This Anna Maria Island beachfront property is steps from Historic Green Village and Anna Maria City Pier, a short 2.4km walk from Bay Boulevard Beach and Bradenton Beach. This 50 square metre holiday home offers two bedrooms, a sofa bed, one bathroom, and amenities including a swimming pool, terrace, garden, parking, and Wi-Fi, accommodating up to four guests and featuring gas grills and an on-site water park.
9.9 54 reviews
Anna Maria, FL
19/07 – 23/07
SG$3529/nighttotal: SG$14116 (4 )
Villa Marisol: Beachfront, Mediterranean Style, W/terrace, Pool, Hot Tub!
4 4
apartment , Anna Maria
This beachfront property is located just a short walk from Anna Maria Beach and Bean Point Beach, with Bradenton Beach and Bayfront Park a 16-kilometre drive away. The property has consistently received excellent ratings for location, cleanliness and overall experience. This four-bedroom holiday home offers 342 square metres of space. Enjoy the private swimming pool, Jacuzzi, terrace, garden, spa, restaurant, fitness centre, tennis court and parking, all within the grounds.
8.0 1 review
Anna Maria, FL
19/07 – 23/07
SG$467/nighttotal: SG$1868 (4 )
Bay Cottage
1 4
house , Anna Maria
Bay Cottage is a detached house located in Anna Maria, 2.1 kilometres from Anna Maria Island and 27 kilometres from Sarasota Bradenton International Airport. This pet-friendly cottage offers 74 square metres of living space with one bedroom, accommodating up to seven guests, and features a fully equipped kitchen, air conditioning, free WiFi, and an outdoor balcony with barbecue facilities.
9.4 71 reviews
Anna Maria, FL
19/07 – 23/07
SG$373/nighttotal: SG$1492 (4 )
1 Mi To Anna Maria Island: Pet-friendly Retreat
2 4
house , Cortez
This holiday home is situated in Cortez, Florida, just 1.8 kilometres from Bradenton Beach and 1.9 kilometres from Cortez Beach. It has consistently received excellent ratings for location, cleanliness, and overall user experience. The property is a spacious two-bedroom house with one bathroom, covering 111 square metres and accommodating up to four guests. It offers a range of amenities, including a fully equipped kitchen, air conditioning, a garden, a spa, parking, and free Wi-Fi, making it ideal for families or groups looking for a comfortable and convenient stay.
9.8 34 reviews
Anna Maria, FL
20/06 – 27/06
SG$370/nighttotal: SG$2590 (7 )
2 Bedroom Townhouse For Unforgettable Vacations!
2 3
apartment , Holmes Beach
This Holmes Beach beachfront condo is situated steps from AMI Paddleboard Adventures and West Coast Surf Shop, and within 10 minutes' drive of Manatee Public Beach and Anna Maria Sound. This 111 square metre (1194 square feet) apartment sleeps six, boasting two bedrooms, two bathrooms, a fully equipped kitchen including a dishwasher, in-unit laundry, and a comfortable sofa bed, plus parking and Wi-Fi.
9.2 54 reviews
Anna Maria, FL
20/06 – 27/06
SG$383/nighttotal: SG$2681 (7 )
Anna Cabana B - 301 Poinsettia
1 2
house , Anna Maria
Anna Cabana B is a self-catering property in Anna Maria, a five-minute walk from Anna Maria Island and a thirteen-minute walk from Anna Maria City Pier, approximately 32 kilometres from The John and Mable Ringling Museum of Art. This one-bedroom, one-bathroom holiday home offers 56 square metres of space, boasting a private swimming pool, spa, fitness centre, and parking, alongside a fully equipped kitchen and air conditioning.
9.2 91 reviews
Anna Maria, FL
20/06 – 27/06
SG$259/nighttotal: SG$1813 (7 )
Getaway Retreat A+b · 4br · Firepit · Bay
2 2
apartment , Bradenton Beach
This holiday home is ideally situated in Bradenton Beach, just a 3km walk from Anna Maria Sound and the beach, and within a 3km radius of Bradenton Beach Marina and Fish Hole Adventure Golf. It has been highly rated by previous guests for its location, cleanliness and overall experience. The property is a spacious 153 square metre house with 4 bedrooms, a sofa bed and a fully equipped kitchen. Guests can enjoy a range of amenities, including a swimming pool, terrace, garden, barbecue grills and free parking.
9.8 38 reviews
Anna Maria, FL
20/06 – 27/06
SG$466/nighttotal: SG$3262 (7 )
Paradise On Palm Lower Unit
1 2
apartment , Anna Maria
This beachfront Anna Maria Island flat is situated a short distance from Pine Street, offering easy access to shops and restaurants. Sleeping four comfortably in two bedrooms (one king-size, one queen-size bed), this self-catering property boasts a private patio, parking, in-unit laundry, and is available for monthly winter lets (January-March), with Saturday/Sunday check-in.
9.8 29 reviews
Anna Maria, FL
20/06 – 27/06
SG$332/nighttotal: SG$2324 (7 )
Updated Ground-level Villa, Pet Friendly And So Close To The Beach! Great Rates!
2 2
apartment , Holmes Beach
This Holmes Beach beachfront villa offers stunning ocean views and is less than 1.6km from Bradenton Beach and Palmetto Avenue Beach, and within 3.2km of the Island Players and Anna Maria Island Museum. This 93 square metre property sleeps four guests in two bedrooms and two bathrooms, boasting a private pool, spa, terrace, garden, BBQ, and fully equipped kitchen including a dishwasher; free Wi-Fi is also provided.
9.9 82 reviews
Anna Maria, FL
19/07 – 23/07
SG$3550/nighttotal: SG$14200 (4 )
Cloud 9 - Beachfront Splendor
1 4
apartment , Anna Maria
This Anna Maria holiday home is situated directly on the beach, just a short walk from Bayfront Park and Anna Maria Beach. The property has received excellent ratings for its location, cleanliness, and overall user experience. The house offers a spacious and comfortable layout, with 5 bedrooms and a floor area of 288 square meters, comfortably accommodating up to 8 guests. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, tennis court, and a fully equipped kitchen.
9.4 7 reviews
Anna Maria, FL
20/06 – 27/06
SG$272/nighttotal: SG$1904 (7 )
Sandy Pointe By Ami Locals
2 3
apartment , Holmes Beach
This two-bedroom apartment in Holmes Beach is ideally located just a 1.6-kilometre walk from Anna Maria Sound, AMI Paddleboard Adventures, and West Coast Surf Shop. The self-catering apartment offers a fully equipped kitchen, a private balcony, and access to a swimming pool, perfect for a relaxing holiday in Florida.
10 6 reviews
Anna Maria, FL
08/10 – 14/10
SG$359/nighttotal: SG$2154 (6 )
Barefoot Bungalow: Steps To Bayfront Park
2 4
apartment , Anna Maria
This Anna Maria Island bungalow enjoys a quiet north-end location, approximately 0.8 km from Bean Point Beach and Bayfront Park, and 1.6 km from Anna Maria City Pier and Pine Avenue's shops and restaurants. The two-bedroom, two-bathroom property sleeps five, offering a recently updated open-plan living area, a fully equipped kitchen with dishwasher, air conditioning, free Wi-Fi, and pet-friendly accommodation; guests can also utilise the nearby free Island Trolley service.
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
9.6 14 reviews
Anna Maria, FL
28/07 – 03/08
SG$2914/nighttotal: SG$17484 (6 )
New Beach House 1 Min To Beach! Heated Pool/spa!
1 11
apartment , Anna Maria
This detached house is situated on the north end of Anna Maria Island, a mere 100 metres from Anna Maria Beach and within easy walking distance of Pine Avenue's shops and eateries. This dog-friendly property accommodates up to 12 guests across five bedrooms, featuring a private heated swimming pool, spa, and a games area with ping-pong and darts, alongside a well-equipped gourmet kitchen and covered outdoor seating with a barbecue.
9.4 10 reviews
Anna Maria, FL
08/10 – 14/10
SG$445/nighttotal: SG$2670 (6 )
Southern Breeze 2
2 4
house , Anna Maria
Southern Breeze 2, a beachfront Anna Maria Island holiday home, is a 7-minute walk from Anna Maria Island and an 11-minute walk (approximately 1.8km) from Anna Maria City Pier, 27km from Sarasota Bradenton International Airport and 32km from The John and Mable Ringling Museum of Art. This 73 square metre property features two bedrooms, one bathroom, sleeps eleven guests, and includes a fully equipped kitchen, private balcony, free Wi-Fi, a swimming pool and fitness centre, perfect for families or groups seeking a beachfront stay.
10 47 reviews
Anna Maria, FL
28/07 – 03/08
SG$677/nighttotal: SG$4062 (6 )
Heated Pool Haven! Fun Games! Near Img & Ami!
1 11
apartment , Bradenton
This Bradenton house, ideally located for exploring Anna Maria Island (9.5km), IMG Academy (8.5km), and Bradenton's city centre (7.5km), offers easy access to Robinson Preserve for outdoor pursuits. The 210 square metre property boasts four bedrooms, three bathrooms, sleeps twelve guests, and includes a private pool, fully equipped kitchen, and amenities such as a foosball table and beach equipment.
9.8 14 reviews
Anna Maria, FL
28/07 – 03/08
SG$804/nighttotal: SG$4824 (6 )
12 Min To Beach, Hot Tub, Pickleball, Game Room
3 11
apartment , West Bradenton
This Palma Sola, Bradenton holiday home is conveniently located near Robinson Preserve (4 minutes' drive), Manatee Public Beach (12 minutes' drive), and IMG Academy (12 minutes' drive), offering easy access to Anna Maria Island beaches within a short drive. This spacious three-bedroom, two-bathroom apartment boasts 141 square metres of living space, sleeping up to 12 guests and including resort-style amenities such as a heated pool, hot tub, pickleball court, and a fully equipped kitchen; plus abundant beach gear and family-friendly features like a pack 'n' play and highchair are provided.
Best family friendly Anna Maria, FL lodging
Among the 2100 accommodations in Anna Maria, FL, here are the 4 best for families
9.8 13 reviews
Anna Maria, FL
28/07 – 03/08
SG$1039/nighttotal: SG$6234 (6 )
Luxurious Retreat W/ Pool & Spa | Steps To Bay!
5 11
apartment , Bradenton
This five-bedroom, five-bathroom holiday home in Bradenton, Florida, enjoys a prime location within walking distance of Palma Sola Bay and Causeway Park, and under 8km from Anna Maria Island's beaches. Offering 465 square metres of living space, the property boasts a spacious layout sleeping up to 16 guests, complete with resort-style amenities including a heated saltwater pool, spa, extensive game rooms, and pet-friendly features.
9.8 35 reviews
Anna Maria, FL
19/07 – 23/07
SG$2065/nighttotal: SG$8260 (4 )
Pool*hot Tub*tiki Bar*pickleball Court*dock
4 4
apartment , Anna Maria
This Anna Maria Island property, a four-bedroom, three-bathroom house, is situated less than 1.6 km from Bay Boulevard Beach, Historic Green Village, and Bayfront Park, and under 1.6 km from Palmetto Avenue Beach and the Anna Maria Island Museum. Offering 252 square metres of space, this waterfront holiday home sleeps eight guests and boasts a private pool, fenced yard, tennis court, and access to on-site amenities including a water park, spa tub, and games room.
9.5 43 reviews
Anna Maria, FL
04/08 – 06/08
SG$1398/nighttotal: SG$2796 (2 )
Isle Relax: Close To Gulf Of Mexico And Pine Ave.
3 2
apartment , Anna Maria
This Anna Maria Island holiday home is centrally located, less than 1.6km from the Anna Maria Island Museum and Historical Park and Anna Maria Beach, and within a 5-minute drive of Island Players and Bradenton Beach. This 147 square metre property boasts three bedrooms, two bathrooms, sleeps eight guests, and includes a private pool, tennis court, and free Wi-Fi.
9.9 130 reviews
Anna Maria, FL
28/07 – 03/08
SG$706/nighttotal: SG$4236 (6 )
Stunning!- Game Room, Pool, Beaches & Full Remodel!
4 11
apartment , Bradenton
This Bradenton holiday home enjoys a coastal location, less than 5km from Blake Medical Center, Smugglers Cove Adventure Golf, and The Bishop Museum of Science and Nature. The 204 square metre property offers four bedrooms, two bathrooms, a private pool, and a fully equipped kitchen, sleeping up to a large family group; on-site amenities include a water park and games room.
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
9.2 14 reviews
Anna Maria, FL
08/10 – 14/10
SG$675/nighttotal: SG$4050 (6 )
Pet-friendly Retreat With Pool And Hot Tub Near The Beach!
3 4
apartment , Anna Maria
This pet-friendly holiday home is situated in Anna Maria, a short walk from the Anna Maria Island Historical Museum and Park, and 6 minutes from The Island Players theatre. Spanning 132 square meters, this apartment accommodates up to six guests with three bedrooms and two bathrooms, and offers a heated swimming pool, hot tub, and balcony, alongside a fully equipped kitchen and air conditioning.
9.6 7 reviews
Anna Maria, FL
20/06 – 27/06
SG$388/nighttotal: SG$2716 (7 )
Main St Gem! Walk To Shops, Dining & Beach! +Heated Pool And Spa
1 2
apartment , Holmes Beach
This Holmes Beach holiday home is a short walk from Bradenton Beach and Anna Maria Sound, and within a 15-minute drive (approx. 10km) of AMI Paddleboard Adventures and West Coast Surf Shop. This 63 square metre property boasts one bedroom, one bathroom, sleeps three, and includes a private hot tub, swimming pool, in-unit laundry, and a fully equipped kitchen with gas grills for outdoor cooking.
Anna Maria, FL
28/07 – 03/08
SG$952/nighttotal: SG$5712 (6 )
Manatee Haven Pool Games Hot Tub Firepit
4 11
apartment , West Bradenton
This 4-bedroom residence is situated in the Palma Sola district of West Bradenton, offering proximity to Anna Maria Island and the Gulf beaches, with the De Soto National Memorial and Palma Sola Botanical Park nearby. This spacious 158 square metre holiday home accommodates up to 12 guests, featuring a fully equipped chef's kitchen, a dedicated workspace, a games room with pool and foosball, an outdoor entertainment area with a heated swimming pool and hot tub, and parking for up to five vehicles.
9.0 4 reviews
Anna Maria, FL
28/07 – 03/08
SG$929/nighttotal: SG$5574 (6 )
Private Oasis W/ Heated Saltwater Pool & Hot Tub
4 11
apartment , Bradenton
This Bradenton residence is located in a quiet, safe neighbourhood, 0.9 kilometres from Bradenton Country Club and 1.6 kilometres from HCA Florida Blake Hospital, with Anna Maria Island beaches approximately 12.9 kilometres away. This spacious 175 square metre holiday home accommodates up to 10 guests with four bedrooms and three bathrooms, featuring a private fenced backyard with a heated saltwater pool, hot tub, fire pit, games room including a foosball table, mini pool table, mini ping pong table, and arcade games, plus a dedicated workspace with high-speed internet and parking for six cars.
Best Anna Maria, FL accommodations with a kitchen
10 195 reviews
Anna Maria, FL
15/08 – 22/08
SG$337/nighttotal: SG$2359 (7 )
Naut 2 Shabby Bungalow - A Sweet And Cozy Getaway On Pine Avenue!
1 3
apartment , Anna Maria
This Anna Maria Island property is situated near the sea, less than a kilometre from Historic Green Village and Bradenton Beach, and a short 0.8 kilometre drive from Bay Boulevard Beach and Bayfront Park. This self-catering holiday home boasts 65 square metres of space, sleeping four guests in one bedroom and one bathroom, and features a private swimming pool, spa, tennis court, and fitness centre, plus free Wi-Fi.
10 22 reviews
Anna Maria, FL
20/06 – 27/06
SG$384/nighttotal: SG$2688 (7 )
Palm Villa By Beach Boutique Rentals
2 3
cottage , Holmes Beach
This charming cottage is situated just a short walk from the beach path in Holmes Beach, offering easy access to the sand and nearby shops and restaurants. The cottage has consistently received excellent ratings for its cleanliness, location, and overall experience, making it a popular choice for travellers. The two-bedroom cottage spans 75 square metres and comfortably accommodates up to five guests. It features a fully equipped kitchen, a private patio with outdoor shower, and a shared laundry facility, ensuring a relaxing and comfortable stay.
9.6 73 reviews
Anna Maria, FL
04/08 – 06/08
SG$3648/nighttotal: SG$7296 (2 )
South Bay Beach House: Bay Front Luxury Beach Villa With Heated Pool
4 2
apartment , Anna Maria
This Anna Maria Island property is centrally located, less than 1.6km from Bay Boulevard Beach and Anna Maria Beach, and a 10-minute drive from Anna Maria City Pier and Bayfront Park. This 265 square metre holiday home sleeps eight guests across four bedrooms and three bathrooms, boasting a private pool, a terrace, a fully equipped kitchen, free Wi-Fi, and access to shared barbecue facilities and a water park.
9.8 12 reviews
Anna Maria, FL
20/06 – 27/06
SG$482/nighttotal: SG$3374 (7 )
102 M² House ∙ 2 Bedrooms ∙ 6 Guests
2 3
house , Anna Maria
This family-friendly detached house, "Sea Breeze Haven", is located on the quiet northern tip of Anna Maria Island, 75 meters from the sugar sand beaches and a short walk or cycle from local restaurants and shops. This ground-level property offers 102 square meters of living space with two bedrooms and two bathrooms, accommodating up to six guests with air conditioning, Wi-Fi, a fully equipped kitchen, and a garden with a patio and gas grill.
