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Anna Maria Island, FL villas
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2864 Villa rentals in Anna Maria Island, FL

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

Among the 2864 accommodations in Anna Maria Island, FL, here are the 4 best villas and beach houses with a pool

191 M² House ∙ 4 Bedrooms ∙ 8 Guests - Anna Maria Island, FL
10 6 reviews
Anna Maria Island, FL
07/02 – 07/06
$496/nighttotal: $1984 (4 )

191 M² House ∙ 4 Bedrooms ∙ 8 Guests

4 5
house , Bradenton
This Bradenton house rental boasts a central location, less than 20 minutes from Sarasota-Bradenton International Airport and a short drive to Anna Maria Island, downtown Bradenton, and Lakewood Ranch.
This 2,050-square-foot vacation home features four bedrooms, two bathrooms, sleeps eight guests, and includes a private pool, spa, and fully equipped kitchen with stainless steel appliances; high-speed Wi-Fi and a smart lock are also provided.
Cozy Beachside Cottage At Tradewinds/1br/pool/steps To Beach.unit1 Available Too - Anna Maria Island, FL
9.8 7 reviews
Anna Maria Island, FL
08/07 – 08/09
$451/nighttotal: $902 (2 )

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

1 2
cottage , Bradenton Beach
This renovated 700 sq ft cottage in Bradenton Beach offers 1 bedroom and 1 bathroom, accommodating up to 4 guests, and is located just steps from the Gulf beaches and a community pool, with Bridge Street Bistro and Anna Maria Oyster Bar within walking distance. Guests can enjoy amenities such as a full kitchen with a dishwasher, air conditioning, internet, and parking, with an option to book a second adjacent unit for larger groups.
90 M² House ∙ 1 Bedroom ∙ 4 Guests - Anna Maria Island, FL
9.9 78 reviews
Anna Maria Island, FL
06/27 – 07/04
$339/nighttotal: $2373 (7 )

90 M² House ∙ 1 Bedroom ∙ 4 Guests

1 2
house , Bradenton Beach
This beachfront condo, located on Anna Maria Island in Bradenton Beach, Florida, boasts stunning Gulf of Mexico views.
The 960-square-foot unit features one king bedroom, two bathrooms, a chef's kitchen, a private lanai, a heated pool, and accommodates up to four guests, with beach access and amenities provided.
Gulf Views & Pool Access: Bradenton Beach Condo! - Anna Maria Island, FL
9.8 74 reviews
Anna Maria Island, FL
08/03 – 08/07
$452/nighttotal: $1808 (4 )

Gulf Views & Pool Access: Bradenton Beach Condo!

2 3
house , Bradenton Beach
This Bradenton Beach apartment is located just steps from Cortez Beach and a 5-minute walk from Coquina Beach, offering easy access to the area's beautiful beaches. Guests consistently rate this rental excellent for location, cleanliness, and overall experience.
This 2-bedroom, 1000-square-foot vacation rental comfortably accommodates up to 6 guests. Enjoy a fully equipped kitchen, air conditioning, free Wi-Fi, a private pool, a Jacuzzi, a garden, and a tennis court.

Best Anna Maria Island, FL houses with a kitchen

Playa Esmeralda Cottage! Add Golf Cart!! - Anna Maria Island, FL
10 2 reviews
Anna Maria Island, FL
07/27 – 07/29
$601/nighttotal: $1202 (2 )

Playa Esmeralda Cottage! Add Golf Cart!!

2 5
house , Bradenton Beach
This Playa Esmeralda Cottage is located in Bradenton Beach, a 2-minute walk from Cortez Beach and 13 miles from Sarasota International Convention Center and The John and Mable Ringling Museum of Art.
This family-friendly house offers 2 bedrooms, 2 bathrooms, complimentary private parking, free WiFi, air conditioning, and a fully equipped kitchen with a dishwasher and oven, with outdoor seating available.
Bella Villa - Anna Maria Island, FL
9.4 14 reviews
Anna Maria Island, FL
06/26 – 06/30
$281/nighttotal: $1124 (4 )

Bella Villa

3 2
house , Bradenton
Bella Villa is a 3-bedroom house located in Bradenton, Florida, just a short drive from Sarasota Bradenton International Airport and The John and Mable Ringling Museum of Art. This rental has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The 1180 square foot house comfortably accommodates up to 6 guests. Enjoy a peaceful escape with amenities like a swimming pool, tennis court, garden, and a patio with lake views.
Luxury Villa Heated Pool, Putt-putt & Bocce - Anna Maria Island, FL
9.3 28 reviews
Anna Maria Island, FL
07/17 – 07/24
$441/nighttotal: $3087 (7 )

Luxury Villa Heated Pool, Putt-putt & Bocce

4 7
house , Bradenton
This recently renovated Bradenton vacation home is conveniently located 7.5 miles from Sarasota Bradenton International Airport and 10 miles from the John and Mable Ringling Museum of Art.
This 1930-square-foot property boasts four bedrooms, three bathrooms, two living rooms, a private heated saltwater pool, an arcade, and can comfortably accommodate up to 14 guests.
172 M² House ∙ 3 Bedrooms ∙ 8 Guests - Anna Maria Island, FL
10 18 reviews
Anna Maria Island, FL
07/02 – 07/06
$496/nighttotal: $1984 (4 )

172 M² House ∙ 3 Bedrooms ∙ 8 Guests

3 5
house , Bradenton
This Bradenton vacation rental is located just off 75th St W, a short drive from the beautiful beaches of Anna Maria Island, Bradenton Beach, and Holmes Beach, and close to Lakewood Ranch, Sarasota, and Tampa. The house has received excellent user ratings and is perfect for families.
This 3-bedroom, 3-bathroom home spans 1840 square feet and comfortably sleeps 8 guests. The home offers a modern coastal design, a private saltwater pool with a screened-in area, a fully equipped kitchen, and family-friendly features like a high chair, a pack-n-play, and a poolside bathroom.

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

Hibiscus Hideaway B - Top Floor Unit - Anna Maria Island, FL
9.7 29 reviews
Anna Maria Island, FL
08/03 – 08/07
$415/nighttotal: $1660 (4 )

Hibiscus Hideaway B - Top Floor Unit

2 3
house , Bradenton Beach
Hibiscus Hideaway B, a Bradenton Beach vacation home, is conveniently located near Cortez Beach, Bradenton Beach, and Coquina Beach, approximately 6.1 miles from the Anna Maria City Pier.
This 3,510-square-foot rental boasts two bedrooms, two bathrooms, a private pool, fitness center, and tennis court, comfortably accommodating small families or groups, and offering free Wi-Fi and parking.
New! Blue Iguana! Tropical Backyard Oasis With Heated Pool, Hot Tub, Fire Table, And More! - Anna Maria Island, FL
Anna Maria Island, FL
07/10 – 07/12
$834/nighttotal: $1668 (2 )

New! Blue Iguana! Tropical Backyard Oasis With Heated Pool, Hot Tub, Fire Table, And More!

3 7
house , Bradenton
This Bradenton vacation home, near Palma Sola Causeway Park (1.8 miles) and 11 miles from the Ringling Museum of Art, offers easy access to area attractions.
This 2,100-square-foot property boasts three bedrooms, two bathrooms, sleeps 19 guests, and features a heated pool, hot tub, and a fully equipped kitchen; nearby amenities include a golf course and Anna Maria City Pier.
Basque Bungalow With Pool, Minutes To Beaches - Anna Maria Island, FL
10 1 review
Anna Maria Island, FL
07/02 – 07/06
$530/nighttotal: $2120 (4 )

Basque Bungalow With Pool, Minutes To Beaches

3 5
house , Bradenton
This Basque-style bungalow in Bradenton, Florida, is located 8.3 miles from the Sarasota International Convention Center and 8.8 miles from the Ringling Museum of Art, offering easy access to Sarasota's cultural attractions and Bradenton's beaches.
This 1,580-square-foot vacation rental boasts three bedrooms, two bathrooms, and accommodates up to 13 guests, featuring a private pool, terrace, garden, and free Wi-Fi; private parking is also available.
Silver Sands #247a - Anna Maria Island, FL
Anna Maria Island, FL
06/28 – 06/29
$532/nightfor 1 night

Silver Sands #247a

1 2
house , Longboat Key
This beachfront condo in Longboat Key offers direct access to the beach and is located 15 miles from the John and Mable Ringling Museum of Art, with Sarasota International Convention Center 17 miles away and Sarasota Bradenton International Airport 16 miles away.
This air-conditioned accommodation features a kitchenette, WiFi, and parking, with a guest capacity of 3, and is close to cycling opportunities and a short drive to major attractions.

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

The Beach Club At Anna Maria #13 - Anna Maria Island, FL
8.0 3 reviews
Anna Maria Island, FL
06/28 – 06/29
$576/nightfor 1 night

The Beach Club At Anna Maria #13

1 2
house , Bradenton Beach
This beachfront house in Bradenton Beach offers immediate access to the shore and is located 12 miles from Sarasota Bradenton International Airport and 14 miles from the Sarasota International Convention Center and John and Mable Ringling Museum of Art.
This non-smoking rental accommodates up to 7 guests with 1 bathroom, featuring a well-equipped kitchen with a dishwasher, microwave, and oven, plus a patio with sea views, a hot tub, fitness room, and complimentary Wi-Fi and parking.
Bridge Street Beach House | Wi-fi | Center Of All - Anna Maria Island, FL
10 3 reviews
Anna Maria Island, FL
06/27 – 07/04
$420/nighttotal: $2940 (7 )

Bridge Street Beach House | Wi-fi | Center Of All

3 2
cottage , Bradenton Beach
This cottage is located in the Bridge Street district of Bradenton Beach, just steps from Bradenton Beach and Anna Maria Sound, and a short walk from Mote Marine Laboratory & Aquarium, Bradenton Beach, and Coquina Beach.
This 650 sq ft cottage accommodates up to 6 guests with 3 bedrooms and 1 bathroom, featuring a full kitchen, air conditioning, a communal pool, hot tub, garden, spa, tennis court, and on-site parking, with bicycles and water sports equipment available for family-friendly activities.
Oma's House W/ Heated Pool Near The Beach And Img - Anna Maria Island, FL
Anna Maria Island, FL
08/03 – 08/07
$364/nighttotal: $1456 (4 )

Oma's House W/ Heated Pool Near The Beach And Img

3 3
house , Bradenton
This West Bradenton vacation home is located 1.8 miles from Palma Sola Causeway Park and 11 miles from the John and Mable Ringling Museum of Art.
This 1560 square foot residence accommodates up to 15 guests with 2 bathrooms, air conditioning, a full kitchen, an outdoor pool, and complimentary WiFi, plus beach gear for nearby coastal exploration.
New Sunshine Getaway Heated Pool Hot Tub Games Villa - Anna Maria Island, FL
10 1 review
Anna Maria Island, FL
07/27 – 07/29
$559/nighttotal: $1118 (2 )

New Sunshine Getaway Heated Pool Hot Tub Games Villa

4 5
house , West Bradenton
This 4-bedroom villa is located in West Bradenton, 1.8 miles from Palma Sola Causeway Park and 13 miles from the John and Mable Ringling Museum of Art.
This spacious house offers a heated outdoor swimming pool, hot tub, complimentary WiFi, and parking, with a floor area of 2350 square feet accommodating up to 23 guests.
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