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

Water Slide & Pool ** Sugarcane Hideaway** - Anna Maria Island, FL
9.2 93 reviews

Water Slide & Pool ** Sugarcane Hideaway**

apartment, Bradenton
This 3-bedroom house is located near the beach in Bradenton, within easy reach of attractions like Blake Medical Center, LECOM Park, and Riverwalk. It has received excellent ratings for location, cleanliness, and overall experience.
The property offers a private garden and a swimming pool, perfect for relaxing after a day exploring Bradenton. Guests can also enjoy the convenience of a fully equipped kitchen, a terrace, and free Wi-Fi.
Spectacular Beach & Dolphin Views!  Huge Private Balcony! 2br/2ba Upstairs Villa - Anna Maria Island, FL
9.9 760 reviews

Spectacular Beach & Dolphin Views! Huge Private Balcony! 2br/2ba Upstairs Villa

apartment, Bradenton Beach
This apartment is located in Bradenton Beach, just steps from the marina and beach, with family-friendly attractions like Fish Hole Adventure Golf within a 10-minute walk. The property enjoys excellent user, location, and cleanliness ratings.
The self-catering accommodation sleeps up to six guests in two bedrooms and includes a well-equipped kitchen. Enjoy the outdoor amenities including a garden, barbecue grills, a jacuzzi, a tennis court, and a balcony with views of the sea.
Lake O Woods Lake Front Gated Private Pool Home, Just 5 miles to the Beach home - Anna Maria Island, FL
9.7 154 reviews

Lake O Woods Lake Front Gated Private Pool Home, Just 5 miles to the Beach home

house, Bradenton
This charming house is located in Lake O Woods, just a short drive from Bradenton's beautiful beaches and the John and Mable Ringling Museum of Art. The property has received excellent ratings for its cleanliness, location, and overall experience.
The house has two bedrooms, a dining area, and a living room, providing ample space for a comfortable stay. Guests can enjoy a private pool, a spa, a garden, and a range of modern amenities, including air conditioning, free Wi-Fi, and a fully equipped kitchen.
Sandy Point 205 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath, Maximum Occupancy Of 4 People. - Anna Maria Island, FL
9.6 118 reviews

Sandy Point 205 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath, Maximum Occupancy Of 4 People.

apartment, Holmes Beach
This two-bedroom apartment is located just a short distance from the Gulf beach in Holmes Beach, offering easy access to the sand and surf. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The apartment is spacious and can comfortably accommodate up to four guests. It comes fully furnished with a kitchen, air conditioning, a swimming pool, a terrace, a garden, and parking. Guests can enjoy the convenience of free trolley access, making it easy to explore the island.

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

Adorable Duplex On Ami! With Pool, Near Bean Point Beach - Anna Maria Island, FL
9.2 57 reviews

Adorable Duplex On Ami! With Pool, Near Bean Point Beach

apartment, Anna Maria
Southern Breeze #5, a ground-floor duplex in Anna Maria, Florida, is situated less than 1.6km from Bean Point Beach and a 1.6km drive from Bayfront Park.
This 73 square metre Anna Maria Island flat offers two king bedrooms, a sleeper sofa, one bathroom, and a fully equipped kitchen, accommodating up to six guests and including access to a shared pool, BBQ and laundry facilities.
The Beach Club At Anna Maria #14 - Anna Maria Island, FL
9.0 4 reviews

The Beach Club At Anna Maria #14

house, Bradenton Beach
This beachfront villa in Bradenton Beach offers direct access to the shore and is situated 22 kilometres from the Sarasota International Convention Centre and the John and Mable Ringling Museum of Art, with Sarasota Bradenton International Airport located 19 kilometres away.
This property accommodates up to seven guests, featuring a well-equipped kitchen with a dishwasher and microwave, air conditioning, a swimming pool, a hot tub, and a fitness centre, with accessible facilities and on-site parking available.
Paradise Retreat  With  Heated Pool-- Need We Say More - Anna Maria Island, FL
9.9 469 reviews

Paradise Retreat With Heated Pool-- Need We Say More

apartment, South Bradenton
This family-friendly property is located in South Bradenton, just a short distance from Arcadeland, Smugglers Cove Adventure Golf, and IMG Academy. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The three-bedroom house spans 102 square metres and comfortably accommodates up to six guests. It offers a range of amenities including a private pool, a fitness centre, a spa, a terrace, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay.
One Particular Harbour 392-201 · Courtyard View · Pet-friendly - Anna Maria Island, FL
9.6 42 reviews

One Particular Harbour 392-201 · Courtyard View · Pet-friendly

apartment, Bradenton
This Bradenton waterfront apartment, situated within 3.2km of Anna Maria Sound and under 4.8km from Manatee Public Beach and Bradenton Beach, offers stunning views.
The 138 square metre property boasts two bedrooms, two bathrooms, sleeps five, and includes a fully equipped kitchen, private balcony, free Wi-Fi, and access to an on-site water park and barbecue grills.

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! Bean Point is a must-see for its stunning sunsets and views. The historic Anna Maria City Pier offers great fishing and people-watching opportunities. For a taste of history, explore the Anna Maria Island Historical Society Museum. And don't miss the picturesque Bridge Street, filled with shops and restaurants.
  • 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 on the Gulf Coast means you'll experience beautiful sunsets and the gentle Gulf breezes. The beaches themselves are a unique natural phenomenon, with their soft, white sand and calm waters perfect for swimming, shelling, and sunbathing. Keep an eye out for the abundant birdlife – you might spot herons, egrets, or even pelicans.
  • 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 for exploring the island. Don't forget your beach towel and a reusable water bottle to stay hydrated in the Florida sun. A camera is also a good idea to capture the beautiful scenery.
  • What are the best holiday 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 budget, expect to spend approximately £150-£300 per day for a couple, covering accommodation, meals, some activities, and local transport. This is just an estimate; you could spend more or less depending on your choices.
  • 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 waterfront dining with classic seafood dishes. For a more casual atmosphere, try the many beachfront cafes and eateries along Pine Avenue. Fresh seafood, especially grouper and stone crab (in season), are must-try specialties.
  • 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 Anna Maria Island Nature Preserve offers lovely walking trails and opportunities for birdwatching. Exploring the quieter beaches away from the main tourist areas, such as the southern end of the island, can be a rewarding experience. Consider renting bikes and cycling the length of the island – it's a great way to see the quieter residential areas.
  • What are the best activities for engaging with locals and understanding their culture on Anna Maria Island, Florida?

    Visiting local shops and markets provides a chance to chat with owners and learn about the area. Dining at smaller, family-run restaurants is another great way to experience local culture. Attending any local events or festivals (check local listings) offers opportunities to interact with residents.
  • What unique natural landscapes and terrain features can travellers explore on Anna Maria Island, Florida?

    Anna Maria Island is known for its beautiful beaches, which are its main natural feature. The island's relatively flat terrain makes it easy to explore on foot or by bicycle. The mangrove forests and coastal wetlands offer diverse ecosystems, though accessing these areas might require some planning.
  • 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. A possible itinerary could include: Day 1: Beach time and exploring Anna Maria City; Day 2: Visit Bean Point and explore Bradenton Beach; Day 3: Explore Holmes Beach and enjoy watersports; Day 4: Relax, shop, and enjoy a final sunset.

Nearby regions

Best Anna Maria Island, FL holiday rentals with a balcony

Fm Shorewalk -Pool, Tennis, Pickle Ball, Near Beaches Anna Maria Island And Img - Anna Maria Island, FL
9.5 35 reviews

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

apartment, Bradenton
This two-bedroom apartment is located in Bradenton, just over 1.5 kilometres from both Arcadeland and IMG Academy, making it ideal for families and sports enthusiasts. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment is 116 square metres in size and can comfortably accommodate up to four guests. It features a fully equipped kitchen, two bathrooms, a washing machine, a patio, a TV, parking, internet access, and table tennis, ensuring a comfortable and enjoyable stay.
Runaway Bay 210 - Anna Maria Island, FL
9.4 26 reviews

Runaway Bay 210

apartment, Bradenton Beach
Runaway Bay 210 apartment is a two-minute walk from Bradenton Beach and under 1.6km from Cortez Beach, offering easy access to Holmes Beach (2.1km) and Anna Maria City Pier (8.5km).
This 100 square metre self-catering flat features one bedroom, one bathroom, a fully equipped kitchen, and a terrace, plus access to a swimming pool, sauna, fitness centre, tennis court, and on-site restaurant.
Ks Shorewalk -Pool, Tennis, Pickle Ball, Near Beaches Anna Maria Island And Img - Anna Maria Island, FL
9.8 17 reviews

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

apartment, Bradenton
This beachfront apartment, near Bradenton, Florida, is located approximately 2.7 kilometres from Smugglers Cove Adventure Golf and the IMG Academy.
The 109-square-metre property boasts two bedrooms, two bathrooms, a fully equipped kitchen, and a private balcony; it comfortably sleeps four guests and offers access to a swimming pool, Jacuzzi, and tennis court.
Beach Walk - 6250 Holmes #31 - Anna Maria Island, FL
9.5 41 reviews

Beach Walk - 6250 Holmes #31

house, Holmes Beach
This charming two-bedroom property is located in Holmes Beach, a short 10-minute walk from Bradenton Beach and Island Gallery West, with Holmes Beach Beaches and Manatee Public Beach within 1.6 kilometres. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The 139 square metre house comfortably accommodates up to six guests, and features a fully equipped kitchen, air conditioning, a private balcony, a swimming pool, a spa, and a garden. Guests can enjoy free Wi-Fi, parking, and easy access to the beach and local attractions.

Best Anna Maria Island, FL holiday rentals with parking

Mello On The Beach - Vitamin Sea - Anna Maria Island, FL
9.8 278 reviews

Mello On The Beach - Vitamin Sea

aparthotel, Holmes Beach
This beachfront apartment hotel in Bradenton Beach, Florida, enjoys a prime location, steps from AMI Paddleboard Adventures, West Coast Surf Shop, and Manatee Public Beach.
The self-catering apartments offer fully equipped kitchens, in-unit laundry, air conditioning, a swimming pool, terrace/balcony, and barbecue grills, ensuring a comfortable stay for guests.
7th Heaven Condo - Anna Maria Island, FL
9.3 60 reviews

7th Heaven Condo

apartment, Longboat Key
7th Heaven condo, a beachfront property on Longboat Key, Florida, offers direct beach access and is situated within 21-26 km of attractions such as the Ringling Museum of Art, the Van Wezel Performing Arts Hall, and Sarasota Bradenton International Airport.
This 69-square-metre one-bedroom apartment features a fully equipped kitchen, private terrace, swimming pool access, free Wi-Fi, and sleeps up to two guests, providing a comfortable stay near Greens of Manatee Golf Club.
Bright Condo In The Palms, Close To Everything! - Anna Maria Island, FL
9.9 104 reviews

Bright Condo In The Palms, Close To Everything!

apartment, Holmes Beach
This Holmes Beach condo, a short walk or cycle from the beach and local restaurants, offers convenient access to Anna Maria Island's attractions.
Sleeping five guests, this two-bedroom, one-bathroom apartment features a fully equipped kitchen with dishwasher, private deck, three bikes, a beach wagon, and modern amenities including new high-impact windows and mattresses.
Anna Maria Island Th - Close To Beach, Pool! - Anna Maria Island, FL
9.6 83 reviews

Anna Maria Island Th - Close To Beach, Pool!

house, Holmes Beach
This Holmes Beach townhouse, newly renovated in Autumn 2023, is situated just 0.32 kilometres from Anna Maria Island's beaches and within walking distance of local restaurants, shops, and pickleball/tennis courts.
The three-bedroom, two-and-a-half-bathroom property sleeps six guests and boasts a well-equipped kitchen, a heated pool, three parking spaces, Roku TVs, Wi-Fi, and a screened porch with outdoor decks and a grill.
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