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Anna Maria Vacation Rentals

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  2. United States of America
  3. Florida
  4. Anna Maria

Our Favorite Vacation Rentals in Anna Maria

  • PassAGrille Anheiser Busch Resort Captain
     2br Home/Apartment
    RedAwning
    From
    $1,230
  • 19 Palms AMI
     Country House
    Booking.com
    From
    $248
  • Dream Lover Boat & Breakfast on Anna Maria Island
    Excellent2br Boat
    HolidayLettings
    From
    $335
  • Pass-A-Grille Anheiser Busch Resort Boat House
     2br Home/Apartment
    RedAwning
    From
    $1,232
  • Tides Inn on the Bay (units 1-3)
     Country House
    Booking.com
    From
    $250
  • Beach Escape with Heated Pool - Sleeps 20
     3br Home/Apartment
    HolidayLettings
    From
    $1,566
  • PassAGrille Anheiser Busch Resort Bay&Captain
     8br Home/Apartment
    RedAwning
    From
    $3,885
  • The Spurge Mansion - Sleeps 20
     5br Country House
    HolidayLettings
    From
    $2,000
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Check prices for these upcoming dates

Anna Maria Vacation Rentals with a Pool

  • PassAGrille Anheiser Busch Resort Captain&Boat
     4br Home/Apartment
    RedAwning
    From
    $2,355
  • Pass-A-Grille Anheiser Busch Resort Bay House
     6br Home/Apartment
    RedAwning
    From
    $2,345
  • Pass-A-Grille Anheiser Busch Resort Bay&Boat
     8br Home/Apartment
    RedAwning
    From
    $3,898
  • Pass-A-Grille Boutique/Anheiser Busch Resort
     10br Home/Apartment
    RedAwning
    From
    $5,466
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Anna Maria Vacation Rentals with Wi-Fi

  • Vibrant Beach Getaway - Built like a Tropical Island - Sleeps 12
     3br Home/Apartment
    Airbnb
    From
    $1,259
  • Tropical Beach House - 2 mins to Anna Maria Beach - Sleeps 6
     2br Home/Apartment
    Airbnb
    From
    $878
  • Sunset Inn Holmes Beach Unit 2
    NiceHome/Apartment
    Airbnb
    From
    $266
  • Luxury Beach Getaway - 6 minutes to the Beach - Sleeps 10
     3br Home/Apartment
    Airbnb
    From
    $1,033
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Anna Maria Pet-Friendly Vacation Rentals

  • Luxury Spacious Home - Perfect Location in Bradenton - Sleep 16
     5br Home/Apartment
    Airbnb
    From
    $1,056
  • Tiny House Paradise - Pool & Spa, Lanai + Beaches
    Excellent2br Home/Apartment
    Airbnb
    From
    $262
  • Stunning Waterviews Beach Escape - Sleeps 8
     3br Home/Apartment
    Airbnb
    From
    $1,259
  • Tropical Beach Getaway - Heated Pool & Fire Pit - Sleeps 18
     4br Home/Apartment
    Airbnb
    From
    $1,104
Show all

Anna Maria Travel Guide

Dreaming of white sand beaches? Anna Maria, Florida is the perfect location for a long weekend getaway. The city of Anna Maria is only 40 miles south of Tampa Bay, and seven miles west of Bradenton beach. This dreamy beach town will take your breath away with its beautiful beach, charming beachfront rental homes, and many things to do and see.

Because Anna Maria is on the gulf coast, the Gulf of Mexico makes the sea a beautiful tinted blue and very warm. This lovely island has it all; a stunning pier, bay walk, colorful beach houses, museums and plenty of beaches to soak in the sun. Because Anna Maria Island vacation rentals have became so popular in the past years, vacation home real estate has skyrocketed -- many people even build houses for the purpose of vacation rentals now.

Things to Do in Anna Maria

The various beaches here are the most popular choices of course, such as the Coquina Beach and the Holmes Beach. White sand, blue water and lots of sunshine are not the only things visitors can enjoy to the fullest at Anna Maria. The top things to do include the Coquina Baywalk, galleries such as the Island Gallery West where many paintings are on display, and the Anna Maria Island Historical Museum which includes plenty of information of the island, such as the sadly destroyed Pier which was ripped apart by a hurricane.

The Pine Avenue is one of the best streets in Anna Maria, which also means it is one of the busiest. The street connects Holmes Beach and the now-destroyed Anna Maria City Pier. There are many little restaurants and coffee shops to enjoy, a community garden, and an Olive Oil Outpost where farmers display their finest oils, vinegars, honey and many more artisan products. For family-friendly fun, visit the Mote Marine Laboratory and Aquarium. Visitors can learn about marine life and the importance of oceans. Many fish, crabs and even sharks can be seen here, and some attractions include touch tanks to discover even more about these wonderful creatures.

Best Places to Stay in Anna Maria

For the most amazing and fun vacation, rent out beach houses and condos. There are plenty of places to stay, great options for families, couples and friends as well. The downtown area of Anna Maria is busier, so if you prefer quiet nights make sure to avoid those locations. Gorgeous beachfront properties are very popular but these accommodations tend to sell out fast, so when you see something you like do not hesitate to book it.

Best Time to Visit Anna Maria

Due to its great location, Anna Maria is always warmer than 60 degrees, and particularly hot in the summer months. October is probably the best month to visit because the weather is very nice with a lot of sunshine, the average temperature above 75 degrees, and not too much rain.

During summer months and in September there is heavy rainfall. So if you prefer dry and sunny weather, June to September is not your best bet for a weekend getaway at Anna Maria.

Food in Anna Maria

There are plenty of great places to check out in Anna Maria! Lots of seafood and Italian restaurants, and if you have a sweet tooth you will not be disappointed. Cute donut shops and dessert bars await visitors. Walk down to the beach and have a nice refreshing drink at one of the seaside restaurants. Many places offer great selections for children as well, so the whole family can tuck into a meal together.

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Price and Availability in Anna Maria

Most expensive
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The cheapest day to stay at a vacation rental in Anna Maria tends to be Tuesday, while the most expensive day tends to be Saturday. Vacation homes in Anna Maria tend to be busiest on Fridays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Anna Maria is in March, while the cheapest month is in November. The most popular time to book a vacation rental in Anna Maria is in the high season in March. Anna Maria has its low season in September, when less people are visiting and the vacation home occupancy rate drops.
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The Weather in Anna Maria

Rainy days
87° 46°
2
86° 45°
1
94° 56°
2
97° 67°
2
99° 73°
6
94° 71°
14
96° 72°
13
96° 69°
2
94° 71°
3
91° 51°
1
84° 48°
3
84° 40°
3
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Rainy days

This climate histogram shows you the weather patterns in Anna Maria. The warmest months in Anna Maria are July and August, when temperatures reach 99 ˚F. The coolest month is December, when temperatures drop to 40 ˚F. The wettest month in Anna Maria is June with 13.92 inches of rain, while the driest month is February with 0.53 inches of rain.

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What Expert Travelers Think

  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum
    Visit Tammymum

  • — When I first opened up the AllTheRooms.com site, I was impressed right away... When I’m traveling, I don’t like to waste time searching multiple engines for accommodations, it gets overwhelming and frustrating fast. I want a unique, comfortable stay for the best deal

    Kaelin
    KaelinKindly Kae
    Visit Kindly Kae

  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad
    Middle Class Dad

Vacation Rentals in Anna Maria

Pick the perfect vacation rental for your trip at AllTheRooms.com. We aggregate Airbnb, RedAwning, Priceline and many more. Anna Maria has 2,750 hotels, vacation rentals and other special places to stay, with prices to suit budget travelers, luxury travelers and everything in between. When traveling on a budget, the cheapest place to stay in Anna Maria is available at $84 per night. On average, a place to stay in Anna Maria will cost you $460 per night.

If you want to stay connected during your trip, then you can choose from over 475 accommodations in Anna Maria that have WiFi. 5 of our accommodations include a breakfast in the price. You can maintain your workout regime by staying at one of 19 accommodations that provide gym facilities. Driving to Anna Maria? Then choose one of the 436 places to stay that comes with a parking spot included. We have 335 places to stay that have a pool or jacuzzi.

AllTheRooms has 144 pet-friendly places to stay in Anna Maria, so if you're traveling with your cat or dog you won't have any problems.

We compare vacation rentals, hotels and other bespoke accommodation types from many providers in Anna Maria, including 430 places to stay from Airbnb, 35 accommodations from RedAwning and 16 places to stay from Priceline

1,162 of our accommodations in Anna Maria have been reviewed and rated. 44% are rated great. You can instantly book any of 1,198 places to stay right now.

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