Holiday Rentals in Anna Maria Island, FL

6231 available vacation rental offers

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Anna Maria Island, FL holiday rentals
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Best Holiday rentals and Airbnb offers 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

Paradise Palms! Holiday Home W/ Pool - Anna Maria Island, FL
9.7 74 reviews

Paradise Palms! Holiday Home W/ Pool

house, Bradenton
This Bradenton townhome offers excellent access to Anna Maria Island's beaches (approx. 8km) and Robinsons Preserve (0.8-2.4km), plus downtown Bradenton's attractions within walking distance.
Sleeping six guests, this two-bedroom, one-bathroom property features a fully equipped kitchen, in-unit laundry, air conditioning, a shared pool, and kid-friendly amenities including a travel cot and high chair.
Pet-friendly Bradenton Home 1.5 Mi To Cortez Beach - Anna Maria Island, FL
10 59 reviews

Pet-friendly Bradenton Home 1.5 Mi To Cortez Beach

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.
4411 Shorewalk 15 Min To Beach And 5 Mins To Img - Anna Maria Island, FL
8.9 1675 reviews

4411 Shorewalk 15 Min To Beach And 5 Mins To Img

house, Bradenton
This two-bedroom house in Bradenton is ideally located just 15 minutes from the beach and 5 minutes from IMG Academy, making it perfect for families or groups looking for a relaxing and convenient stay. The house has consistently received excellent ratings for its location, cleanliness, and overall experience.
The house is spacious and comfortable, providing a relaxing retreat after a day of exploring the area. Guests can enjoy a range of amenities, including a private pool, a hot tub, and a fully equipped kitchen.
Best Location! Heated Pool~steps To Beach/shops! - Anna Maria Island, FL
10 25 reviews

Best Location! Heated Pool~steps To Beach/shops!

apartment, Holmes Beach
This 1-bedroom villa, located in Islands West Resort, offers direct access to Holmes Beach, just a 2-minute walk away, and is conveniently situated within 500 metres of local shops and eateries.
This dog-friendly holiday let can accommodate up to four guests, featuring a king bed and a queen sleeper sofa, and provides access to a shared heated swimming pool, a private BBQ grill, and essential beach gear for your convenience.

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 Sunsets - Studio - Anna Maria Island, FL
9.2 271 reviews

Anna Maria Sunsets - Studio

studio, Bradenton Beach
This one-bedroom flat is situated on Bradenton Beach, just a short walk from the Anna Maria Sound and Bradenton Beach Marina.
The self-catering apartment sleeps up to four guests and offers a swimming pool, parking, and free Wi-Fi, making it perfect for a relaxing beach getaway.
The Beach Club At Anna Maria #12 - Anna Maria Island, FL
9.0 1 review

The Beach Club At Anna Maria #12

house, Bradenton Beach
The Beach Club At Anna Maria #12 is a beachfront property in Bradenton Beach, offering direct access to the beach and situated 19 kilometres from Sarasota Bradenton International Airport and 23 kilometres from the Sarasota International Convention Centre and John and Mable Ringling Museum of Art.
This apartment accommodates up to three guests and features a well-equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, jacuzzi, garden, fitness centre, tennis court, and private parking, with disabled facilities and complimentary WiFi also available.
Runaway Bay 185 - 1357300 - Anna Maria Island, FL
9.3 203 reviews

Runaway Bay 185 - 1357300

apartment, Bradenton Beach
Runaway Bay 185 - 1357300 is located in Bradenton Beach, just a short walk from the main beach area and less than a mile from Cortez Beach. This property has received excellent ratings for location, cleanliness and overall user experience.
The apartment has a floor area of 100 square metres and includes a well-equipped kitchen, a private patio, and access to a range of amenities, such as a swimming pool, tennis court, fitness centre, sauna, spa, and restaurant.
Lp Shorewalk -Pool, Tennis, Pickle Ball, Near Beaches Anna Maria Island And Img - Anna Maria Island, FL
9.2 10 reviews

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

apartment, Bradenton
This Bradenton seaside apartment, near IMG Academy and other attractions within 5km, offers stunning ocean views.
The 109 square metre property boasts two bedrooms, four bathrooms, a private balcony, and access to a swimming pool, jacuzzi, tennis court, and garden; accommodating up to four guests.

Frequently asked questions about holiday rentals in Anna Maria Island, FL

  • What are the must-see sights on Anna Maria Island, Florida?

    For must-see sights on Anna Maria Island, you definitely want to check out the Anna Maria Island Historical Museum to learn about the island's history. The picturesque Anna Maria City Pier is a great spot for fishing and enjoying the views. Bean Point is famous for its stunning sunsets and views of the coastline. And don't forget the beautiful beaches themselves – they're the main attraction!
  • What are the best Airbnb and vacation rentals in Anna Maria Island, FL?

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

    Anna Maria Island boasts incredible natural beauty. The beaches are renowned for their pristine, white sand and calm, clear waters. You'll see abundant wildlife, from shorebirds to dolphins. The island's position in the Gulf of Mexico means you can witness beautiful sunsets almost every night. The mangrove forests provide a unique ecosystem to explore, too.
  • 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 be doing a lot of exploring. Don't forget your beach towel and a reusable water bottle to stay hydrated in the Florida sun. A camera is also a must to capture the stunning scenery.
  • What are the best vacation rentals with a pool in Anna Maria Island, FL?

    Standard 2 Bedroom B, Heated & Chilled Pool - -private Outdoor Living With Grill and Anna Maria Island Beach Palms 2b are the best vacation rentals with a pool 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 trip, you could expect to spend around £150-£300 per day for a couple, covering accommodation, meals, some activities, and local transport. Budget travellers could manage on less, while luxury travellers will spend considerably more.
  • What are the best rentals for families and kids 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 popular choice for upscale dining, known for its fresh seafood. Rod & Reel Pier offers casual dining with stunning waterfront views and classic seafood options. The Sandbar Restaurant is another popular spot for its laid-back atmosphere and delicious seafood. Fresh seafood is a must-try on the island, along with key lime pie – a Florida classic.
  • What are the best rentals or Airbnbs with a jacuzzi in Anna Maria Island, FL?

  • What are some less-famous attractions on Anna Maria Island, Florida that are worth a visit?

    The Leffis Key Preserve offers a beautiful nature trail for birdwatching and exploring the local ecosystem. Exploring the smaller, quieter beaches away from the main tourist areas can provide a more tranquil experience. Take a stroll along the bayfront and admire the charming architecture of the older homes.
  • What are the best activities for engaging with locals and understanding their culture on Anna Maria Island, Florida?

    Chatting with staff at local businesses, like the smaller shops or restaurants, is a great way to get a feel for the island's atmosphere. Visiting the Anna Maria Island Historical Museum can provide insight into the community's history. Attending any local events or farmers' markets (when available) will give you a chance to interact with residents.
  • What unique natural landscapes and terrain features can travellers explore on Anna Maria Island, Florida?

    The island's main feature is its beautiful beaches, with soft white sand and calm waters. The mangrove forests offer a unique ecosystem to explore, with opportunities for kayaking or paddleboarding. The coastline provides diverse habitats, from sandy beaches to tidal flats.
  • 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 explore Anna Maria Island at a relaxed pace. One could spend a day exploring the beaches, another visiting the Anna Maria City Pier and the Historical Museum, and a third exploring the nature preserves and enjoying watersports. A fourth day could be spent simply relaxing and enjoying the island's atmosphere.

Nearby regions

Best Anna Maria Island, FL holiday rentals with a balcony

Step From The Beach.renovated Ground Floor Unit 63 - Anna Maria Island, FL
9.5 315 reviews

Step From The Beach.renovated Ground Floor Unit 63

studio, Longboat Key
This studio apartment is located on Longboat Key, just a 2-minute walk from the beach and 19 kilometres from the John and Mable Ringling Museum of Art. It has received excellent ratings for its location, cleanliness and overall experience.
The apartment is on the ground floor, offering easy access and a private balcony. Guests have access to a range of amenities including a well-equipped kitchen, a swimming pool, a jacuzzi, a tennis court and free parking.
Cozy Beachside Cottage At Tradewinds/1br/pool/steps To Beach.unit1 Available Too - Anna Maria Island, FL
9.8 12 reviews

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

cottage, Bradenton Beach
This newly renovated 1-bedroom, 1-bathroom cottage in Bradenton Beach is just a few steps from Bradenton Beach and the community pool, offering easy access to local boutiques, Bridge Street Bistro, and Anna Maria Oyster Bar.
This 65 square meter holiday home accommodates up to four guests and features a full kitchen with a fridge, microwave, and dishwasher, air conditioning, Wi-Fi, and private parking, with the option to book an adjacent unit for larger groups.
Luxury 2br/2ba Condo Minutes From Ami, Beaches & Img - Anna Maria Island, FL
10 10 reviews

Luxury 2br/2ba Condo Minutes From Ami, Beaches & Img

apartment, South Bradenton
This two-bedroom, two-bathroom flat in Bradenton is situated 3 kilometres from Smugglers Cove Adventure Golf and 5 kilometres from DeSoto Square mall, offering easy access to St. Armands Circle, Mall at University Town Centre, Coquina Beach, Bean Point Beach, and The Bishop Museum of Science and Nature.
This 109-square-metre apartment accommodates up to five guests and features air conditioning, Wi-Fi, a fully equipped kitchen with a microwave and dishwasher, a swimming pool, a jacuzzi, a terrace/balcony, and on-site parking.
2 Mi To Anna Maria Island: Newly Built Home! - Anna Maria Island, FL
9.4 5 reviews

2 Mi To Anna Maria Island: Newly Built Home!

house, Cortez
This Cortez holiday home, newly built in Bradenton, is situated 3.2km from Anna Maria Island's beaches, 21km from Sarasota's cultural attractions including the Ringling Museum of Art, and 18km from Sarasota Bradenton International Airport.
The 38 square metre property offers one bedroom, one bathroom, sleeps seven guests, and includes a fully equipped kitchen with fridge and microwave, air conditioning, Wi-Fi, a garden, parking, and a washing machine.

Best Anna Maria Island, FL holiday rentals with parking

Getaway Retreat A · Firepit · 1 Block To Bay - Anna Maria Island, FL
9.2 91 reviews

Getaway Retreat A · Firepit · 1 Block To Bay

apartment, Holmes 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.
Bayside Retreat With Pool And Bay Views! Near - Anna Maria Island, FL
9.3 564 reviews

Bayside Retreat With Pool And Bay Views! Near

house, Anna Maria
This charming coastal property is located just a short walk from both Bay Boulevard Beach and Anna Maria Beach, offering easy access to the beautiful surroundings. It's also within a 5-minute walk of the Anna Maria City Pier and Bayfront Park, making it a perfect base for exploring the area. The property has consistently received excellent ratings for user experience, location and cleanliness.
The house features two bedrooms, providing ample space for a small family or group of friends. It includes a fully equipped kitchen, a relaxing patio, a comfortable sofa bed for additional guests, and access to a water park and barbecue grills.
Amazing View, Updated Beachfront Condo - Anna Maria Island, FL
9.4 280 reviews

Amazing View, Updated Beachfront Condo

apartment, Bradenton Beach
This apartment is located in Bradenton Beach, just a 5-minute walk from the beach, Anna Maria Sound, and Aluna Wellness Centre & Spa, offering a peaceful and convenient location close to local amenities. The property has consistently received excellent ratings for location, cleanliness, and overall guest experience.
This comfortable apartment offers 46 square metres of space and can accommodate up to 3 guests. Guests can enjoy access to a swimming pool, parking, and a kitchen equipped with a fridge, freezer, microwave oven, and coffee/tea maker.
Playa Esmeralda Suite 3 - Anna Maria Island, FL
9.0 20 reviews

Playa Esmeralda Suite 3

apartment, Bradenton Beach
Playa Esmeralda Unit D, a Bradenton Beach flat, is a two-minute walk from Cortez Beach, 9.3km from Anna Maria City Pier, and 23km from attractions such as The John and Mable Ringling Museum of Art and the Van Wezel Performing Arts Hall.
This 42-square-metre one-bedroom apartment sleeps seven, features free Wi-Fi and private parking, a fully equipped kitchen with oven and microwave, and air conditioning.
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