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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

Captain's Quarters Spinnakers - 202 - 56th 1 - Anna Maria Island, FL
9.9 298 reviews

Captain's Quarters Spinnakers - 202 - 56th 1

house, Holmes Beach
This vacation home is located in Holmes Beach, just a short walk from Bradenton Beach and Island Gallery West, with other beaches also within a mile. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience. This vacation rental comfortably accommodates six guests and features a well-equipped kitchen, a private pool, a water park, and a balcony with a smart TV. Enjoy barbecue grills, a spa, and easy access to the beach, making this an ideal choice for families and groups seeking a relaxing and fun-filled getaway.
The Beach On Longboat Key #106 - Anna Maria Island, FL
No reviews

The Beach On Longboat Key #106

house, Longboat Key
This beachfront villa in Longboat Key offers direct access to Longboat Key Beach and is 11 miles from the John and Mable Ringling Museum of Art.
This 340 square foot vacation home accommodates up to 3 guests with 1 bathroom, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, garden, fitness center, tennis court, and private parking.
Sleeps 12 Game Room Theatre Tiki Bar Pool - Anna Maria Island, FL
No reviews

Sleeps 12 Game Room Theatre Tiki Bar Pool

house, Bradenton
This vacation home in Cedar Hammock, Bradenton, is located 6.8 miles from Sarasota Bradenton International Airport and within 8.5 miles of the Sarasota International Convention Center and the John and Mable Ringling Museum of Art.
This 1980 square foot house offers 4 bedrooms accommodating up to 12 guests, with amenities including a private pool, tiki bar, home theater, game room, casino access, free WiFi, and on-site parking.
Lakeside Retreat - Anna Maria Island, FL
10 2 reviews

Lakeside Retreat

house, West Bradenton
Lakeside Retreat, a 3-bedroom West Bradenton home, is located 1.6 miles from Palma Sola Causeway Park and 11 miles from Sarasota Bradenton International Airport.
This 1,320-square-foot vacation rental sleeps 11 guests and boasts a private balcony with stunning sea views, a pool, tennis court, and on-site massage services.

Best Anna Maria Island, FL houses with a kitchen

A Piece Of Paradise - Anna Maria Island, FL
10 2 reviews

A Piece Of Paradise

house, West Bradenton
This beachfront vacation home in West Bradenton, Florida, is conveniently located 10 miles from Sarasota Bradenton International Airport (SRQ), 12 miles from The Ringling Museum of Art, and approximately 30 miles from The Dali Museum and the Chihuly Collection.
This 1810-square-foot property boasts three bedrooms, two bathrooms, and accommodates up to 17 guests, featuring a private pool, balcony, free Wi-Fi, and free parking; enjoy easy beach access and a fully equipped kitchen.
Great Location Near Manatee Beach 1br At Casa Coco - Anna Maria Island, FL
9.5 180 reviews

Great Location Near Manatee Beach 1br At Casa Coco

house, Holmes Beach
This beachfront home in Holmes Beach is just steps from West Coast Surf Shop and AMI Paddleboard Adventures, with Manatee Public Beach and Bradenton Beach a short walk away. The property has excellent ratings for location, cleanliness, and overall experience. This vacation rental offers a comfortable and convenient stay with one bathroom and a fully equipped kitchen. Enjoy the outdoor patio, the private pool, and the convenience of laundry facilities, all while being close to the beach and local attractions.
Resort Condo W/ Beach Access On Anna Maria Island! - Anna Maria Island, FL
9.3 33 reviews

Resort Condo W/ Beach Access On Anna Maria Island!

house, Bradenton Beach
This Bradenton Beach apartment is located a short walk from Cortez Beach and a 16-minute walk from Coquina Beach, providing easy access to the area's beautiful beaches.
The 1,080 square foot unit features two bedrooms, two bathrooms, and a balcony with stunning sea views, perfect for families or groups of friends looking for a comfortable and convenient Bradenton Beach vacation rental.
Palm Shell Villa - Pool - Pickleball - Hot Tub - Anna Maria Island, FL
No reviews

Palm Shell Villa - Pool - Pickleball - Hot Tub

house, Bradenton
Palm Shell Villa in Bradenton is situated approximately 10 miles from the Sarasota International Convention Center and the John and Mable Ringling Museum of Art, with Sarasota Bradenton International Airport just over 8 miles away.
This 2130 square foot house offers 4 bedrooms and 3 bathrooms, accommodating up to 22 guests with amenities including a private swimming pool, hot tub, full kitchen, air conditioning, free WiFi, and on-site parking.

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

Steps To Beach - Seagrass Sunsets By Seabreeze Vacation - Anna Maria Island, FL
10 2 reviews

Steps To Beach - Seagrass Sunsets By Seabreeze Vacation

house, Bradenton Beach
This vacation home in Ilexhurst offers unbeatable proximity, located literally steps from Bradenton Beach and 14 miles from the John and Mable Ringling Museum of Art.
This 720 square foot rental features 2 bedrooms, 2 bathrooms, and accommodates up to 11 guests with amenities including air conditioning, a swimming pool, a terrace, free WiFi, and free private parking.
Lakefront 2br Condo Near Img - Pool, Pickleball, Tennis - Anna Maria Island, FL
9.3 3 reviews

Lakefront 2br Condo Near Img - Pool, Pickleball, Tennis

house, Bradenton
This Bradenton lakefront condo is conveniently located 6 miles from Sarasota Bradenton International Airport and 8 miles from both the Sarasota International Convention Center and the Ringling Museum of Art.
This 1,170-square-foot property features two bedrooms and two bathrooms, accommodating up to four guests and offering amenities such as a swimming pool, spa, fitness center, and private balcony, plus nearby pickleball and tennis courts.
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 house in Bradenton is located 6 miles from Bradenton Beach, 7.9 miles from the Sarasota International Convention Center, and 8 miles from the John and Mable Ringling Museum of Art.
This 1170 sq ft accommodation offers 2 bedrooms and 2 bathrooms for up to 9 guests, featuring a private pool, hot tub, full kitchen with dishwasher, air conditioning, and free parking.
Minutes To Anna Maria - Canal Hangout Onsite Apartment - Anna Maria Island, FL
9.8 4 reviews

Minutes To Anna Maria - Canal Hangout Onsite Apartment

house, Bradenton
This Bradenton vacation home, an eight-minute walk from Palma Sola Causeway Park and twelve miles from Sarasota Bradenton International Airport, offers convenient access to Anna Maria Island.
The 200-square-foot property features one bedroom, one bathroom, sleeps six guests, includes a fully equipped kitchen, free Wifi, a private entrance, and a washer.

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

Casa Bella - 5br, Waterfront, Pool, Spa -9 Min Anna Maria - Anna Maria Island, FL
9.9 145 reviews

Casa Bella - 5br, Waterfront, Pool, Spa -9 Min Anna Maria

house, West Bradenton
Casa Bella, a waterfront vacation home in West Bradenton, is situated 9 miles from Anna Maria Island City Pier, 1.8 miles from Palma Sola Causeway Park, and 11 miles from Sarasota Bradenton International Airport.
This 2,400-square-foot property boasts five bedrooms, three bathrooms, a private pool and jacuzzi, and a fully equipped kitchen; guests can enjoy water activities, relax in the garden, and utilize free parking.
Breezy Livin' Speakeasy Pool Hot Tub Game Room - Anna Maria Island, FL
10 1 review

Breezy Livin' Speakeasy Pool Hot Tub Game Room

house, Bradenton
This vacation home in West Bradenton is located 7.5 miles from Sarasota Bradenton International Airport, 9.3 miles from the Sarasota International Convention Center, and 9.4 miles from the John and Mable Ringling Museum of Art.
This 2290 square foot rental accommodates up to 15 guests and features a private outdoor swimming pool, hot tub, game room, on-site casino and speakeasy, a fully equipped kitchen, free WiFi, and on-site parking.
Set In Sand - Anna Maria Island, FL
No reviews

Set In Sand

house, Bradenton Beach
Set in Sand is a beachfront home in Bradenton Beach, Florida, located 4.7 miles from Anna Maria City Pier and 15 miles from The John and Mable Ringling Museum of Art.
This 2,810-square-foot vacation rental boasts seven bedrooms, six bathrooms, and accommodates up to 27 guests, featuring a private pool, fitness center, and free Wi-Fi.
Tarpon Pointe - Anna Maria Island, FL
No reviews

Tarpon Pointe

house, Anna Maria
This beachfront Anna Maria Island rental, Tarpon Pointe, is a 9-minute walk from Anna Maria Island and a 5-minute walk from the Anna Maria City Pier, offering stunning sea views and proximity to Sarasota Bradenton International Airport (18 miles).
This 2,220-square-foot house features four bedrooms, three bathrooms, and accommodates up to 19 guests, complete with a private pool, fitness center, free Wi-Fi, and free parking.
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