria Island?

Among the facilities available on Holidu, it appears that the cottages on Anna Maria Island offer everything that vacationers wish for! Here, the cottages generally have a variety of amenities, the most popular being: air-conditioning (100%), internet (100%), and barbecue (67%)...Are you convinced yet?

How do travelers usually rate cottages on Anna Maria Island?

On average, the cottages are rather well rated. According to the Holidu database, 33% of cottages have a rating average of 4.5 stars. This is a quite high percentage which allows us to confirm that there are quite a few that are very comfortable and will be the perfect choice for your next vacation.

Are the cottages on Anna Maria Island child-friendly?

According to the Holidu data, 50% of cottages on Anna Maria Island are suitable for vacations with children, so you won't face any issues in finding the perfect cottage for you and your family.

Are the cottages on Anna Maria Island suitable for travelers and their furry friends?

Definitely! On Anna Maria Island, 67% of the cottages offer the possibility for travelers to take their pets with them, 33% also have a garden!

Do the cottages on Anna Maria Island tend to come with an internet connection?

Of course! According to Holidu, 100% of cottages on Anna Maria Island have Wi-Fi. This means that you will be able to access your emails and favorite social media sites at any time!

Do the cottages on Anna Maria Island generally come equipped with a pool?

Certainly! According to Holidu's data, 67% of cottages on Anna Maria Island are equipped with a pool. It is the perfect destination for spending hot summer days by the pool! 67% even have a barbecue!

Are the cottages on Anna Maria Island suitable for stays with the whole family or rather for a vacation as a couple?

According to Holidu, 83% of cottages are perfect for families with up to four people. Approximately 50% of the cottages here include at least two separate bedrooms. This is the ideal destination for families of four!

Are Cottages in Anna Maria Island the best option for a luxurious trip?

Some cottages are, but others aren't as luxurious. So if you are looking for that special accommodation, don't delay in making a reservation because only 67% have a pool, while 100% have air conditioning none have a sauna. However, if it's space you're looking for, 83% of the cottages can accommodate four or more adults, and 33% have a garden.

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