Find Vacation Rentals in Anna Maria Island

Anna Maria
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Popular Anna Maria Island Vacation Rentals

Find the perfect Anna Maria Island vacation rental

House Anna Maria
e.g. 12/10 - 12/17 (Sat - Sat)
-56%
$1,328
$588 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (7 ratings)
Anna Maria, Manatee County, Florida, United States
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HomeToGo
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House Anna Maria
e.g. 9/17 - 9/24 (Sat - Sat)
-51%
$824
$406 per night
House ∙ 6 guests ∙ 2 bedrooms
4.9
"Excellent" (53 ratings)
Anna Maria, Manatee County, Florida, United States
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HomeToGo
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Cottage Anna Maria
e.g. 10/29 - 11/5 (Sat - Sat)
-54%
$776
$355 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (107 ratings)
Anna Maria, Manatee County, Florida, United States
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HomeToGo
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House Anna Maria
e.g. 9/24 - 10/1 (Sat - Sat)
-52%
$1,675
$807 per night
House ∙ 10 guests ∙ 4 bedrooms
4.9
"Excellent" (9 ratings)
Anna Maria, Manatee County, Florida, United States
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HomeToGo
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House Anna Maria
e.g. 10/1 - 10/8 (Sat - Sat)
-51%
$1,095
$540 per night
House ∙ 10 guests ∙ 5 bedrooms
4.7
"Outstanding" (34 ratings)
Anna Maria, Manatee County, Florida, United States
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HomeToGo
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House Anna Maria
e.g. 9/7 - 9/14 (Wed - Wed)
-22%
$671
$523 per night
House ∙ 6 guests ∙ 3 bedrooms
4.8
"Excellent" (50 ratings)
Anna Maria, Manatee County, Florida, United States
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Vacasa
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House Anna Maria
e.g. 9/17 - 9/24 (Sat - Sat)
-60%
$938
$375 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (94 ratings)
Anna Maria, Manatee County, Florida, United States
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HomeToGo
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House Anna Maria
e.g. 9/17 - 9/24 (Sat - Sat)
$213 per night
House ∙ 4 guests ∙ 2 bedrooms
Anna Maria, Manatee County, Florida, United States
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HomeToGo
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House Anna Maria
e.g. 12/1 - 12/8 (Thu - Thu)
$372 per night
House ∙ 8 guests ∙ 3 bedrooms
4.9
"Excellent" (65 ratings)
Anna Maria, Manatee County, Florida, United States
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Vacasa
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Vacation rentals with Wi-Fi

House Internet Anna Maria
e.g. 10/29 - 11/5 (Sat - Sat)
-41%
$501
$298 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (37 ratings)
Anna Maria, Manatee County, Florida, United States
Internet
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HomeToGo
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House Internet Anna Maria
e.g. 9/10 - 9/17 (Sat - Sat)
-44%
$993
$555 per night
House ∙ 8 guests ∙ 4 bedrooms
4.8
"Excellent" (33 ratings)
Anna Maria, Manatee County, Florida, United States
Internet
Details
HomeToGo
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House Internet Anna Maria
e.g. 10/1 - 10/8 (Sat - Sat)
-54%
$679
$314 per night
House ∙ 8 guests ∙ 4 bedrooms
4.8
"Excellent" (19 ratings)
Anna Maria, Manatee County, Florida, United States
Internet
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Vacation rentals and apartments with air conditioning

Villa Aircondition Anna Maria
e.g. 9/18 - 9/25 (Sun - Sun)
-69%
$812
$249 per night
Villa ∙ 6 guests ∙ 2 bedrooms
4.6
"Outstanding" (26 ratings)
Anna Maria, Manatee County, Florida, United States
Aircondition
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House Aircondition Anna Maria
e.g. 12/3 - 12/10 (Sat - Sat)
$282 per night
House ∙ 6 guests ∙ 3 bedrooms
Anna Maria, Manatee County, Florida, United States
Aircondition
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House Aircondition Anna Maria
e.g. 10/1 - 10/8 (Sat - Sat)
-50%
$771
$384 per night
House ∙ 6 guests ∙ 3 bedrooms
4.7
"Outstanding" (42 ratings)
Anna Maria, Manatee County, Florida, United States
Aircondition
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Apartments and vacation rentals with a kitchen

House Kitchen Anna Maria
e.g. 11/26 - 12/3 (Sat - Sat)
$213 per night
House ∙ 4 guests ∙ 2 bedrooms
Anna Maria, Manatee County, Florida, United States
Kitchen
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House Kitchen Anna Maria
e.g. 9/17 - 9/24 (Sat - Sat)
-43%
$605
$345 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (15 ratings)
Anna Maria, Manatee County, Florida, United States
Kitchen
Details
HomeToGo
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House Kitchen Anna Maria
e.g. 5/8 - 5/15 (Mon - Mon)
$362 per night
House ∙ 6 guests ∙ 3 bedrooms
Anna Maria, Manatee County, Florida, United States
Free cancellation
Kitchen
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Frequently Asked Questions

How much does it cost to book a vacation rental in Anna Maria Island?

The price per night in Anna Maria Island starts at $184.

Can I see all vacation rentals that are available in Anna Maria Island?

Currently, there are 3,085 vacation rentals available for you to compare and book.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Anna Maria Information

About Anna Maria

40 miles south of Tampa is Anna Maria, a beautiful island that is bordered by the Gulf of Mexico to the west and Sarasota Bay to the south. This vacation hotspot was formerly discovered by the Timucan and Caloosan Native Americans, followed by the Spanish explorers. Nowadays the island is known for its white sand beaches, amazing weather, and its small year-round population of less than 2000 people. It’s the perfect tropical vacation getaway without having to fly to the Caribbean.

Things to Do in Anna Maria

Anna Maria offers visitors a charming old coastal village feeling when they visit this beautiful place filled with history and sightseeing. To learn more about the town’s interesting history, stop by the Anna Maria Historical Society on Pine Avenue, where admission is free and guests can read up on the fascinating informational archives about the island. Anna Maria is known for having gorgeous beaches year-round at the northern tip of the island; parking tends to be challenging and some of them are more secluded, making them more easily accessible by foot or bike. Check out the beaches on the Gulf of Mexico, Bean Point, and the Tampa Bay beaches at Bay Front Park. Go for a stroll on Anna Maria City Pier, which was built in 1911 and boasts stunning views of the beaches and marine wildlife. The City of Anna Maria hosts various events throughout the year on Pine Avenue that feature great food, live music and vendors. Some of the annual events include Food and Wine on Pine, Sandbar Easter Egg Hunt, Bay Fest, and Christmas on Pine. If you’re looking to do something other than go to the beach, other activities include catching a performance at Players Theater, checking out literature at Little Free Library, and taking a fitness or dance class at the Community Center. Go shopping on Bridge Street, which is located at the other end of the island in Bradenton Beach and has lots of shopping and dining options, offering great views of the Gulf of Mexico and Sarasota Bay.

Day Trips Near Anna Maria

If you’re traveling with family and are looking for some kid-friendly options, Orlando is two hours north east of Anna Maria Island and is home to Disney World, SeaWorld, and Universal Theme Parks. Tampa is an hour north of Anna Maria Island and has plenty of fun things to do, including the Florida Aquarium, Big Cat Rescue sanctuary, Raymond James Stadium, and Lowry Park Zoo.

Anna Maria Accommodation

There are many beautiful homes that are available to rent for your vacation in Anna Maria. The Pine Avenue area is a popular place for a home rental and offers close proximity to the beach and the main shopping and restaurants. The Holmes Beach area is located right on the Gulf of Mexico and has lots of cute cottages, bungalows, and larger beach homes that offer stunning ocean views and are just steps from the sand. The Bradenton Beach area is on the opposite side of the island from the main Anna Maria center and has gulf front condos that offer direct beach access and unobstructed views.

Transportation in Anna Maria

Due to the island’s geography and some of the beaches being harder to access by foot, one great way to travel around Anna Maria is by renting a bicycle. Another fun form of transportation is renting a luxury golf cart rental, which are available in a variety of styles and sizes that are street legal and offer a comfortable, leisurely way to get around the island. If you rent a vehicle from Lux Carts, 10-percent of proceeds are donated to local charities including the Anna Maria Island Elementary School.

Popular Day Trips Near Anna Maria Island

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