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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

Fabulous View Of Pond!  Steps To Pools/tennis & Clubhouse! Fall Rates 99 Dollars - Anna Maria Island, FL
9.6 203 reviews

Fabulous View Of Pond! Steps To Pools/tennis & Clubhouse! Fall Rates 99 Dollars

apartment, Bradenton
This ground floor condo is located in the Shorewalk Vacation Villas in Bradenton, Florida, just a short walk from the resort's amenities, including pools, tennis courts, and BBQ grills. This vacation rental has consistently received excellent ratings from previous guests.
This two-bedroom, two-bathroom condo offers 1000 square feet of space, comfortably accommodating up to four guests. The condo boasts a range of amenities, including a fully equipped kitchen, a private balcony, and access to the resort's numerous recreational facilities, such as a swimming pool, jacuzzi, and fitness center.
177 M² House ∙ 3 Bedrooms ∙ 8 Guests - Anna Maria Island, FL
9.9 25 reviews

177 M² House ∙ 3 Bedrooms ∙ 8 Guests

house, Bradenton
Bloom Lagoon is located in Northwest Bradenton, just a short drive from the beautiful beaches of Anna Maria Island and close to popular destinations like Lakewood Ranch, Sarasota, and Tampa. This vacation rental has received excellent user ratings, making it a popular choice for travelers.
The 1890 square foot house has 4 bedrooms, 2 bathrooms, and can comfortably accommodate up to 8 guests. This family-friendly rental offers a private heated pool, a fully stocked kitchen, and a comfortable living space with a smart TV and fast Wi-Fi.
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.
Two Bedroom Cottage With Tropical Landscaping Surrounding Private Heated Pool! - Anna Maria Island, FL
10 17 reviews

Two Bedroom Cottage With Tropical Landscaping Surrounding Private Heated Pool!

cottage, Holmes Beach
This smoke-free cottage is located in Holmes Beach, just a mile from Bradenton Beach, Palmetto Avenue Beach, and the Island Players theater. Guests rave about the cottage's excellent rating and its convenient location, making it a great choice for a relaxing beach vacation. This two-bedroom cottage comfortably sleeps five guests and features a private pool, outdoor barbecue grills, and a fully equipped kitchen. Enjoy a refreshing dip in the pool, relax on the patio, and explore the nearby beaches and attractions.

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

Bloom Lagoon! Tropical Home With Heated Pool And Grill! Pet Friendly! - Anna Maria Island, FL
9.2 5 reviews

Bloom Lagoon! Tropical Home With Heated Pool And Grill! Pet Friendly!

house, Bradenton
This Bradenton vacation home, near Palma Sola Causeway Park (1.6 miles) and within 30 miles of The Ringling Museum, The Dali Museum, and Tropicana Field, offers convenient access to major attractions.
This 1,910-square-foot property boasts three bedrooms, two bathrooms, sleeps up to 15 guests, and features a heated pool, grill, and fully equipped kitchen with a dishwasher, plus free Wi-Fi.
Paradise At Shorewalk - Anna Maria Island, FL
10 57 reviews

Paradise At Shorewalk

apartment, Bradenton
This Bradenton condo, located less than two miles from Smugglers Cove Adventure Golf and IMG Academy, offers easy beach access.
The 1170-square-foot, two-bedroom, two-bathroom unit sleeps six and features a fully equipped kitchen, private patio, swimming pool, Jacuzzi, tennis court, and free Wi-Fi.
Charming Ground Level Resort Style 3 Units Condo  Of A Triplex- Unit A - Anna Maria Island, FL
10 31 reviews

Charming Ground Level Resort Style 3 Units Condo Of A Triplex- Unit A

cottage, Holmes Beach
The Charming Ground Level Resort Style 3 Units Condo Of A Triplex- Unit A is located in Bradenton Beach, just a short walk from Island Gallery West and a 5-minute drive from Holmes Beach Beaches. This smoke-free vacation rental is highly rated by guests and offers a comfortable and convenient stay.
This ground-level condo has 2 bedrooms, 1 bathroom, and can accommodate up to 6 guests. The 990 square foot space includes a private pool, a fully equipped kitchen, a terrace, and a garden, making it ideal for families or groups seeking a relaxing retreat.
Cozy Beachside Cottage At Tradewinds/1br/pool/steps To Beach.unit1 Available Too - Anna Maria Island, FL
9.8 13 reviews

Cozy Beachside Cottage At Tradewinds/1br/pool/steps To Beach.unit1 Available Too

cottage, Bradenton Beach
This renovated 700 sq ft cottage in Bradenton Beach offers 1 bedroom and 1 bathroom, accommodating up to 4 guests, and is located just steps from the Gulf beaches and a community pool, with Bridge Street Bistro and Anna Maria Oyster Bar within walking distance. Guests can enjoy amenities such as a full kitchen with a dishwasher, air conditioning, internet, and parking, with an option to book a second adjacent unit for larger groups.

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

The Sapphire Sea Star - Anna Maria Island, FL
8.4 6 reviews

The Sapphire Sea Star

house, Cortez
The Sapphire Sea Star vacation rental is located in Bradenton, Florida, approximately six miles from the Greens of Manatee Golf Club and eight miles from Anna Maria City Pier.
This 1720-square-foot home features two bedrooms, two bathrooms, two living rooms, a fully equipped kitchen, a private patio with pool views, and free Wi-Fi; it comfortably accommodates families or groups.
Adorable Cottage With Covered Balconies And Private Pool - Anna Maria Island, FL
9.8 48 reviews

Adorable Cottage With Covered Balconies And Private Pool

cottage, Anna Maria
This house is located on Anna Maria Island, within walking distance of Anna Maria Beach and Anna Maria Island Museum and Historical Park. It has an excellent user rating.
The house has a floor area of 1300 square feet and can accommodate up to 8 guests. It has 3 bedrooms, 2 bathrooms, a fully equipped kitchen, a washing machine, a sofa bed, a refrigerator, a TV, and air conditioning. It also has a private pool, a parking space, and access to a water park. The house is situated in a smoke-free environment and allows pets.
Beautiful 2 Bedroom 2 Bath Fully Furnished Condo Close To Beaches - Anna Maria Island, FL
9.6 52 reviews

Beautiful 2 Bedroom 2 Bath Fully Furnished Condo Close To Beaches

apartment, Bradenton
This Bradenton rental is conveniently located just a mile from Arcadeland and a mile and a half from IMG Academy, making it an ideal spot for families and groups visiting the area. The apartment has received excellent ratings from previous guests, highlighting its comfortable accommodations and convenient amenities.
The 2-bedroom, 2-bathroom apartment offers 1170 square feet of space, accommodating up to 6 guests. The rental features a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, a tennis court, and a spa, providing plenty of opportunities for relaxation and recreation.
Pool, Elevator, Close To Beach! - Blue Pineapple - Anna Maria Island, FL
9.5 24 reviews

Pool, Elevator, Close To Beach! - Blue Pineapple

apartment, Holmes Beach
This beachfront Holmes Beach vacation home offers easy access to Bradenton Beach, Palmetto Avenue Beach, and the Island Players, all within one mile.
The 4-bedroom, 2.5-bathroom residence sleeps 8 guests and boasts a private pool, fully equipped kitchen, laundry facilities, and proximity to a water park, Island Gallery West, and the Anna Maria Island Museum and Historical Park.

Best Anna Maria Island, FL vacation rentals with parking

Florida Palms Heaven Near Img Academy & Beaches - Anna Maria Island, FL
9.3 3 reviews

Florida Palms Heaven Near Img Academy & Beaches

apartment, Bradenton
This Bradenton apartment rental is conveniently located near IMG Academy and Bradenton's beaches, 8.1 miles from the Ringling Museum of Art and 6.2 miles from Sarasota Bradenton International Airport.
This 1180-square-foot, two-bedroom, two-bathroom unit sleeps four and features a private garden, a pool, a hot tub, free Wi-Fi, on-site parking, and a well-equipped kitchen.
3/2 Home Heated Pool/close To Anna M. Beaches/ Img - Anna Maria Island, FL
9.5 73 reviews

3/2 Home Heated Pool/close To Anna M. Beaches/ Img

apartment, Bradenton
This Bradenton vacation home is located just under a mile from Blake Medical Center and within a 3-mile radius of both Arcadeland and LECOM Park. It has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The home offers 3 bedrooms and 2 bathrooms, spanning 1590 square feet, comfortably accommodating up to 6 guests. Enjoy a private pool, a spa tub, barbecue grills, a fully equipped kitchen, and free WiFi, all within a smoke-free environment.
Pond-side 4br Oasis W/ Private Pool + Pickleball! - Anna Maria Island, FL
9.9 114 reviews

Pond-side 4br Oasis W/ Private Pool + Pickleball!

apartment, Bradenton
This pet-friendly designer home is located in Bradenton, a short distance from the downtown area, the River Walk, and the Village of the Arts. The property has received excellent ratings for location, cleanliness, and overall user experience.
This 4-bedroom, 3-bathroom vacation rental spans 2,200 square feet and comfortably accommodates up to 10 guests. Enjoy amenities like a private pool, a spacious backyard, a fully equipped kitchen, and beach gear provided for your convenience.
Beach Castle 12 - Anna Maria Island, FL
9.6 43 reviews

Beach Castle 12

apartment, Longboat Key
Beach Castle Resort #12 By Rva is located on Longboat Key, just a mile from the beach and Cannons Marina, offering a peaceful escape near the water. The resort consistently receives excellent ratings for its location, cleanliness, and overall experience.
This two-bedroom condo comfortably sleeps six guests and features a fully equipped kitchen, a sofa bed, and a terrace. Guests can enjoy amenities like a swimming pool, a jacuzzi, a tennis court, and free WiFi, making it a great choice for families or groups looking for a relaxing beach vacation.