Anna Maria Vacation Rentals

Our Favorite Vacation Rentals in Anna Maria

  • Bridge Villa 1 Bradenton Beach
     Country House
    RedAwning
    From
    $176
  • Emerald Seas
     Country House
    Booking.com
    From
    $690
  • Beach Dreams "Tangerine Dreams Villa "
     Cottage
    Flipkey
    From
    $250
  • Holiday Island 2BR w/ Pool, Hot Tub, Tennis & Dock
     2br Home/Apartment
    RedAwning
    From
    $362
  • Heron Hideaway
     Home/Apartment
    Booking.com
    From
    $178
  • "Sea Story" A two bedroom cottage minutes walking to beach.
    Excellent2br Cottage
    Flipkey
    From
    $317
  • Pass-A-Grille St Pete Beach Bungalow 105-1 By Tech Travel
     2br Home/Apartment
    RedAwning
    From
    $400
  • Sun Villa - Steps to Beaches - Family Retreat
     Villa
    Booking.com
    From
    $119

Check prices for these upcoming dates

Anna Maria Vacation Rentals with a Pool

  • Historic Pass-A-Grille Beach Club Gulf Way 701-5 By Tech Travel
     2br Home/Apartment
    RedAwning
    From
    $450
  • Sea Club I
    Good24br Home/Apartment
    Booking.com
    From
    $186
  • Luxury Beach Cottage for Families
    Excellent3br Home/Apartment
    Airbnb
    From
    $605
  • Beautiful Beach Paradise - Walk to the beach - Heated Pool
     3br Home/Apartment
    Airbnb
    From
    $1,192

Anna Maria Vacation Rentals with Wi-Fi

  • Historic Pass-A-Grille Beach Studio 3110 By Tech Travel
     Cottage
    RedAwning
    From
    $197
  • St Pete Beach House Catty Corner to Don Cesar By Tech Travel
     3br Home/Apartment
    RedAwning
    From
    $404
  • Bridge Villa 5 Bradenton Beach
     Country House
    RedAwning
    From
    $243
  • Bridge Villa 4 Bradenton Beach
     Country House
    RedAwning
    From
    $229

Anna Maria Pet-Friendly Vacation Rentals

  • NEW! Canalfront Bradenton Home w/ Dock & Pool!
     3br Home/Apartment
    HolidayLettings
    From
    $384
  • Dog-friendly, renovated home w/ outdoor pool, patio and screened lanai
     3br Home/Apartment
    HolidayLettings
    From
    $322
  • Bradenton House w/Screened Lanai & Private Pool!
     4br Home/Apartment
    HolidayLettings
    From
    $347
  • Paradise Retreat -- Need We Say More
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $233

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.

Price and Availability in Anna Maria

Most expensive
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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.

The Weather in Anna Maria

Rainy days
94 º72
6
92 º54
1
89 º44
2
85 º42
8
80 º30
3
80 º30
3
80 º30
3
89 º52
3
92 º61
7
94 º70
4
93 º69
8
95 º71
5
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Anna Maria. The hottest month in Anna Maria is May, when temperatures peak at 95 ˚F. The coolest month is October, when temperatures drop to 30 ˚F. The wettest month in Anna Maria is January with 8.1 inches of rain, while the driest month is March with 1.1 inches of rain.

What Expert Travelers Think

  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen
  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE
  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston

Destinations near Anna Maria

  • Kissimmee133,451 Properties
  • Davenport54,599 Properties
  • Panama City Beach32,189 Properties
  • Champions Gate20,289 Properties
  • Destin16,763 Properties
  • Orlando14,510 Properties
  • Miramar Beach13,211 Properties
  • Fort Myers Beach12,987 Properties
  • Siesta Key8,858 Properties
  • St. Augustine8,336 Properties
  • Marco Island7,877 Properties
  • Hollywood7,871 Properties
  • Holmes Beach7,740 Properties
  • Cape Coral7,488 Properties
  • Clermont6,944 Properties
  • New Smyrna Beach6,159 Properties
  • Sanibel5,999 Properties
  • Santa Rosa Beach5,948 Properties
  • Sunny Isles Beach5,947 Properties
  • Miami Beach5,876 Properties
  • Celebration5,641 Properties
  • Haines City5,415 Properties
  • Naples4,884 Properties
  • Bradenton Beach4,804 Properties
  • Miami4,508 Properties
  • Madeira Beach4,419 Properties
  • Bonita Springs4,396 Properties
  • Daytona Beach4,315 Properties
  • Key West4,311 Properties
  • Pompano Beach3,547 Properties
  • Pensacola Beach3,449 Properties
  • Indian Shores3,359 Properties
  • Fort Walton Beach3,319 Properties
  • Treasure Island3,309 Properties
  • Bradenton3,285 Properties
  • Fort Myers3,047 Properties
  • Sarasota2,968 Properties
  • Indian Rocks Beach2,854 Properties
  • St. Pete Beach2,843 Properties
  • Palm Coast2,825 Properties
  • Daytona Beach Shores2,767 Properties
  • Hallandale Beach2,611 Properties
  • St. Augustine Beach2,460 Properties
  • Tallahassee2,317 Properties
  • Tampa2,311 Properties
  • Fort Lauderdale2,201 Properties
  • Marathon2,067 Properties
  • Key Largo1,950 Properties
  • Longboat Key1,918 Properties
  • Cocoa Beach1,917 Properties
  • Captiva1,768 Properties
  • Gainesville1,727 Properties
  • Ormond Beach1,726 Properties
  • Pensacola1,634 Properties
  • Englewood1,623 Properties
  • Clearwater Beach1,585 Properties
  • Venice1,579 Properties
  • The Villages1,561 Properties
  • Placida1,544 Properties
  • Delray Beach1,507 Properties
  • Key Colony Beach1,493 Properties
  • Islamorada1,438 Properties
  • North Bay Village1,426 Properties
  • Fernandina Beach1,395 Properties
  • Oakland Park1,384 Properties
  • Clearwater1,364 Properties
  • Wilton Manors1,296 Properties
  • Lake Buena Vista1,293 Properties
  • St. George Island1,284 Properties
  • Dania Beach1,260 Properties
  • Fort Pierce1,259 Properties
  • Deerfield Beach1,231 Properties
  • Cape Canaveral1,227 Properties
  • West Palm Beach1,176 Properties
  • Tavernier1,108 Properties
  • Lake Worth1,097 Properties
  • Dunedin1,067 Properties
  • Boca Raton1,061 Properties
  • Jacksonville1,061 Properties
  • Vero Beach1,035 Properties
  • Redington Shores972 Properties
  • Weston964 Properties
  • Bay Lake956 Properties
  • Rotonda West953 Properties
  • Ponte Vedra Beach914 Properties
  • Port St. Joe886 Properties
  • Surfside880 Properties
  • Port Charlotte879 Properties
  • Jensen Beach858 Properties
  • Mexico Beach847 Properties
  • Winter Garden839 Properties
  • Edgewater837 Properties
  • Navarre772 Properties
  • Stuart763 Properties
  • Coral Gables754 Properties
  • Port St. Lucie744 Properties
  • Lauderdale-by-the-Sea732 Properties
  • Punta Gorda721 Properties
  • Boca Grande721 Properties
  • Panama City712 Properties
  • Estero699 Properties
  • North Captiva682 Properties
  • Aventura672 Properties
  • Doral667 Properties
  • Ocala657 Properties
  • Lakeland654 Properties
  • Flagler Beach627 Properties
  • Jupiter616 Properties
  • Matlacha608 Properties
  • Gulfport605 Properties
  • Port Orange590 Properties
  • Nokomis584 Properties
  • Palm Beach Gardens582 Properties
  • North Redington Beach576 Properties
  • Ruskin569 Properties
  • Orange Park566 Properties
  • Melbourne565 Properties
  • Largo565 Properties
  • St. Petersburg557 Properties
  • Temple Terrace547 Properties
  • Palm Beach547 Properties
  • Boynton Beach533 Properties
  • Inverness525 Properties
  • Hudson523 Properties
  • Palm Beach Shores521 Properties
  • Miami Springs516 Properties
  • Miramar512 Properties
  • Plantation498 Properties
  • Crystal River487 Properties
  • Wellington471 Properties
  • New Port Richey461 Properties
  • Winter Haven455 Properties
  • Winter Park452 Properties
  • Altamonte Springs437 Properties
  • Redington Beach436 Properties
  • Spring Hill434 Properties
  • Sebastian433 Properties
  • Brandon431 Properties
  • Sunrise428 Properties
  • Singer Island413 Properties
  • Belleair Beach413 Properties
  • North Fort Myers410 Properties
  • Homosassa408 Properties
  • North Port403 Properties
  • Palm Harbor402 Properties
  • Sebring402 Properties
  • Key Biscayne402 Properties
  • Mount Dora377 Properties
  • Pembroke Pines370 Properties
  • Wesley Chapel365 Properties
  • Titusville338 Properties
  • Ponce Inlet335 Properties
  • Lake Placid326 Properties
  • Tarpon Springs322 Properties
  • Lutz321 Properties
  • Melbourne Beach317 Properties
  • Lake Mary313 Properties
  • Palm Bay308 Properties
  • Lake City308 Properties
  • Lady Lake305 Properties
  • Lehigh Acres303 Properties
  • Davie303 Properties
  • North Miami299 Properties
  • Bokeelia296 Properties
  • Sanford292 Properties
  • Riviera Beach289 Properties
  • Jacksonville Beach285 Properties
  • Satellite Beach276 Properties
  • Gulf Breeze273 Properties
  • Bal Harbour271 Properties
  • Indialantic267 Properties
  • Steinhatchee262 Properties
  • Port Richey257 Properties
  • Seminole254 Properties
  • Homestead251 Properties
  • Cocoa251 Properties
  • Lantana251 Properties
  • Miami Shores245 Properties
  • Coral Springs227 Properties
  • Apopka226 Properties
  • Okeechobee223 Properties
  • Lake Wales221 Properties
  • Highland Beach218 Properties
  • Juno Beach208 Properties
  • Florida City205 Properties
  • Merritt Island203 Properties
  • Port Saint Lucie201 Properties
  • Big Pine Key180 Properties
  • Brooksville179 Properties
  • Cedar Key176 Properties
  • DeLand170 Properties
  • Duck Key166 Properties
  • Niceville161 Properties
  • Dunnellon154 Properties
  • Leesburg153 Properties
  • Neptune Beach143 Properties
  • Ocoee122 Properties
  • Carrabelle115 Properties
  • Wildwood107 Properties
  • Apalachicola104 Properties
  • Atlantic Beach99 Properties
  • Miami Gardens88 Properties
  • North Miami Beach88 Properties
  • Land O' Lakes54 Properties
  • Ellenton37 Properties