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Anna Maria Island, FL villas
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3777 Villa rentals in Anna Maria Island, FL

Best Anna Maria Island, FL villas and beach houses with a pool

Among the 3777 accommodations in Anna Maria Island, FL, here are the 4 best villas and beach houses with a pool

Bay To Beach: Amazing Views Of Gulf & Bay By Anna Maria Life Vacation Rentals - Anna Maria Island, FL
9.6 51 reviews

Bay To Beach: Amazing Views Of Gulf & Bay By Anna Maria Life Vacation Rentals

house, Bradenton Beach
This Holmes Beach vacation rental is located just a mile from Bradenton Beach and Island Gallery West, and within two miles of Palmetto Avenue Beach, Island Players, and Holmes Beach Beaches. This property has received excellent ratings for user experience, location, and cleanliness.
The house features two bedrooms and two bathrooms, with a total floor area of 1500 square feet, and can accommodate up to six guests. Amenities include a private pool, fenced yard, fully equipped kitchen, free Wi-Fi, air conditioning, and a spa.
Bradenton Beach Resort Style Getaway-walk To Beach - Anna Maria Island, FL
9.7 128 reviews

Bradenton Beach Resort Style Getaway-walk To Beach

house, Bradenton Beach
This Bradenton Beach vacation rental is a two-minute walk from Bradenton Beach and 0.7 miles from Cortez Beach, offering easy access to the Gulf Coast and proximity to Anna Maria City Pier (5.3 miles) and the Greens of Manatee Golf Club (9.3 miles).
This 2,100-square-foot house features three bedrooms, a fully equipped kitchen with a dishwasher, a private patio, a swimming pool, a jacuzzi, and free Wi-Fi, comfortably accommodating families or groups.
2 Hot Tubs+pool+putting Green+sleeps 16 - Anna Maria Island, FL
9.3 3 reviews

2 Hot Tubs+pool+putting Green+sleeps 16

house, Bradenton
This Bradenton vacation home is conveniently located near Palma Sola Causeway Park, 6.5 miles from the Greens of Manatee Golf Club, and 9.3 miles from Sarasota Bradenton International Airport.
This 2,910-square-foot house features five bedrooms, three bathrooms, sleeps up to sixteen guests, and includes a private pool, spa, and on-site mini-golf.
Palma Sola Pool Home, Minutes To Ami - Anna Maria Island, FL
10 2 reviews

Palma Sola Pool Home, Minutes To Ami

house, Bradenton
This 3-bedroom, 2-bathroom house is located in Palma Sola, Bradenton, a 15-minute walk from Palma Sola Causeway Park and approximately 11 miles from Sarasota International Convention Center and the John and Mable Ringling Museum of Art.
This vacation home accommodates up to 11 guests and features a private swimming pool, air conditioning, a fully equipped kitchen, complimentary WiFi, and free private parking.

Best Anna Maria Island, FL houses with a kitchen

Shorewalk 202 - By Skyrun Anna Maria - Anna Maria Island, FL
9.5 2 reviews

Shorewalk 202 - By Skyrun Anna Maria

house, Bradenton
This Anna Maria vacation home offers convenient access to cycling routes and attractions within the Bradenton region.
This 1170 sq ft rental accommodates up to 11 guests with 2 bathrooms, a fully equipped kitchen, air conditioning, WiFi, a private pool, and outdoor play equipment.
Walk To Beach: Home W/ Porch On Anna Maria Island! - Anna Maria Island, FL
9.3 39 reviews

Walk To Beach: Home W/ Porch On Anna Maria Island!

house, Holmes Beach
This Holmes Beach rental is a 9-minute walk from Holmes Beach's town center, a 12-minute walk from Bradenton Beach, and a 4-mile drive from Anna Maria City Pier.
This 930-square-foot condo features two bedrooms, two bathrooms, a fully equipped kitchen with a dishwasher, free Wi-Fi, a terrace, and a private parking space, comfortably accommodating families or groups.
A Coastal Paradise - Anna Maria Island, FL
8.0 1 review

A Coastal Paradise

house, West Bradenton
This beachfront West Bradenton vacation home is 1.6 miles from Palma Sola Causeway Park and 9.3 miles from Sarasota Bradenton International Airport.
The 1,590-square-foot property boasts three bedrooms, two bathrooms, sleeps up to 13 guests, and features a private pool, balcony, free Wi-Fi, and free parking.
8 Mi To Beaches: Bradenton Home W/ Poolside Oasis! - Anna Maria Island, FL
10 37 reviews

8 Mi To Beaches: Bradenton Home W/ Poolside Oasis!

house, Bradenton
This Bradenton vacation home is located just a short drive from the John and Mable Ringling Museum of Art and a few miles from the Greens of Manatee Golf Club, offering easy access to both cultural attractions and outdoor activities. Guests consistently rate this property as excellent, praising its comfortable and convenient features. This 2-bedroom rental, spanning 1330 square feet, comfortably accommodates up to 6 guests. Enjoy a private pool, a fully equipped kitchen with a dishwasher and oven, a washing machine, a cable flat-screen TV, free Wi-Fi, and a relaxing atmosphere.

Frequently Asked Questions about villa rentals in Anna Maria Island, FL

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

    Anna Maria Island boasts beautiful beaches like Bean Point, known for its stunning sunsets and calm waters, perfect for swimming and shelling. The Anna Maria Island Historical Society Museum offers a glimpse into the island's past. For nature lovers, the Anna Maria Island Nature Preserve is a must-see, offering walking trails and opportunities for birdwatching. The charming shops and restaurants of Pine Avenue in Anna Maria are also a popular destination.
  • What are the best villa rentals in Anna Maria Island, FL?

    Among the villa rentals in Anna Maria Island, FL, Standard 2 Bedroom B, Do You Love The Beach? and Bay Breeze Cottages #3 are the most popular ones.

  • Is Anna Maria Island known for mountains, beaches, forests, or other types of landscapes?

    Anna Maria Island is primarily known for its beautiful beaches and laid-back coastal atmosphere. While there aren't mountains or extensive forests, the island features stretches of natural beach, mangrove estuaries, and tranquil residential areas. The landscape is predominantly flat and characterized by its coastal charm.
  • What are the best villa rentals with a pool in Anna Maria Island, FL?

    Standard 2 Bedroom B, Do You Love The Beach? and Bay Breeze Cottages #3 are the best villa rentals with a pool in Anna Maria Island, FL.

  • What are the most surprising and hidden attractions on Anna Maria Island?

    One surprising gem is the Leffis Key Preserve, a small, secluded area accessible by kayak or paddleboard, offering incredible views and wildlife sightings. Exploring the back streets and residential areas can also reveal charming hidden cottages and glimpses of old Florida architecture. The smaller beaches away from the main areas can offer a more secluded beach experience.
  • What are the best villa rentals with a jacuzzi in Anna Maria Island, FL?

    The best villa rentals with a jacuzzi in Anna Maria Island, FL are Standard 2 Bedroom B, “New” - Large 3 Bed 2 Bath W/ Private Pool and Playa Esmeralda Home Bradenton Beach Now Open.

  • What are some unique ways to learn about the culture of Anna Maria Island by engaging with its people?

    Chatting with locals at the various small, independently owned shops and restaurants on Pine Avenue or Bridge Street provides a genuine taste of island life. Attending a local event, like a farmers market (if available), allows for interaction with residents. The Anna Maria Island Historical Society Museum also offers insights through exhibits and potentially guided tours.
  • What are the best villa rentals for families and kids in Anna Maria Island, FL?

    The best villa rentals for families and kids in Anna Maria Island, FL are Do You Love The Beach?, Bradenton Beach Club 225 By Seabreeze Vacation and Beach Pool House Family Vacation Home.

  • How much time should you set aside to thoroughly explore Anna Maria Island?

    To truly experience Anna Maria Island, at least 3-4 days is recommended. This allows for ample time to relax on the beaches, explore the various neighborhoods, visit the attractions, and enjoy the island's laid-back pace. A longer stay would allow for more in-depth exploration and relaxation.
  • What are the best pet friendly villa rentals in Anna Maria Island, FL?

  • Is there anything you might not think to pack for a trip to Anna Maria Island?

    While it's a tropical location, evenings can get cool, especially during the winter months. A light jacket or sweater might be a good idea. Don't forget reef-safe sunscreen to protect the coral reefs and your skin. Also, consider packing insect repellent, especially for exploring natural areas.
  • What are the best villa rentals with parking in Anna Maria Island, FL?

    Standard 2 Bedroom B, Do You Love The Beach? and Bay Breeze Cottages #3 are the best villa rentals with parking in Anna Maria Island, FL.

  • What cultural experiences or workshops on Anna Maria Island offer something different?

    Specific workshops and cultural events vary seasonally. Check local listings for art classes, shelling workshops, or historical society events. The island's art galleries often host exhibits and events that showcase local artists. Keep an eye out for announcements from the Anna Maria Island Historical Society.
  • Are there any food festivals on Anna Maria Island where you can try local food?

    Anna Maria Island doesn't have large-scale, regularly scheduled food festivals like some larger cities. However, many restaurants offer fresh, locally sourced seafood and other dishes. Check local event listings for smaller, seasonal events that may feature local food vendors.
  • What seasonal natural events, such as migrations or blooming periods, occur on Anna Maria Island?

    During the winter months, many migratory birds can be seen in the area. Spring brings the blooming of various flowers and plants. The exact timing varies each year, but the Anna Maria Island Nature Preserve is a great place to observe these seasonal changes.
  • What exclusive experiences are available when visiting Anna Maria Island?

    Private boat tours or sunset cruises offer an exclusive way to experience the island's coastline. Kayaking or paddleboarding through the mangroves provides a unique perspective on the natural environment. Staying in a beachfront vacation rental offers a more secluded and luxurious experience compared to hotels.

Nearby regions

Best Anna Maria Island, FL houses with air conditioning

176 M² House ∙ 3 Bedrooms ∙ 8 Guests - Anna Maria Island, FL
9.3 10 reviews

176 M² House ∙ 3 Bedrooms ∙ 8 Guests

house, West Bradenton
This West Bradenton residence is situated in a quiet Northwest Bradenton neighborhood, a short drive to Anna Maria Island's beaches, shops, and restaurants, and convenient for exploring Bradenton's historic downtown and waterfront parks.
This 1880 square foot house offers 3 bedrooms and 2 bathrooms, accommodating up to 8 guests with a bright, open floor plan, a private heated pool, a fully fenced yard, and provided beach gear.
An Island Getaway At Palm Tree Villas - Anna Maria Island, FL
9.3 330 reviews

An Island Getaway At Palm Tree Villas

house, Holmes Beach
This Holmes Beach house is located near popular tourist attractions and landmarks, including Captain Mike's Fishing Charters, Bradenton Beach Marina, Robinson Preserve, and Anna Maria City Pier, making it an excellent choice for travelers looking to explore the area. The house has received very good user ratings and excellent location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The house features a kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, a swimming pool, a terrace or balcony, a garden, and parking. It also offers amenities such as an outdoor pool, free Wi-Fi, a TV and patio in each unit, barbecue facilities, and laundry facilities.
Tropical 3bd 2bth Poolside Retreat Near Beaches - Anna Maria Island, FL
10 2 reviews

Tropical 3bd 2bth Poolside Retreat Near Beaches

house, Bradenton
This 3-bedroom, 2-bathroom vacation home in Palma Sola Park, Bradenton, is an 18-minute walk from Palma Sola Causeway Park and 11 miles from the John and Mable Ringling Museum of Art and Sarasota International Convention Center.
This 1540 square foot house accommodates up to 14 guests with a fully equipped kitchen, air conditioning, a swimming pool, a garden, and complimentary WiFi.
Near Beaches & Img Academy, Mins To Downtown Oasis Villa Retreat - Anna Maria Island, FL
9.8 40 reviews

Near Beaches & Img Academy, Mins To Downtown Oasis Villa Retreat

house, Bradenton
Oasis Villa Retreat is a vacation home in Bradenton, Florida, located 7.9 miles from the renowned John and Mable Ringling Museum of Art, with excellent user and location ratings. The two-bedroom, four-guest villa offers ground-floor convenience and ample space, along with a fully equipped kitchen, refreshing outdoor swimming pool, and on-site parking. Guests can also enjoy complimentary Wi-Fi, air conditioning, and proximity to attractions like Tropicana Field and The Dali' Museum.

Best Anna Maria Island, FL villas and beach houses with jacuzzi

Beach Castle Resort #26 - Anna Maria Island, FL
No reviews

Beach Castle Resort #26

house, Longboat Key
This Longboat Key vacation home is situated a 4-minute walk from Longboat Key Beach and 14 miles from the Ringling Museum.
This 640 square foot, air-conditioned cottage accommodates up to 7 guests and features a well-equipped kitchen, a heated swimming pool, a hot tub, and complimentary WiFi and private parking.
Suncoast Retreat - Anna Maria Island, FL
No reviews

Suncoast Retreat

house, Bradenton
Suncoast Retreat, a one-bedroom house in Bradenton, Florida, is conveniently located 3.5 miles from the Greens of Manatee Golf Club and 6.2 miles from Sarasota Bradenton International Airport, offering easy access to Sarasota attractions like the Sarasota International Convention Center and The Ringling Museum of Art.
This Bradenton vacation rental boasts two bathrooms, sleeps seven guests, and includes a private pool, jacuzzi, free Wi-Fi, and a fully equipped kitchen with a dishwasher and microwave; nearby activities include golfing and cycling.
Beach Loft - Heated Pool & Spa Slide Fire Pit - Anna Maria Island, FL
No reviews

Beach Loft - Heated Pool & Spa Slide Fire Pit

house, Bradenton
This Bradenton vacation home is located 9.3 miles from Sarasota Bradenton International Airport and a 13-minute walk from Palma Sola Causeway Park.
This 800 square foot house accommodates up to 7 guests and features a heated pool with a waterslide, a hot tub, an outdoor fire pit, and complimentary WiFi.
Echo Of The Seas - Anna Maria Island, FL
No reviews

Echo Of The Seas

house, Bradenton
Echo of the Seas, a Bradenton house rental, is conveniently located 6.2 miles from Sarasota Bradenton International Airport (SRQ) and offers easy access to attractions like the Ringling Museum of Art (8.5 miles away).
This one-bedroom, two-bathroom vacation home sleeps seven, features a private pool and jacuzzi, free parking, and a fully equipped kitchen with a dishwasher; nearby activities include golfing at the Greens of Manatee Golf Club (3.4 miles) and exploring Sarasota's cultural scene.