Holiday Rentals in Anna Maria Island, FL

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Anna Maria Island, FL holiday rentals
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6231 Holiday Rentals and Airbnb in Anna Maria Island, FL

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

Sea Salt Retreat! Private Pool Home In Bradenton Just 5 Miles From Anna Maria! - Anna Maria Island, FL
Anna Maria Island, FL
28/06 – 03/07
NZ$881/nighttotal: NZ$4405 (5 )

Sea Salt Retreat! Private Pool Home In Bradenton Just 5 Miles From Anna Maria!

3 8
house , West Bradenton
This West Bradenton detached house offers a convenient location, situated 8 kilometres from Anna Maria Island and 2.25 kilometres from Palma Sola Causeway Park, with Sarasota Bradenton International Airport 16 kilometres away.
This family-friendly residence, spanning 175 square metres, features three bedrooms, two bathrooms, and accommodates fifteen guests, boasting a private swimming pool, a fully equipped kitchen with a dishwasher and microwave, air conditioning, and complimentary WiFi and parking.
5 Stars! ⭐️? Hottub&pool-4br/2ba  5 Miles To Beach! - Anna Maria Island, FL
9.8 137 reviews
Anna Maria Island, FL
27/07 – 29/07
NZ$671/nighttotal: NZ$1342 (2 )

5 Stars! ⭐️? Hottub&pool-4br/2ba 5 Miles To Beach!

4 5
apartment , West Bradenton
This family-friendly vacation home is located in West Bradenton, just 2.7 kilometres from Blake Medical Center and within a 10 kilometre radius of attractions like Arcadeland and the Bishop Museum of Science and Nature. This property has received excellent reviews for its location, cleanliness, and overall experience.
This four-bedroom, two-bathroom property offers a comfortable and spacious environment for families. Enjoy amenities like a private pool, spa tub, game room, fully equipped kitchen, free Wi-Fi, and a washing machine, as well as easy access to the beach.
New! Blue Iguana! Tropical Backyard Oasis With Heated Pool, Hot Tub, Fire Table, And More! - Anna Maria Island, FL
Anna Maria Island, FL
28/06 – 03/07
NZ$1216/nighttotal: NZ$6080 (5 )

New! Blue Iguana! Tropical Backyard Oasis With Heated Pool, Hot Tub, Fire Table, And More!

3 8
house , Bradenton
This Bradenton holiday home is situated 2.9 kilometres from Palma Sola Causeway Park, offering easy access to attractions such as the Ringling Museum of Art (17.7 kilometres away).
The 195-square-metre property boasts three bedrooms, two bathrooms, sleeps up to 19 guests, and includes a heated pool, hot tub, fire pit, children's playground, free Wi-Fi, and a fully equipped kitchen.
Near Ami-heated Pool-hot Tub-game Room-putting G - Anna Maria Island, FL
9.9 120 reviews
Anna Maria Island, FL
03/08 – 07/08
NZ$681/nighttotal: NZ$2724 (4 )

Near Ami-heated Pool-hot Tub-game Room-putting G

1 3
apartment , West Bradenton
This Palma Sola, West Bradenton holiday home is ideally situated, less than 20km from Anna Maria Island's beaches and within a 24km radius of Palma Sola Botanical Gardens and IMG Academy.
Sleeping up to 10 guests, this three-bedroom, two-bathroom property boasts a heated pool, hot tub, games room with pool table and arcade games, a fully equipped kitchen, and ample outdoor space with a Traeger grill and various games; beach essentials are also provided.

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

Coconut Cottage~private Heated Pool~block To Shops - Anna Maria Island, FL
10 56 reviews
Anna Maria Island, FL
27/06 – 28/06
NZ$1957/nightfor 1 night

Coconut Cottage~private Heated Pool~block To Shops

1 8
apartment , Anna Maria
Coconut Cottage, a three-bedroom holiday home on Anna Maria Island's north end, is located a short 0.8 km walk from Pine Avenue's shops and restaurants and the beach.
This pet-friendly property sleeps eight, boasting a private heated pool, fully equipped kitchen with granite worktops, and is close to Palmetto Avenue Beach; an adjacent cottage, Kiwi Cottage, can also be rented for larger groups.
Luxury 7br|gulf & Bay Views +1 Min Walk To Beach - Anna Maria Island, FL
9.8 38 reviews
Anna Maria Island, FL
27/06 – 28/06
NZ$6849/nightfor 1 night

Luxury 7br|gulf & Bay Views +1 Min Walk To Beach

1 8
apartment , Bradenton Beach
This luxurious seven-bedroom Bradenton Beach holiday home is located less than 0.16 kilometres from the beach, offering easy access to playgrounds and parks.
Sleeping up to 15 guests, this property boasts a state-of-the-art kitchen, private heated pool and hot tub, rooftop deck with Gulf and Bay views, and six-and-a-half bathrooms.
"The Salty Sugaree"-6 Miles To Beach, 1 Mile To Img, & Multiple Resort Pools! - Anna Maria Island, FL
10 15 reviews
Anna Maria Island, FL
02/07 – 05/07
NZ$476/nighttotal: NZ$1428 (3 )

"The Salty Sugaree"-6 Miles To Beach, 1 Mile To Img, & Multiple Resort Pools!

2 6
apartment , South Bradenton
"The Salty Sugaree" condo resort in Bradenton, Florida, is situated approximately 3.2km from IMG Academy and 3.2km from Smugglers Cove Adventure Golf.
This two-bedroom, two-bathroom property sleeps six guests and boasts a balcony, fully equipped kitchen, swimming pool, hot tub, and tennis court, offering convenient self-catering and family-friendly amenities.
Private Heated Pool Home W/arcade Games 15 Min To Beach! - Anna Maria Island, FL
9.6 74 reviews
Anna Maria Island, FL
27/06 – 04/07
NZ$1004/nighttotal: NZ$7028 (7 )

Private Heated Pool Home W/arcade Games 15 Min To Beach!

3 2
apartment , 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?

    Anna Maria Island boasts beautiful beaches, of course! The northern end, near Bean Point, offers stunning sunsets. The Anna Maria City Pier is a classic spot for fishing and people-watching. For history buffs, the Island's Historical Society Museum is a worthwhile visit. And don't forget the charming shops and restaurants of Anna Maria's downtown area.
  • What are the best Airbnb and holiday rentals in Anna Maria Island, FL?

  • Are there any unique natural phenomena on Anna Maria Island, Florida?

    The island's position means you'll see incredible sunsets over the Gulf of Mexico. The beaches themselves are a natural wonder, with their white sand and calm waters perfect for swimming and shelling. Keep an eye out for the diverse birdlife – you might spot herons, pelicans, and even the occasional osprey.
  • 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 likely be doing a lot of exploring. Don't forget your beach towel and a reusable water bottle to stay hydrated in the Florida sun.
  • What are the best holiday rentals with a pool in Anna Maria Island, FL?

  • What famous events or festivals are happening on Anna Maria Island, Florida?

    Anna Maria Island doesn't have huge, internationally renowned festivals. However, the annual Anna Maria Island Summer Concert Series offers free outdoor concerts throughout the summer months. Check local listings closer to your travel dates for smaller, community events.
  • What are the best rentals for families and kids 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 experience, you might budget around £150-£300 per day for a couple, covering accommodation (consider renting a condo or small house for better value), meals at local restaurants, some activities, and transportation (car rental is recommended for exploring the island fully).
  • What are the best rentals or Airbnbs with a jacuzzi 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 fine-dining option known for its fresh seafood. Rod & Reel Pier offers casual dining with fantastic waterfront views. For more casual fare, try the Anna Maria Oyster Bar, known for its, well, oysters! Fresh seafood is a must-try specialty on the island, along with key lime pie – a Florida classic.
  • What are some less-famous attractions on Anna Maria Island, Florida that are worth a visit?

    The Anna Maria Island Nature Preserve offers lovely walking trails and opportunities for birdwatching. Exploring the quieter beaches south of the main tourist areas can be a rewarding experience. You might also enjoy a leisurely bike ride along the island's scenic pathways.
  • What are the best activities for engaging with locals and understanding their culture on Anna Maria Island, Florida?

    Chatting with staff at local businesses, especially smaller, family-run shops and restaurants, is a great way to get a feel for the island's culture. Attend a local event or concert if one is happening during your visit. Simply strolling through the residential areas and observing the relaxed island lifestyle can be insightful.
  • What unique natural landscapes and terrain features can travellers explore on Anna Maria Island, Florida?

    The island's main feature is its beautiful beaches, of course. The Anna Maria Island Nature Preserve offers a different perspective with its mangrove forests and coastal habitats. The various bayside areas offer calm waters for kayaking and paddleboarding.
  • 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 get a feel for the island. Spend a day exploring the beaches, another exploring the north and south ends, and perhaps a day dedicated to relaxing and enjoying the local restaurants. Consider a boat trip or kayaking to experience the waters.

Nearby regions

Best Anna Maria Island, FL holiday rentals with a balcony

Mycataleya Comfy Condo Near Beach (Bradenton) - Anna Maria Island, FL
9.2 28 reviews
Anna Maria Island, FL
17/07 – 20/07
NZ$378/nighttotal: NZ$1134 (3 )

Mycataleya Comfy Condo Near Beach (Bradenton)

2 2
apartment , Bradenton
This Bradenton apartment is conveniently located just 10 kilometres from Sarasota Bradenton International Airport and 13.7 kilometres from the John and Mable Ringling Museum of Art.
The 100 square metre property boasts two bedrooms, two bathrooms, sleeps seven guests, and features a private balcony with river views, a full kitchen, and access to on-site amenities including a swimming pool, hot tub, tennis court, and table tennis.
Heated Pool, Game Room, Mini Golf, 9 Min To Img - Anna Maria Island, FL
9.8 16 reviews
Anna Maria Island, FL
27/07 – 29/07
NZ$940/nighttotal: NZ$1880 (2 )

Heated Pool, Game Room, Mini Golf, 9 Min To Img

3 5
apartment , Bradenton
This Bradenton holiday home is situated near IMG Academy, a 21-kilometre drive from Anna Maria Island's beaches and Bradenton Motorsports Park.
The three-bedroom, two-bathroom property sleeps nine, boasting a private tropical garden with a heated pool, mini-golf, and covered patio, plus a games room with table tennis and table football, and abundant beach equipment.
The Palms #3   Beach, Pool & Trolley  No Car Needed - Anna Maria Island, FL
9.6 59 reviews
Anna Maria Island, FL
27/06 – 04/07
NZ$508/nighttotal: NZ$3556 (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.
2br Cedars East #814bay Views & Tennis By Rva - Anna Maria Island, FL
8.6 23 reviews
Anna Maria Island, FL
11/07 – 25/07
NZ$641/nighttotal: NZ$8974 (14 )

2br Cedars East #814bay Views & Tennis By Rva

2 7
apartment , Longboat Key
This holiday home on Longboat Key is just 1.6 kilometres from Longboat Key Beaches and Cannons Marina, and 4.3 kilometres from Jewfish Key, offering easy access to the island's attractions. Guests have consistently rated this property as "very good".
The property has two bedrooms and a floor area of 134 square metres, providing ample space for a comfortable stay. Amenities include a fully equipped kitchen, three bathrooms, a washing machine, a sofa bed, a TV, books, air conditioning, a swimming pool, a garden, parking, and internet access.

Best Anna Maria Island, FL holiday rentals with parking

Coquina Cheer On Anna Maria Island - Anna Maria Island, FL
9.7 3 reviews
Anna Maria Island, FL
03/08 – 07/08
NZ$478/nighttotal: NZ$1912 (4 )

Coquina Cheer On Anna Maria Island

1 3
house , Bradenton Beach
Coquina Cheer, a self-catering property in Bradenton Beach, Florida, is a 3-minute walk from Cortez Beach, 19 kilometres from Sarasota Bradenton International Airport, and 23 kilometres from the Sarasota International Convention Center.
This one-bedroom house offers 56 square metres of space, sleeping up to six guests and boasting a private terrace, swimming pool, BBQ facilities, and proximity to various watersports.
Sleeps 10 - Heated Pool & Slide - Games-min To Img - Anna Maria Island, FL
Anna Maria Island, FL
28/06 – 03/07
NZ$765/nighttotal: NZ$3825 (5 )

Sleeps 10 - Heated Pool & Slide - Games-min To Img

3 8
house , South Bradenton
This Bradenton holiday home is located in South Bradenton, offering convenient access to IMG Academy, cycling routes, and local attractions, with a casino also available on site.
This 116 square meter residence accommodates up to 14 guests and features air conditioning, a fully equipped kitchen with a dishwasher and microwave, a heated outdoor swimming pool with a slide, Wi-Fi, and on-site parking.
Ed Shorewalk -Pool, Tennis, Pickle Ball, Near Beaches Anna Maria Island And Img - Anna Maria Island, FL
9.6 91 reviews
Anna Maria Island, FL
17/07 – 20/07
NZ$404/nighttotal: NZ$1212 (3 )

Ed Shorewalk -Pool, Tennis, Pickle Ball, Near Beaches Anna Maria Island And Img

2 2
apartment , Bradenton
This Bradenton waterfront apartment, a five-minute drive from IMG Academy and fifteen minutes from Anna Maria Island and Longboat Key beaches, offers easy access to local attractions.
The 110 square metre property features two bedrooms, four bathrooms, and accommodates four guests, boasting a private terrace, swimming pool, jacuzzi, and tennis court access within a resort complex.
Pet-friendly Bradenton Home 1 5 Mi To Cortez Beach - Anna Maria Island, FL
10 57 reviews
Anna Maria Island, FL
03/08 – 07/08
NZ$386/nighttotal: NZ$1544 (4 )

Pet-friendly Bradenton Home 1 5 Mi To Cortez Beach

2 3
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.
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