Old Florida Style! Beachfront Duplex, Steps To The Sand! Quiet Street
1 2
apartment , Holmes Beach
This Holmes Beach beachfront apartment offers direct beach access and is less than 2km from Bradenton Beach, Palmetto Avenue Beach, and Island Gallery West, with Island Players and the Anna Maria Island Museum within 3km. The self-catering flat features one bedroom, one bathroom, sleeps four, includes a fully equipped kitchen, patio with BBQ, and offers excellent guest ratings for cleanliness and location.
8.0 2 reviews
Anna Maria, FL
27/06 – 04/07
SG$1610/nighttotal: SG$11270 (7 )
Hibiscus Haven On Anna Maria Island
4 9
apartment , Anna Maria
Hibiscus Haven, a four-bedroom holiday home, is situated directly across from the water on Anna Maria Island, mere steps from the Gulf beaches and close to the free island trolley stops, offering immediate access to Pine Avenue boutiques and waterfront dining. This pet-friendly property boasts a private heated swimming pool and spa, a fully equipped modern kitchen, and accommodates up to 10 guests with three King Suites and a Bunk Room, ensuring a comfortable stay for families and groups.
9.9 65 reviews
Anna Maria, FL
04/08 – 06/08
SG$1064/nighttotal: SG$2128 (2 )
Birdsong-steps To Bean Point Beach Heated Pool!
1 2
apartment , Anna Maria
This Anna Maria Island holiday home is situated a short 0.5km stroll from the beach, offering easy access to Anna Maria Island's attractions. Sleeping up to six guests, this recently remodelled (2025) two-bedroom, two-bathroom apartment boasts a private fenced backyard with a heated pool, outdoor dining area with BBQ, and all modern conveniences including a fully equipped kitchen and free Wi-Fi.
9.8 48 reviews
Anna Maria, FL
28/07 – 03/08
SG$743/nighttotal: SG$4458 (6 )
Heated Pool + Game Room | 10 Min To Beach & Img
1 11
apartment , Bradenton
This four-bedroom, two-bathroom Bradenton holiday home is situated in a peaceful neighbourhood, approximately 16 kilometres from Anna Maria Island's beaches, 18 kilometres from IMG Academy, and 18 kilometres from Robinson Preserve. Sleeping up to 14 guests, the property boasts a private heated pool, a games room with arcade games, foosball and air hockey, plus beach essentials including chairs, towels, and a cooler; free parking for four cars is also available.
Anna Maria, FL
27/06 – 04/07
SG$986/nighttotal: SG$6902 (7 )
Beach Time Ami
5 9
house , Holmes Beach
Beach Time AMI, a beachfront property in Holmes Beach, Florida, is a 6-minute walk from Anna Maria Island, 3.2km from Anna Maria City Pier, and approximately 26km from Sarasota Bradenton International Airport. This five-bedroom, three-bathroom holiday home boasts 307 square metres of living space, offering two living rooms, a fully equipped kitchen, a private pool, free Wi-Fi, and parking, comfortably accommodating up to 19 guests.
10 2 reviews
Anna Maria, FL
27/06 – 04/07
SG$564/nighttotal: SG$3948 (7 )
Lakeside Beach House · Pool · Outdoor Kitchen
3 5
apartment , Holmes Beach
This Holmes Beach flat is located on a natural canal in a quiet residential area, offering convenient access to the beach, library, and eateries in the northern part of town, approximately 1.6 kilometres away. This newly renovated three-bedroom, two-bathroom property accommodates six guests and features a private heated pool, an outdoor kitchen with a stereo system, complimentary beach gear, and a fishing pier on a canal known for snook.
10 34 reviews
Anna Maria, FL
05/07 – 11/07
SG$1124/nighttotal: SG$6744 (6 )
Seashell Oasis: 2.5 Blocks To Gulf! Dog Friendly, Pool By Anna Maria Life
4 11
apartment , Bradenton Beach
This Bradenton Beach holiday home, situated between the Gulf of Mexico (0.4 km) and the Bay (0.16 km), offers unparalleled access to both stunning beaches and Bradenton Beach's local amenities. This spacious 243 square metre property boasts four king-size bedrooms, five bathrooms, a private heated pool, and ample parking for six cars, comfortably accommodating up to nine guests and including a fenced yard for pets.
9.2 62 reviews
Anna Maria, FL
10/09 – 13/09
SG$429/nighttotal: SG$1287 (3 )
Duplex On North End Of Anna Maria Island! With Pool And Grill
2 4
apartment , Anna Maria
This two-bedroom duplex is located on the southern end of Anna Maria Island, a 10-minute walk from Bean Point Beach and a 10-minute drive from Bayfront Park. It is rated excellent by previous guests. The 73 square metre duplex sleeps up to six guests and features a well-equipped kitchen, a shared pool, a laundry room, and a garden. Guests can enjoy the tropical décor and relax on the large sectional sofa or explore the nearby shops and restaurants on Pine Avenue.
9.5 232 reviews
Anna Maria, FL
15/08 – 17/08
SG$624/nighttotal: SG$1248 (2 )
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay
1 4
apartment , Anna Maria
This charming cottage is located on the North End of Anna Maria Island, just a short walk from Pine Avenue, City Pier, and a variety of restaurants. Guests have consistently rated the cottage as excellent for its location, cleanliness, and overall experience. The cottage spans 107 square metres and comfortably accommodates up to six guests in its three bedrooms and two bathrooms. Enjoy a private dock with waterfront views, a spacious deck for outdoor dining, a fully equipped kitchen, and access to Netflix and WiFi.
10 4 reviews
Anna Maria, FL
24/07 – 01/08
SG$2254/nighttotal: SG$18032 (8 )
Oasis~2min Walk To Gulf,3 King+twin Bunk,salt Pool+spa,golf,bikes,bocce+cornhole
3 7
apartment , Anna Maria
This Anna Maria Island holiday home, located at the quiet northern end, is a two-minute walk from the Gulf beach and a three-minute cycle from Bean Point and Pine Avenue. This 146 square metre (1570 square feet) property boasts three bedrooms, three bathrooms, sleeps eight guests, and offers a heated saltwater pool, spa, private fenced yard, three-hole putting green, and comprehensive beach and pool equipment.
9.3 543 reviews
Anna Maria, FL
21/06 – 26/06
SG$541/nighttotal: SG$2705 (5 )
Resort-style Pool Steps From The Bay And Pine Ave!
1 3
house , Anna Maria
This charming coastal property is located just a short walk from both Bay Boulevard Beach and Anna Maria Beach, offering easy access to the beautiful surroundings. It's also within a 5-minute walk of the Anna Maria City Pier and Bayfront Park, making it a perfect base for exploring the area. The property has consistently received excellent ratings for user experience, location and cleanliness. The house features two bedrooms, providing ample space for a small family or group of friends. It includes a fully equipped kitchen, a relaxing patio, a comfortable sofa bed for additional guests, and access to a water park and barbecue grills.
Anna Maria, FL
29/06 – 30/06
SG$745/nightfor 1 night
The Beach Club At Anna Maria #1
1 2
house , Bradenton Beach
This beachfront holiday home in Bradenton Beach offers direct access to the shore and is located just a few steps from the beach itself, approximately 19 kilometres from Sarasota Bradenton International Airport and 22 kilometres from the Sarasota International Convention Centre and the John and Mable Ringling Museum of Art. This holiday cottage, accommodating up to seven guests, features a well-equipped kitchen with a dishwasher and microwave, air conditioning, complimentary WiFi, a swimming pool, a hot tub, and a fitness centre, with cycling opportunities available nearby.
Best Anna Maria, FL lodgings with a pool
Among the 2100 accommodations in Anna Maria, FL, here are the 4 best ones with a pool
9.5 49 reviews
Anna Maria, FL
03/07 – 06/07
SG$1505/nighttotal: SG$4515 (3 )
Private Home Situated Near Bean Point With Spacious Heated Pool!
2 3
apartment , Anna Maria
This Anna Maria Island holiday home is situated a short walk (under 0.8km) from Anna Maria Beach, Bean Point Beach, and Bradenton Beach, and within a 2.4km radius of Bay Boulevard Beach and Bayfront Park. This 137 square metre property boasts two bedrooms, two bathrooms, sleeps five guests, and includes a private pool, tennis court, and fully equipped kitchen; nearby attractions include an on-site water park and arcade.
9.8 11 reviews
Anna Maria, FL
31/10 – 10/11
SG$345/nighttotal: SG$3450 (10 )
Stays On North End Of Anna Maria Island! Duplex With Pool And Bbq Grill!
2 2
apartment , Anna Maria
Southern Breeze #2, a ground-floor duplex in Anna Maria, Florida, is less than 1.6km from Bean Point Beach and under 1.6km from Bayfront Park. This Anna Maria Island holiday home boasts 73 square metres of living space, featuring two king-size bedrooms, a sofa bed, one bathroom, a fully equipped kitchen, and a shared pool; sleeping up to six guests.
9.8 59 reviews
Anna Maria, FL
21/06 – 26/06
SG$432/nighttotal: SG$2160 (5 )
Tradewinds Deluxe North Cottage
1 3
apartment , Bradenton Beach
This one-bedroom apartment in Bradenton Beach is located within walking distance of the beach, the Anna Maria Island Pier, and the Bridge Street district. This self-catering property features a full kitchen, a private deck, and can comfortably accommodate up to four guests.
10 4 reviews
Anna Maria, FL
29/06 – 30/06
SG$2436/nightfor 1 night
Casa Del Sol | Rooftop Deck, Pool + Ocean Views
1 2
apartment , Anna Maria
This modern, newly built apartment on the North End of Anna Maria Island offers exceptional proximity to the beach, just a 30-second walk away, and is minutes from the shops and restaurants on Pine Avenue. This family-friendly accommodation for up to eight guests boasts a private swimming pool, jacuzzi, garden, a fully equipped kitchen, and complimentary luxury bikes, with 24/7 local support ensuring a convenient stay.
Best family friendly Anna Maria, FL lodging
Among the 2100 accommodations in Anna Maria, FL, here are the 4 best for families
Anna Maria, FL
28/07 – 03/08
SG$743/nighttotal: SG$4458 (6 )
214 M² House ∙ 4 Bedrooms ∙ 12 Guests
4 11
house , Cortez
This Palma Sola property, in Cortez, Florida, is situated approximately 8 kilometres from Anna Maria Island's beaches. This four-bedroom, three-bathroom house offers 213 square metres of living space, boasting a private tropical backyard with a heated pool, Tiki bar, and outdoor kitchen; it sleeps up to 12 guests and includes amenities such as Wi-Fi, parking, and a fully equipped kitchen.
10 64 reviews
Anna Maria, FL
21/06 – 26/06
SG$2144/nighttotal: SG$10720 (5 )
Bimini Bay Breeze: Canal Front | Close To Beach And Pine St. | Pool/spa |
4 3
apartment , Anna Maria
This luxurious Anna Maria Island property, a short 0.32-kilometre stroll from the Gulf of Mexico beaches and Pine Avenue's amenities, boasts direct canal access with a 10,000-pound boat lift. The 264-square-metre holiday home offers four bedrooms, four bathrooms, sleeps eight guests, and includes a heated pool, spa, outdoor kitchen, putting green, crow's nest with panoramic views, and kayaks/paddleboards for exploring the waterways.
8.5 20 reviews
Anna Maria, FL
31/10 – 10/11
SG$401/nighttotal: SG$4010 (10 )
Briney Breezes - Old Florida Living With Modern Comforts
3 2
apartment , Anna Maria
This Anna Maria Island property is centrally located, less than 1.6km from Historic Green Village, Anna Maria Beach, and Bean Point Beach, and within a 10-minute drive of Bay Boulevard Beach and the Anna Maria Island Museum and Historical Park. This 195 square metre holiday home sleeps eight guests and boasts a private pool, Jacuzzi, tennis court, fitness centre, and fully equipped kitchen, plus barbecue facilities; nearby attractions include an on-site water park.
Anna Maria, FL
05/07 – 11/07
SG$606/nighttotal: SG$3636 (6 )
4 Br/3 Ba Heated Pool And Hot Tub By Fvc
4 11
apartment , Bradenton
This Bradenton property is conveniently located 8 kilometres from Anna Maria Island beaches, 5 kilometres from IMG Academy and downtown Bradenton's spring training facilities, and 1.6 kilometres from G.T. Bray Park. This spacious 234 square metre flat accommodates up to 12 guests across four bedrooms, featuring a separate mother-in-law suite with a full kitchen, a private heated pool and jacuzzi in the backyard, and modern coastal decor.
Frequently asked questions about accommodations in Anna Maria, FL
What are the must-see sites in or near Anna Maria, FL?
Anna Maria Island is a gem! You have to visit the historic City Pier, it's a great spot to watch the sunset. The Anna Maria Island Historical Museum is a must-see for anyone interested in the island's history. And if you're looking for something a bit more adventurous, take a trip to the nearby Coquina Beach, known for its beautiful white sand and clear blue waters.
What are the best accommodations in Anna Maria, FL?
The easiest way to get to Anna Maria is to fly into Sarasota Bradenton International Airport (SRQ), which is about a 20-minute drive. You can also fly into Tampa International Airport (TPA), which is about an hour's drive. Once you're on the island, getting around is easy, as it's small and very walkable. You can also rent bikes or golf carts for a fun way to explore.
What are the best accommodations with a pool in Anna Maria, FL?
What outdoor activities can visitors enjoy in and around Anna Maria, FL?
Anna Maria is a paradise for outdoor enthusiasts! You can spend your days swimming, sunbathing, and kayaking in the Gulf of Mexico. There are also plenty of opportunities for fishing, paddleboarding, and even dolphin watching tours. For a change of pace, explore the mangrove forests on a guided eco-tour.
What are the best accommodations with a jacuzzi in Anna Maria, FL?
When is the ideal time to plan a trip to Anna Maria, FL?
The best time to visit Anna Maria is during the spring (March-May) or autumn (September-November) when the weather is pleasant and the crowds are smaller. Summer (June-August) can get very hot and humid, while winter (December-February) is the peak season with higher prices and more crowds.
What are the best accommodations for families and kids in Anna Maria, FL?
What are the best walking or cycling routes in Anna Maria, FL?
The Anna Maria Island Nature Trail is a beautiful, paved path that runs along the coast, offering stunning views of the Gulf. For a more scenic route, try the Pine Avenue Trail, which winds through the heart of Anna Maria, passing by charming shops and restaurants. You can also explore the island's many side streets and discover hidden gems.
What are the best pet friendly accommodations in Anna Maria, FL?
What nearby towns or cities can be explored from Anna Maria, FL?
If you're looking to venture beyond Anna Maria, you can easily visit the nearby cities of Bradenton, Sarasota, and St. Petersburg. Bradenton is home to the South Florida Museum and the Bishop Museum of Science and Nature. Sarasota is known for its art scene, with the Ringling Museum and the Van Wezel Performing Arts Hall. St. Petersburg offers a vibrant downtown area, beautiful beaches, and the Salvador Dali Museum.
What are the best accommodations with parking in Anna Maria, FL?
What amenities can travelers expect from accommodations in Anna Maria, FL?
Anna Maria offers a range of accommodation options, from charming bed and breakfasts to luxurious beachfront hotels. Many accommodations offer amenities like swimming pools, hot tubs, and private balconies. You'll also find plenty of restaurants, shops, and entertainment options within walking distance of most hotels.
Destinations nearby
Best Anna Maria, FL accommodations with a balcony
10 1 review
Anna Maria, FL
24/07 – 01/08
SG$1695/nighttotal: SG$13560 (8 )
197 M² House ∙ 4 Bedrooms ∙ 8 Guests
4 7
house , Anna Maria
Pirates Lookout, a carriage house on Anna Maria Island's northern end, is situated steps from the Rod & Reel Pier and a short distance from Pine Avenue's shops and restaurants. This pet-friendly, newly renovated three-bedroom property boasts 139 square metres of floor space, sleeping up to six guests, and offers direct bay beach access with kayaks and paddleboards, plus a fully equipped kitchen, laundry facilities, and beach equipment.
9.9 78 reviews
Anna Maria, FL
15/08 – 17/08
SG$2455/nighttotal: SG$4910 (2 )
New Bay Dreamin 4 Bedroom Private Pool Spa Beach Front Property Home
4 4
house , Anna Maria
This beachfront property is located in Anna Maria, a 24-kilometre drive from The John and Mable Ringling Museum of Art and a 15-minute walk from the island's main district. This four-bedroom, 258 square metre home offers a private pool and spa, a fully equipped kitchen, and free private parking.
9.4 5 reviews
Anna Maria, FL
04/08 – 06/08
SG$872/nighttotal: SG$1744 (2 )
Isla Living, 3 Bed, Canal, Pool
3 2
house , Anna Maria
Isla Living, a recently renovated three-bedroom holiday home, is situated in Anna Maria, a 5-minute walk from Anna Maria Island and a 19-kilometre drive from Sarasota Bradenton International Airport. This 120-square-metre property sleeps up to 11 guests and boasts a private pool, garden, free Wi-Fi, and a fully equipped kitchen; nearby activities include fishing and canoeing, with Anna Maria City Pier a short walk away.
9.6 199 reviews
Anna Maria, FL
04/08 – 06/08
SG$1887/nighttotal: SG$3774 (2 )
May, June Specials ,Beachfront, Private Beach On The Waterfront, Bring Your Dog
3 2
apartment , Anna Maria
This beachfront property is located in Anna Maria, just a short walk from the Anna Maria City Pier and Pine Avenue, with easy access to the free trolley. This three-bedroom, two-bathroom apartment offers a spacious 189 square metre living area with direct beach access, a private deck, and a luxurious master suite with a Jacuzzi tub.
Best Anna Maria, FL accommodations with a kitchen
9.4 110 reviews
Anna Maria, FL
28/07 – 03/08
SG$1380/nighttotal: SG$8280 (6 )
Canalfront Home, Saltwater Pool, Near Beaches And Shopping - Sunrise Shore
5 11
apartment , Anna Maria
This five-bedroom property is situated on Anna Maria Island, just a short distance from Anna Maria Beach and within a mile of Island Players, offering a peaceful and convenient location for your stay. The property has received excellent ratings for user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay. The property comfortably accommodates up to 11 guests and features a fully equipped kitchen, a private pool, a water park, a terrace, and a garden for your enjoyment. Guests can also benefit from direct beach access, a fitness centre, and parking.
9.8 8 reviews
Anna Maria, FL
21/06 – 26/06
SG$333/nighttotal: SG$1665 (5 )
Paradise Awaits By Coastal Chic Vacations
2 3
apartment , Bradenton
This Anna Maria Island condo, a short 3.2km drive from Manatee Beach and a 6.4km drive from other Anna Maria Island beaches, offers a luxurious escape near Bradenton, Florida. The 140 square metre, two-bedroom, two-bathroom apartment sleeps five guests, boasting a fully equipped kitchen, private lanai, resort-style amenities including a heated pool and jacuzzi, and access to a private beach club and fitness centre for longer stays.
10 1 review
Anna Maria, FL
28/07 – 03/08
SG$705/nighttotal: SG$4230 (6 )
Open For Spring Break! Dockside Oasis On The Canal
3 11
house , Cortez
This waterside dwelling in Bradenton offers a unique canal-side experience, located 17.7 kilometres from the Sarasota International Convention Centre and the John and Mable Ringling Museum of Art, and 11.3 kilometres from Greens of Manatee Golf Club. This accommodation for 19 guests features a well-equipped kitchen, air conditioning, free WiFi, private parking, and a terrace, with a bedroom and two bathrooms, ideal for those seeking a dockside retreat with easy access to local attractions.
Anna Maria, FL
28/07 – 03/08
SG$1362/nighttotal: SG$8172 (6 )
Recently Renovated With Large Pool On The North End Of Ami
4 11
house , Anna Maria
This Anna Maria Island holiday home, a five-minute walk from the beach and 0.8 kilometres from the Anna Maria City Pier, offers easy access to Anna Maria Island's attractions. This four-bedroom property boasts 117 square metres of living space, sleeps up to 23 guests, includes a private pool, and features a fully equipped kitchen with a dishwasher, air conditioning, and cable TV.