Anna Maria vacation rentals

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Best Anna Maria vacation rentals

Most recommended vacation rentals in Anna Maria

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Blissful Bay at Bayside Bungalow - Anna Maria - Building
Blissful Bay at Bayside Bungalow
Anna Maria, FL
8.7Very good(14)
Parking
Free Wi-Fi
Pool
Pet friendly
$615+
Check availability
Bayside Cutie at Bayside Bungalow: Anna Maria Island Getaway Near Pine Avenue! - Anna Maria - Living room
Bayside Cutie at Bayside Bungalow: Anna Maria Island Getaway Near Pine Avenue!
Anna Maria, FL
$607+
Check availability
Anna Maria Island Beach Palms 6b - Anna Maria - Balcony
Anna Maria Island Beach Palms 6b
Anna Maria, FL
9.2Wonderful(11)
Parking
Free Wi-Fi
$421+
Check availability
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand! - Anna Maria - Pool
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!
Anna Maria, FL
Free Wi-Fi
Pool
$444+
Check availability
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand! - Anna Maria - Pool
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!
Anna Maria, FL
Free Wi-Fi
Pool
$529+
Check availability
Convenient & Well-Located Condo w/Shared Washer/Dryer, Pool, and Free WiFi - Anna Maria - Pool
Convenient & Well-Located Condo w/Shared Washer/Dryer, Pool, and Free WiFi
Anna Maria, FL
Pool
$332+
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Bay Haven - Anna Maria - Living room
Bay Haven
Anna Maria, FL
9.0Wonderful(23)
Parking
Free Wi-Fi
Pet friendly
$374+
Check availability
Seaside - Anna Maria - Balcony
Seaside
Anna Maria, FL
6.3Okay(6)
Parking
Free Wi-Fi
$955+
Check availability
A Place in Paradise Unit A - Anna Maria - Living room
A Place in Paradise Unit A
Anna Maria, FL
9.7Wonderful(15)
Free Wi-Fi
Pet friendly
$259+
Check availability
Minnow 1 1 Bedroom Cottage by RedAwning - Anna Maria - Beach
Minnow 1 1 Bedroom Cottage by RedAwning
Anna Maria, FL
9.0Wonderful(2)
Free Wi-Fi
$370+
Check availability
Budget-friendly beach condo with pool access, washer/dryer, WiFi & full kitchen - Anna Maria - Beach
Budget-friendly beach condo with pool access, washer/dryer, WiFi & full kitchen
Anna Maria, FL
Pool
$249+
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Sunrise Garden Resort - Anna Maria
Sunrise Garden Resort
Anna Maria, FL
7.9Good(351)
Free Wi-Fi
Pool
Pet friendly
$315+
Check availability
Barefoot by the Bay at Bayside Bungalow - Anna Maria
Barefoot by the Bay at Bayside Bungalow
Anna Maria, FL
9.0Wonderful(3)
Parking
Free Wi-Fi
Pool
Pet friendly
$622+
Check availability
South Bay Inn - Anna Maria
South Bay Inn
Anna Maria, FL
9.0Wonderful(46)
$271+
Check availability
21 Palms - Anna Maria
21 Palms
Anna Maria, FL
7.0Good(40)
$246+
Check availability
Bay Breezes at Bayside Bungalow - Anna Maria
Bay Breezes at Bayside Bungalow
Anna Maria, FL
8.9Very good(3)
Parking
Free Wi-Fi
Pool
$678+
Check availability
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$246 - $1,065$1,065 - $1,883$1,883 - $2,702$2,702 - $3,520$3,520+ per night

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KAYAK’s insights for vacation rentals in Anna Maria

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Anna Maria with confidence.

Which month has the cheapest vacation rental rates in Anna Maria?

Vacation rentals are cheapest in Anna Maria in September, with average rates of $347. In comparison, December is the most expensive month, with prices at $1,059.

What is the cheapest day of the week to book a vacation rental in Anna Maria?

Sunday offers the lowest rates in Anna Maria, with an average nightly price of $490. The highest prices are found on Saturday, with average rates at $924.

How early should you book a vacation rental in Anna Maria?

Book at least 11 days before your stay begins to get the best price for your Anna Maria vacation rental.
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Good to know

Low season

September

High season

December

Average price (weeknight)

$611

Average price (weekend night)

$844
Cheapest month to stay with an average 46% drop in price.
Most expensive month to stay with an average 64% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Anna Maria vacation rental deals

  • Beachfront, pet friendly, pool, and air-conditioned are the most popular vacation rental property amenities in Anna Maria
  • The best vacation rental properties in Anna Maria are Canal-front Gem with Pool and Hot Tub in Anna Maria (9.4, 26 reviews), South Bay Inn (9.1, 46), and Bay Haven (9.0, 23), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Anna Maria, you should consider visiting during the low season. The cheapest vacation homes in Anna Maria can be found in September and November.
  • The cheapest night for renting a vacation home in Anna Maria is Sunday. In contrast, the most expensive is Saturday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Anna Maria for 3 days.
  • The cheapest Anna Maria vacation rental found on KAYAK in the last 2 weeks was $398, while the most expensive was $398.

FAQs when booking a vacation home in Anna Maria

  • How much is a vacation rental for a week in Anna Maria?

    The average price for a weekly Anna Maria vacation rental found by KAYAK users in the last 2 weeks is $5,163.

  • How much is a vacation rental for a month in Anna Maria?

    The average price for a monthly Anna Maria vacation rental found by KAYAK users in the last 2 weeks is $22,129.

  • What types of vacation rentals are available in Anna Maria?

    There are loads of different property types that you can make your vacation home in Anna Maria. You’ll find apartments, bungalows, cabins, condos, cottages, houses, homestays, houseboats and villas.

  • What are some of the most-loved vacation rentals available in Anna Maria?

    There are many types of properties available for Anna Maria vacation rentals. If you’re looking for something special, vacation rentals most loved by KAYAK users are Queen's Gate Resort and Beach Dreams Resort.

  • Are there any pet-friendly vacation rentals in Anna Maria?

    There are a number of dog and pet-friendly Anna Maria vacation rentals, with around 16% allowing you to bring your pet along with you.

  • How much is a vacation rental in Anna Maria for tonight?

    In the last 72 hours, users have found Anna Maria vacation rentals for tonight for as low as $540. Search here for similar prices

  • How can I find vacation rentals near me in Anna Maria?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Anna Maria?

Our map will help you find the perfect place to stay in Anna Maria by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Anna Maria

Anna Maria vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Anna Maria. Find cheap vacation homes to rent in Anna Maria. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Anna Maria that suits you best.

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