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Anna Maria Island, FL vacation rentals
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Best Vacation rentals and Airbnb offers in Anna Maria Island, FL

Best family friendly Anna Maria Island, FL vacation rentals

Among the 9208 accommodations in Anna Maria Island, FL, here are the 4 best family friendly rentals

*Casa Bella* Waterfront View! 2br, W/2 Pools, Mins To Img/beach/anna Maria Isl - Anna Maria Island, FL
9.8 66 reviews

*Casa Bella* Waterfront View! 2br, W/2 Pools, Mins To Img/beach/anna Maria Isl

apartment, Bradenton
This lakefront condo is located in the Shorewalk resort in Bradenton, just minutes from the beaches of Anna Maria Island, Siesta Key, and Longboat Key. The property has excellent user ratings and offers a comfortable and convenient stay for travelers.
This 2-bedroom, 2-bathroom vacation rental comfortably sleeps up to 6 guests and features a fully equipped kitchen, washer and dryer, and a screened lanai with lake views. The resort offers a variety of amenities, including two heated swimming pools, a hot tub, tennis courts, a fitness center, a clubhouse, and BBQ grills.
Cortez Gardens Cottage 11, Renovated, Close To Beach, 3-bed, 2 Bath 10 People - Anna Maria Island, FL
8.9 74 reviews

Cortez Gardens Cottage 11, Renovated, Close To Beach, 3-bed, 2 Bath 10 People

apartment, Bradenton
This 3-bedroom apartment is located in Bradenton, just 9 miles from the John and Mable Ringling Museum of Art and a short drive from the beach. The apartment has received excellent ratings for location, cleanliness, and overall experience.
The apartment comfortably accommodates up to 10 guests and includes a fully equipped kitchen with a dishwasher and oven. Enjoy the peace and quiet of the street, relax in the garden, and stay connected with free Wi-Fi and private parking.
Beach And Sunset View From Your Balcony - Anna Maria Island, FL
9.7 224 reviews

Beach And Sunset View From Your Balcony

apartment, Longboat Key
This Longboat Key apartment is just a short drive from the John and Mable Ringling Museum of Art and Mote Marine Laboratory, making it a great base for exploring the area. The apartment has consistently received excellent ratings for its location, cleanliness, and overall experience.
The one-bedroom, one-bathroom apartment comfortably accommodates up to six guests and features a fully equipped kitchen, a private balcony with ocean views, a swimming pool, a garden, and access to bike rentals, mini-golf, and a picnic area.
Best Beach Getaway  Steps From The Gulf  Of Mexico - Anna Maria Island, FL
9.9 77 reviews

Best Beach Getaway Steps From The Gulf Of Mexico

apartment, Bradenton Beach
This Bradenton Beach condo is a short 5-minute walk from Bradenton Beach and Anna Maria Sound, and less than 15 minutes from the Aluna Wellness Center & Spa and Bradenton Beach Marina.
The one-bedroom, one-bathroom unit sleeps four, boasts a fully equipped kitchen, private terrace, access to a resort-style pool, fitness center, and tennis court, plus free parking and Wi-Fi.

Best Anna Maria Island, FL vacation rentals with a pool

Among the 9208 accommodations in Anna Maria Island, FL, here are the 4 best rentals with a pool

Beach Escape | Pool | Walk Everywhere - Anna Maria Island, FL
9.8 41 reviews

Beach Escape | Pool | Walk Everywhere

apartment, Bradenton Beach
This Bradenton Beach condo offers a fantastic location directly across the street from Anna Maria Island's beaches, minutes from Holmes Beach and Anna Maria, and a short drive from Longboat Key and Sarasota.
The one-bedroom, one-bathroom unit sleeps four with a queen bed, sleeper sofa, fully equipped kitchen including a dishwasher, free Wi-Fi, and access to a community pool and grill; enjoy the open and airy interior design and flat-screen TVs.
Mycataleya Beautiful Florida Condo (Bradenton) - Anna Maria Island, FL
9.4 46 reviews

Mycataleya Beautiful Florida Condo (Bradenton)

apartment, Bradenton
This Bradenton condo, near the Greens of Manatee Golf Club (3.3 miles) and Sarasota Bradenton International Airport (6.2 miles), offers convenient access to area attractions including The John and Mable Ringling Museum of Art and The Dali Museum.
This recently renovated 1,080-square-foot unit features two bedrooms, two bathrooms with a hot tub, a private terrace, and accommodates up to seven guests, boasting a fully equipped kitchen, swimming pool, and tennis court.
Vacation Home With Pool And Bbq Near Anna Maria Island - Anna Maria Island, FL
10 6 reviews

Vacation Home With Pool And Bbq Near Anna Maria Island

apartment, Bradenton
This pet-friendly vacation home in Bradenton, Florida, is a 21-minute drive from Tampa Bay and a 38-minute drive from Lido Beach, offering easy access to beaches like Coquina Beach and Bean Point Beach, as well as attractions such as Smugglers Cove Adventure Golf and The Bishop Museum of Science and Nature.
This 1,400-square-foot house features four bedrooms, two bathrooms, and accommodates up to nine guests, boasting a fully equipped kitchen, a private garden, and amenities including Wi-Fi, air conditioning, and a washer/dryer.
Ami, 2 Heated Pools, Img, 2 Hot Tubs, Pickleball - Anna Maria Island, FL
10 1 review

Ami, 2 Heated Pools, Img, 2 Hot Tubs, Pickleball

house, Bradenton
This vacation rental in Bradenton is located 7.9 miles from the Sarasota International Convention Center and the John and Mable Ringling Museum of Art, and 6.2 miles from Sarasota Bradenton International Airport.
This 2-bedroom, 2-bathroom house with a 1170 sq ft floor area accommodates up to 11 guests and features a private terrace, two heated swimming pools, two hot tubs, a garden, tennis court, and complimentary WiFi.

Frequently Asked Questions about vacation 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 Bean Point is a must-see for its stunning sunsets and views. The Anna Maria City Pier is a great place to fish or just relax and watch the Gulf. Historic Bridge Street in Bradenton Beach offers unique shops and restaurants. And don't forget to explore the nature preserves like the Anna Maria Island Nature Preserve and the Leffis Key Preserve.
  • What are the best Airbnb and vacation rentals in Anna Maria Island, FL?

    Standard 2 Bedroom B, Spectacular Beach & Dolphin Views Huge Private Balcony 2br/2ba Upstairs Villa and Anna Maria Island Beach Palms 2b are the most popular Airbnb and vacation rentals in Anna Maria Island, FL among travelers.

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

    The island's location on the Gulf Coast means you'll see amazing sunsets. The beaches are known for shelling, with a variety of shells washing ashore. You might even spot dolphins playing in the waters near the shore. Birdwatching is also popular, with various species frequenting the island's natural areas.
  • What are the most popular Airbnbs in Anna Maria Island, FL?

  • What essentials should you bring along for a trip to Anna Maria Island, Florida?

    Pack light clothing, swimwear, sunscreen, sunglasses, a hat, and comfortable walking shoes. Don't forget insect repellent, especially for evenings. A beach umbrella and beach chairs will make your beach days more enjoyable. And of course, a camera to capture those amazing sunsets!
  • What are the best vacation rentals with a pool in Anna Maria Island, FL?

    Standard 2 Bedroom B, Anna Maria Island Beach Palms 2b and Do You Love The Beach? are the best vacation 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 large-scale, internationally known festivals. However, throughout the year, smaller local events take place, including the annual Christmas boat parade and various art walks. Check local event listings closer to your travel dates for the most up-to-date information.
  • 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 can vary greatly depending on your travel style. For a comfortable trip, expect to spend around $150-$300 per person per day. This includes mid-range accommodation, meals, some activities, and local transportation. Budget-conscious travelers could likely manage on less, while luxury travelers will spend significantly more.
  • 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 establishment known for its fresh seafood. Rod & Reel Pier offers casual dining with waterfront views. Many restaurants feature fresh seafood, which is a local specialty. Key lime pie is a must-try dessert, reflecting Florida's citrus heritage.
  • What are some less-famous attractions on Anna Maria Island, Florida that are worth the visit?

    The Anna Maria Island Historical Society Museum offers a glimpse into the island's past. Exploring the quieter beaches away from the main tourist areas provides a more peaceful experience. Take a leisurely bike ride along the island's scenic paths. Consider kayaking or paddleboarding through the mangroves.
  • What are the best activities for engaging with locals and understanding their culture on Anna Maria Island, Florida?

    Visiting local shops and art galleries allows you to interact with business owners. Attending smaller community events offers opportunities to meet residents. Simply striking up conversations with people you meet on the beach or in restaurants can provide insights into island life. The laid-back atmosphere makes it easy to connect with people.
  • What unique natural landscapes and terrain features can travelers explore on Anna Maria Island, Florida?

    Anna Maria Island features beautiful beaches with soft, white sand. The mangrove forests provide unique ecosystems to explore via kayak or paddleboard. The island's relatively flat terrain makes it easy to explore on foot or by bike.
  • How many days are ideal for visiting Anna Maria Island, Florida, and what are some itinerary suggestions?

    Three to five days is a good amount of time to explore Anna Maria Island at a relaxed pace. Spend a day relaxing on the beach, another exploring Bridge Street, and perhaps a day kayaking or visiting the nature preserves. Consider a sunset cruise for a memorable experience.

Nearby regions

Best Anna Maria Island, FL vacation rentals with a balcony

Near Beaches & Img Academy, Mins To Downtown - Anna Maria Island, FL
9.8 23 reviews

Near Beaches & Img Academy, Mins To Downtown

apartment, Bradenton
This 2-bedroom, 2-bathroom condo in Bradenton is located within walking distance of restaurants, grocery stores, bowling, and a movie theater, and is just a short drive to Anna Maria Island beaches.
This well-equipped rental sleeps up to 4 guests and features a full kitchen with stainless steel appliances, a 55" 4K HD TV, a lanai with a Foosball table and dartboard, and smart lock entry for easy access.
Shorewalk 202/4625 - Bradenton-condo 2 Bedroom/ 2 - Anna Maria Island, FL
10 26 reviews

Shorewalk 202/4625 - Bradenton-condo 2 Bedroom/ 2

apartment, Bradenton
This 2-bedroom, 2-bathroom apartment in Bradenton is conveniently located just a 5-minute drive from the IMG campus and a 15-minute drive from the beaches of Anna Maria Island and Longboat Key. This rental has received excellent ratings for location, cleanliness, and user experience.
The home is spacious and can comfortably accommodate up to 4 guests. This vacation rental offers a range of amenities, including a private screened porch, a fully equipped kitchen, a washer and dryer, and access to resort-style amenities like swimming pools, Jacuzzis, tennis courts, and more.
Lp Shorewalk, Near Anna Maria Island Beaches And Img, Pools, Tennis, Pickleball - Anna Maria Island, FL
9.2 10 reviews

Lp Shorewalk, Near Anna Maria Island Beaches And Img, Pools, Tennis, Pickleball

apartment, Bradenton
This Bradenton beachfront condo boasts stunning ocean views and is conveniently located near IMG Academy, Smugglers Cove Adventure Golf, and the IMG Bollettieri Tennis Academy, all within three miles.
The 1,170-square-foot unit features two bedrooms, four bathrooms, a fully equipped kitchen, in-unit laundry, a private balcony, and access to a swimming pool, hot tub, tennis court, and garden; it comfortably sleeps four guests.
Fm-near Beaches And Img, Pool, Tennis, Pickleball - Anna Maria Island, FL
9.5 36 reviews

Fm-near Beaches And Img, Pool, Tennis, Pickleball

apartment, Bradenton
This Bradenton apartment is located just over a mile from Arcadeland and IMG Academy, offering easy access to entertainment and sports facilities. The apartment consistently receives excellent ratings for location, cleanliness, and overall user experience.
The two-bedroom apartment spans 1250 square feet and comfortably accommodates up to four guests. It features a fully equipped kitchen, two bathrooms, a patio, a washing machine, a TV, table tennis, internet access, and parking.

Best Anna Maria Island, FL vacation rentals with parking

Cozy Seashore! Only 15 Min From Ami Beaches, Relaxing Pond Views, Free Wifi - Anna Maria Island, FL
9.4 72 reviews

Cozy Seashore! Only 15 Min From Ami Beaches, Relaxing Pond Views, Free Wifi

apartment, Bradenton
This 2-bedroom condo is located in the Shorewalk resort in Bradenton, just minutes from IMG Academies, shopping, dining, and the beaches of Anna Maria Island. The property has received excellent reviews from previous guests, highlighting its comfortable accommodations and convenient location.
This 1170 square foot apartment can comfortably accommodate up to 4 guests. Enjoy access to two large heated pools, two Jacuzzis, tennis courts, a basketball court, a children's playground, and shuffleboard, along with a screened lanai, a well-equipped kitchen, and a full-sized washer and dryer.
3 Dolphins In Bradenton - Anna Maria Island, FL
9.2 37 reviews

3 Dolphins In Bradenton

apartment, Bradenton
This Bradenton vacation rental is conveniently located near the coast, just a short drive from Blake Medical Center, arcadeland, and Manatee Golf Course. The property has consistently received excellent ratings for its location, cleanliness, and overall guest experience. This three-bedroom house offers 1600 square feet of space, comfortably accommodating up to six guests. Enjoy a relaxing stay with access to a private pool, fitness center, concierge services, and a variety of other amenities, including a fully equipped kitchen, a terrace, and a garden.
Very Close To Img Academy, Beaches, Restaurants, Shopping And Grocery Stores. - Anna Maria Island, FL
9.6 65 reviews

Very Close To Img Academy, Beaches, Restaurants, Shopping And Grocery Stores.

apartment, Bradenton
This family-friendly Bradenton condo is conveniently located near the beach, within 2 miles of Smugglers Cove Adventure Golf and IMG Academy. It has excellent user ratings, making it a popular choice for travelers. This 2-bedroom, 2-bathroom condo offers 1000 square feet of space and can comfortably accommodate up to 5 guests. Amenities include a fully equipped kitchen, a washer and dryer, a swimming pool, a spa tub, a tennis court, and a patio.
Beach Town 1 Bedroom Apt. - Anna Maria Island, FL
9.2 64 reviews

Beach Town 1 Bedroom Apt.

apartment, Holmes Beach
This one-bedroom apartment in Holmes Beach is just a 2.5-block walk from the world-renowned beaches, offering a peaceful setting with a small lake in the back.
The apartment features a recently renovated bathroom, a shared backyard with a front and back porch, and is ideal for small families or couples seeking a relaxing getaway.
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