Best Vacation rentals and Airbnb offers in Anna Maria, FL
9.9 68 reviews
Anna Maria, FL
06/20 – 06/27
$213/nighttotal: $1491 (7 )
Island Retreat By Seabreeze Vacation
1 2
apartment , Holmes Beach
This Holmes Beach vacation rental boasts a prime beachfront location, a 5-minute walk from West Coast Surf Shop and AMI Paddleboard Adventures, and a 10-minute drive from Manatee Public Beach and Bradenton Beach. This 680-square-foot house features one bedroom, one bathroom, a fully equipped kitchen, in-unit laundry, a balcony, and accommodates up to four guests comfortably with a sofa bed, plus amenities including a spa and fitness center.
9.6 34 reviews
Anna Maria, FL
06/20 – 06/27
$250/nighttotal: $1750 (7 )
Liddie's Place: Gulf Front Sun Plaza West Condo, Pool, Tennis By Anna Maria Life Vacation Rentals
2 2
apartment , Holmes Beach
This Holmes Beach beachfront house offers direct beach access and is a 10-minute walk from Bradenton Beach and Island Gallery West, less than a mile from Holmes Beach and Manatee Public Beaches. This 1,090-square-foot vacation rental boasts three bedrooms, two bathrooms, sleeps six, and includes a private pool, spa, tennis court, and free WiFi.
9.7 312 reviews
Anna Maria, FL
08/04 – 08/06
$346/nighttotal: $692 (2 )
Ideal Beach Hideaway Pool Condo Located Between The Island Marina And Beach
1 2
house , Bradenton Beach
This waterfront condo is situated in Bradenton Beach, within walking distance of Bradenton Beach and Cortez Beach. It has excellent user, location, and cleanliness ratings. The condo has one bedroom, one bathroom, and can accommodate up to four guests. It features a fully equipped kitchen, a private outdoor patio, and access to on-site barbecue grills. Guests can also enjoy the swimming pool and garden.
9.8 81 reviews
Anna Maria, FL
07/19 – 07/23
$1231/nighttotal: $4924 (4 )
Bon Ami: North End Ami, Pool Home, Short Walk To Bean Point By Anna Maria Life Vacation Rentals
3 4
house , Anna Maria
Bon Ami, a 1,500-square-foot Anna Maria Island house rental, is conveniently located a 5-minute walk from Anna Maria City Pier and a short drive from the Ringling Museum of Art. This pet-friendly home boasts two bathrooms, a private pool, spa, fitness center, and a fully equipped kitchen including a dishwasher, microwave, and refrigerator, perfect for a relaxing vacation.
9.7 109 reviews
Anna Maria, FL
06/20 – 06/27
$766/nighttotal: $5362 (7 )
Bean Point Bungalow! Pet Friendly Home With Pool And Walk To Beach
3 2
apartment , Anna Maria
This Anna Maria vacation home is located just a short 5-minute walk from Bean Point Beach and Anna Maria Beach, offering easy access to the beautiful Florida coastline. Guests consistently rate this property as excellent for its cleanliness, location, and overall experience. The home features 3 bedrooms spanning 2200 square feet, providing ample space for families or groups. Amenities include a private pool, a shared bathroom, a fully equipped kitchen, a washer and dryer, a balcony with a TV, barbecue grills, and access to a water park, ensuring a comfortable and entertaining stay.
Anna Maria, FL
07/28 – 08/03
$2253/nighttotal: $13518 (6 )
Villa La Concha~west Of Gulf Steps To The Beach!
6 11
apartment , Anna Maria
This Anna Maria rental property is located a 1-minute walk from Anna Maria Beach and a short distance from Pine Avenue shops and dining. This 3750 sq ft vacation home offers 6 bedrooms, 5 bathrooms, and sleeps 12 with a private heated pool, spa, game room with Ping Pong and Foosball, and BBQ grill.
9.7 719 reviews
Anna Maria, FL
08/04 – 08/06
$457/nighttotal: $914 (2 )
Bay Breeze Cottages #3
1 2
apartment , Anna Maria
This Anna Maria vacation rental is located a short 5-minute walk from Anna Maria Beach and Bayfront Park, with Bean Point Beach and Bradenton Beach within a 10-minute reach. The house features a private pool, a fully equipped kitchen, a washing machine, a sofa bed, a balcony, a TV, and a barbecue grill, perfect for a comfortable and convenient stay.
9.5 141 reviews
Anna Maria, FL
08/04 – 08/06
$211/nighttotal: $422 (2 )
"Paradise" By The Private (Heated) Pool Light!
1 2
apartment , Cortez
This Cortez vacation rental, located one mile from the Gulf Coast beaches, offers a secluded tropical escape. The property features a private heated pool, large screened lanai, BBQ grill, outdoor shower, complete kitchenette, queen-sized bed, updated bathroom, Wi-Fi, Smart TV, washer, dryer, and accommodates two guests.
9.7 74 reviews
Anna Maria, FL
08/04 – 08/06
$805/nighttotal: $1610 (2 )
Perfect Island Location! Heated Pool And Plenty Of Room For The Entire Family
3 2
apartment , 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.
9.5 62 reviews
Anna Maria, FL
06/20 – 06/27
$244/nighttotal: $1708 (7 )
Resort Style Condo By The Beach With Heated Pool At Runaway Bay
1 2
apartment , Bradenton Beach
This smoke-free condo is located in Bradenton Beach, within walking distance of Anna Maria Sound, Aluna Wellness Center & Spa, and Bradenton Beach itself. The "Resort Style Condo By The Beach With Heated Pool At Runaway Bay" has excellent user, location, and cleanliness ratings. The one-bedroom, one-bathroom condo has 700 square feet and can accommodate up to four guests. Amenities include a full kitchen, a washing machine, free WiFi, a sofa bed, a heated pool, tennis courts, and a music library.
9.8 38 reviews
Anna Maria, FL
06/20 – 06/27
$363/nighttotal: $2541 (7 )
Paradise On Palm Lower Unit
1 3
apartment , Anna Maria
This Anna Maria Island beachfront rental is a two-bedroom, one-bathroom unit located one block from Pine Avenue, offering easy access to Anna Maria's shops and restaurants. The 2-bedroom condo sleeps four comfortably with a king and queen bed, features a private patio, washer/dryer, dishwasher, and designated parking; monthly winter rentals (January-March) are available with Saturday/Sunday check-in only.
9.6 104 reviews
Anna Maria, FL
07/28 – 08/03
$437/nighttotal: $2622 (6 )
Coco's Beach House Residential Home W/ Pool
3 11
apartment , Bayshore Gardens
Coco's Beach House, a pet-friendly vacation home in Bayshore Gardens, Florida, offers convenient access to Sarasota-Bradenton International Airport (SRQ), Downtown Sarasota, and Downtown Bradenton, all within a 15-minute radius of area beaches. This three-bedroom, two-bathroom rental sleeps up to ten guests, boasting a private heated pool (no extra charge), ample parking for six cars plus RVs/boats, a fully equipped kitchen, and modern amenities including Roku TV and Wi-Fi.
Best Anna Maria, FL vacation rentals with a balcony
9.8 124 reviews
Anna Maria, FL
07/19 – 07/23
$363/nighttotal: $1452 (4 )
Tropical Haven *A
2 4
apartment , Cortez
This Bradenton condo, located near Anna Maria Sound, Bradenton Beach Marina, Fish Hole Adventure Golf, Bridge Street, and the Historic Bridge Street Pier (all within 3 miles), offers convenient access to Cortez area attractions. This 1100-square-foot apartment features two bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen, private balcony, free WiFi, swimming pool, and parking.
9.8 255 reviews
Anna Maria, FL
08/04 – 08/06
$379/nighttotal: $758 (2 )
Anna Maria Beach Condo 1/1
1 2
apartment , Bradenton Beach
This smoke-free condo is located on Bradenton Beach, just steps from Anna Maria Sound and Bradenton Beach, with Aluna Wellness Center & Spa and Bradenton Beach Marina within a 10-minute walk. The apartment has received excellent reviews from previous guests, ensuring a comfortable and enjoyable stay. The one-bedroom, one-bathroom unit comes equipped with a kitchen featuring a microwave, dishwasher, and coffee maker, as well as a washing machine, TV, and hair dryer. The apartment also offers access to a swimming pool, parking, and internet, making it a convenient and relaxing option for a Bradenton Beach getaway.
9.6 37 reviews
Anna Maria, FL
08/04 – 08/06
$1165/nighttotal: $2330 (2 )
Ami Du Soleil | 1 Block 2 Beach, Big Heated & Shaded Saltwater Pool, Lanai, Grill, Walk To Restaurants, Cafes, Shops, Bars
4 2
apartment , Anna Maria
This Anna Maria Island vacation rental is steps from Bradenton Beach and a short walk to the Island Players, less than a mile from Bean Point and Anna Maria beaches. The 1910-square-foot home features three bedrooms and three bathrooms, accommodating eight guests, and includes a private pool, fenced yard, and fully equipped kitchen with all major appliances.
9.7 68 reviews
Anna Maria, FL
07/28 – 08/03
$1393/nighttotal: $8358 (6 )
Waterfront Estate, Dock, Heated Pool/spa & More!
5 11
apartment , Bradenton
Palma Sola Bay House is located in Bradenton, just a short walk from Palma Sola Causeway Park and a drive from the John and Mable Ringling Museum of Art. This vacation rental has received excellent ratings for its location, cleanliness, and overall experience. This 5-bedroom home comfortably accommodates large families or groups of friends. Guests can enjoy a private pool, balcony, fully equipped kitchen, free parking, Wi-Fi, air conditioning, and cable TV.
Our Favorite Family-Friendly Vacation Rentals in Anna Maria, FL
These family-friendly vacation rentals in Anna Maria, FL offer spacious layouts and easy access to local beaches.
9.8 17 reviews
Anna Maria, FL
08/04 – 08/06
$1083/nighttotal: $2166 (2 )
8 Palms: Gorgeous Heated Pool And Lounge Area, With Putt-putt!
3 2
apartment , Anna Maria
This Anna Maria Island vacation home offers easy access to Anna Maria Beach, a 15-minute walk from the Anna Maria Island Museum and Historic Green Village, and a short drive from Bean Point Beach. The 1,120-square-foot property features three bedrooms, two bathrooms, sleeps eight, and includes a private pool, Jacuzzi, tennis court, and fully equipped kitchen; barbecue grills are available for outdoor cooking.
Anna Maria, FL
06/20 – 06/27
$228/nighttotal: $1596 (7 )
Anna Maria's Dream: Ground Level, Close To Everything!
2 2
apartment , Holmes Beach
This 2-bedroom, 2-bathroom cottage in Holmes Beach is a 10-minute walk to the Gulf beach and a 2-minute walk to tennis courts, pickleball courts, and a playground. This family-friendly rental accommodates up to 6 guests and features a sunroom with an additional twin bed and trundle, a backyard with a dining table, air conditioning, and parking for 2 cars.
10 18 reviews
Anna Maria, FL
07/19 – 07/23
$645/nighttotal: $2580 (4 )
Best Location! North End Of Anna Maria, Fl , Steps To Beach & Dining , Unit B
2 4
apartment , Anna Maria
This Anna Maria Island duplex is located on the quiet north end of the island, just steps from Bean Point Beach and a short walk to the Rod and Reel Pier. It has earned excellent user ratings for its comfortable accommodations. The two-bedroom, one-bathroom unit offers 990 square feet of space and comfortably sleeps four guests. This Anna Maria Island rental includes amenities like a private heated pool, beach chairs, umbrellas, and coolers, as well as a fully equipped kitchen and free WiFi.
Frequently Asked Questions about vacation rentals in Anna Maria, FL
What are some interesting places to visit in or near Anna Maria, FL?
Anna Maria Island is full of charm! You've got to check out the historic City Pier in Bradenton Beach, where you can often see dolphins playing. For a taste of local history, visit the Anna Maria Island Museum. And if you're looking for a unique shopping experience, head over to the Pine Avenue shops in Anna Maria.
What are the best Airbnb and vacation rentals in Anna Maria, FL?
Which walking or cycling routes are the best in Anna Maria, FL?
The paved path along the Gulf Drive is a popular choice for walking and biking, offering stunning views of the beach. For a more scenic route, try the Anna Maria Island Nature Trail, where you can spot native wildlife. And if you want to explore the island's history, take a walk down the historic streets of Anna Maria.
What are the most popular Airbnbs in Anna Maria, FL?
What sports or outdoor activites can visitors enjoy in and around Anna Maria, FL?
Anna Maria Island is a paradise for outdoor enthusiasts! You can swim, sunbathe, and surf on the beautiful beaches. Try your hand at paddleboarding or kayaking in the calm waters of the Gulf. And for a more adventurous experience, rent a boat and explore the nearby islands.
What are the best vacation rentals with a pool in Anna Maria, FL?
What other towns or cities can be easily accessed from Anna Maria, FL?
You can easily reach nearby cities like Bradenton, Sarasota, and St. Petersburg from Anna Maria Island. Bradenton is just a short drive away and offers a variety of attractions, including the South Florida Museum and the Bishop Museum of Science and Nature. Sarasota is known for its art scene and beautiful beaches, while St. Petersburg is home to the Dali Museum.
What are the best rentals for families and kids in Anna Maria, FL?
What amenities are commonly available in vacation rentals in Anna Maria, FL?
Most vacation rentals in Anna Maria offer a range of amenities to make your stay comfortable. You can expect to find private pools, hot tubs, fully equipped kitchens, laundry facilities, and even private balconies or patios. Many rentals also offer access to beach chairs, umbrellas, and other beach essentials.
What are the best rentals or Airbnbs with a jacuzzi in Anna Maria, FL?
What time of year is best to rent a vacation rental Anna Maria, FL?
The best time to visit Anna Maria Island really depends on your preferences. If you're looking for warm weather and sunshine, the peak season runs from December to April. For a more relaxed and budget-friendly experience, consider visiting during the shoulder seasons, from May to June or September to November.
Destinations nearby
Best Anna Maria, FL vacation rentals with parking
9.4 565 reviews
Anna Maria, FL
08/04 – 08/06
$304/nighttotal: $608 (2 )
South Bay Inn 1
1 2
apartment , Anna Maria
This waterfront condo in Anna Maria offers stunning Gulf of Mexico views and is just minutes from Anna Maria Beach, Bayfront Park, and the Anna Maria City Pier. It has received excellent ratings for its location, cleanliness, and user experience. The apartment features a fully equipped kitchen, a comfortable living area with a sofa bed, laundry facilities, free parking, and internet access. Guests can enjoy the swimming pool, terrace/balcony, and garden. Pets are allowed, making it a great choice for families traveling with furry friends.
10 7 reviews
Anna Maria, FL
07/28 – 08/03
$526/nighttotal: $3156 (6 )
Spacious 4br Retreat W/ 2 King Suites ~ Heated Saltwater Pool ~ Near Ami/img!
4 11
apartment , West Bradenton
This Palma Sola, West Bradenton vacation rental is conveniently located near Anna Maria Island (6.5 miles), IMG Academy (7 miles), and LECOM Park (5.4 miles), offering easy access to beaches and attractions. This four-bedroom, four-bathroom home sleeps twelve, boasting a heated saltwater pool, screened patio, private fenced yard with games, WiFi, washer/dryer, and ample parking for trailers or campers.
9.9 130 reviews
Anna Maria, FL
07/28 – 08/03
$549/nighttotal: $3294 (6 )
Stunning!- Game Room, Pool, Beaches & Full Remodel!
4 11
apartment , Bradenton
This Bradenton vacation home, near the Gulf of Mexico and within three miles of Blake Medical Center, Smugglers Cove Adventure Golf, and The Bishop Museum of Science and Nature, offers convenient access to area attractions. This 2200-square-foot property features four bedrooms, two bathrooms, a private pool, and a fully equipped kitchen, comfortably accommodating larger families or groups with amenities including free Wi-Fi and on-site parking.
10 34 reviews
Anna Maria, FL
07/28 – 08/03
$594/nighttotal: $3564 (6 )
Heated Pool Haven! Fun Games! Near Img & Ami!
4 11
apartment , Bradenton
This Bradenton vacation home, located near Bradenton Beach and just three miles from Blake Medical Center and De Soto National Memorial, offers convenient access to both healthcare and historical sites. This spacious 2,250-square-foot house features four bedrooms, three bathrooms, and can comfortably accommodate up to twelve guests, boasting a private pool, fenced yard, free Wi-Fi, and proximity to a water park.
Neighborhoods and points of interest in Anna Maria, FL
Browse Vacation Rentals with a Pool in Anna Maria, FL
Complement your beach days with a dip in the pool at these premier vacation rentals in Anna Maria, FL.
9.0 73 reviews
Anna Maria, FL
08/04 – 08/06
$817/nighttotal: $1634 (2 )
Beach To Bay Getaway
4 2
house , Anna Maria
This vacation home is a 13-minute walk from Anna Maria Island and a 9-minute walk from Anna Maria City Pier, putting you close to the island's main attractions. This property has received excellent ratings for location, cleanliness, and overall experience. This 4-bedroom dwelling comfortably accommodates up to 8 guests. Enjoy a private pool, a fully equipped kitchen, free Wi-Fi, air conditioning, and nearby cycling trails.
9.0 24 reviews
Anna Maria, FL
08/04 – 08/06
$1023/nighttotal: $2046 (2 )
Bellablu: A Waterfront Haven, The Ideal Retreat For Your Next Getaway!
4 2
apartment , Anna Maria
This Anna Maria Island vacation home is centrally located, less than a mile from Bay Boulevard Beach and Anna Maria Beach, and a 15-minute drive from Anna Maria City Pier and Bayfront Park. This four-bedroom, four-bathroom rental boasts a private pool, fitness center, tennis court, and is equipped with free WiFi, a full kitchen, and can comfortably accommodate eight guests, perfect for families seeking a relaxing beach getaway.
9.7 78 reviews
Anna Maria, FL
07/19 – 07/23
$351/nighttotal: $1404 (4 )
Sugary Sands 1 Bed Condo And One Block To Beach!
1 4
apartment , Bradenton Beach
This Bradenton Beach condo boasts a prime waterfront location, steps from the Bradenton Beach Marina, Bridge Street's shops and restaurants, and a short walk from the Bridge Street Pier. The 590-square-foot unit features one bedroom, one bathroom, sleeps four, includes a fully equipped kitchen, in-unit laundry, a balcony, and access to a swimming pool; enjoy nearby attractions like Fish Hole Adventure Golf.
9.3 34 reviews
Anna Maria, FL
07/19 – 07/23
$3121/nighttotal: $12484 (4 )
Precious Memories 753 Jacaranda Rd
5 4
house , Anna Maria
Precious Memories, a 3,120-square-foot Anna Maria Island vacation home, is a short walk from Anna Maria Island's beaches and the Anna Maria City Pier, and is 18 miles from Sarasota Bradenton International Airport. This pet-friendly rental boasts a private pool, jacuzzi, spa, fitness center, and tennis court, along with a fully equipped kitchen and all the comforts of home.
Top-Rated Oceanfront Vacation Rentals in Anna Maria, FL
Discover charming seaside vacation rentals in Anna Maria, FL near the coast. Browse our favorite coastal picks to find your perfect beach-town match.
9.6 13 reviews
Anna Maria, FL
07/28 – 08/03
$603/nighttotal: $3618 (6 )
Funky Flamingo! Beach Gear And Heated Pool
4 11
apartment , Bradenton
9.6 185 reviews
Anna Maria, FL
06/20 – 06/27
$198/nighttotal: $1386 (7 )
Steps To Gulf. Shared Heated Pool. Holmes Beach.
1 2
apartment , Holmes Beach
8.5 11 reviews
Anna Maria, FL
07/19 – 07/23
$374/nighttotal: $1496 (4 )
Gone Coastal: *3 Mins To Beach *Pet-friendly
2 4
apartment , Anna Maria
9.9 36 reviews
Anna Maria, FL
07/28 – 08/03
$735/nighttotal: $4410 (6 )
Bay View,manatees,pool, Recroom,large Home,fishing
1 11
apartment , Bradenton
Top-Rated 5-Star Vacation Rentals in Anna Maria, FL
Refined interiors and prime locations make these luxury waterfront vacation rentals in Anna Maria, FL the ideal choice for your stay.
8.0 1 review
Anna Maria, FL
07/19 – 07/23
$363/nighttotal: $1452 (4 )
Bay Cottage
1 4
house , Anna Maria
Best Vacation Rentals with a Steam Room in Anna Maria, FL
Maximize your recovery with an on-site sauna, a standard feature at these premier Anna Maria, FL vacation rentals.
