Search 105,200+ Vacation Rentals

Anna Maria Island Vacation Rentals & Beach Rentals - 232 Rentals Available

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

232 Vacation rentals

(4)

1 / 26

Bradenton Beach Apartment

  • 1
  • 6
  • min stay varies
  • Air conditioning

$265.00

Excellent (4 reviews)

Book

from $265.00 / night

(1)

1 / 33

Anna Maria Island Villa

  • 2
  • 3
  • min stay varies
  • Child friendly

Responds fast! Avg. 3 hours 20 minutes

$175.00

Excellent (1 reviews)

Book

from $175.00 / night

1 / 24

Holmes Beach House

  • 4
  • 10
  • 4 nights min
  • Nearest beach 0.01 mi
  • Swimming pool
  • Child friendly

$750.00

Inquire

from $750.00 / night

(3)

1 / 33

Bradenton Beach Cottage

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
“My husband and I spent the weekend in this cottage to celebrate his milestone birthday. We found it to be very comfortable and welcoming. I especially love the sunroom for my morning coffee and yoga. We were pleasantly surprised at how comfortable...”
- Review left on 11/23/2017

$150.00

Very Good (3 reviews)

Book

from $150.00 / night

(1)

1 / 49

Holmes Beach House

  • 6
  • 12
  • min stay varies
  • Nearest beach 0.01 mi
  • Swimming pool
  • Child friendly

$599.00

Excellent (1 reviews)

Inquire

from $599.00 / night

1 / 20

Bradenton Beach Condo

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$329.00

Book

from $329.00 / night

(29)

1 / 87

Bradenton Beach Condo

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“It was a great experience. The condo was close to perfect. It was a great spot close to the beach and many restuarants and shops. The Island was perfect with free trolly service and very clean roads and ammenities. The Ocean views and the white...”
- Review left on 06/05/2016

$160.00

Very Good (29 reviews)

Book

from $160.00 / night

1 / 33

Bradenton Beach House

  • 6
  • 14
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$399.00

Inquire

from $399.00 / night

1 / 8

Anna Maria Island Apartment

  • 2
  • 6
  • min stay varies
  • Child friendly
  • Air conditioning

$220.00

Book

from $220.00 / night

1 / 70

Anna Maria Island Condo

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

$200.00

Book

from $200.00 / night

1 / 19

Holmes Beach House

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$259.00

Inquire

from $259.00 / night

(1)

1 / 31

Anna Maria Island Cottage

  • 1
  • 3
  • min stay varies
  • Beach/lakeside relaxation

$195.00

Excellent (1 reviews)

Book

from $195.00 / night

(1)

1 / 21

Anna Maria House

  • 3
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

Responds fast! Avg. 1 hour 21 minutes

$501.00

Excellent (1 reviews)

Book

from $501.00 / night

1 / 24

Holmes Beach House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$700.00

Inquire

from $700.00 / night

1 / 34

Bradenton Beach Condo

  • 2
  • 6
  • min stay varies
  • Child friendly

$150.00

Book

from $150.00 / night

(1)

1 / 8

Anna Maria Island Condo

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$150.00

Excellent (1 reviews)

Book

from $150.00 / night

(23)

1 / 29

Anna Maria House

  • 4
  • 8
  • 28 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

Responds fast! Avg. 1 hour 43 minutes

“Whether you are a couple or three families under one roof, the layout of this home fits the bill. Three eating areas, three gathering areas plus the pool area is amazing. Newer homes on the island have five bedrooms....great...right but there is...”
- Review left on 06/25/2015

$175.00

Very Good (23 reviews)

Book

from $175.00 / night

(15)

1 / 26

Anna Maria Island House

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 12 minutes

“Gorgeous, beautiful home away from home. This home has everything you and your family will need. The granite kitchen is fully equipped and beautiful. I was able to make a full Thanksgiving dinner with everything that was supplied in the home! Our...”
- Review left on 11/30/2016

$450.00

Excellent (15 reviews)

Book

from $450.00 / night

(9)

1 / 100

Anna Maria Island Condo

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Hidden Oasis is a lovely property - nicely decorated, very clean, very well-kept, and equipped with pretty much everything you might need or want. It also has a fantastic view of the gulf and the beach; and this view is visible from the living room...”
- Review left on 03/16/2017

$200.00

Excellent (9 reviews)

Book

from $200.00 / night

1 / 53

Holmes Beach House

  • 6
  • 14
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$499.00

Inquire

from $499.00 / night

(5)

1 / 93

Anna Maria Island House

  • 4
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“We enjoyed our stay at this property. The home is well decorated and all rooms are very spacious. The master bedroom is enormous with jacuzzi and large walk-in shower. The other bedrooms are very spacious too. Our manager resolved a few minor...”
- Review left on 08/10/2016

$360.00

Excellent (5 reviews)

Book

from $360.00 / night

1 / 19

Bradenton Beach Cottage

  • 1
  • 3
  • min stay varies
  • Car not necessary
  • Air conditioning

Responds fast! Avg. 3 hours 20 minutes

$175.00

Book

from $175.00 / night

1 / 34

Holmes Beach House

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$251.00

Inquire

from $251.00 / night

(2)

1 / 20

Holmes Beach Townhouse

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“We enjoyed this house. It was just a short walk to the beach. It was the perfect size for our family of four. The decorations were very pretty and beachy! The pool and outside landscaping was gorgeous! It came supplied with a beach wagon which was a...”
- Review left on 04/21/2016

$225.00

Excellent (2 reviews)

Inquire

from $225.00 / night

(5)

1 / 92

Anna Maria Island Condo

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“The unit was well equipped with a good kitchen and lots of seating. TV's where great. We have two kids so we needed a place that could work for at home cooking as well. The location was perfect for us. The balcony was a perfect place for having a...”
- Review left on 01/05/2016

$157.00

Very Good (5 reviews)

Book

from $157.00 / night

(23)

1 / 23

Anna Maria Island Cottage

  • 2
  • 5
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden

Responds fast! Avg. 2 hours 25 minutes

“Songbird is a little slice of heaven with everything we needed to have a comfortable stay. We stayed for one week. Joel, the owner, is very thoughtful, and accommodating, and he makes it known that he is there for you if you need him. Which is so...”
- Review left on 05/20/2017

$120.00

Excellent (23 reviews)

Book

from $120.00 / night

1 / 45

Anna Maria Island Condo

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$172.00

Book

from $172.00 / night

(21)

1 / 11

Holmes Beach Townhouse

  • 2
  • 6
  • 7 nights min
  • Nearest beach 0.05 mi
  • Swimming pool
  • Child friendly
“This was my family's first visit to Anna Maria Island and it won't be our last. We loved the beaches, restaurants, and amazing sunsets. The Gulf View Townhouse was clean and centrally located, and it was an added bonus to have a pool on the...”
- Review left on 07/19/2016

$150.00

Very Good (21 reviews)

Book

from $150.00 / night

(8)

1 / 84

Anna Maria Island Condo

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
“Impeccable beach house! All the amenities one would want. Great Weber gas grill, (almost) private pool, brand new kitchen, brand new front loader washer/dryer (free). Cross the street and you're on the public beach, or drive 10 min north or south...”
- Review left on 11/23/2016

$157.00

Excellent (8 reviews)

Book

from $157.00 / night

(2)

1 / 19

Holmes Beach House

  • 5
  • 12
  • min stay varies
  • Nearest beach 0.02 mi
  • Swimming pool
  • Child friendly

$501.00

Excellent (2 reviews)

Inquire

from $501.00 / night

(2)

1 / 36

Bradenton Beach Cottage

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$150.00

Excellent (2 reviews)

Book

from $150.00 / night

(1)

1 / 78

Anna Maria Island Condo

  • 1
  • 3
  • 6 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“As this was my first time to Anna Maria I was pleasantly surprised how very nice it is. My accommodations were above what I expected. The location is perfect for going to the beach, shopping, dining, or just relaxing by the pool. I enjoyed my stay so...”
- Review left on 03/10/2015

$120.00

Excellent (1 reviews)

Book

from $120.00 / night

1 / 48

Anna Maria Island House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$130.00

Book

from $130.00 / night

1 / 14

Bradenton Beach Townhouse

  • 2
  • 6
  • min stay varies
  • Ask about children
  • Air conditioning

$220.00

Book

from $220.00 / night

(2)

1 / 25

Holmes Beach Townhouse

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$259.00

Excellent (2 reviews)

Inquire

from $259.00 / night

1 / 14

Anna Maria House

  • 2
  • 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

Responds fast! Avg. 1 hour 21 minutes

$501.00

Book

from $501.00 / night

1 / 51

Anna Maria Apartment

  • 5
  • 12
  • 4 nights min
  • Child friendly

$799.00

Inquire

from $799.00 / night

(3)

1 / 25

Anna Maria Island Condo

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“We had a wonderful week at the tropical sunset condo I count the days to go back with my husband and two little kids (4.5 & 1.5) We loved everything in this condo and the beach was so beautiful! We saw Manatees at the road and reel Pier and Dolphins...”
- Review left on 05/24/2016

$143.00

Excellent (3 reviews)

Inquire

from $143.00 / night

1 / 79

Bradenton Beach Condo

  • 2
  • 6
  • min stay varies
  • Child friendly

$150.00

Book

from $150.00 / night

1 / 19

Holmes Beach Townhouse

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$199.00

Inquire

from $199.00 / night

About Anna Maria Island

Laidback and oozing “old Florida” charm, Anna Maria Island is a slice of paradise located on Florida’s famous Gulf Coast. With picturesque beaches known around the world for their beautiful white sand and waters of the clearest turquoise blue, it’s not hard to relax and unwind while on this island in the Gulf of Mexico.
Only seven miles long, the island is divided into three cities: Holmes Beach, Bradenton Beach, and Anna Maria. This gives vacationers plenty of choices when it comes to choosing what to do and where to stay while visiting. An Anna Maria Island vacation rental right on the beach is the perfect option as home base since chain restaurants are pleasantly absent and the area remains untainted by numerous high rise buildings.

Climate

The average year-round temperature in Anna Maria Island is a comfortable 75 degrees making it an ideal destination to visit during any month. In the winter, the skies are cloudless and temperatures range from 75 degrees during the daytime to 50 degrees overnight. Trade winds influence the spring months with sunny, dry days that reach up to 90 degrees. Hot summer temperatures mixed with gentle breezes and cooling rains give way to glorious weather throughout late fall.

Transit

The best way to tour this intimate seven-mile island is by hopping aboard the Anna Maria Island Trolley. It runs north to south from the Anna Maria City Pier to Coquina Beach stopping every few blocks for riders to hop on and off. The best part about it is that it is completely free to riders and offers the perfect opportunity for a burst of refreshing air conditioning on the way to the next activity. Parking can be scarce throughout the island, so the trolley is both a scenic ride and a necessity.

Attractions

Part of Anna Maria Island’s charm is its well-preserved natural beauty. The Anna Maria Island Butterfly Park is a perfect place to see butterflies and plants local to the area. Similarly, the island’s scenic shoreline is an attraction in itself. For people who love to visit the beach and soak up sun, Anna Maria Island has several gorgeous beaches to enjoy.

·       Bean Point is at the very northern tip of the island and is a local secret offering stunning views of the sunset from its pristine and tranquil beach.
·       Manatee Beach is a large public beach with lifeguards on duty and ample beach space for undisturbed bliss.
·       Cortez Beach has calm waters and light surf and is a family-oriented destination. Although no lifeguards are on duty here, it’s one of the best beaches on Anna Maria Island.

The local museums and art galleries are popular attractions as well and great alternatives to outdoor activities. After a morning spent relaxing in an Anna Maria Island vacation rental, people can spend a fun 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. Other indoor attractions include The Studio, where exhibits, workshops and lectures are held, as well as Bradenton’s Village of the Arts where artists live and work.

Shopping & Dining

Anna Maria Island offers a variety of shopping options ranging from eclectic seaside shops to popular outlets. Pine Avenue, “the greenest little main street in America,” is lined with boutiques leading up to the City Pier, and Holmes Beach has blocks of shops filled with adorable keepsakes. Mixed in amongst the folksy storefronts is an array of award-winning dining options as well. Whether you’re looking for a grouper sandwich at a casual beachside joint, or a romantic waterfront experience, Anna Maria Island has many options to choose from. With tables in the sand, the Sandbar is always a good choice for a quintessential island meal.

Events

When planning a trip to Anna Maria Island, make arrangements to stay in a vacation rental during one of the city’s awesome annual events. Anna Maria Island 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. In March, Island CityFest features a kids’ zone, arts, crafts and more. Later in Spring, the Bridge Street Merchants host the Blues, Brews & BBQ event for locals and visitors to enjoy. Outdoor Market Sundays take place November through April, and Winterfest in December wraps up the year’s festivities. On Anna Maria Island, fun events happen year-round, so there will always be something to do.

Free from commercialism and where shoes are optional, Anna Maria Island is a premier beach destination that visitors flock to year-round. Book a vacation rental to live the laidback lifestyle of a true Anna Maria Islander and fully experience the island’s Floridian charm. The beaches are beckoning!
Read More