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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

Nautical Nest  Cozy Poolside Condo, Near Beaches! - Anna Maria Island, FL
9.2 5 reviews

Nautical Nest Cozy Poolside Condo, Near Beaches!

apartment, Bradenton
This West Bradenton condo is conveniently located 6.8 miles from Anna Maria Island beaches, a short walk from the Shoppes of Bradenton Commons, and near IMG Academy.
The 910-square-foot apartment features two bedrooms, two bathrooms, sleeps four guests, and includes a fully equipped kitchen, private lanai, and access to resort amenities like heated pools and a hot tub.
Steps To Beach - Seagrass Sunsets By Seabreeze Vacation - Anna Maria Island, FL
10 2 reviews

Steps To Beach - Seagrass Sunsets By Seabreeze Vacation

house, Bradenton Beach
This vacation home in Ilexhurst offers unbeatable proximity, located literally steps from Bradenton Beach and 14 miles from the John and Mable Ringling Museum of Art.
This 720 square foot rental features 2 bedrooms, 2 bathrooms, and accommodates up to 11 guests with amenities including air conditioning, a swimming pool, a terrace, free WiFi, and free private parking.
Peaceful Lakeview Condo  2 Pools  Minutes To Img & Beaches - Anna Maria Island, FL
9.8 70 reviews

Peaceful Lakeview Condo 2 Pools Minutes To Img & Beaches

apartment, Bradenton
This Bradenton apartment is conveniently located near the beach, just a short drive from attractions like Arcadeland and IMG Academy. It boasts excellent guest ratings and is perfect for families or groups of friends.
The 1170 square foot apartment has two bedrooms and two bathrooms, comfortably accommodating up to four guests. Enjoy a range of amenities, including a swimming pool, Jacuzzi, tennis court, and a fully equipped kitchen, along with free Wi-Fi and a private terrace or balcony.
Sunny Bella Rosa  Pools, Spas, Near Img & Beaches - Anna Maria Island, FL
9.8 225 reviews

Sunny Bella Rosa Pools, Spas, Near Img & Beaches

apartment, South Bradenton
This lakeside condo in South Bradenton is a great choice for families visiting IMG Tennis Academy and the nearby beaches. The condo has excellent user, location and cleanliness ratings. The floor area is 1280 square feet, with 2 bedrooms and 2 bathrooms. The condo has a coastal Florida ambiance, with stunning lake views from the screened lanai.
The condo is fully furnished and has all the amenities you need, including a kitchen with appliances, three TVs with cable, and a washer/dryer. The resort-style amenities include swimming pools, tennis courts, and a playground. The condo also provides beach essentials like umbrellas, towels, and chairs.

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

Beautiful Condo With Pool, Steps To The Beach! - Anna Maria Island, FL
9.6 59 reviews

Beautiful Condo With Pool, Steps To The Beach!

apartment, Holmes Beach
This Holmes Beach vacation rental is just a 10-minute walk from Bradenton Beach and Anna Maria Sound, offering easy access to the area's beautiful beaches and activities. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience.
This 2-bedroom home provides comfortable accommodation for up to 6 guests with 750 square feet of living space. Enjoy a private water park, a fully equipped kitchen, barbecue grills, and a relaxing balcony, perfect for enjoying the Florida sunshine.
The Beach Club At Anna Maria #6 - Anna Maria Island, FL
No reviews

The Beach Club At Anna Maria #6

house, Bradenton Beach
This beachfront vacation home in Bradenton Beach offers direct access to the shore and is located 12 miles from Sarasota Bradenton International Airport and 14 miles from the Sarasota International Convention Center and the John and Mable Ringling Museum of Art.
This 7-guest capacity residence features a swimming pool, jacuzzi, garden, fitness center, tennis court, and a well-equipped kitchen, with complimentary high-speed WiFi and free private parking, ideal for enjoying cycling activities near Bradenton Beach.
Paradise Retreat - Anna Maria Island, FL
9.9 469 reviews

Paradise Retreat

apartment, Bradenton
This family-friendly vacation rental is located in South Bradenton, just a short drive from popular attractions like Arcadeland and Smugglers Cove Adventure Golf, and within a 5-minute drive of IMG Academy. The property has received excellent ratings for location, cleanliness, and overall user experience.
This 3-bedroom, 1-bathroom home comfortably accommodates 6 guests and spans 1100 square feet. Enjoy a private pool, a fitness center, and a fully equipped kitchen, perfect for preparing meals and enjoying outdoor dining on the lanai.
Breezy Livin' Speakeasy Pool Hot Tub Game Room - Anna Maria Island, FL
10 1 review

Breezy Livin' Speakeasy Pool Hot Tub Game Room

house, Bradenton
This vacation home in West Bradenton is located 7.5 miles from Sarasota Bradenton International Airport, 9.3 miles from the Sarasota International Convention Center, and 9.4 miles from the John and Mable Ringling Museum of Art.
This 2290 square foot rental accommodates up to 15 guests and features a private outdoor swimming pool, hot tub, game room, on-site casino and speakeasy, a fully equipped kitchen, free WiFi, and on-site parking.

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

10 Mins To Ami/img - 4/bd Pool Home - Anna Maria Island, FL
9.4 61 reviews

10 Mins To Ami/img - 4/bd Pool Home

apartment, West Bradenton
This apartment is located in West Bradenton, just a short 12-minute drive from the beaches and close to the city center. It has an excellent user rating and offers a comfortable and convenient stay for travelers.
The apartment is spacious, with 1910 square feet of living space, 4 bedrooms, and 3 bathrooms, comfortably accommodating up to 13 guests. It features a fully equipped kitchen, a private backyard with a pool, a terrace, and a garden, as well as free high-speed Wi-Fi, parking for up to 4 cars, and other amenities for a relaxing and enjoyable stay.
Hc Shorewalk -Pool, Tennis, Pickle Ball, Near Beaches Anna Maria Island And Img - Anna Maria Island, FL
10 3 reviews

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

apartment, Bradenton
This Bradenton condo boasts a prime seaside location 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, two bathrooms, a fully equipped kitchen, in-unit laundry, a private balcony, and access to a swimming pool, jacuzzi, tennis court, and garden; comfortably accommodating four guests.
Gulf And Bay Views! With Pool, Stroll To The Beach - Anna Maria Island, FL
9.2 28 reviews

Gulf And Bay Views! With Pool, Stroll To The Beach

apartment, Bradenton Beach
This Bradenton Beach apartment is just a short walk from the beautiful Anna Maria Sound and Bradenton Beach, offering easy access to the area's stunning beaches and waterfront activities. The apartment enjoys excellent user, location, and cleanliness ratings.
The 1190 square foot apartment features two bedrooms, two bathrooms, a fully equipped kitchen, a balcony, and a TV. It also offers access to a swimming pool, jacuzzi, spa, and restaurant, as well as a water park and a garden.
Castaway Cottage: Near Img And Beaches - Anna Maria Island, FL
No reviews

Castaway Cottage: Near Img And Beaches

apartment, Bradenton
This Bradenton vacation rental, near Cortez Beach and St. Armands Circle, provides easy access to both the Florida Maritime Museum at Cortez and the shopping and dining of St. Armands.
This 1,600-square-foot home features four bedrooms, two bathrooms, accommodates up to ten guests, and includes a private pool, community water park access, a full kitchen, laundry facilities, and a balcony.

Best Anna Maria Island, FL vacation rentals with parking

'Ocean Breeze Oasis' W/ Boat Dock & Slip On Canal! - Anna Maria Island, FL
9.4 110 reviews

'Ocean Breeze Oasis' W/ Boat Dock & Slip On Canal!

house, Bayshore Gardens
This Bayshore Gardens vacation home, located in Bradenton near Sarasota Bradenton International Airport (1.9 miles) and Van Wezel Performing Arts Hall (3.9 miles), offers convenient access to area attractions.
The 1450-square-foot property features three bedrooms, a private boat dock, a swimming pool, a jacuzzi, free bicycles, and a fully equipped kitchen, comfortably accommodating families or groups.
Home With Private Heated Pool - Anna Maria Island, FL
10 182 reviews

Home With Private Heated Pool

apartment, South Bradenton
This single-family home is located in South Bradenton, just 6.6 miles from Anna Maria Island beach and 2 miles from IMG Academy, offering easy access to both the beach and the popular sports academy. The home has received excellent user ratings, indicating a positive experience for previous guests. This 940-square-foot property comfortably accommodates up to 5 guests and features a modern open floor plan. Enjoy the convenience of a private pool, fenced yard, and modern amenities like smart TVs, a RING doorbell, Wi-Fi, and an outdoor grill.
Mycataleya Beautiful Florida Condo (Bradenton) - Anna Maria Island, FL
9.5 54 reviews

Mycataleya Beautiful Florida Condo (Bradenton)

apartment, Bradenton
This 2-bedroom condo is located in a resort-style community just a 2-minute walk from the clubhouse, pools, spas, tennis courts, and BBQ facilities. The property enjoys excellent user, location, and cleanliness ratings.
The unit offers a comfortable layout for up to 4 guests and features a king-size bed in the master bedroom and twin beds in the second bedroom. You'll enjoy access to a range of on-site amenities including a fitness center, swimming pool, Jacuzzi, and garden, as well as convenient features like a full-size washer and dryer, a large-screen smart TV, and free Wi-Fi.
Luxury 3/3 Margaritaville  Resort - Anna Maria Island, FL
9.9 219 reviews

Luxury 3/3 Margaritaville Resort

apartment, Bradenton
This luxurious 3-bedroom condo is located in a new development in Bradenton, just a short walk from a large lagoon with a two-mile walking path. The property has received excellent ratings for user experience, location, and cleanliness.
The 1750 square foot apartment has a gourmet kitchen, high-end mattresses, furniture, and electronics. It also offers access to a large heated pool, splash pad, tot-lot, outdoor kitchen, and a marina with wet slip and dry storage.
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