Compare best Airbnb in Anna Maria Island, FL from 100+ providers!
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Best Vacation rentals and Airbnb offers in Anna Maria Island, FL
9.7 14 reviews
Anna Maria Island, FL
06/27 – 06/28
$1300/nightfor 1 night
Nirvana Sunset~across From Beach, Heated Pool/spa!
4 8
apartment , Holmes Beach
This Holmes Beach residence is located on Avenue E, offering convenient access to the Gulf coast within a residential neighborhood. This family-friendly rental accommodates up to 8 guests and features a private heated pool, a rooftop deck with Gulf views, a chef's kitchen with GE Monogram appliances, and complimentary beach amenities.
9.2 91 reviews
Anna Maria Island, FL
08/30 – 09/03
$285/nighttotal: $1140 (4 )
Getaway Retreat A+b · 4br · Firepit · Bay
2 5
apartment , Bradenton Beach
This Bradenton Beach vacation home is just a 5-minute walk from Anna Maria Sound and the beach, making it ideal for enjoying the area's natural beauty. Guests consistently rate the property as very good for cleanliness, location, and overall experience. The home has 4 bedrooms and a sofa bed, providing ample space for families or groups of friends, and it features a fully equipped kitchen, a private pool, and a terrace with a garden, perfect for relaxing and enjoying the Florida sunshine.
10 67 reviews
Anna Maria Island, FL
07/18 – 07/25
$226/nighttotal: $1582 (7 )
Near Img - Shorewalk Unit 202 By Seabreeze Vacation
2 2
apartment , Bradenton
This Bradenton apartment is conveniently located near the sea, just a short distance from both Arcadeland and the IMG Academy. It has earned an excellent user rating, indicating a high level of satisfaction from previous guests. The two-bedroom apartment comfortably accommodates four guests. It features a fully equipped kitchen, a balcony, a spa tub, and access to a swimming pool, tennis court, and barbecue grills, ensuring a comfortable and enjoyable stay.
Anna Maria Island, FL
06/27 – 06/28
$1142/nightfor 1 night
Casa Del Sol
1 8
apartment , South Bradenton
This South Bradenton house is located 2 miles from the downtown Bradenton waterfront, 15 miles from Anna Maria Island beaches, and 20 miles from the Ringling Museum of Art and Sarasota Jungle Gardens. This 4-bedroom, 2-bathroom rental accommodates up to 8 guests and features internet, a kitchen, air conditioning, a swimming pool, and parking.
10 34 reviews
Anna Maria Island, FL
07/17 – 07/24
$373/nighttotal: $2611 (7 )
Pool & Play Oasis~ All The Amenities & Near Ami!
1 7
apartment , West Bradenton
This 3-bedroom apartment in West Bradenton is located 8 minutes from Manatee Public Beach on Anna Maria Island, 11 minutes from Bradenton Beach, and 9 minutes from Robinson Nature Preserve. This rental offers a private heated pool, hot tub, game room with a pool table, foosball, and dartboard, a putting green, and a basketball hoop, accommodating up to 10 guests with included beach gear, linens, and towels.
9.1 163 reviews
Anna Maria Island, FL
07/08 – 07/15
$263/nighttotal: $1841 (7 )
Gulfside 2br Condosilver Sands #257s
1 2
apartment , Longboat Key
Silver Sands #257s Resort By Rva is located on Longboat Key, a short walk from Longboat Key Beaches and Cannons Marina, with Coquina Beach and Bradenton Beach within a short drive. This property has received excellent user ratings for location and overall experience, with a very good rating for cleanliness. The condo offers two bedrooms, a sofa bed, and a fully equipped kitchen. Enjoy amenities like a swimming pool, tennis court, garden, barbecue grills, and free Wi-Fi.
10 2 reviews
Anna Maria Island, FL
06/27 – 06/28
$995/nightfor 1 night
Free Heated Pool, Mini Golf Course, Full Arcade, Hot Tub, Ami 6 Miles, Img 3 Mi
3 8
apartment , South Bradenton
This South Bradenton rental is ideally situated just three miles from IMG Academy and six miles from Anna Maria Island, offering easy access to beaches and attractions. This 1500-square-foot apartment sleeps nine guests and boasts three bedrooms, two bathrooms, a private pool, and access to on-site amenities including a heated pool, mini golf, and a fitness center.
10 8 reviews
Anna Maria Island, FL
07/02 – 07/05
$1765/nighttotal: $5295 (3 )
Family - Hottub - Sauna - Pickleball - Game Room
5 6
apartment , Bradenton
This 5-bedroom, 3-bathroom vacation home in Bradenton is located a short drive from Bradenton Beach and Anna Maria Island, and is close to downtown Bradenton attractions and IMG Academy. This spacious rental offers a private backyard oasis with a pool, hot tub, and sauna, along with extensive recreational amenities including pickleball, basketball, mini golf, and bowling, accommodating up to 16 guests.
10 4 reviews
Anna Maria Island, FL
07/02 – 07/05
$1386/nighttotal: $4158 (3 )
Designer Pool Home Guest House Near Ami
4 6
apartment , West Bradenton
This West Bradenton vacation home, located in Palma Sola, is a 10-minute drive from Anna Maria Island beaches and 5-15 minutes from Downtown Bradenton and IMG Academy. The 2,600-square-foot property features four bedrooms, four bathrooms, and sleeps up to 11 guests, boasting a heated pool, spa, a 4-person arcade game, and beach gear for family fun.
10 53 reviews
Anna Maria Island, FL
07/11 – 07/25
$426/nighttotal: $5964 (14 )
Riverside Château | Pool, Game Room + Near Ami
4 7
apartment , West Bradenton
This four-bedroom West Bradenton home, located 2.7 miles from Downtown Bradenton, 4.6 miles from IMG Academy, and 7.4 miles from Anna Maria Island beaches, offers a secluded retreat near major attractions. This vacation rental boasts a private heated saltwater pool, game room, fully equipped kitchen, and beach gear, comfortably accommodating up to 12 guests with amenities like pack 'n plays and a highchair.
9.6 91 reviews
Anna Maria Island, FL
07/17 – 07/24
$195/nighttotal: $1365 (7 )
Ed-pool, Tennis, Pickle Ball, Near Beaches And Img, Shorewalk Condo 2 Bedroom/2 Bath Lake View
2 2
apartment , Bradenton
This Bradenton waterfront condo, located five minutes from IMG Academy and fifteen minutes from Anna Maria Island and Longboat Key beaches, offers easy access to area attractions. The 1,170-square-foot unit features two bedrooms, four bathrooms, and accommodates four guests, boasting a private terrace, swimming pool, Jacuzzi, and tennis court access.
10 2 reviews
Anna Maria Island, FL
06/28 – 07/03
$431/nighttotal: $2155 (5 )
172 M² House ∙ 3 Bedrooms ∙ 8 Guests
3 8
house , West Bradenton
This West Bradenton rental is located in the Palma Sola area, approximately 6 miles from Anna Maria Island beaches and 3 miles from Palma Sola Causeway, with nearby access to De Soto National Memorial Park and Robinson Preserve. This 1840 sq ft house accommodates up to 8 guests with 3 bedrooms and 2 bathrooms, featuring a screened-in heated pool and spa, a fully stocked kitchen, and kid-friendly amenities.
Best family friendly Anna Maria Island, FL vacation rentals
Among the 6231 accommodations in Anna Maria Island, FL, here are the 4 best family friendly rentals
10 2 reviews
Anna Maria Island, FL
06/27 – 06/28
$985/nightfor 1 night
Fenced Dog-friendly Coastal Home With Pool & Game Room
4 8
house , Bayshore Gardens
This house in Bayshore Gardens is situated 5.2 miles from the John and Mable Ringling Museum of Art and the Sarasota International Convention Center, and 4.8 miles from Greens of Manatee Golf Club, offering convenient access to local attractions and Sarasota Bradenton International Airport, just 3.1 miles away. This accommodation features 4 bedrooms and 3 bathrooms, accommodating up to 19 guests with amenities including a fully equipped kitchen with a dishwasher and microwave, air conditioning, free Wi-Fi, and an outdoor swimming pool and fireplace.
9.6 250 reviews
Anna Maria Island, FL
06/28 – 06/29
$899/nightfor 1 night
Newly Renovated Sea Breeze Cottage With Private Dock, Easy Access To Bimini Bay
2 2
cottage , Anna Maria
This waterfront cottage is conveniently located on Anna Maria Island, just a 15-minute walk from Bay Boulevard Beach, Anna Maria City Pier, and Bayfront Park, making it easy to access the island's top attractions. Guests rave about the excellent location, cleanliness, and overall experience. The 1100 square foot cottage comfortably sleeps up to 6 guests in its 2 bedrooms and 2 bathrooms. Enjoy a fully equipped kitchen, a relaxing jacuzzi, and a private terrace or balcony for outdoor dining and relaxation.
This Palmetto vacation rental offers 4 bedrooms and 2 bathrooms, accommodating up to 8 guests and is conveniently located near fishing, a marina, Emerson Point Preserve (a 14-minute walk, approximately 7,392 feet), and the Manatee County Agricultural Museum (a 6-minute drive). This pet-friendly house features a private pool, garden, fire pit, barbecue, foosball, Wi-Fi, a full kitchen with an oven, stovetop, refrigerator, coffee maker, ice maker, and microwave, plus an in-unit washer and dryer for guest convenience.
9.3 3 reviews
Anna Maria Island, FL
06/28 – 07/03
$521/nighttotal: $2605 (5 )
Bloom Lagoon! Tropical Home With Heated Pool And Grill! Pet Friendly!
3 8
house , Bradenton
This Bradenton vacation home, near Palma Sola Causeway Park (1.6 miles) and within 30 miles of The Ringling Museum, The Dali Museum, and Tropicana Field, offers convenient access to major attractions. This 1,910-square-foot property boasts three bedrooms, two bathrooms, sleeps up to 15 guests, and features a heated pool, grill, and fully equipped kitchen with a dishwasher, plus free Wi-Fi.
Best Anna Maria Island, FL vacation rentals with a pool
Among the 6231 accommodations in Anna Maria Island, FL, here are the 4 best rentals with a pool
9.5 1699 reviews
Anna Maria Island, FL
08/30 – 09/03
$236/nighttotal: $944 (4 )
Anna Maria Island Beach Palms 2b
2 5
apartment , Bradenton Beach
This beachfront rental is located in Bradenton Beach, just a short distance from Bradenton Beach, Cortez Beach, and Coquina Beach, offering easy access to the area's best attractions. The apartment has received excellent ratings for its location, cleanliness, and overall experience. The rental features a private heated pool, a garden with a balcony, and a fully equipped kitchen. Enjoy a range of amenities, including a playground for kids, free Wi-Fi and parking, and access to cycling trails.
9.8 58 reviews
Anna Maria Island, FL
07/11 – 07/25
$337/nighttotal: $4718 (14 )
Heated Pool/spacious Lanai/near Ami Beaches & Img
1 7
apartment , Bradenton
This Bradenton vacation home, near Anna Maria Island (15 minutes), IMG Academy (10 minutes), and Robinson Preserve (9 minutes), offers easy access to beaches, sports facilities, and nature. The four-bedroom, two-bathroom house sleeps eight, features a recently retiled pool, a large screened lanai, a fully equipped kitchen, high-speed internet (500 Mbps), and numerous family-friendly amenities including a firepit, games (foosball, ping pong, cornhole, Connect Four), and beach gear.
8.9 134 reviews
Anna Maria Island, FL
06/28 – 06/29
$444/nightfor 1 night
Silver Sands #245a Resort By Rva
1 2
apartment , Longboat Key
Silver Sands #245a Resort By Rva is located on Longboat Key, just a short walk from Longboat Key Beaches and Cannons Marina, offering a peaceful escape from the hustle and bustle of city life. The resort consistently receives excellent ratings for its cleanliness, location, and overall user experience. This smoke-free apartment building provides guests with comfortable accommodations featuring a fully equipped kitchen, a washing machine, and a TV with a DVD player. Enjoy the Florida sunshine and socialize in the tranquil garden and barbecue grills, or take advantage of the resort's amenities like the swimming pool, tennis court, and free Wi-Fi.
9.9 411 reviews
Anna Maria Island, FL
09/24 – 09/27
$414/nighttotal: $1242 (3 )
Paradise Cove -- A Perfect Beach Getaway
3 8
apartment , Bradenton
This family-friendly vacation rental is located in Bradenton, just a short distance from attractions like Smugglers Cove Adventure Golf, arcadeland, and The Bishop Museum of Science and Nature. The property has received excellent ratings for its location, cleanliness, and overall experience. This 3-bedroom home with a sofa bed offers ample space for families or groups of friends. It features a private pool and patio, a fully equipped kitchen, a fireplace, and outdoor amenities like a garden and barbecue grills for enjoying the Florida sunshine.
Frequently Asked Questions about vacation rentals in Anna Maria Island, FL
What are the must-see sights on Anna Maria Island, Florida?
Anna Maria Island boasts beautiful beaches, of course! The Bean Point is a must-see for its stunning sunsets and views. The Anna Maria City Pier is a great place to fish or just relax and watch the Gulf. Historic Bridge Street in Bradenton Beach offers unique shops and restaurants. And don't forget to explore the nature preserves like the Anna Maria Island Nature Preserve and the Leffis Key Preserve.
What are the best Airbnb and vacation rentals in Anna Maria Island, FL?
Are there unique natural phenomena on Anna Maria Island, Florida?
The island's location on the Gulf Coast means you'll see amazing sunsets. The beaches are known for shelling, with a variety of shells washing ashore. You might even spot dolphins playing in the waters near the shore. Birdwatching is also popular, with various species frequenting the island's natural areas.
What are the most popular Airbnbs in Anna Maria Island, FL?
What essentials should you bring along for a trip to Anna Maria Island, Florida?
Pack light clothing, swimwear, sunscreen, sunglasses, a hat, and comfortable walking shoes. Don't forget insect repellent, especially for evenings. A beach umbrella and beach chairs will make your beach days more enjoyable. And of course, a camera to capture those amazing sunsets!
What are the best vacation rentals with a pool in Anna Maria Island, FL?
What famous events or festivals are happening on Anna Maria Island, Florida?
Anna Maria Island doesn't have large-scale, internationally known festivals. However, throughout the year, smaller local events take place, including the annual Christmas boat parade and various art walks. Check local event listings closer to your travel dates for the most up-to-date information.
What are the best rentals for families and kids in Anna Maria Island, FL?
What is the average daily budget you should plan for (accommodation, food, transportation, activities) on Anna Maria Island, Florida?
A daily budget can vary greatly depending on your travel style. For a comfortable trip, expect to spend around $150-$300 per person per day. This includes mid-range accommodation, meals, some activities, and local transportation. Budget-conscious travelers could likely manage on less, while luxury travelers will spend significantly more.
What are the best rentals or Airbnbs with a jacuzzi in Anna Maria Island, FL?
Where can you find the best restaurants serving local dishes on Anna Maria Island, Florida, and what are the must-try specialties?
The Beach Bistro is a fine-dining establishment known for its fresh seafood. Rod & Reel Pier offers casual dining with waterfront views. Many restaurants feature fresh seafood, which is a local specialty. Key lime pie is a must-try dessert, reflecting Florida's citrus heritage.
What are some less-famous attractions on Anna Maria Island, Florida that are worth the visit?
The Anna Maria Island Historical Society Museum offers a glimpse into the island's past. Exploring the quieter beaches away from the main tourist areas provides a more peaceful experience. Take a leisurely bike ride along the island's scenic paths. Consider kayaking or paddleboarding through the mangroves.
What are the best activities for engaging with locals and understanding their culture on Anna Maria Island, Florida?
Visiting local shops and art galleries allows you to interact with business owners. Attending smaller community events offers opportunities to meet residents. Simply striking up conversations with people you meet on the beach or in restaurants can provide insights into island life. The laid-back atmosphere makes it easy to connect with people.
What unique natural landscapes and terrain features can travelers explore on Anna Maria Island, Florida?
Anna Maria Island features beautiful beaches with soft, white sand. The mangrove forests provide unique ecosystems to explore via kayak or paddleboard. The island's relatively flat terrain makes it easy to explore on foot or by bike.
How many days are ideal for visiting Anna Maria Island, Florida, and what are some itinerary suggestions?
Three to five days is a good amount of time to explore Anna Maria Island at a relaxed pace. Spend a day relaxing on the beach, another exploring Bridge Street, and perhaps a day kayaking or visiting the nature preserves. Consider a sunset cruise for a memorable experience.
Nearby regions
Best Anna Maria Island, FL vacation rentals with a balcony
9.9 108 reviews
Anna Maria Island, FL
09/24 – 09/27
$444/nighttotal: $1332 (3 )
Pond-side 4br Oasis W/ Private Pool + Pickleball!
4 8
apartment , Bradenton
This pet-friendly designer home is located in Bradenton, a short distance from the downtown area, the River Walk, and the Village of the Arts. The property has received excellent ratings for location, cleanliness, and overall user experience. This 4-bedroom, 3-bathroom vacation rental spans 2,200 square feet and comfortably accommodates up to 10 guests. Enjoy amenities like a private pool, a spacious backyard, a fully equipped kitchen, and beach gear provided for your convenience.
Anna Maria Island, FL
06/27 – 06/28
$531/nightfor 1 night
Mid Mod Getaway
3 6
house , West Bradenton
This 1700 sq ft, 3-bedroom house in West Bradenton offers a private pool, garden views, and complimentary bikes, located 11-12 miles from Sarasota International Convention Center, John and Mable Ringling Museum of Art, and Sarasota Bradenton International Airport. This family-friendly vacation rental accommodates up to 11 guests with a well-equipped kitchen, free WiFi, and indoor/outdoor play areas, making it ideal for exploring the West Bradenton area.
9.8 53 reviews
Anna Maria Island, FL
11/06 – 11/08
$418/nighttotal: $836 (2 )
Beach Castle Resort, Pool, Private Beach And Bayfront
2 2
apartment , Longboat Key
Beach Castle Resort, a Longboat Key condo offering stunning waterfront views, is located less than a mile from Longboat Key beaches and Cannons Marina, with Jewfish Key a short 3.1-mile drive away. This 710-square-foot one-bedroom, one-bathroom unit sleeps four and boasts a fully equipped kitchen, Smart TV, in-unit laundry, and access to resort amenities including a pool, tennis court, spa, and concierge services.
Anna Maria Island, FL
06/27 – 07/04
$139/nighttotal: $973 (7 )
Yacht Time
1 2
yacht , Bradenton
The Yacht Time cottage, a pet-friendly boat rental in Bradenton, Florida, is located 5 miles from the city center, offering a quiet escape. This one-bathroom vessel accommodates two guests and features a microwave, air conditioning, a terrace, a garden, barbecue area, and on-site parking.
Best Anna Maria Island, FL vacation rentals with parking
10 6 reviews
Anna Maria Island, FL
06/28 – 07/03
$431/nighttotal: $2155 (5 )
191 M² House ∙ 4 Bedrooms ∙ 8 Guests
4 8
house , Bradenton
This Bradenton house rental boasts a central location, less than 20 minutes from Sarasota-Bradenton International Airport and a short drive to Anna Maria Island, downtown Bradenton, and Lakewood Ranch. This 2,050-square-foot vacation home features four bedrooms, two bathrooms, sleeps eight guests, and includes a private pool, spa, and fully equipped kitchen with stainless steel appliances; high-speed Wi-Fi and a smart lock are also provided.
9.8 58 reviews
Anna Maria Island, FL
07/08 – 07/15
$188/nighttotal: $1316 (7 )
Luxury Lakefront Condo, Resort Amenities, 10 Minutes To Beach
2 2
apartment , Bradenton
This lakefront condo is located in the Shorewalk Resort Complex in Bradenton, a short 10-minute drive from the Gulf of Mexico beaches and approximately 6 minutes from IMG Academies. This property has earned an excellent user rating, ensuring a comfortable and enjoyable stay. This two-bedroom, two-bathroom apartment spans 1250 square feet, comfortably accommodating up to four guests. The condo offers numerous amenities, including a fully-equipped kitchen, a private lanai with lake views, access to two heated pools, two hot tubs, two tennis courts, and a clubhouse with various activities.
9.3 65 reviews
Anna Maria Island, FL
07/17 – 07/24
$171/nighttotal: $1197 (7 )
Simply Adorable, Spacious And Cozy Beach Home
2 2
apartment , Cortez
This Cortez vacation home is located near the beach, within 3 miles of Arcadeland, Manatee Golf Course, and Blake Medical Center, and within 6 miles of IMG Academy and Anna Maria Sound, offering easy access to various activities and amenities. The house has received excellent ratings for location, cleanliness, and user experience. The property features two bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy the Florida sunshine with the outdoor charcoal grills, prepare meals in the fully equipped kitchen, and stay connected with free Wi-Fi throughout the house and public areas.
10 17 reviews
Anna Maria Island, FL
06/27 – 07/04
$195/nighttotal: $1365 (7 )
Eh-near Beaches And Img, Pool, Tennis, Pickleball
2 2
apartment , Bradenton
This Bradenton condo, located in the Shorewalk complex, offers easy access to Anna Maria Island and Longboat Key beaches (15-minute drive) and IMG Academy (5-minute drive). The 1170-square-foot apartment features two bedrooms, two bathrooms, and sleeps four, boasting resort amenities including heated pools, Jacuzzis, and tennis/pickleball courts.
