Anna Maria: Vacation Rental By Owner

Showing 20 Of 337 Vacation Rentals
  • Property-1 Image 1
    House $884 / Nightly
    • 5 Bed
    • 6 Baths
    • (20)
    Anna Maria, FL

    Just updated 2020, with state of the art finishes! 5 BR 2 King Sleep Sofas, 1.5 Chaise Lounger, 5 BA Duplex with direct views of Skyway Bridge and Tampa Bay in... ...more

  • Property-2 Image 1
    House Select Dates for Price
    • 4 Bed
    • 2 Baths
    • (10) Excellent
    Anna Maria, FL

    ******Please Read our Property Manager Notes Below ****** BEFORE YOU BOOK: We rent Saturday to Saturday…Usually. If you are interested in starting or ending on a... ...more

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

    Kick off your shoes and promise yourself not to put them on again. Take off your watch and tell time by the location of the sun. Watch the sailboats bob by and... ...more

  • Property-4 Image 1
    Cottage Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (68)
    Anna Maria, FL

    Sea breeze cottage is located at north end of anna maria island. Brand new renovation, 2 bedroom with 2 bath room, with private dock, sailboat direct to bimini... ...more

  • Property-5 Image 1
    House $1,291 / Nightly
    • 4 Bed
    • 5 Baths
    • (67)
    Anna Maria, FL

    Welcome to 'Sky way view', one of the most exclusive homes on Anna Maria Island. It is located in one of the most spectacular spots on Anna Maria Island on South... ...more

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

    Come enjoy a large home/duplex on one of Anna Maria’s tranquil family beaches. Emerald Shores is perfect for large family gatherings. It is a six-bedroom, four... ...more

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

    Before you Book: Usually, we prefer to rent Saturday to Saturday. Want to rent starting or ending on a different day? Contact us before you book by clicking the... ...more

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

    ******Please Read our Property Manager Notes Below ****** BEFORE YOU BOOK: We rent Saturday to Saturday…Usually. If you are interested in starting or ending on a... ...more

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

    PLUMFISH - A gorgeous water front cottage, nestled between the mangroves, overlooking the Hammock Bayou. Canal side. Private deck on the water. North End... ...more

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

    Minimum Stays Required Based on Dates - Inquire Directly Note: Municipal Declarations require the public to wear a mask when social distancing is not possible.... ...more

  • Property-11 Image 1
    House Select Dates for Price
    • 3 Bed
    • 2 Baths
    • (27) Wonderful
    Anna Maria, FL

    Anna’s Cottage is a completely renovated island home that is perfectly located on Spring Avenue in the city of Anna Maria. Only 2 blocks west is the beautiful... ...more

  • Property-12 Image 1
    House Select Dates for Price
    • 4 Bed
    • 4 Baths
    • (6) Very Good
    Anna Maria, FL

    Located just a short walk away from bustling Pine Avenue and beautiful white sand beaches, this vacation rental is perfect for anyone looking for a relaxing... ...more

  • Property-13 Image 1
    House $699 / Nightly
    • 3 Bed
    • 3 Baths
    • (22)
    Anna Maria, FL

    o Description ? It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. ? With canal access, you have the... ...more

  • Property-14 Image 1
    House Select Dates for Price
    • 4 Bed
    • 3 Baths
    • (71) Wonderful
    Anna Maria, FL

    Relaxing 'Home Away from Home' Tropical Paradise - 3 Houses from the beach. Located on the quiet, North end of the Island. Perfect location for Amazing Sunsets... ...more

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

    This brand new rebuild on Anna Maria Island located within Anna Maria city has 3 Bedrooms, 3 Bathrooms home plus loft that is professionally decorated throughout,... ...more

  • Property-16 Image 1
    House $952 / Nightly
    • 4 Bed
    • 4 Baths
    • (58)
    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
    • 3 Bed
    • 2 Baths
    Anna Maria, FL

    Welcome to Sea Mist! Elevated 3 Bed, 2 Bath in Anna Maria, Florida just STEPS to Pine Avenue & Anna Maria City Pier This home is under new management so does... ...more

  • Property-18 Image 1
    House Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (8) Wonderful
    Anna Maria, FL

    Welcome to Decked Out! 2 bed 2 bath, Sleeps 4 (Max: 6) Anna Maria, FL 34217 A gorgeous home filled with luxurious furnishings, high-end touches, and smart... ...more

  • Property-19 Image 1
    House Select Dates for Price
    • 4 Bed
    • 6 Baths
    • (30)
    Anna Maria, FL

    Sea La Vie Beach House Newly Constructed Single Family Waterfront Home with Pool & Spa on Deepwater Canal 4 Bedroom, 4 1/2 Bath Anna Maria, FL 2825 sq. ft. ?... ...more

  • Property-20 Image 1
    House Select Dates for Price
    • 4 Bed
    • 4 Baths
    • (5) Exceptional
    Anna Maria, FL

    Welcome to Salty Pirate! Newly Renovated Single Family Waterfront Home with Pool & Spa 4 Bedroom, 3 Bath Anna Maria, FL 2512 sq. ft. Need more room? Reserve... ...more

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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 July, where prices hit an average of $78 a night. In June, prices will hit an average low of $271 per night.