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

Escape To An Island Adventure! Free Bikes & Beach Items - Anna Maria Island, FL
10 152 reviews

Escape To An Island Adventure! Free Bikes & Beach Items

house, Anna Maria
This charming house is located just a 32-kilometre drive from The John and Mable Ringling Museum of Art and a short 5-minute walk from Anna Maria Island's beautiful beaches. It has received excellent ratings for location, cleanliness, and user experience.
The 139 square metre house has two bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy the fully equipped kitchen, air conditioning, and the convenience of an on-site restaurant, plus a terrace, garden, and free bikes for exploring the island.
Spacieuse Maison, Piscine Chauffee, Pres Ana Maria - Anna Maria Island, FL
9.8 74 reviews

Spacieuse Maison, Piscine Chauffee, Pres Ana Maria

apartment, West Bradenton
This West Bradenton holiday home, a 15-minute drive (approx. 24km) from Anna Maria Island, enjoys a peaceful residential setting near the Warner East Bayou.
The four-bedroom, two-bathroom property sleeps eight guests and boasts a spacious open-plan layout including two living rooms, a fully equipped kitchen with dishwasher, a private heated swimming pool, and a tropical garden; access to all premises (excluding the shed) is provided.
Water Slide & Pool ** Sugar Shack** - Anna Maria Island, FL
9.4 166 reviews

Water Slide & Pool ** Sugar Shack**

apartment, Bradenton
This Bradenton property is conveniently located within 5 kilometres of Blake Medical Center, LECOM Park, and Riverwalk, offering easy access to the area's attractions. The property has consistently received excellent guest ratings for its location, cleanliness, and overall experience.
The house features three bedrooms, providing comfortable accommodation for families or groups of friends. Guests can enjoy a range of amenities, including a private garden, a swimming pool, a jacuzzi, and a fully equipped kitchen.
Beachwalker Apartment:  Duplex Within 100 Steps To The Sand. - Anna Maria Island, FL
9.3 63 reviews

Beachwalker Apartment: Duplex Within 100 Steps To The Sand.

apartment, Holmes Beach
This holiday home is located in Holmes Beach, just a short walk from Bradenton Beach and within a 16km drive of Manatee Public Beach and Anna Maria Sound. The property has received excellent ratings for location, cleanliness, and overall guest experience.
The 42 square metre house has one bedroom and one bathroom, comfortably accommodating two guests. It offers a range of amenities including a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, and parking.

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

Anna Maria Beach Condo 1/1 - Anna Maria Island, FL
9.8 220 reviews

Anna Maria Beach Condo 1/1

apartment, Bradenton Beach
This house is located in Bradenton Beach, just a short walk from Anna Maria Sound and Bradenton Beach, with Aluna Wellness Center & Spa and Bradenton Beach Marina within a 15-minute drive. The accommodation has excellent user ratings and is perfect for a relaxing getaway.
This one-bedroom property can accommodate up to four guests and features a private swimming pool, a fully equipped kitchen, air conditioning, and internet access. You can enjoy the beach, go kayaking or paddleboarding, or simply relax in the tranquil surroundings.
Near Beaches & Img Academy, Mins To Downtown - Anna Maria Island, FL
10 22 reviews

Near Beaches & Img Academy, Mins To Downtown

apartment, Bradenton
This Bradenton flat offers excellent access to Anna Maria Island beaches (12.8-20.9 kilometres) and IMG Academy (8 kilometres), with shops, restaurants, and entertainment within walking distance.
This two-bedroom, two-bathroom flat accommodates four guests and features a fully equipped kitchen with new stainless steel appliances, a 4K HD television, complimentary Wi-Fi, and an attached lanai/game room with a foosball table and dart board.
143 M² House ∙ 3 Bedrooms ∙ 6 Guests - Anna Maria Island, FL
No reviews

143 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Bradenton
This West Bradenton property is situated approximately 19km from Anna Maria Island and 18km from Bradenton Beach, offering easy access to Beachway Plaza and Sarasota Bradenton International Airport.
The 142 square metre house boasts three bedrooms, two bathrooms, sleeps six guests, and includes a private heated pool (extra charge), a fully equipped kitchen, and a screened lanai with BBQ facilities.
Ab Shorewalk -Pool, Tennis, Pickle Ball, Near Beaches Anna Maria Island And Img - Anna Maria Island, FL
9.2 7 reviews

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

apartment, Bradenton
This Bradenton lakeside apartment, five minutes from IMG Academy and fifteen minutes (approx. 24km) from Anna Maria Island and Longboat Key beaches, offers convenient access to local attractions.
The 109 square metre, two-bedroom, two-bathroom property sleeps four guests and boasts a private terrace, swimming pool, Jacuzzi, and tennis court, alongside a fully equipped kitchen and air conditioning.

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

Getaway Retreat A+b · 4br · Firepit · Bay - Anna Maria Island, FL
9.2 91 reviews

Getaway Retreat A+b · 4br · Firepit · Bay

apartment, Bradenton Beach
This holiday home is ideally situated in Bradenton Beach, just a 3km walk from Anna Maria Sound and the beach, and within a 3km radius of Bradenton Beach Marina and Fish Hole Adventure Golf. It has been highly rated by previous guests for its location, cleanliness and overall experience.
The property is a spacious 153 square metre house with 4 bedrooms, a sofa bed and a fully equipped kitchen. Guests can enjoy a range of amenities, including a swimming pool, terrace, garden, barbecue grills and free parking.
Cd Shorewalk -Pool, Tennis, Pickle Ball, Near Beaches Anna Maria Island And Img - Anna Maria Island, FL
10 3 reviews

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

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.
Ck Shorewalk -Pool, Tennis, Pickle Ball, Near Beaches Anna Maria Island And Img - Anna Maria Island, FL
9.6 49 reviews

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

apartment, Bradenton
This apartment is situated on a lake in Bradenton, just 5km from IMG Academy, Smugglers Cove Adventure Golf, IMG Bollettieri Tennis Academy, IMG Soccer Academy, and State College of Florida. It has received excellent ratings for its location, cleanliness, and overall user experience.
This 2-bedroom apartment can comfortably accommodate up to 4 guests and offers 116 square metres of living space. Amenities include a fully equipped kitchen, air conditioning, a private patio, a swimming pool, a jacuzzi, a spa, a tennis court, and parking.
Resort Retreat W/ Pools! 6 Mi To Bradenton Beach - Anna Maria Island, FL
No reviews

Resort Retreat W/ Pools! 6 Mi To Bradenton Beach

house, Bradenton
This detached house in Bradenton is situated approximately 9.6 kilometres from Bradenton Beach, with the Sarasota International Convention Centre and the John and Mable Ringling Museum of Art both within 12.8 kilometres.
This 109 square metre accommodation offers a private patio, air conditioning, a fully equipped kitchen with a dishwasher, and an outdoor swimming pool and hot tub, comfortably accommodating up to nine guests.

Best Anna Maria Island, FL holiday rentals with parking

Beachy Chic!  1st Floor Condo-pool-close To Beach - Anna Maria Island, FL
9.8 118 reviews

Beachy Chic! 1st Floor Condo-pool-close To Beach

apartment, Bradenton Beach
This newly renovated Bradenton Beach condo, a short walk from the beach and close to local restaurants and shops, offers a convenient location for exploring this Florida coastal town.
The first-floor apartment sleeps four guests in two bedrooms (with flexible twin/king bed arrangement in the second), boasts a fully equipped kitchen with stainless steel appliances and small appliances including a Keurig coffee machine, and includes beach gear (six chairs, two umbrellas, wagon, towels) for ultimate beach convenience.
Romantic Island Getaway! Just Steps From The Beach - Anna Maria Island, FL
8.6 4 reviews

Romantic Island Getaway! Just Steps From The Beach

cottage, Bradenton Beach
This Bradenton Beach holiday home is a five-minute walk from Anna Maria Sound and Bradenton Beach, and within a 15-minute radius of the Aluna Wellness Centre & Spa and Bradenton Beach Marina.
The 50 square metre self-catering property sleeps four, featuring one bedroom, one bathroom, a fully equipped kitchen (including oven, hob, fridge and microwave), a sofa bed, air conditioning, a swimming pool, parking, and outdoor barbecue grills; guests can enjoy stunning sea views and easy beach access.
Newly Renovated 2 Bed With Beach Supplies, Trailer Space, Walk To Beach - Anna Maria Island, FL
10 1 review

Newly Renovated 2 Bed With Beach Supplies, Trailer Space, Walk To Beach

house, Cortez
This newly renovated two-bedroom bungalow in Cortez is located 1.8 kilometres from Cortez Beach and within 19 kilometres of The John and Mable Ringling Museum of Art.
This 111 square metre residence accommodates up to seven guests, offering a fully equipped kitchen, one bathroom, free WiFi, air conditioning, a garden, and private parking, with beach supplies provided for your convenience.
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