Holiday Rentals in Anna Maria, FL

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Anna Maria, FL holiday rentals
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1981 Holiday rentals and Airbnb in Anna Maria, FL

Best family friendly Anna Maria, FL holiday rentals

Among the 1981 accommodations in Anna Maria, FL, here are the 4 best family friendly rentals

Sleeps 12 | Pool, Game Room Fun & Hot Tub - Anna Maria, FL
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.
No Busy Roads To Cross To Get To The Beach! 5 Min Walk To Beach! Sleeps 6 - Anna Maria, FL
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.
Luxury ~ Heated Pool  ~ Games ~ Near Ami, Img, Srq - Anna Maria, FL
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.
Cd Shorewalk -Pool, Tennis, Pickle Ball, Near Beaches Anna Maria Island And Img - Anna Maria, FL
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

235 M² House ∙ 4 Bedrooms ∙ 8 Guests - Anna Maria, FL
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.
Paradise Inn - Anna Maria, FL
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.
Heated Pool Haven! Fun Games! Near Img & Ami! - Anna Maria, FL
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.
Montego Bay - Anna Maria, FL
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

Spectacular Beach & Dolphin Views!  Huge Private Balcony! 2br/2ba Upstairs Villa - Anna Maria, FL
9.9 745 reviews
Anna Maria, FL
15/07 – 17/07
519 €/nighttotal: 1038 € (2 )

Spectacular Beach & Dolphin Views! Huge Private Balcony! 2br/2ba Upstairs Villa

2 5
apartment , Bradenton Beach
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.
Anna Maria Home With Pool And Rooftop Deck! 5-min Walk To Beach - Coconut Breeze - Anna Maria, FL
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.
Steps Away To Beaches And The Gulf, Snowbird Friendly, Ac, Free Wifi And Parking - Anna Maria, FL
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.
64 M² Condo ∙ 1 Bedroom ∙ 4 Guests - Anna Maria, FL
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

Bay Vista At Bayside Bungalow - Anna Maria, FL
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.
Coral Escape - Anna Maria, FL
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.
112 M² House ∙ 3 Bedrooms ∙ 6 Guests - Anna Maria, FL
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.
Luxury Home With Rooftop Deck, Pool- Florida Fling - Anna Maria, FL
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.
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