Anglers Bay At One Particular Harbour 392-103 · Lagoon Views · 5-night Min
3 7
apartment , Bradenton
This three-bedroom, three-bathroom condo in One Particular Harbour, Bradenton, offers stunning lagoon views and is located minutes from Anna Maria Island's beaches. The 155 square metre (1667 square foot) property features a spacious open-plan living area, a fully equipped kitchen, and a private screened balcony, accommodating up to six guests and providing access to resort-style amenities including a heated pool and private beach club perks for stays of 30 nights or more.
9.9 43 reviews
Anna Maria, FL
24/07 – 29/07
380 €/nighttotal: 1900 € (5 )
Nautical Escape! Private Pool Home With A Tropical Backyard Oasis!
4 9
apartment , West Bradenton
This West Bradenton holiday home enjoys a convenient location, approximately 16 kilometres from Sarasota Bradenton International Airport and 19 kilometres from The John and Mable Ringling Museum of Art, offering easy access to beaches and a boat ramp. The four-bedroom property boasts a private pool, free Wi-Fi, a fully equipped kitchen, and free private parking, comfortably accommodating families or groups and providing all the amenities needed for a relaxing West Bradenton getaway.
9.7 99 reviews
Anna Maria, FL
24/07 – 27/07
392 €/nighttotal: 1176 € (3 )
Tortuga 2 Bedroom Deluxe Partial View
2 5
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.
10 76 reviews
Anna Maria, FL
02/07 – 05/07
782 €/nighttotal: 2346 € (3 )
Pool & Sports Court | Near Anna Maria + Beaches
1 9
apartment , Bradenton
This luxurious Bradenton holiday home is situated approximately 16km from Bradenton Beach and Anna Maria Island, also within 16km of the Riverwalk and IMG Academy, offering easy access to local attractions. Sleeping up to 10 guests in 3 bedrooms and 2 bathrooms, this self-catering property boasts a private heated pool, a unique pickleball/basketball court, a fully equipped kitchen with stainless steel appliances, and complimentary beach gear including chairs, towels, and a cooler; a 2023 Ford Bronco car rental option is also available.
8.5 2 reviews
Anna Maria, FL
15/07 – 17/07
550 €/nighttotal: 1100 € (2 )
Southern Breeze 5
2 5
house , Anna Maria
Southern Breeze 5, a beachfront property on Anna Maria Island, is a 6-minute walk from the island and 27 kilometres from Sarasota Bradenton International Airport. This two-bedroom, one-bathroom holiday home boasts 73 square metres of floor space, sleeps up to 11 guests, includes a fully equipped kitchen, private pool, fitness centre, and free Wi-Fi, and is a 12-minute walk from Anna Maria City Pier.
Anna Maria, FL
27/06 – 04/07
192 €/nighttotal: 1344 € (7 )
Waterfront Villa Delphina
2 5
apartment , Holmes Beach
This canal-front villa in Holmes Beach offers direct water access, with two kayaks provided for exploring the canals, and is a mere 400 metres from Holmes Beach and the Gulf beaches, placing you within walking distance of dining, shopping, and island trolley stops. This accommodation accommodates up to six guests across two king bedrooms, each with an en-suite bathroom featuring a walk-in shower, and includes a full-size sleeper sofa, with amenities such as in-unit laundry, air conditioning, and two dedicated parking spaces.
10 57 reviews
Anna Maria, FL
10/07 – 13/07
179 €/nighttotal: 537 € (3 )
Pet-friendly Bradenton Home 1 5 Mi To Cortez Beach
2 4
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.
9.6 49 reviews
Anna Maria, FL
03/07 – 06/07
1136 €/nighttotal: 3408 € (3 )
Bean Point Beach Cottage: North End Pool Home, Close To Beach & Bay By Anna Maria Life
3 3
house , Anna Maria
Bean Point Beach Cottage is situated in Anna Maria, Florida, a short 32km drive from The John and Mable Ringling Museum of Art and within walking distance of Anna Maria City Pier and Anna Maria Island. This 111 square metre property boasts two bathrooms, a fully equipped kitchen including a dishwasher, a private swimming pool, spa, fitness centre, and parking, perfect for a relaxing beach holiday.
9.3 73 reviews
Anna Maria, FL
24/07 – 27/07
344 €/nighttotal: 1032 € (3 )
Private Pool Home- Near Beaches-room For Boat Or Jet Ski Parking
3 5
apartment , Bradenton
This Bradenton property is conveniently situated just 5km from Blake Medical Center, De Soto National Memorial and Robinson Preserve, offering easy access to both the beach and local attractions. The house has received excellent user ratings and very good ratings for location and cleanliness. This 3-bedroom, 2-bathroom home is ideal for families or groups of up to 6 guests, offering 143 square metres of comfortable living space. The property includes a private pool, a fully equipped kitchen, laundry facilities, a garden and parking, ensuring a relaxing and enjoyable stay.
9.7 68 reviews
Anna Maria, FL
05/07 – 11/07
535 €/nighttotal: 3210 € (6 )
Stunning Saltwater Pool And Spa With Mature Fl Landscaping For Complete Privacy.
4 11
apartment , Bradenton
This spacious apartment is ideally situated near Holmes Beach, downtown Bradenton, and the natural beauty of Robinson's Preserve and GT Bray Park, offering easy access to both beachside relaxation and cultural attractions. The property consistently receives excellent ratings for user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay. The apartment features a generous 265 square metres of living space, comfortably accommodating families or groups. With four bedrooms, three bathrooms, a private pool, spa, and a fully equipped kitchen, guests can enjoy a luxurious and relaxing retreat, complete with all the comforts of home.
Anna Maria, FL
02/07 – 05/07
269 €/nighttotal: 807 € (3 )
Nautical Nest W/dock
2 6
apartment , Bradenton
This Bradenton flat offers waterfront living on a saltwater canal, located just 4.8 kilometres from the beaches of Anna Maria Island and a 5-15 minute walk to downtown Bradenton and Robinsons Preserve. This two-bedroom accommodation sleeps up to six guests and features air conditioning, a fully equipped kitchen, an in-unit washer and dryer, and access to a shared swimming pool, with complimentary boat docking available for vessels under 25 feet.
9.8 19 reviews
Anna Maria, FL
24/07 – 29/07
235 €/nighttotal: 1175 € (5 )
Palm Tree Home - Private Pool Haven, Pet-friendly!
3 9
apartment , Bradenton
This Bradenton holiday home is ideally situated less than 1.6km from Bradenton Riverwalk, the Bishop Museum of Science and Nature, and the Manatee Performing Arts Centre, and under 3.2km from LECOM Park and Manatee Memorial Hospital. The 140 square metre property boasts three bedrooms, two bathrooms, sleeps nine guests, and includes a private pool, fully equipped kitchen, laundry facilities, and patio – perfect for exploring Bradenton's attractions.
Best family friendly Anna Maria, FL holiday rentals
Among the 1981 accommodations in Anna Maria, FL, here are the 4 best family friendly rentals
9.8 154 reviews
Anna Maria, FL
24/07 – 29/07
422 €/nighttotal: 2110 € (5 )
Sleeps 12 | Pool, Game Room Fun & Hot Tub
4 9
apartment , Bradenton
This four-bedroom holiday home is located in Bradenton, just a short drive (8 km) from Anna Maria Island, Bradenton Beach, and Coquina Beach. The property offers a private pool and hot tub, a games room with a pool table and arcade machine, and a fully equipped kitchen, making it ideal for families and groups of up to 12 guests.
9.8 53 reviews
Anna Maria, FL
27/06 – 04/07
495 €/nighttotal: 3465 € (7 )
No Busy Roads To Cross To Get To The Beach! 5 Min Walk To Beach! Sleeps 6
3 5
apartment , Holmes Beach
This Holmes Beach holiday home is situated mid-island, a short walk (approximately 0.8 km) from the beach and close to the trolley stop providing easy access to Pine Avenue and Coquina Beach, renowned as one of the world's top beaches. The 121 square metre property boasts a spacious open-plan layout, sleeps six guests comfortably, and includes a private heated pool (November 15th–April 15th), a fully equipped kitchen, beach amenities, and a convenient in-unit washer/dryer.
9.9 28 reviews
Anna Maria, FL
24/07 – 29/07
505 €/nighttotal: 2525 € (5 )
Luxury ~ Heated Pool ~ Games ~ Near Ami, Img, Srq
1 9
apartment , Bradenton
Palma Paradise, a five-bedroom Bradenton villa, is situated a short drive (approx. 16km) from Anna Maria Island and 24km from Longboat Key, offering easy access to local beaches and attractions. This self-catering property sleeps eleven guests and boasts a private heated saltwater pool and spa, a fully equipped games room with air hockey and arcade games, and provides beach equipment including chairs, umbrellas, and coolers.
10 2 reviews
Anna Maria, FL
03/07 – 06/07
205 €/nighttotal: 615 € (3 )
Cd Shorewalk -Pool, Tennis, Pickle Ball, Near Beaches Anna Maria Island And Img
2 3
apartment , Bradenton
This Bradenton apartment, near IMG Academy (a 5-minute drive away), offers easy access to Anna Maria Island and Longboat Key beaches (approximately 24km). The 106 square metre, two-bedroom, two-bathroom property sleeps four, boasting a terrace, garden, and access to resort amenities including heated pools, tennis/pickleball courts, and a clubhouse with BBQ grills.
Best Anna Maria, FL holiday rentals with a pool
Among the 1981 accommodations in Anna Maria, FL, here are the 4 best rentals with a pool
Anna Maria, FL
02/07 – 05/07
2162 €/nighttotal: 6486 € (3 )
235 M² House ∙ 4 Bedrooms ∙ 8 Guests
4 6
house , Anna Maria
Serendipity Deux is a luxury beach villa on Anna Maria Island, offering premium beach access and proximity to Rod & Reel Pier, Pine Avenue, and Bean Point. This spacious 235 square metre property accommodates up to 8 guests in 4 bedrooms, featuring a swimming pool, jacuzzi, fitness centre, and included bicycles, a kayak, and paddleboards for exploring the 11 kilometre island.
9.9 28 reviews
Anna Maria, FL
24/07 – 27/07
272 €/nighttotal: 816 € (3 )
Paradise Inn
3 5
apartment , Cortez
Paradise Inn, a three-bedroom house in the Bradenton/Cortez/Anna Maria Island area, is a minute from restaurants, 4.8km from Anna Maria Island's beaches, and 8km from Bridge Street. This single-storey property sleeps six, boasts a private pool and garden, a walk-in shower, and an adjustable bed, making it suitable for families and senior guests; nearby attractions include IMG Academy, a ten-minute drive away.
10 47 reviews
Anna Maria, FL
24/07 – 29/07
482 €/nighttotal: 2410 € (5 )
Heated Pool Haven! Fun Games! Near Img & Ami!
1 9
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.
Anna Maria, FL
05/07 – 11/07
1054 €/nighttotal: 6324 € (6 )
Montego Bay
5 11
house , Anna Maria
This holiday home in Montego Bay, Anna Maria, is a 5-minute walk from Anna Maria Island and a 10-minute walk to Anna Maria City Pier, with The John and Mable Ringling Museum of Art located 30.56 kilometres away. This spacious 242 square metre holiday home accommodates up to 23 guests across 5 bedrooms and 4 bathrooms, featuring a private swimming pool, a balcony with sea views, a well-equipped kitchen with a dishwasher and microwave, complimentary high-speed WiFi, and free private parking.
Frequently asked questions about holiday rentals in Anna Maria, FL
What are some interesting places to visit in or near Anna Maria, FL?
Anna Maria Island is packed with things to see and do. The historic Anna Maria City Pier is a must-visit, offering stunning views of the Gulf of Mexico. For a bit of nature, check out the Bean Point Preserve, a haven for birdwatching and enjoying the beach. If you're looking for a bit of history, the Anna Maria Island Museum is a great place to learn about the island's past.
What are the best Airbnb and holiday rentals in Anna Maria, FL?
Which walking or cycling routes are the best in Anna Maria, FL?
For a scenic stroll, try the Pine Avenue Walkway, which runs along the waterfront. If you're feeling adventurous, you can cycle the entire length of Anna Maria Island on the dedicated bike path, taking in the beautiful beaches and charming neighbourhoods. Don't forget to stop at the Anna Maria City Pier for a break and to enjoy the views.
What are the most popular Airbnbs in Anna Maria, FL?
What sports or outdoor activites can visitors enjoy in and around Anna Maria, FL?
Anna Maria Island is a paradise for watersports enthusiasts. You can try your hand at kayaking, paddleboarding, or even kitesurfing in the calm waters of the Gulf of Mexico. Fishing is also very popular, with plenty of charter boats available for deep-sea adventures. For a more relaxed experience, why not rent a beach cruiser and explore the island at your own pace?
What are the best holiday rentals with a pool in Anna Maria, FL?
What other towns or cities can be easily accessed from Anna Maria, FL?
Anna Maria Island is perfectly located for exploring the surrounding area. You can easily drive to Bradenton, which is home to the South Florida Museum and the Bishop Museum of Science and Nature. Sarasota, known for its vibrant arts scene and beautiful beaches, is also within easy reach. For a day trip, consider visiting the St. Armand's Circle in Sarasota, a popular shopping and dining destination.
What are the best rentals for families and kids in Anna Maria, FL?
What amenities are commonly available in vacation rentals in Anna Maria, FL?
Vacation rentals in Anna Maria Island are typically well-equipped with modern amenities to make your stay comfortable. Most rentals offer private pools, hot tubs, fully equipped kitchens, laundry facilities, and high-speed internet. Many also have balconies or patios with stunning views of the Gulf of Mexico.
What are the best rentals or Airbnbs with a jacuzzi in Anna Maria, FL?
What time of year is best to rent a vacation rental Anna Maria, FL?
The best time to visit Anna Maria Island is during the shoulder seasons, from April to May and September to October. The weather is still warm and sunny, but the crowds are smaller and prices are more affordable. If you're looking for a more lively experience, you can visit during the peak season, from December to April, but be prepared for higher prices and larger crowds.
Destinations nearby
Best Anna Maria, FL holiday rentals with a balcony
This apartment is located in Bradenton Beach, just steps from the marina and beach, with family-friendly attractions like Fish Hole Adventure Golf within a 10-minute walk. The property enjoys excellent user, location, and cleanliness ratings. The self-catering accommodation sleeps up to six guests in two bedrooms and includes a well-equipped kitchen. Enjoy the outdoor amenities including a garden, barbecue grills, a jacuzzi, a tennis court, and a balcony with views of the sea.
9.4 16 reviews
Anna Maria, FL
27/07 – 01/08
1155 €/nighttotal: 5775 € (5 )
Anna Maria Home With Pool And Rooftop Deck! 5-min Walk To Beach - Coconut Breeze
4 9
apartment , Anna Maria
This four-bedroom Anna Maria Island holiday home is situated a 0.5km stroll from Bean Point Beach, close to Pine Avenue's shops and restaurants. Offering 210 square metres of space, this property boasts four ensuite bedrooms sleeping twelve, a private heated saltwater pool and spa, rooftop deck, outdoor kitchen, pool table, and beach equipment, all within easy reach of Anna Maria's attractions.
10 6 reviews
Anna Maria, FL
15/08 – 17/08
463 €/nighttotal: 926 € (2 )
Steps Away To Beaches And The Gulf, Snowbird Friendly, Ac, Free Wifi And Parking
2 4
apartment , Anna Maria
This Anna Maria Island holiday home is centrally located, within a 1.6km walk of Bean Point and Anna Maria beaches, and a similar distance from Bradenton Beach and Bayfront Park. The 213 square metre property boasts two bedrooms, two bathrooms, and can comfortably accommodate four guests, featuring a fully equipped kitchen, private balcony, in-house laundry, and parking.
9.2 16 reviews
Anna Maria, FL
27/06 – 04/07
238 €/nighttotal: 1666 € (7 )
64 M² Condo ∙ 1 Bedroom ∙ 4 Guests
1 2
apartment , Bradenton Beach
This Anna Maria Island holiday apartment, situated within the Runaway Bay community, boasts direct beach access and is a short drive from Bradenton's historical sites and museums. The 64 square metre self-catering flat offers one bedroom, one bathroom, sleeps four, and includes a king-size bed, queen-size sofa bed, fully equipped kitchen, screened balcony overlooking a pond, and access to Runaway Bay's amenities such as a swimming pool (currently under repair), tennis courts, and a fishing pier; beach chairs, toys and a wagon are provided.
Best Anna Maria, FL holiday rentals with parking
8.5 2 reviews
Anna Maria, FL
29/06 – 30/06
1000 €/nightfor 1 night
Bay Vista At Bayside Bungalow
1 2
house , Anna Maria
Bay Vista at Bayside Bungalow, a beachfront property in Anna Maria, Florida, is a 12-minute walk from Anna Maria Island and 29 kilometres from Sarasota Bradenton International Airport. This three-bedroom, two-bathroom holiday home boasts 111 square metres of floor space, sleeps up to 11 guests, includes a fully equipped kitchen, swimming pool, fitness centre, and free Wi-Fi, and offers stunning sea views.
Anna Maria, FL
27/06 – 04/07
1213 €/nighttotal: 8491 € (7 )
Coral Escape
6 9
house , Holmes Beach
Coral Escape, a substantial villa in Holmes Beach, offers a prime location just 3 minutes' walk from Anna Maria Island's shores and 4.8 kilometres from Anna Maria City Pier. This property boasts 441 square metres of living space with 6 bedrooms and 4 bathrooms, accommodating up to 23 guests, and features a kitchen with a fridge, microwave oven, and dishwasher, alongside air conditioning, a swimming pool, terrace, garden, and private parking.
Anna Maria, FL
24/07 – 27/07
519 €/nighttotal: 1557 € (3 )
112 M² House ∙ 3 Bedrooms ∙ 6 Guests
3 5
house , Anna Maria
Key Lime Cottage offers a prime location on North Shore Drive, Anna Maria Island, just a short 200-metre walk to the Gulf beaches. This 186-square-metre holiday home comfortably accommodates up to eight guests with three bedrooms and two bathrooms, featuring a private hot tub, a fenced garden, and complimentary beach gear including paddle boards and bicycles.
9.6 10 reviews
Anna Maria, FL
27/07 – 01/08
1635 €/nighttotal: 8175 € (5 )
Luxury Home With Rooftop Deck, Pool- Florida Fling
7 9
apartment , Bradenton Beach
This beachfront property in Bradenton Beach, Florida, is a short walk (under 1.6km) from Bridge Street and Cortez Beach, and less than 0.8km from Fish Hole Adventure Golf. This seven-bedroom, eight-bathroom holiday home boasts 257 square metres of living space, a private pool, jacuzzi, and terrace, accommodating up to 14 guests, with all mod cons including a fully equipped kitchen and free Wi-Fi.