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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

Island Vacay -1 Block Walk-quiet Street To Beach - Anna Maria Island, FL
Anna Maria Island, FL
07/18 – 07/25
$281/nighttotal: $1967 (7 )

Island Vacay -1 Block Walk-quiet Street To Beach

1 2
house , Holmes Beach
This Holmes Beach vacation rental is situated a 2-minute walk from Holmes Beach, 4 miles from Anna Maria City Pier, and 12 miles from Sarasota Bradenton International Airport.
This 650 sq ft, 1-bedroom, 1-bathroom cottage accommodates up to 7 guests and features air conditioning, a full kitchen, free WiFi, a private entrance, and a balcony, with a swimming pool on-site.
Riverbend Cottage - Anna Maria Island, FL
Anna Maria Island, FL
07/17 – 07/24
$332/nighttotal: $2324 (7 )

Riverbend Cottage

2 2
house , Bradenton
Riverbend Cottage, a house in Bradenton, is located 8.1 miles from Sarasota Bradenton International Airport.
This 21,530 square foot cottage offers 2 bedrooms, 2 bathrooms, accommodates 8 guests, and features air conditioning, Wi-Fi, a full kitchen, a swimming pool, and a garden.
Holmes Beach Retreat! Condo In Margaritaville With Amazing Views Of The Bay! - Anna Maria Island, FL
9.0 2 reviews
Anna Maria Island, FL
07/11 – 07/25
$559/nighttotal: $7826 (14 )

Holmes Beach Retreat! Condo In Margaritaville With Amazing Views Of The Bay!

3 7
house , Bradenton
This Holmes Beach condo, located within Bradenton's Margaritaville resort, is 5.2 miles from Anna Maria City Pier and 14 miles from Sarasota Bradenton International Airport.
This 1,670-square-foot vacation rental boasts three bedrooms, three bathrooms, sleeps up to 13 guests, and includes a private balcony, pool access, a fully equipped kitchen, and free Wi-Fi.
Luxury 3br Home With Heated Pool, Pickleball And Game Room - Anna Maria Island, FL
10 2 reviews
Anna Maria Island, FL
07/02 – 07/05
$1128/nighttotal: $3384 (3 )

Luxury 3br Home With Heated Pool, Pickleball And Game Room

3 6
house , Bradenton
This luxury house in Bradenton is situated 10 miles from the Sarasota International Convention Center and the John and Mable Ringling Museum of Art.
This 1910 square foot home accommodates up to 13 guests with 3 bedrooms and 2 bathrooms, featuring a private heated pool, on-site game room with billiards, table tennis, and squash, an outdoor fireplace, free WiFi, and free private parking.

Best Anna Maria Island, FL houses with a kitchen

Beach N Bay Home - Anna Maria Island, FL
9.9 49 reviews
Anna Maria Island, FL
06/27 – 07/04
$532/nighttotal: $3724 (7 )

Beach N Bay Home

1 2
house , Anna Maria
Beach N Bay home, located in Anna Maria, Florida, offers convenient proximity to Anna Maria Island (a 6-minute walk) and the Anna Maria City Pier (a 7-minute walk).
This pet-friendly 830-square-foot house features two bedrooms, one bathroom, a fully equipped kitchen with a dishwasher, a private patio, and access to a swimming pool and Jacuzzi.
232 M² House ∙ 6 Bedrooms ∙ 12 Guests - Anna Maria Island, FL
9.9 47 reviews
Anna Maria Island, FL
06/27 – 07/04
$1445/nighttotal: $10115 (7 )

232 M² House ∙ 6 Bedrooms ∙ 12 Guests

6 2
house , Holmes Beach
This six-bedroom, 6.5-bathroom Holmes Beach house on 42nd Street is a short walk from Holmes Beach's pristine sands, restaurants, and shops.
This luxurious vacation rental boasts a private heated saltwater pool, spa, fitness center, and tennis court, accommodating up to twelve guests with amenities including free Wi-Fi, beach towels, and pack 'n plays.
Open For Spring Break! Dockside Oasis On The Canal - Anna Maria Island, FL
10 1 review
Anna Maria Island, FL
07/03 – 07/05
$1556/nighttotal: $3112 (2 )

Open For Spring Break! Dockside Oasis On The Canal

3 10
house , Cortez
This canal-side vacation home in Bradenton, Florida, is situated 11 miles from the Sarasota International Convention Center and the John and Mable Ringling Museum of Art, offering dockside access for a waterside experience.
This pet-friendly house accommodates up to 19 guests with 2 bathrooms, featuring a full kitchen, air conditioning, a swimming pool, terrace, free Wi-Fi, and private parking, located 7 miles from the Greens of Manatee Golf Club.
Shorewalk 2 Bedroom 2 Bathroom Near Img And Bradenton Beach - Anna Maria Island, FL
8.0 35 reviews
Anna Maria Island, FL
08/03 – 08/07
$196/nighttotal: $784 (4 )

Shorewalk 2 Bedroom 2 Bathroom Near Img And Bradenton Beach

1 3
house , Bradenton
This Bradenton villa, near IMG Academy and Bradenton Beach, offers convenient access to Sarasota Bradenton International Airport (6.8 miles) and The John and Mable Ringling Museum of Art (8.5 miles).
This 1,130-square-foot property features two bedrooms, one bathroom, accommodates up to 15 guests, and includes a private pool, jacuzzi, tennis court, and fully equipped kitchen.

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

Almost There - Anna Maria Island, FL
9.6 54 reviews
Anna Maria Island, FL
07/17 – 07/20
$397/nighttotal: $1191 (3 )

Almost There

2 2
house , Bradenton
This Bradenton house is a short drive from the Palma Sola Causeway Park and the John and Mable Ringling Museum of Art, offering easy access to both natural beauty and cultural attractions. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The two-bedroom home spans 1230 square feet and features a private pool, garden view, patio, fully equipped kitchen, air conditioning, free Wi-Fi, and parking. Guests can relax by the pool, explore nearby cycling trails, and prepare meals in the well-equipped kitchen, making this a great option for families or groups.
Tides Inn On The Bay Vacation Homes - Anna Maria Island, FL
9.7 153 reviews
Anna Maria Island, FL
07/17 – 07/20
$327/nighttotal: $981 (3 )

Tides Inn On The Bay Vacation Homes

1 2
house , Bradenton Beach
Tides Inn on the Bay Vacation Homes is ideally located steps away from Cortez Beach and a short walk from Bradenton Beach. It boasts excellent user, location, and cleanliness ratings.
The house features one bathroom, a fully equipped kitchen, air conditioning, and a terrace or balcony. Guests can also enjoy a barbecue on the sun terrace, or go fishing nearby. Free Wi-Fi and private parking are also available.
Seaside Bliss - Anna Maria Island, FL
Anna Maria Island, FL
11/06 – 11/08
$338/nighttotal: $676 (2 )

Seaside Bliss

1 2
house , Bradenton
Seaside Bliss, a Bradenton vacation home, is conveniently located approximately 8 miles from the Ringling Museum of Art and Sarasota Convention Center, and 6.2 miles from Sarasota Bradenton International Airport (SRQ).
This one-bedroom, two-bathroom rental boasts a private pool, jacuzzi, free parking, and a fully equipped kitchen including a dishwasher and microwave, comfortably accommodating up to seven guests with in-unit laundry and free Wi-Fi.
Minutes To Ami Pool Arcade Games Sleeps 11 - Anna Maria Island, FL
Anna Maria Island, FL
07/03 – 07/05
$1066/nighttotal: $2132 (2 )

Minutes To Ami Pool Arcade Games Sleeps 11

4 10
house , Bradenton
This Bradenton house rental is located 1.8 miles from Palma Sola Causeway Park and 11 miles from Sarasota International Convention Center and the John and Mable Ringling Museum of Art.
This 1640 square foot home offers four bedrooms, three bathrooms, and accommodates up to 11 guests, featuring a private swimming pool, a fully equipped kitchen with a dishwasher, and on-site water park access.

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

Hey Sunshine - Hosted By Skyrun Anna Maria - Anna Maria Island, FL
10 1 review
Anna Maria Island, FL
07/17 – 07/24
$610/nighttotal: $4270 (7 )

Hey Sunshine - Hosted By Skyrun Anna Maria

4 7
house , Bradenton
This Bradenton vacation rental is situated a 13-minute walk from Palma Sola Causeway Park, 12 miles from the John and Mable Ringling Museum of Art and the Sarasota International Convention Center, and 30 miles from Tropicana Field.
This 2600 square foot house accommodates up to 15 guests with 4 bedrooms and 4 bathrooms, featuring a private swimming pool, hot tub, full kitchen with a dishwasher and microwave, air conditioning, Wi-Fi, and parking.
The Beach Club At Anna Maria #3 - Anna Maria Island, FL
10 1 review
Anna Maria Island, FL
08/03 – 08/07
$341/nighttotal: $1364 (4 )

The Beach Club At Anna Maria #3

1 3
house , Bradenton Beach
This beachfront house in Bradenton Beach offers direct access to the shore and is located 12 miles from Sarasota Bradenton International Airport.
This accommodation features a well-equipped kitchen, a patio with sea views, a swimming pool, jacuzzi, fitness center, and tennis court, accommodating up to 7 guests with complimentary WiFi and parking.
Tropical Oasis 10th - Anna Maria Island, FL
10 5 reviews
Anna Maria Island, FL
08/30 – 09/03
$368/nighttotal: $1472 (4 )

Tropical Oasis 10th

3 5
house , Bradenton
Tropical Oasis 10th, a Bradenton vacation home, is located 1.7 miles from Palma Sola Causeway Park and 8.7 miles from Sarasota Bradenton International Airport.
This 1,540-square-foot property features three bedrooms, two bathrooms, sleeps eleven guests, and includes a private pool, hot tub, outdoor fireplace, and free Wi-Fi.
Lazy Pelican Home - Anna Maria Island, FL
9.0 2 reviews
Anna Maria Island, FL
06/27 – 07/04
$762/nighttotal: $5334 (7 )

Lazy Pelican Home

2 2
house , Holmes Beach
Lazy Pelican, a Holmes Beach house rental, is a 7-minute walk from Anna Maria Island and 1.7 miles from the Anna Maria City Pier, offering easy access to Holmes Beach attractions.
This 1,560-square-foot vacation home features two bedrooms, two bathrooms, a swimming pool, free Wi-Fi, and a fully equipped kitchen with a dishwasher, comfortably accommodating small families or groups.
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