Enter a destination to search

Anna Maria: Vacation Rental By Owner

Search result 1 to 20 Of 249
  • Property-1 Image 1
    House Select Dates for Price
    • 4Bed
    • 3Baths
    Anna Maria, FL

    Welcome to The Salty Dog. This luxury Key West style home has it all. Expansive bay views, private heated pool, extra large master suite with a double shower and... ...more

  • Property-2 Image 1
    House Select Dates for Price
    • 2Bed
    • 1Baths
    Anna Maria, FL

    The Ibis unit at the Blue Dolphin Inn, located at 780 Jacaranda in the Historic Village of Anna Maria is a wonderful two bedroom, one bath downstairs unit... ...more

  • Property-3 Image 1
    House Select Dates for Price
    • 3Bed
    • 2Baths
    Anna Maria, FL

    The Flamingo unit at the Blue Dolphin Inn, located at 780 Jacaranda in the Historic Village of Anna Maria is a wonderful and spacious three bedroom, two bath... ...more

  • Property-4 Image 1
    House Select Dates for Price
    • 3Bed
    • 4Baths
    • (10) Wonderful
    Anna Maria, FL

    Coconut Bayou is a 3 bedroom, 3.5 bath Key West style beauty with all the comforts you may think of. The kitchen is gorgeous and spacious - a dream for every chef... ...more

  • Property-5 Image 1
    House Select Dates for Price
    • 2Bed
    • 1Baths
    • (13)
    Anna Maria, FL

    The location of Aquaville A is just fantastic: Enjoy a short walk away from everything at the prestigious North End of Anna Maria Island: From the famous beach,... ...more

  • Property-6 Image 1
    House Select Dates for Price
    • 3Bed
    • 2Baths
    • (7) Exceptional
    Anna Maria, FL

    Lay-by at the Point Lay-by at the Point, located on the north end of Anna Maria Island, is a fantastic place to start your vacation. This three-bedroom,... ...more

  • Property-7 Image 1
    House Select Dates for Price
    • 2Bed
    • 2Baths
    • (5) Exceptional
    Anna Maria, FL

    ISLAND TIME Welcome to Island Time, Leave the clocks behind! This beautiful Anna Maria Island cottage offers a sparkling private pool, gorgeous outdoor... ...more

  • Property-8 Image 1
    House Select Dates for Price
    • 2Bed
    • 2Baths
    • (2) Exceptional
    Anna Maria, FL

    DREAMSCAPE Welcome to Dreamscape! Just two blocks from the most pristine beaches of the north end of Anna Maria Island, you’ll find Dreamscape! A two bedroom,... ...more

  • Property-9 Image 1
    House Select Dates for Price
    • 2Bed
    • 2Baths
    • (5) Very Good
    Anna Maria, FL

    BAREFOOT CROSSINGS Welcome To Barefoot Crossings! Just a five minute walk from the postcard perfect beaches Anna Maria is famous for you’ll find Barefoot... ...more

  • Property-10 Image 1
    House Select Dates for Price
    • 2Bed
    • 3Baths
    Anna Maria, FL

    A MERMAID'S LAIR A beautiful brand new pool and tropical outdoor area await you in the newest of our vacation rentals, A Mermaid''s Lair! Located on the quiet... ...more

  • Property-11 Image 1
    Villa Select Dates for Price
    • 2Bed
    • 1Baths
    Anna Maria, FL

    21 PALMS A Tastefully decorated with an island flair! You'll love this adorable two bedroom/one bath half duplex on the north end of Anna Maria Island! Just 3... ...more

  • Property-12 Image 1
    House $320 / Nightly
    • 2Bed
    • 1Baths
    • (50) Wonderful
    Anna Maria, FL

    NEWLY REMODELED BATHROOM (pics not up yet on site) - Situated at the quiet north end of Anna Maria Island. Removed from the condos, hotels, and crowds. We are... ...more

  • Property-13 Image 1
    Villa Select Dates for Price
    • 3Bed
    • 2Baths
    • (1) Exceptional
    Anna Maria, FL

    ANNA MARIA BEACH HOUSE If you are looking for the perfect spot to vacation on Anna Maria Island, look no further! This beautiful 3 bedroom, 2 bath, Anna Maria... ...more

  • Property-14 Image 1
    Villa Select Dates for Price
    • 3Bed
    • 2Baths
    Anna Maria, FL

    ANNA MARIA BAY SIDE If you are looking for the picture-perfect spot to vacation on Anna Maria Island, look no further! This beautiful 3 bedroom, 2 bath, Anna... ...more

  • Property-15 Image 1
    House Select Dates for Price
    • 3Bed
    • 3Baths
    • (27) Exceptional
    Anna Maria, FL

    Tucked Away is a newly renovated custom home with everything you could possibly need for the vacation of a life time. The incredibly private setting includes a... ...more

  • Property-16 Image 1
    House $952 / Nightly
    • 4Bed
    • 4Baths
    • (57)
    Anna Maria , FL

    Beach chic meets casual elegance in this brand new three story house only steps away from the best beach on Anna Maria Island. Ocean views await you from almost... ...more

  • Property-17 Image 1
    House Select Dates for Price
    • 2Bed
    • 2Baths
    • (2) Exceptional
    Anna Maria, FL

    A contemporary aesthetic combined with a top-notch location is sure to make Pelican Bay a favorite part of your Anna Maria vacation! Tucked away at the north... ...more

  • Property-18 Image 1
    House Select Dates for Price
    • 4Bed
    • 3Baths
    • (11) Very Good
    Anna Maria, FL

    You'll be right at home in this tastefully designed 4-bedroom 3-bath ground floor cottage, nestled at the corner of Alamanda and North Bay Boulevard, just half a... ...more

  • Property-19 Image 1
    Cottage Select Dates for Price
    • 4Bed
    • 3Baths
    Anna Maria, FL

    Enjoy a simple, old fashioned seaside vacation in this adorable duplex west of Gulf Drive and just two houses from the beach in the quaint village of Anna Maria.... ...more

  • Property-20 Image 1
    House Select Dates for Price
    • 2Bed
    Anna Maria, FL

    Property Location When you stay at this vacation home in Anna Maria, you'll be next to a golf course, within a 15-minute drive of Manatee Public Beach and... ...more

Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Anna Maria. Many accommodations in Anna Maria provide "Non Smoking Only", there are 310, or there are 294 of Vacation Rentals in Anna Maria with a "Children Welcome", there are also 248 with "Fishing", which is another great reason to visit Anna Maria.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Anna Maria. The most expensive month of the next 12 months is in January, where prices hit an average of $82 a night. In , prices will hit an average low of $0 per night.