Best Holiday rentals and Airbnb offers in Anna Maria Island, FL
9.5 62 reviews
Anna Maria Island, FL
27/06 – 04/07
SG$295/nighttotal: SG$2065 (7 )
Resort Style Condo By The Beach With Heated Pool At Runaway Bay
1 2
apartment , Bradenton Beach
This smoke-free apartment is located in Bradenton Beach, just a short walk from Anna Maria Sound, Aluna Wellness Center & Spa, and the beach itself. It has received excellent ratings for location, cleanliness, and overall experience. The apartment has one bedroom and one bathroom, providing space for up to four guests. It comes equipped with a kitchen, laundry facilities, free Wi-Fi, a TV, a comfortable sofa bed, and access to a heated swimming pool, tennis courts, and a music library.
9.5 240 reviews
Anna Maria Island, FL
03/08 – 07/08
SG$496/nighttotal: SG$1984 (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.
This Palma Sola holiday home, situated within 2km of De Soto National Memorial and Palma Sola Botanical Park, and 2.1km from Robinson Preserve, offers convenient access to West Bradenton's key attractions. The 218 square metre property boasts four bedrooms, sleeping up to sixteen guests, and features a private pool, fully equipped kitchen, laundry facilities, barbecue grills, and a patio; on-site amenities include an arcade/game room and garden.
9.8 224 reviews
Anna Maria Island, FL
07/10 – 14/10
SG$194/nighttotal: SG$1358 (7 )
Shorewalk Sunny Bella Rosa 2br Villa 2 Pools & Hot Tubs Near Img / Beaches
2 4
apartment , Bradenton
This two-bedroom apartment is located in South Bradenton, just 1.6 kilometres from the IMG Tennis Academy and a 15-20 minute drive from Anna Maria, Bradenton, and Longboat Key beaches. It has consistently received excellent ratings for its location, cleanliness, and overall experience. The apartment offers 119 square metres of living space, comfortably accommodating up to four guests. Enjoy a range of amenities including a swimming pool, Jacuzzi, tennis court, and a fully equipped kitchen, ensuring a relaxing and enjoyable stay.
9.8 58 reviews
Anna Maria Island, FL
11/07 – 25/07
SG$434/nighttotal: SG$6076 (14 )
Heated Pool/spacious Lanai/near Ami Beaches & Img
1 7
apartment , Bradenton
This spacious Bradenton pool house, near Anna Maria Island (approx. 24km), IMG Academy (approx. 16km), and Robinson Preserve (approx. 14km), offers a tranquil family-friendly escape. The four-bedroom, two-bathroom property sleeps eight, boasting a fully equipped kitchen, private pool, extensive games, high-speed Wi-Fi (500 Mbps), and a screened lanai perfect for relaxation.
10 17 reviews
Anna Maria Island, FL
24/09 – 27/09
SG$346/nighttotal: SG$1038 (3 )
Pool+spa+3.5 Baths+outdoor Grill
1 8
apartment , Bradenton
This Bradenton flat offers a central location, situated between 11 and 29 kilometres from Bradenton Beach and Siesta Key, and a short drive to SRQ Airport, IMG Academy (approximately 4.2 kilometres) and Riverwalk Park (approximately 6.6 kilometres). This family-friendly property accommodates up to 10 guests with 3 bedrooms and 3 bathrooms, featuring a private pool, inground spa, a well-equipped kitchen, and two sets of washers and dryers, with provided beach chairs and a cooler for excursions.
10 4 reviews
Anna Maria Island, FL
28/06 – 03/07
SG$548/nighttotal: SG$2740 (5 )
164 M² House ∙ 3 Bedrooms ∙ 8 Guests
3 8
house , West Bradenton
This West Bradenton holiday home is located in the exclusive Harbour Hills community, a short drive (approximately 10km) from Anna Maria Island and less than 5km from the Palma Sola Causeway. The 175 square metre property boasts three bedrooms, two bathrooms, sleeping eight guests comfortably, and features a fully equipped kitchen, private swimming pool, and outdoor entertainment area complete with a 75" Smart TV, grill, fire pit, and putting green.
10 57 reviews
Anna Maria Island, FL
17/07 – 20/07
SG$298/nighttotal: SG$894 (3 )
Pet-friendly Bradenton Home 1.5 Mi To Cortez Beach
2 2
house , Cortez
This property is situated in Bradenton, Florida, approximately 5 kilometres from the beach and 10 kilometres from the Greens of Manatee Golf Club. It enjoys excellent ratings for location, cleanliness, and overall user experience. This two-bedroom home spans 93 square metres and comfortably accommodates up to four guests. It features a fully equipped kitchen, air conditioning, a private terrace, a garden, a spa, and parking.
9.8 31 reviews
Anna Maria Island, FL
11/07 – 25/07
SG$416/nighttotal: SG$5824 (14 )
Private Pool Oasis Near Img & Ami
3 7
apartment , Bradenton
This Bradenton holiday home is ideally situated near IMG Academy, approximately 10-13km from Anna Maria Island's beaches and 18km from Sarasota Bradenton International Airport. Sleeping up to eight guests, the property boasts three bedrooms, two bathrooms, a private heated pool, covered patio, fully equipped kitchen, abundant beach gear, and family-friendly amenities including a travel cot, high chair, and children's tableware; plus outdoor games like cornhole and Connect 4.
9.3 34 reviews
Anna Maria Island, FL
27/06 – 04/07
SG$531/nighttotal: SG$3717 (7 )
Jerry's Gem Home
3 2
house , West Bradenton
Jerry's Gem is located in Bradenton, just 13.7 kilometres from the Greens of Manatee Golf Club and 22.5 kilometres from the John and Mable Ringling Museum of Art. The property has received excellent ratings for user experience, location, and cleanliness. This three-bedroom holiday home spans 167 square metres. It boasts a private pool, air conditioning, a fully equipped kitchen, free private parking, an outdoor patio, and is close to cycling routes.
9.9 390 reviews
Anna Maria Island, FL
11/07 – 25/07
SG$347/nighttotal: SG$4858 (14 )
Casa Del Río! Beaches, Img, Boating & Riverwalk.
3 7
apartment , Bradenton
This Bradenton property is conveniently located in the River District, just a short walk from the Riverwalk, the Bishop Museum, and LECOM Park. The house has received excellent ratings for location, cleanliness, and overall user experience. The 126 square metre house can comfortably accommodate up to 7 guests in its three bedrooms and two bathrooms. The property offers a range of amenities, including a fully equipped kitchen, a garden, a patio with barbecue grills, and a spa, ensuring a relaxing and enjoyable stay.
9.8 70 reviews
Anna Maria Island, FL
28/06 – 29/06
SG$539/nightfor 1 night
Peaceful Lakeview Condo 2 Pools Minutes To Img & Beaches
3 2
apartment , Bradenton
This Bradenton apartment is situated just 1.8 kilometres from Arcadeland and 2.2 kilometres from IMG Academy, offering easy access to these popular attractions. It has received excellent user ratings, making it a popular choice for travellers. This two-bedroom apartment spans 109 square metres and comfortably accommodates up to four guests. Enjoy a range of amenities including a swimming pool, jacuzzi, terrace, garden, tennis court, and parking, perfect for a relaxing and enjoyable stay.
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 22 reviews
Anna Maria Island, FL
27/07 – 29/07
SG$366/nighttotal: SG$732 (2 )
Coastal Confort Home.10 Min To Anna María Island.
1 5
apartment , Bradenton
This Bradenton apartment, located in a quiet neighbourhood a short distance (a few kilometres) from Anna Maria Island's beaches and Bradenton's shops and restaurants, offers a convenient base for exploring the area. Sleeping up to eight guests, this three-bedroom, two-bathroom property boasts a fully equipped kitchen, air conditioning, private garden, and on-site parking.
9.0 5 reviews
Anna Maria Island, FL
28/06 – 03/07
SG$937/nighttotal: SG$4685 (5 )
Lake O' Woods! Gated Private Pool Home!
4 8
house , Bradenton
This Bradenton property, near Lake O'Woods, is conveniently located 12 kilometres from Sarasota Bradenton International Airport and 16 kilometres from The John and Mable Ringling Museum of Art. The 279 square metre house boasts four bedrooms, three bathrooms, and can comfortably accommodate up to 19 guests, featuring a private pool, spa, and fully equipped kitchen within a gated community.
10 2 reviews
Anna Maria Island, FL
02/07 – 05/07
SG$714/nighttotal: SG$2142 (3 )
Rest Easy, Htd Pool, Tiki Hut, 11 Min To Beach
3 6
apartment , Bradenton
This family home is located in a quiet Bradenton neighbourhood, 17.7 kilometres from the beaches of Anna Maria Island, 12.8 kilometres from IMG Academy and 24.1 kilometres from Robinson Nature Preserve. This 154 square metre apartment sleeps up to six guests and offers three bedrooms, two bathrooms, a heated saltwater swimming pool, two firepits, a Weber BBQ grill, complimentary beach gear and free driveway parking for four cars.
10 7 reviews
Anna Maria Island, FL
28/06 – 29/06
SG$1512/nightfor 1 night
Sea Glass North End • 2bed/2 Bath Steps To Beach
1 2
apartment , Anna Maria
Sea Glass Cottage, a two-bedroom flat on the north end of Anna Maria Island, is located just 160 metres from Bean Point Beach and a 2-minute walk to the Fern Street beach access. This family-friendly accommodation for six features a private heated swimming pool, a chef's kitchen with Wolf and Sub-Zero appliances, and beach-ready essentials, all within easy reach of the serene shoreline ideal for swimming and shelling.
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
9.6 188 reviews
Anna Maria Island, FL
27/06 – 04/07
SG$407/nighttotal: SG$2849 (7 )
Steps To Gulf. Shared Heated Pool. Holmes Beach.
1 2
apartment , Holmes Beach
This holiday home is located just a short stroll from the beach in Bradenton Beach, a peaceful area with easy access to shops and restaurants. The property has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience. The spacious home offers a comfortable and well-equipped living space with a fully equipped kitchen, a relaxing patio, and a private swimming pool. Guests can enjoy a range of on-site amenities including a fitness centre, tennis court, and barbecue facilities, as well as the convenience of a dedicated parking space.
9.6 107 reviews
Anna Maria Island, FL
27/07 – 29/07
SG$543/nighttotal: SG$1086 (2 )
Captain America Dream
3 5
house , Bradenton
This charming house is located in Bradenton, Florida, just a short drive from Sarasota Bradenton International Airport and the John and Mable Ringling Museum of Art. It has consistently received excellent ratings for its location, cleanliness, and overall user experience. The property offers three bedrooms and two bathrooms, comfortably accommodating up to six guests. Guests can enjoy a private pool, a children's playground, a fully equipped kitchen, free Wi-Fi, a garden, and the opportunity to explore the area by bike.
9.2 45 reviews
Anna Maria Island, FL
27/06 – 04/07
SG$279/nighttotal: SG$1953 (7 )
Beach Home With Pool Access And Private Patio With Bbq Grill! - Little Dream
1 2
apartment , Holmes Beach
This Holmes Beach holiday home is a short walk from Bradenton Beach and Island Gallery West, and within 3.2km of Holmes Beach Beaches and Manatee Public Beach. This self-catering property boasts 42 square metres of space, sleeping up to four guests in one bedroom and one bathroom, and features a fully equipped kitchen, swimming pool, and free Wi-Fi.
9.6 74 reviews
Anna Maria Island, FL
28/06 – 03/07
SG$747/nighttotal: SG$3735 (5 )
New Private 3 Bedroom Pool Home Sleeps 10 Short Drive To Local Beaches Home
3 8
house , Bradenton
This charming house is situated in Bradenton, just 2.7km from Palma Sola Causeway Park, 18km from the Ringling Museum of Art, and 48km from Tropicana Field. The property has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience. The three-bedroom home spans 153 square metres and comfortably accommodates up to 10 guests. Enjoy a private pool, free parking, a fully equipped kitchen, air conditioning, and free Wi-Fi, making it the perfect base for exploring Bradenton and its surrounding attractions.
Frequently asked questions about holiday rentals in Anna Maria Island, FL
What are the must-see sights on Anna Maria Island, Florida?
For must-see sights on Anna Maria Island, you definitely want to check out the Anna Maria Island Historical Museum to learn about the island's history. The picturesque Anna Maria City Pier is a great spot for fishing and enjoying the views. Bean Point is famous for its stunning sunsets and views of the coastline. And don't forget the beautiful beaches themselves – they're the main attraction!
What are the best Airbnb and vacation rentals in Anna Maria Island, FL?
Are there any unique natural phenomena on Anna Maria Island, Florida?
Anna Maria Island boasts incredible natural beauty. The beaches are renowned for their pristine, white sand and calm, clear waters. You'll see abundant wildlife, from shorebirds to dolphins. The island's position in the Gulf of Mexico means you can witness beautiful sunsets almost every night. The mangrove forests provide a unique ecosystem to explore, too.
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, and insect repellent. Comfortable walking shoes are a must, as you'll be doing a lot of exploring. Don't forget your beach towel and a reusable water bottle to stay hydrated in the Florida sun. A camera is also a must to capture the stunning scenery.
What are the best vacation 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 expect to spend around £150-£300 per day for a couple, covering accommodation, meals, some activities, and local transport. Budget travellers could manage on less, while luxury travellers will spend considerably more.
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 upscale dining, known for its fresh seafood. Rod & Reel Pier offers casual dining with stunning waterfront views and classic seafood options. The Sandbar Restaurant is another popular spot for its laid-back atmosphere and delicious seafood. Fresh seafood is a must-try on the island, along with key lime pie – a Florida classic.
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 a beautiful nature trail for birdwatching and exploring the local ecosystem. Exploring the smaller, quieter beaches away from the main tourist areas can provide a more tranquil experience. Take a stroll along the bayfront and admire the charming architecture of the older homes.
What are the best activities for engaging with locals and understanding their culture on Anna Maria Island, Florida?
Chatting with staff at local businesses, like the smaller shops or restaurants, is a great way to get a feel for the island's atmosphere. Visiting the Anna Maria Island Historical Museum can provide insight into the community's history. Attending any local events or farmers' markets (when available) will give you a chance to interact with residents.
What unique natural landscapes and terrain features can travellers explore on Anna Maria Island, Florida?
The island's main feature is its beautiful beaches, with soft white sand and calm waters. The mangrove forests offer a unique ecosystem to explore, with opportunities for kayaking or paddleboarding. The coastline provides diverse habitats, from sandy beaches to tidal flats.
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 explore Anna Maria Island at a relaxed pace. One could spend a day exploring the beaches, another visiting the Anna Maria City Pier and the Historical Museum, and a third exploring the nature preserves and enjoying watersports. A fourth day could be spent simply relaxing and enjoying the island's atmosphere.
Nearby regions
Best Anna Maria Island, FL holiday rentals with a balcony
9.2 7 reviews
Anna Maria Island, FL
27/07 – 29/07
SG$382/nighttotal: SG$764 (2 )
Spacious Shorewalk 2b-2b Condo Near Anna Maria Island, Beaches & Img Academy
2 5
resort , Bradenton
This resort is situated in Bradenton, just 13 kilometres from The John and Mable Ringling Museum of Art and 10 kilometres from Sarasota Bradenton International Airport, offering easy access to both cultural attractions and transport links. It has consistently received excellent ratings for location, cleanliness, and overall user experience. The spacious two-bedroom apartment offers 111 square metres of living space and can comfortably accommodate up to 10 guests. This family-friendly resort features a swimming pool, jacuzzi, garden, fitness centre, and free Wi-Fi, ensuring a relaxing and enjoyable stay for all.
9.2 12 reviews
Anna Maria Island, FL
17/07 – 24/07
SG$467/nighttotal: SG$3269 (7 )
156 M² House ∙ 3 Bedrooms ∙ 8 Guests
3 7
house , Cortez
This modern 3-bedroom smart home is situated in the Hunters Point district of Cortez, Florida, offering convenient access to Anna Maria Island beaches and the historic Cortez Village, known for its fresh seafood. This 155 square metre residence accommodates up to eight guests, featuring a dedicated games room with pool and foosball, a private patio with a grill, an in-house elevator, a Tesla EV charger, and high-speed Wi-Fi.
Anna Maria Island, FL
17/07 – 24/07
SG$443/nighttotal: SG$3101 (7 )
Stunning 3 Bedroom Coastal Getaway
3 7
apartment , Bradenton
This condo is located in the gated One Particular Harbour community in Bradenton, 1.6 kilometres from Anna Maria Island beaches and less than 1 kilometre from Neal Preserve nature trails. This 155 square metre apartment offers three bedrooms and three bathrooms for up to seven guests, featuring a fully equipped kitchen, air conditioning, a swimming pool, a spa, a terrace, and parking within the resort-style community.
9.0 6 reviews
Anna Maria Island, FL
24/09 – 27/09
SG$576/nighttotal: SG$1728 (3 )
Relax Gateway Near Img Private Pool And Beach
3 8
apartment , Bradenton
This Bradenton flat is located just 4.8 kilometres from Anna Maria Island, offering easy access to Sarasota attractions and De Soto Park, with Sarasota Airport a 20-minute drive away. This three-bedroom, two-bathroom residence accommodates up to ten guests and features a private heated pool, a modern kitchen, an office room, and free parking for two vehicles.
Best Anna Maria Island, FL holiday rentals with parking
9.9 68 reviews
Anna Maria Island, FL
27/06 – 04/07
SG$348/nighttotal: SG$2436 (7 )
Island Retreat By Seabreeze Vacation
1 2
apartment , Holmes Beach
This Holmes Beach holiday home is situated near Anna Maria Sound, a short 0.8km walk from West Coast Surf Shop and AMI Paddleboard Adventures, and under 1.6km from Manatee Public Beach and Bradenton Beach. The 63 square metre property offers one bedroom, one bathroom, a fully equipped kitchen, private balcony, free Wi-Fi, on-site parking, and sleeps up to two guests with a sofa bed; nearby activities include watersports and beach relaxation.
10 34 reviews
Anna Maria Island, FL
17/07 – 24/07
SG$480/nighttotal: SG$3360 (7 )
Pool & Play Oasis~ All The Amenities & Near Ami!
1 7
apartment , West Bradenton
This West Bradenton apartment, ideally located approximately 13 kilometres from Anna Maria Island's beaches and a short drive from attractions such as IMG Academy and Robinson Preserve, offers a convenient base for exploring the area. Sleeping up to 10 guests, this three-bedroom, two-bathroom property boasts a private heated pool and hot tub, a putting green, basketball court, and a fully equipped games room with pool table, foosball, and dartboard, along with beach essentials provided.
9.3 199 reviews
Anna Maria Island, FL
18/07 – 25/07
SG$328/nighttotal: SG$2296 (7 )
Runaway Bay 185 - 1357300
2 2
apartment , Bradenton Beach
Runaway Bay 185 - 1357300 is located in Bradenton Beach, just a short walk from the main beach area and less than a mile from Cortez Beach. This property has received excellent ratings for location, cleanliness and overall user experience. The apartment has a floor area of 100 square metres and includes a well-equipped kitchen, a private patio, and access to a range of amenities, such as a swimming pool, tennis court, fitness centre, sauna, spa, and restaurant.
9.6 59 reviews
Anna Maria Island, FL
27/06 – 04/07
SG$380/nighttotal: SG$2660 (7 )
The Palms #3 Beach, Pool & Trolley No Car Needed
2 2
apartment , Holmes Beach
This holiday home is located in Holmes Beach, just under a kilometre from Bradenton Beach, Anna Maria Sound, and AMI Paddleboard Adventures, offering easy access to the area's many attractions. The property has consistently received excellent user ratings for its location, cleanliness, and overall experience. The two-bedroom house spans 70 square metres and comfortably accommodates up to six guests. It features a fully equipped kitchen, a private swimming pool, a spa, a garden, and a terrace, providing everything you need for a relaxing and enjoyable stay.
