
Anna Maria Beach, Anna Maria
10/09 – 10/13
$409/nighttotal: $1636 (4 )
Island Gem B Home
2 2house , Anna Maria
Island Gem B, a two-bedroom, one-bathroom house in Anna Maria, offers convenient access to Anna Maria Island and the Anna Maria City Pier, a six-minute walk away, and is located within 20 miles of The John and Mable Ringling Museum of Art and Sarasota Bradenton International Airport.
This Anna Maria vacation rental boasts a fully equipped kitchen with a dishwasher, in-house laundry, air conditioning, a private patio, and access to a swimming pool; it comfortably sleeps up to four guests and includes free Wi-Fi and pet-friendly accommodations.
This Anna Maria vacation rental boasts a fully equipped kitchen with a dishwasher, in-house laundry, air conditioning, a private patio, and access to a swimming pool; it comfortably sleeps up to four guests and includes free Wi-Fi and pet-friendly accommodations.

Anna Maria Beach, Anna Maria
10/09 – 10/13
$389/nighttotal: $1556 (4 )
Sea Spray 2: *Pet-friendly *Steps To The Beach *Close To Shops, Restaurants
2 2apartment , Anna Maria
This Anna Maria Island rental is located in the North End, just west of Gulf Drive and a short walk from the beautiful Gulf Beach. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The 800 square foot apartment can comfortably accommodate up to four guests with two bedrooms and one bathroom. Enjoy amenities such as a fully equipped kitchen, air conditioning, a shared outdoor space with a grill, and a shared laundry room.
The 800 square foot apartment can comfortably accommodate up to four guests with two bedrooms and one bathroom. Enjoy amenities such as a fully equipped kitchen, air conditioning, a shared outdoor space with a grill, and a shared laundry room.

Anna Maria Beach, Anna Maria
08/23 – 09/03
$314/nighttotal: $3454 (11 )
2nd House From The Beach With No Roads To Cross
2 2apartment , Anna Maria
This Anna Maria Island beachfront home offers direct beach access and is a 10-minute walk from Bradenton Beach and Bean Point, and a 15-minute walk or drive from Anna Maria Beach and Bay Boulevard Beach.
This 960-square-foot vacation rental features two bedrooms, two bathrooms, a fully equipped kitchen, a private fenced yard, a fireplace, a swimming pool, a spa, a tennis court, and free WiFi; it comfortably sleeps a family and allows pets.
This 960-square-foot vacation rental features two bedrooms, two bathrooms, a fully equipped kitchen, a private fenced yard, a fireplace, a swimming pool, a spa, a tennis court, and free WiFi; it comfortably sleeps a family and allows pets.

Anna Maria Beach, Anna Maria
08/23 – 09/03
$217/nighttotal: $2387 (11 )
Tranquil Palm: Perfect North-end Location
2 2apartment , Anna Maria
This Anna Maria Island rental is a three-bedroom, one-bathroom duplex conveniently located in the north end, a five-minute walk from Pine Avenue's shops and restaurants, and near the Anna Maria Island Community Center.
The 910-square-foot unit features a fully equipped kitchen, a cozy patio, and accommodates up to four guests, with pets allowed (dogs under 40 lbs, max 2, fee applies).
The 910-square-foot unit features a fully equipped kitchen, a cozy patio, and accommodates up to four guests, with pets allowed (dogs under 40 lbs, max 2, fee applies).

Anna Maria Beach, Anna Maria
10/12 – 10/18
$300/nighttotal: $1800 (6 )
Shell Cottage -With Shared Pool, 200 Feet From The Beach
1 2cottage , Anna Maria
This charming cottage is located on Anna Maria Island, just a short walk from Bradenton Beach and Bean Point Beach, offering a peaceful escape with easy access to the island's beautiful shores. Guests consistently rate this cottage as excellent, highlighting its comfortable accommodations and convenient location.
The cottage features one bedroom and one bathroom, comfortably accommodating two guests. Enjoy the fully equipped kitchen, outdoor patio, and access to a swimming pool, making this cottage an ideal choice for a relaxing and enjoyable stay.
The cottage features one bedroom and one bathroom, comfortably accommodating two guests. Enjoy the fully equipped kitchen, outdoor patio, and access to a swimming pool, making this cottage an ideal choice for a relaxing and enjoyable stay.

Anna Maria Beach, Anna Maria
10/09 – 10/13
$378/nighttotal: $1512 (4 )
Adorable Duplex On Ami! With Pool, Near Bean Point Beach
2 2apartment , Anna Maria
This Anna Maria Island ground-level duplex is located less than a 10-minute walk from Bean Point Beach and a 10-minute drive from Bayfront Park, offering easy access to Pine Avenue's shops and restaurants.
This 790-square-foot, two-bedroom, one-bathroom unit sleeps six guests and features a newly remodeled interior, a fully equipped kitchen, a shared community pool, and a professional linen program.
This 790-square-foot, two-bedroom, one-bathroom unit sleeps six guests and features a newly remodeled interior, a fully equipped kitchen, a shared community pool, and a professional linen program.

Anna Maria Beach, Anna Maria
10/09 – 10/13
$375/nighttotal: $1500 (4 )
Cute & Cozy Getaway At North End Of Anna Maria Island. 5-min Walk To The Beach!
2 2apartment , Anna Maria
This Anna Maria Island vacation home offers a prime location, a short walk from Anna Maria Beach and Bradenton Beach, and within a 10-minute drive of Bean Point Beach and Bayfront Park.
This 750-square-foot villa boasts two bedrooms, one bathroom, sleeps four guests, and includes a private pool, spa, fitness center, and gas grills, plus free WiFi and on-site water park access.
This 750-square-foot villa boasts two bedrooms, one bathroom, sleeps four guests, and includes a private pool, spa, fitness center, and gas grills, plus free WiFi and on-site water park access.

Anna Maria Beach, Anna Maria
10/12 – 10/18
$266/nighttotal: $1596 (6 )
Apartment ∙ 1 Bedroom ∙ 3 Guests
1 2apartment , Anna Maria
This ground-floor condo, 'Barefoot Mermaid 3,' is located on the north end of Anna Maria Island, 50 feet from the Gulf of Mexico beaches and a short walk to Pine Avenue's dining and shopping.
This newly renovated 1-bedroom, 1-bathroom unit offers comfortable accommodations for up to 3 guests with a queen bed and sofa bed, featuring a tropical theme, polished terrazzo floors, a flat-screen TV, free high-speed internet, and access to a common laundry area and golf cart charging station.
This newly renovated 1-bedroom, 1-bathroom unit offers comfortable accommodations for up to 3 guests with a queen bed and sofa bed, featuring a tropical theme, polished terrazzo floors, a flat-screen TV, free high-speed internet, and access to a common laundry area and golf cart charging station.

Anna Maria Beach, Anna Maria
10/09 – 10/13
$276/nighttotal: $1104 (4 )
2 Br Home With Internet And Washer And Dryer
2 2apartment , Anna Maria
This Anna Maria rental cottage is located steps from the beach and bay, with nine dining and entertainment options within a short walk.
This 2-bedroom, 1-bathroom villa accommodates up to 4 guests and features a screened-in lanai, a spacious living area with a sectional sofa, a well-equipped kitchen with new appliances, and is pet-friendly for one dog under 20lbs.
This 2-bedroom, 1-bathroom villa accommodates up to 4 guests and features a screened-in lanai, a spacious living area with a sectional sofa, a well-equipped kitchen with new appliances, and is pet-friendly for one dog under 20lbs.

Anna Maria Beach, Anna Maria
10/12 – 10/18
$339/nighttotal: $2034 (6 )
Charming Cottage With Modern Amenities Close To Beach W/ Pool, Beach Gear, Bikes
1 2apartment , Anna Maria
This Anna Maria Island apartment is a short walk from Bradenton Beach and Palmetto Avenue Beach, making it perfect for beach lovers. Guests rave about the excellent location and amenities. The apartment features a fully equipped kitchen and comfortable living space. Enjoy the on-site swimming pool, spa, and barbecue grills, or relax on your private terrace.

Anna Maria Beach, Anna Maria
10/09 – 10/13
$345/nighttotal: $1380 (4 )
Barefoot Bungalow: Steps To Bayfront Park
2 2apartment , Anna Maria
This Anna Maria Island bungalow, located in the quiet north end, is a five-minute walk from Bean Point Beach and Bayfront Park, and a ten-minute walk or bike ride from Anna Maria City Pier and Pine Avenue.
The two-bedroom, two-bathroom home sleeps five, features a recently updated kitchen with a fridge, microwave, and dishwasher, plus air conditioning, a fitness center, and allows two well-trained dogs under 40 lbs (a $150 non-refundable pet fee applies per pet).
The two-bedroom, two-bathroom home sleeps five, features a recently updated kitchen with a fridge, microwave, and dishwasher, plus air conditioning, a fitness center, and allows two well-trained dogs under 40 lbs (a $150 non-refundable pet fee applies per pet).

Anna Maria Beach, Anna Maria
10/12 – 10/18
$350/nighttotal: $2100 (6 )
Dog Friendly Cottage - One Block To The Bay!
2 2apartment , Anna Maria
This Anna Maria Island beachfront vacation home is steps from Bay Boulevard Beach, the Anna Maria City Pier, and Historic Green Village, with Bayfront Park and the Anna Maria Island Museum and Historical Park within a 10-minute drive.
This 540-square-foot rental boasts two bedrooms, a sofa bed, one bathroom, a fully equipped kitchen, and a private lanai, accommodating up to four guests and offering on-site amenities such as a water park and gas grills.
This 540-square-foot rental boasts two bedrooms, a sofa bed, one bathroom, a fully equipped kitchen, and a private lanai, accommodating up to four guests and offering on-site amenities such as a water park and gas grills.











