6231 Holiday rentals and Airbnb in Anna Maria Island, FL
9.5 240 reviews
Anna Maria Island, FL
03/08 – 07/08
A$548/nightTotal: A$2192 (4 )
3 Bedrooms with Gulf Views Unit A Steps Away From Beach villa
3 3
house , Bradenton Beach
This charming villa is located just a short walk from the beautiful Bradenton Beach, with easy access to nearby beaches like Holmes Beach and Cortez Beach. The property has received excellent ratings for location, cleanliness, and overall user experience. The 139 square metre villa can comfortably accommodate up to 6 guests and features three bedrooms and two bathrooms. You can enjoy a range of amenities, including a private balcony, a fully equipped kitchen, air conditioning, a spa, and free parking.
10 4 reviews
Anna Maria Island, FL
10/07 – 12/07
A$933/nightTotal: A$1866 (2 )
Stay Muse, 4br Retreat, Pool, Fire Pit & Mini Golf
1 7
apartment , Bradenton
This four-bedroom, two-bathroom holiday home in Bradenton offers comfortable accommodation for up to 12 guests, featuring a private backyard with a swimming pool, mini golf, and fire pit, as well as a dedicated game room with ping pong and arcade machines. Families will appreciate the provided crib, high chair, and children's dinnerware, while pet owners can bring small to medium dogs, and all guests benefit from high-speed WiFi and ample parking for up to four vehicles.
9.9 145 reviews
Anna Maria Island, FL
03/08 – 07/08
A$469/nightTotal: A$1876 (4 )
Waterfront Bradenton Home Heated Pool And Fire Pit
3 3
house , Cortez
This Bradenton waterfront property boasts stunning views, situated 13.2 km from Anna Maria City Pier and 16 km from Sarasota Bradenton International Airport. The 155 square metre house offers three bedrooms, a fully equipped kitchen including dishwasher and microwave, a heated pool, spa, and private parking, perfect for families or groups seeking a relaxing getaway near Anna Maria Island.
9.7 81 reviews
Anna Maria Island, FL
02/07 – 06/07
A$685/nightTotal: A$2740 (4 )
Sea Salt Retreat! Private Pool Home In Bradenton Just 5 Miles From Anna Maria!
3 5
apartment , West Bradenton
This holiday home is located in Bradenton, just 8 kilometres from the beach and a short drive from Palma Sola Causeway Park, which is 2.2 kilometres away. The property has received excellent ratings for location, cleanliness and overall user experience. The accommodation is 175 square metres in size and offers a range of amenities including a private pool, air conditioning, a fully equipped kitchen, a washing machine, free private parking, an outdoor patio, and access to cycling trails in the area.
9.9 73 reviews
Anna Maria Island, FL
07/10 – 14/10
A$354/nightTotal: A$2478 (7 )
Ami Sand Dollar - 6403 B Holmes
1 4
house , Holmes Beach
This one-bedroom holiday home is situated in Holmes Beach, just a 2.4 kilometre walk from Bradenton Beach and Island Gallery West. The 93 square metre property features a private pool, a fenced-in yard, a full kitchen and a washing machine, as well as access to a nearby water park.
9.5 65 reviews
Anna Maria Island, FL
03/08 – 07/08
A$298/nightTotal: A$1192 (4 )
Kapok In Bradenton
2 3
apartment , Cortez
This family-friendly holiday home is situated in Bradenton, just 3km from the Florida Maritime Museum at Cortez, H2O Watersportz, and Anna Maria Sound. The property has excellent user, location and cleanliness ratings. This two-bedroom home, with a floor area of 155 square metres, comfortably accommodates up to four guests. Amenities include a fully equipped kitchen, three bathrooms, a washing machine, a balcony, a TV, a fitness centre, concierge services, a garden, barbecue grills, a tennis court, and parking.
9.7 99 reviews
Anna Maria Island, FL
27/06 – 28/06
A$711/nightfor 1 night
Tortuga 2 Bedroom Deluxe Partial View
2 6
apartment , Bradenton Beach
This Bradenton Beach flat is conveniently located near the beach and bay, offering easy access to local attractions. The 111.5 square metre self-catering apartment sleeps up to four guests and features a full kitchen, lanai with partial sea views, in-unit laundry, and a luxurious bathroom with jacuzzi tub.
9.2 93 reviews
Anna Maria Island, FL
11/07 – 25/07
A$409/nightTotal: A$5726 (14 )
Water Slide & Pool ** Sugarcane Hideaway**
3 7
apartment , Bradenton
This 3-bedroom house is located near the beach in Bradenton, within easy reach of attractions like Blake Medical Center, LECOM Park, and Riverwalk. It has received excellent ratings for location, cleanliness, and overall experience. The property offers a private garden and a swimming pool, perfect for relaxing after a day exploring Bradenton. Guests can also enjoy the convenience of a fully equipped kitchen, a terrace, and free Wi-Fi.
10 75 reviews
Anna Maria Island, FL
27/06 – 28/06
A$1292/nightfor 1 night
Heated Pool•mini Golf•arcade•spa•ami 6mi•img
3 8
apartment , South Bradenton
This three-bedroom, two-bathroom South Bradenton holiday home is situated in a peaceful neighbourhood, approximately 13 kilometres from Anna Maria Island, 6 kilometres from IMG Academy, and 10 kilometres from the Bradenton Riverwalk. Sleeping up to nine guests, the property boasts a private heated swimming pool, hot tub, mini-golf course, outdoor cinema, backyard arcade, fully equipped kitchen with beach essentials, and amenities including Netflix and high-speed internet.
8.8 93 reviews
Anna Maria Island, FL
05/01 – 12/01
A$269/nightTotal: A$1883 (7 )
Bay View Inn 202
1 2
apartment , Bradenton Beach
Bay View Inn 202 is located in Bradenton Beach, just a short walk from Cortez Beach and less than a kilometre from Coquina Beach, offering a peaceful setting close to the beach. The hotel has received very good user ratings, with excellent location and cleanliness scores. The apartment is 51 square metres and can accommodate up to four guests. It features a kitchen, a terrace, a garden, a swimming pool, parking, and free Wi-Fi, as well as a comfortable seating area and a private bathroom.
9.4 50 reviews
Anna Maria Island, FL
05/01 – 12/01
A$440/nightTotal: A$3080 (7 )
Coastal Comfort Beach Castle #26 By Rva
1 2
apartment , Longboat Key
Beach Castle Resort #26 By Rva is located on the waterfront of Longboat Key, just under 2 kilometres from Longboat Key Beaches and Cannons Marina, and about 5 kilometres from Jewfish Key. This smoke-free apartment building has excellent ratings for location, cleanliness and user experience. The apartment has one bedroom and one bathroom, accommodating up to four guests. It offers a full kitchen, a TV with a DVD player, a comfortable sofa bed, laundry facilities, a spa tub, a swimming pool, a tennis court and free parking.
9.0 51 reviews
Anna Maria Island, FL
28/06 – 29/06
A$634/nightfor 1 night
Charming 1-bedroom, Beachfront Condo In Marvelous Longboat Key
1 2
apartment , Longboat Key
This beachfront Longboat Key flat offers stunning Gulf views and is located steps from the beach, with St. Armands Circle and the Mall at University Town Centre a short drive away. The one-bedroom, one-bathroom apartment sleeps four guests and features a full kitchen, private balcony, access to a heated pool, and complimentary parking; nearby attractions include Lido Beach, Bradenton Beach, Mote Marine Laboratory & Aquarium, and Marie Selby Botanical Gardens.
Best family friendly Anna Maria Island, FL holiday rentals
Among the 6231 accommodations in Anna Maria Island, FL, here are the 4 best family friendly rentals
10 6 reviews
Anna Maria Island, FL
26/06 – 30/06
A$686/nightTotal: A$2744 (4 )
191 M² House ∙ 4 Bedrooms ∙ 8 Guests
4 2
house , Bradenton
This Bradenton property, centrally located within a short drive (under 32km) of Sarasota-Bradenton International Airport and Anna Maria Island, offers easy access to beaches, Sarasota, Tampa, and Lakewood Ranch. This four-bedroom, two-bathroom house boasts 190 square metres of living space, sleeping up to eight guests and featuring a private pool, spa, and fully equipped kitchen; high-speed Wi-Fi and a self check-in smart lock are also provided.
10 205 reviews
Anna Maria Island, FL
27/07 – 29/07
A$520/nightTotal: A$1040 (2 )
Sunshine Oasis With Heated Saltwater Pool
3 5
apartment , Bradenton
This three-bedroom apartment is located just 9.6km from Anna Maria Island, a popular destination for its beautiful beaches and charming atmosphere, and within easy reach of Bradenton's other attractions. The apartment offers a fully equipped kitchen, a private backyard with a saltwater pool, and a two-stall garage with a security camera, making it ideal for families or groups of up to six people.
9.4 165 reviews
Anna Maria Island, FL
27/07 – 29/07
A$658/nightTotal: A$1316 (2 )
Water Slide & Pool ** Sugar Shack**
3 5
apartment , Bradenton
This Bradenton property is conveniently located within 5 kilometres of Blake Medical Center, LECOM Park, and Riverwalk, offering easy access to the area's attractions. The property has consistently received excellent guest ratings for its location, cleanliness, and overall experience. The house features three bedrooms, providing comfortable accommodation for families or groups of friends. Guests can enjoy a range of amenities, including a private garden, a swimming pool, a jacuzzi, and a fully equipped kitchen.
9.9 56 reviews
Anna Maria Island, FL
28/06 – 29/06
A$339/nightfor 1 night
Between The Tides Ami
1 2
apartment , Cortez
This cosy one-bedroom apartment in Sunny Shores/Sagamore Estates, Cortez, is situated approximately 1.6 kilometres from Anna Maria Island's Gulf Coast beaches and the historic Cortez Fishing Village. Sleeping four, it offers a compact open-plan layout with a kitchen (fridge, freezer, microwave), laundry facilities, a screened lanai and patio, plus access to a clubhouse with gym equipment and a pool table; beach essentials are provided.
Best Anna Maria Island, FL holiday rentals with a pool
Among the 6231 accommodations in Anna Maria Island, FL, here are the 4 best rentals with a pool
9.5 53 reviews
Anna Maria Island, FL
17/07 – 24/07
A$312/nightTotal: A$2184 (7 )
Beautiful Florida Condo Near Beach In Bradenton
2 2
apartment , Bradenton
This two-bedroom apartment is situated in a resort-style community in Bradenton, just a short walk from the clubhouse, pools, spas, tennis courts, and BBQ facilities. It has received excellent ratings for its location, cleanliness, and overall experience. The apartment comfortably accommodates four guests and features a king-size bed in the master bedroom and twin beds in the second bedroom. Guests can enjoy a range of amenities, including a fully equipped kitchen, a washer and dryer, free Wi-Fi, and access to a swimming pool, jacuzzi, fitness centre, and garden.
9.0 1 review
Anna Maria Island, FL
26/06 – 30/06
A$573/nightTotal: A$2292 (4 )
Aqua Breeze
3 2
house , Bradenton
Aqua Breeze, a Bradenton holiday home, is conveniently located 12 kilometres from Sarasota Bradenton International Airport and 15 kilometres from the Ringling Museum of Art. This three-bedroom, two-bathroom property boasts 145 square metres of living space, accommodating up to 11 guests and featuring a private swimming pool, tennis court, and balcony; an ATM is also available on-site.
9.7 80 reviews
Anna Maria Island, FL
28/06 – 29/06
A$852/nightfor 1 night
Sugary Sands 1 Bed Condo And One Block To Beach!
1 2
apartment , Bradenton Beach
This Bradenton Beach apartment boasts a prime waterfront location, steps from Bradenton Beach Marina, Bridge Street, and Fish Hole Adventure Golf, with Bradenton Beach and the Historic Bridge Street Pier within 800 metres. The 55 square metre flat features one bedroom, one bathroom, sleeps four, and includes a fully equipped kitchen, laundry facilities, a balcony, free Wi-Fi, and access to a swimming pool and garden.
10 83 reviews
Anna Maria Island, FL
17/07 – 24/07
A$498/nightTotal: A$3486 (7 )
Driftwood & Sunsets - Modern Beach House - Heated Pool - Minutes From The Beach
3 7
apartment , Bradenton
This family-friendly holiday home is located in Bradenton, just a few kilometres from Blake Medical Center and arcadeland, and less than 10 kilometres from the Bishop Museum of Science and Nature and Smugglers Cove Adventure Golf. The property has received excellent ratings for user experience, location, and cleanliness. The house has 3 bedrooms and 2 bathrooms, offering comfortable accommodation for up to 8 guests across 177 square metres. This property has a range of amenities, including a private pool, spa, BBQ facilities, a garden, and a terrace, making it ideal for families and groups looking for a relaxing and enjoyable stay.
Frequently asked questions about holiday 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! Bean Point is a must-see for its stunning views and iconic lighthouse. The Anna Maria City Pier offers great fishing and sunset views. For a bit of history, explore the historic Anna Maria City and its charming cottages. The Island's nature preserves, like the Anna Maria Island Nature Preserve, are also worth exploring.
What are the best Airbnb and holiday rentals in Anna Maria Island, FL?
Are there any unique natural phenomena on Anna Maria Island, Florida?
The island's location means you'll see incredible sunsets over the Gulf of Mexico. The beaches themselves are a unique natural phenomenon – the soft, white sand and the diversity of seashells are something special. Keep an eye out for the diverse birdlife in the mangroves and nature preserves.
What are the most popular Airbnbs in Anna Maria Island, FL?
What essentials should you bring to Anna Maria Island, Florida?
Pack light clothing, swimwear, sunscreen (essential!), sunglasses, a hat, insect repellent, and comfortable walking shoes. Don't forget your reusable water bottle to stay hydrated in the Florida sun. A beach towel and beach bag are also a must.
What are the best holiday rentals with a pool 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 will vary greatly depending on your travel style. For a mid-range trip, you could budget around £150-£300 per day for a couple, covering accommodation, meals, some activities and local transport. Budget accommodation and self-catering can significantly reduce costs.
What are the best rentals for families and kids 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 popular choice for fine dining. Rod & Reel Pier offers casual waterfront dining with fresh seafood. For more casual options, explore the many cafes and restaurants along Pine Avenue in Anna Maria. Fresh seafood is a must-try, especially the stone crab claws (seasonal) and grouper sandwiches.
What are the best rentals or Airbnbs with a jacuzzi in Anna Maria Island, FL?
What are some less-famous attractions on Anna Maria Island, Florida that are worth a visit?
The Leffis Key Preserve offers beautiful nature trails and is less crowded than some of the more popular spots. Exploring the quieter sections of the beaches away from the main access points can offer a more secluded experience. Take a bike ride along the island's many scenic paths.
What are the best activities for engaging with locals and understanding their culture on Anna Maria Island, Florida?
Visiting local shops and markets is a great way to interact with residents. Many smaller restaurants and cafes offer a more intimate setting to chat with locals. Attending smaller, community events (check local listings) can provide opportunities to meet people.
What unique natural landscapes and terrain features can travellers explore on Anna Maria Island, Florida?
Anna Maria Island features beautiful beaches, of course, with the Gulf of Mexico on one side and Tampa Bay on the other. The mangrove forests and the various nature preserves offer unique ecosystems to explore. The island itself is quite flat, making it easy to walk or cycle around.
How many days are ideal for a visit to Anna Maria Island, Florida, and what are some itinerary suggestions?
Three to four days is a good amount of time to enjoy the island at a relaxed pace. A possible itinerary could include beach time, exploring Anna Maria City, visiting the Anna Maria Island Nature Preserve, and enjoying some water activities. Consider a sunset cruise or a dolphin watching tour.
Nearby regions
Best Anna Maria Island, FL holiday rentals with a balcony
8.6 38 reviews
Anna Maria Island, FL
27/07 – 29/07
A$579/nightTotal: A$1158 (2 )
2nd-floor Duplex Near Beach With Heated Pool, Grill, Balcony, & W/d
2 5
apartment , Bradenton Beach
This Bradenton Beach apartment, a two-bedroom duplex, is situated two blocks from the beach and less than 1.6km from Bridge Street, home to attractions such as The Fish Hole miniature golf and the Bridge Street Clock Tower. The 70 square metre property boasts a coastal-themed open-plan layout, sleeping up to seven guests and featuring a fully equipped kitchen, two bathrooms, a private balcony, free parking for two cars, a shared heated outdoor pool (requiring 24-hour notice), and a gas grill with an outdoor shower.
10 1 review
Anna Maria Island, FL
03/08 – 07/08
A$387/nightTotal: A$1548 (4 )
Cabana Beach Club #5b
1 3
house , Longboat Key
This holiday home, Cabana Beach Club #5B, is situated in Longboat Key, a mere 200 metres from Longboat Key Beach, 24 kilometres from the John and Mable Ringling Museum of Art, and 27 kilometres from the Sarasota International Convention Centre. This property accommodates up to seven guests and features a swimming pool, a balcony with pool views, a kitchen equipped with a fridge, microwave oven, and dishwasher, air conditioning, complimentary private parking, and free WiFi, with disabled facilities and cycling opportunities available nearby.
9.2 7 reviews
Anna Maria Island, FL
18/07 – 25/07
A$280/nightTotal: A$1960 (7 )
Ab Shorewalk -Pool, Tennis, Pickle Ball, Near Beaches Anna Maria Island And Img
2 2
apartment , Bradenton
This Bradenton lakeside apartment, five minutes from IMG Academy and fifteen minutes (approx. 24km) from Anna Maria Island and Longboat Key beaches, offers convenient access to local attractions. The 109 square metre, two-bedroom, two-bathroom property sleeps four guests and boasts a private terrace, swimming pool, Jacuzzi, and tennis court, alongside a fully equipped kitchen and air conditioning.
9.2 41 reviews
Anna Maria Island, FL
07/08 – 09/08
A$320/nightTotal: A$640 (2 )
Mycataleya Beautiful Florida Condo (Bradenton)
2 2
apartment , Bradenton
This Bradenton condo, near the Greens of Manatee Golf Club (5.3 km) and Sarasota Bradenton International Airport (10 km), offers easy access to the Ringling Museum of Art (13.5 km) and other local attractions. The 100 square metre, two-bedroom property sleeps seven guests and boasts two bathrooms with a hot tub, a private terrace, a fully equipped kitchen, and access to a swimming pool, jacuzzi, and tennis court.
Best Anna Maria Island, FL holiday rentals with parking
9.6 26 reviews
Anna Maria Island, FL
05/01 – 12/01
A$340/nightTotal: A$2380 (7 )
Labella Casa: Games, Updated Beachy Chic Home Moments To The Gulf!
3 2
apartment , Holmes Beach
This Holmes Beach holiday home is situated near the sea, a 2.4km stroll from Bradenton Beach and Island Gallery West, and within 3.2km of AMI Paddleboard Adventures and Holmes Beach's shores. This 153 square metre property boasts three bedrooms, two bathrooms, sleeps six guests, and includes a private pool, Jacuzzi, tennis court, and fully equipped kitchen; plus nearby family-friendly attractions like an arcade.
Anna Maria Island, FL
10/07 – 12/07
A$540/nightTotal: A$1080 (2 )
Family Getaway Near Img & Beaches. 3br Home W/ Backyard & Gt Bray Park Access
3 7
apartment , Bradenton
This Bradenton flat is situated adjacent to GT Bray Park, a mere 5 kilometre drive from the beaches of Anna Maria Island and within easy reach of IMG Academy and the cultural attractions of Sarasota. This 3-bedroom, 2-bathroom dwelling accommodates up to 8 guests and features a private screened lanai, garden, air conditioning, and parking, with local shops and dining within walking distance.
10 18 reviews
Anna Maria Island, FL
11/07 – 25/07
A$444/nightTotal: A$6216 (14 )
172 M² House ∙ 3 Bedrooms ∙ 8 Guests
3 7
house , Bradenton
This three-bedroom house is located in Northwest Bradenton, just a short drive (around 10km) from the beaches of Anna Maria Island, Bradenton Beach, and Holmes Beach. The property has received excellent user ratings and is perfect for families or groups of up to 8 people. The house spans 171 square metres and offers a private saltwater pool with a screened-in area and a covered deck. Guests can enjoy a fully equipped kitchen, a spacious backyard with a bathroom, and a modern coastal design.
10 2 reviews
Anna Maria Island, FL
27/06 – 28/06
A$1415/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 family-friendly apartment in South Bradenton, Florida, is situated in a quiet neighbourhood, approximately 13 kilometres from Anna Maria Island and 6 kilometres from the IMG Academy. This three-bedroom, two-bathroom dwelling boasts 139 square metres of space, sleeps nine guests, and includes a fully equipped kitchen, private pool, hot tub, and access to on-site amenities such as mini-golf and an outdoor cinema.
