
Anna Maria Beach, Anna Maria
10/18 – 10/28
$350/nighttotal: $3500 (10 )
Love Shack On The Water Most Desirable Location On Ami
2 4apartment , Anna Maria
This Anna Maria Island rental is located on Pine Avenue, a prime spot steps from Anna Maria City Pier, shops, restaurants, and the free Island Trolley.
The two-bedroom, two-bathroom condo sleeps six, features a fully equipped kitchen with dishwasher, offers stunning Tampa Bay views from its patio, and is near Coquina Beach and the historic Roser Chapel.
The two-bedroom, two-bathroom condo sleeps six, features a fully equipped kitchen with dishwasher, offers stunning Tampa Bay views from its patio, and is near Coquina Beach and the historic Roser Chapel.

Anna Maria Beach, Anna Maria
10/12 – 10/18
$396/nighttotal: $2376 (6 )
Perfect Island Location! Heated Pool And Plenty Of Room For The Entire Family
3 2apartment , Anna Maria
This Anna Maria Island vacation home is centrally located, a five-minute walk from the Anna Maria Island Museum and Island Players, and under ten minutes from Historic Green Village and Bay Boulevard Beach.
This three-bedroom, two-bathroom house sleeps eight guests and boasts a private pool, tennis court, barbecue grills, free WiFi, and is close to an on-site water park.
This three-bedroom, two-bathroom house sleeps eight guests and boasts a private pool, tennis court, barbecue grills, free WiFi, and is close to an on-site water park.

Anna Maria Beach, Anna Maria
08/24 – 08/30
$361/nighttotal: $2166 (6 )
Barefoot Mermaid 4, Steps To The Beach
1 2apartment , Anna Maria
Barefoot Mermaid 4, a ground-floor unit on Anna Maria Island's north end, is less than 50 feet from the Gulf of Mexico beach and a short walk from Pine Avenue's shops and restaurants.
This one-bedroom, one-bathroom condo sleeps up to four (two adults, two children/teens) and features a queen bed, daybed, and cot, plus a full kitchen, free high-speed internet, access to a shared laundry, and a starter amenity kit; nearby Saturday morning beach yoga is offered.
This one-bedroom, one-bathroom condo sleeps up to four (two adults, two children/teens) and features a queen bed, daybed, and cot, plus a full kitchen, free high-speed internet, access to a shared laundry, and a starter amenity kit; nearby Saturday morning beach yoga is offered.

Anna Maria Beach, Anna Maria
10/18 – 10/28
$269/nighttotal: $2690 (10 )
Bos Beach Bungalow
1 4house , Anna Maria
Bo's Beach Bungalow is a two-bedroom, one-bathroom house in Anna Maria, Florida, a 12-minute walk from Anna Maria City Pier and a 2-minute walk from Anna Maria Island, offering easy beach access and proximity to local attractions.
This 900-square-foot vacation rental sleeps seven guests and includes free Wi-Fi, air conditioning, a kitchen with a fridge and microwave, and a fitness center.
This 900-square-foot vacation rental sleeps seven guests and includes free Wi-Fi, air conditioning, a kitchen with a fridge and microwave, and a fitness center.

Anna Maria Beach, Anna Maria
08/24 – 08/30
$236/nighttotal: $1416 (6 )
Apartment ∙ 2 Bedrooms ∙ 4 Guests
2 2apartment , Anna Maria
Barefoot Mermaid 2, a ground-floor condo on the north end of Anna Maria Island, is located just 50 feet from the Gulf of Mexico beaches and a short walk from Pine Avenue's shops and restaurants. This 2-bedroom, 1-bathroom rental accommodates up to 4 guests and features air conditioning, internet, parking, and a shared laundry area, with twin beds convertible to a king upon request.

Anna Maria Beach, Anna Maria
10/12 – 10/18
$333/nighttotal: $1998 (6 )
Slo Mocean
2 2house , Anna Maria
Slo M'Ocean, a beachfront Anna Maria Island rental, is a 2-minute walk from Anna Maria City Pier and a 13-minute walk from Anna Maria Island's center, offering stunning ocean views.
This 540-square-foot house features two bedrooms, one bathroom, and accommodates up to seven guests, boasting a fully equipped kitchen, private balcony, in-unit laundry, free Wi-Fi, and free parking.
This 540-square-foot house features two bedrooms, one bathroom, and accommodates up to seven guests, boasting a fully equipped kitchen, private balcony, in-unit laundry, free Wi-Fi, and free parking.

Anna Maria Beach, Anna Maria
10/12 – 10/18
$281/nighttotal: $1686 (6 )
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
08/21 – 08/28
$273/nighttotal: $1911 (7 )
Perfect Modern Cottage, Short Walk To The Beach, Outdoor Deck, Beach Gear!
2 2apartment , Anna Maria
The Canary Cottage is located in Anna Maria City, just two blocks from popular restaurants and a short walk to the beach. It has received excellent user ratings, making it a popular choice for travelers. This two-bedroom, two-bathroom cottage offers 860 square feet of space and comfortably sleeps six guests. The cottage features a fully equipped kitchen, air conditioning, a private terrace, a garden, a spa, and parking.

Anna Maria Beach, Anna Maria
10/18 – 10/28
$226/nighttotal: $2260 (10 )
Endless Summer- On Pine Ave, Steps To Beach & Pier W/ Water View & Dock
2 4apartment , Anna Maria
This Anna Maria Island waterfront condo, located on Pine Avenue, offers easy walking access to Anna Maria City Pier, the beach, and numerous restaurants and shops.
This 830-square-foot, two-bedroom, one-bathroom apartment sleeps four and features a private dock perfect for kayaking and fishing, a terrace, free parking, and a full kitchen with a dishwasher.
This 830-square-foot, two-bedroom, one-bathroom apartment sleeps four and features a private dock perfect for kayaking and fishing, a terrace, free parking, and a full kitchen with a dishwasher.

Anna Maria Beach, Anna Maria
08/24 – 08/30
$812/nighttotal: $4872 (6 )
Mermaids Purse~private Pool! 40 Steps To Beach!
2 2apartment , Anna Maria
This Anna Maria Island condo is situated just 40 steps from Palmetto Beach, offering direct access without crossing any roads, and is a 5-minute walk to Pine Avenue's shops and dining.
This 1600 square foot residence accommodates up to 6 guests, featuring 2 bedrooms, 2 bathrooms, a private heated pool, a dog-friendly policy, and provided beach essentials.
This 1600 square foot residence accommodates up to 6 guests, featuring 2 bedrooms, 2 bathrooms, a private heated pool, a dog-friendly policy, and provided beach essentials.

Anna Maria Beach, Anna Maria
10/18 – 10/28
$419/nighttotal: $4190 (10 )
Ev Charger, Blue Lagoon By Seabreeze Vacation
2 4apartment , Anna Maria
This beachfront Anna Maria Island vacation home boasts stunning sea views, situated less than a mile from the Island Players and under a 10-minute drive from Bradenton Beach and the Anna Maria Island Museum and Historical Park.
The four-bedroom house, sleeping multiple guests, includes a fully equipped kitchen, free Wi-Fi, a sofa bed, private pool, spa, fitness center, and ample parking; enjoy nearby Anna Maria Beach and its attractions.
The four-bedroom house, sleeping multiple guests, includes a fully equipped kitchen, free Wi-Fi, a sofa bed, private pool, spa, fitness center, and ample parking; enjoy nearby Anna Maria Beach and its attractions.

Anna Maria Beach, Anna Maria
10/18 – 10/28
$285/nighttotal: $2850 (10 )
A Place In Paradise Unit B
2 4house , Anna Maria
A Place in Paradise Unit B, a beachfront Anna Maria Island rental, is a 4-minute walk from Anna Maria Island and an 11-minute walk from the Anna Maria City Pier.
This 830-square-foot house features two bedrooms, two bathrooms, and sleeps seven, offering free Wi-Fi, a full kitchen with dishwasher, and a private entrance; enjoy nearby beach access and water activities.
This 830-square-foot house features two bedrooms, two bathrooms, and sleeps seven, offering free Wi-Fi, a full kitchen with dishwasher, and a private entrance; enjoy nearby beach access and water activities.













