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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

Holmes Beach Retreat: Walk To Beach & Dining! - Anna Maria Island, FL
9.4 13 reviews
Anna Maria Island, FL
01/05 – 01/12
$258/nighttotal: $1806 (7 )

Holmes Beach Retreat: Walk To Beach & Dining!

2 2
house , Holmes Beach
This Holmes Beach vacation rental is conveniently located an 8-minute walk from Anna Maria Island's beaches and 1.7 miles from Holmes Beach's shops and restaurants.
This 990-square-foot home features two bathrooms, a fully equipped kitchen with a dishwasher, in-unit laundry, a private balcony, free Wi-Fi, and a private entrance, perfect for a relaxing getaway.
The Beach On Longboat Key #101 - Anna Maria Island, FL
Anna Maria Island, FL
08/16 – 08/17
$632/nightfor 1 night

The Beach On Longboat Key #101

1 5
house , Longboat Key
This beachfront house in Longboat Key offers direct beach access and stunning sea views, located 11 miles from the John and Mable Ringling Museum of Art.
This accommodation sleeps 11 guests and features 1 bedroom, a living room, a fully equipped kitchen, 2 bathrooms, air conditioning, a swimming pool, terrace, garden, fitness center, tennis court, and free private parking.
Paradise Palms - Chic Prime Spot W Pool - Anna Maria Island, FL
8.5 38 reviews
Anna Maria Island, FL
08/15 – 08/22
$140/nighttotal: $980 (7 )

Paradise Palms - Chic Prime Spot W Pool

2 1
house , Bradenton
This Bradenton vacation home, Paradise Palms, offers convenient access to Palma Sola Causeway Park, an 8-minute walk away, and is within easy driving distance of Anna Maria City Pier and The John and Mable Ringling Museum of Art.
This 950-square-foot property features two bedrooms, two bathrooms, sleeps up to 11 guests, and includes a private pool, garden, BBQ, free Wi-Fi, and a fully equipped kitchen with a fridge, microwave, and dishwasher.
Shorewalk 202 - By Skyrun Anna Maria - Anna Maria Island, FL
9.0 1 review
Anna Maria Island, FL
08/02 – 08/09
$227/nighttotal: $1589 (7 )

Shorewalk 202 - By Skyrun Anna Maria

1 2
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.

Best Anna Maria Island, FL houses with a kitchen

Lake O' Woods! Gated Private Pool Home! - Anna Maria Island, FL
9.0 5 reviews
Anna Maria Island, FL
07/10 – 07/12
$896/nighttotal: $1792 (2 )

Lake O' Woods! Gated Private Pool Home!

4 7
house , Bradenton
This Bradenton vacation home is conveniently located 7.5 miles from Sarasota Bradenton International Airport and within a 10-30 mile radius of attractions like The John and Mable Ringling Museum of Art, Tropicana Field, and The Dali Museum.
This 3000-square-foot property boasts a spacious four-bedroom layout, accommodating up to 19 guests, and features a private pool, spa, and fully equipped kitchen; free Wi-Fi is available throughout.
The Beach Club At Anna Maria #4 And #5 - Anna Maria Island, FL
10 1 review
Anna Maria Island, FL
08/16 – 08/17
$779/nightfor 1 night

The Beach Club At Anna Maria #4 And #5

1 5
house , Bradenton Beach
This beachfront villa 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 property accommodates 19 guests with 3 bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, a garden, a fitness center, a tennis court, and complimentary private parking and free WiFi.
Florida Vibes - Anna Maria Island, FL
Anna Maria Island, FL
06/20 – 06/27
$436/nighttotal: $3052 (7 )

Florida Vibes

4 8
house , West Bradenton
This 4-bedroom, 2-bathroom house in West Bradenton offers a private swimming pool and is located 1.7 miles from Palma Sola Causeway Park.
This vacation home features air conditioning, a fully equipped kitchen, and on-site amenities including a water park and garden, with convenient access to Sarasota International Convention Center (13 miles), John and Mable Ringling Museum of Art, and The Dali' Museum.
'Colorful Cottage' W/ Lanai: 7 Mi To Cortez Beach! - Anna Maria Island, FL
Anna Maria Island, FL
07/10 – 07/12
$442/nighttotal: $884 (2 )

'Colorful Cottage' W/ Lanai: 7 Mi To Cortez Beach!

3 7
house , Bradenton
This Bradenton vacation rental is conveniently located just 7 miles from the beautiful beaches and 10 miles from the renowned Ringling Museum of Art.
This 3-bedroom, 2-bathroom house offers a comfortable stay for up to 6 guests, with amenities including a fully equipped kitchen, a private swimming pool, and a relaxing patio.

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

Private Historical Completely Renovated Cottage With  60 Ft Dock On Sarasota Bay - Anna Maria Island, FL
10 105 reviews
Anna Maria Island, FL
07/16 – 07/23
$205/nighttotal: $1435 (7 )

Private Historical Completely Renovated Cottage With 60 Ft Dock On Sarasota Bay

1 4
cottage , Cortez
This golf cottage in Cortez is conveniently located within walking distance of the Florida Maritime Museum at Cortez and Anna Maria Sound. With excellent user ratings, this 1-bedroom, 1-bathroom cottage accommodates up to 4 guests comfortably.
The cottage features a fully equipped kitchen, a comfortable living space with a sofa bed and a balcony, and a garden with barbecue grills for outdoor relaxation and dining. The cottage also offers free WiFi, laundry facilities, and proximity to golf courses for added convenience.
Hav Anna Holiday 211 Periwinkle Plaza - Anna Maria Island, FL
9.7 65 reviews
Anna Maria Island, FL
06/20 – 06/27
$760/nighttotal: $5320 (7 )

Hav Anna Holiday 211 Periwinkle Plaza

1 8
house , Anna Maria
Hav Anna Holiday 211 Periwinkle Plaza is a pet-friendly Anna Maria Island vacation home, a 4-minute walk from the beach and 1.1 miles from the Anna Maria City Pier.
This 1,510-square-foot house features two bathrooms, a swimming pool, spa, fitness center, and a fully equipped kitchen including a dishwasher, plus free internet access; nearby attractions include the John and Mable Ringling Museum of Art (18 miles away) and Sarasota Bradenton International Airport (17 miles away).
Beach House W/ Pool: 3 Mi To Anna Maria Island! - Anna Maria Island, FL
9.4 107 reviews
Anna Maria Island, FL
01/05 – 01/12
$405/nighttotal: $2835 (7 )

Beach House W/ Pool: 3 Mi To Anna Maria Island!

3 2
house , Cortez
This canalfront vacation home is located in Bradenton, just a short drive from Cortez, a charming fishing village known for its seafood restaurants, art galleries, and scenic waterfront. The property has excellent user, location, and cleanliness ratings.
This three-bedroom, two-bathroom house offers 1990 square feet of space for up to six guests. You'll enjoy a private heated pool, a fully equipped kitchen, air conditioning, Wi-Fi, cable TV, a patio with garden views, and a boat dock.
Sand Dollar Beach Side Villa - Anna Maria Island, FL
9.5 65 reviews
Anna Maria Island, FL
06/20 – 06/27
$346/nighttotal: $2422 (7 )

Sand Dollar Beach Side Villa

2 2
house , Holmes Beach
This Holmes Beach vacation rental is located just steps from Anna Maria Island, an 8-minute walk from the town center and 1.2 miles from Bradenton Beach. Guests consistently rate the location, cleanliness, and overall experience as excellent.
The 870-square-foot home has two bedrooms and comfortably accommodates six guests. Enjoy a private patio, a fully equipped kitchen, a swimming pool, and a spa, all while taking advantage of the free parking and Wi-Fi.

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

La Plage - Gulf Views! Heated Pool & Spa! Elevator By Anna Maria Life Vacation Rentals - Anna Maria Island, FL
Anna Maria Island, FL
06/20 – 06/27
$903/nighttotal: $6321 (7 )

La Plage - Gulf Views! Heated Pool & Spa! Elevator By Anna Maria Life Vacation Rentals

1 2
house , Holmes Beach
La Plage is a vacation home in Holmes Beach offering direct access to Anna Maria Island, just steps away, with Gulf views and proximity to Sarasota International Convention Center, located 16 miles away.
This 3200 square foot residence accommodates up to 6 guests with 3 bedrooms, a fully equipped kitchen, a private elevator, a heated swimming pool, a hot tub, and a terrace with sea views, all featuring air conditioning and free private parking.
Kicback Cabana By Beach Retreats - Anna Maria Island, FL
9.8 35 reviews
Anna Maria Island, FL
01/05 – 01/12
$441/nighttotal: $3087 (7 )

Kicback Cabana By Beach Retreats

3 2
house , Holmes Beach
This Holmes Beach vacation rental is a 4-minute walk from Anna Maria Island's beaches, 1.4 miles from the Anna Maria City Pier, and 17 miles from Sarasota Bradenton International Airport.
This three-bedroom home boasts a private hot tub, a swimming pool, and a fully equipped kitchen, plus convenient access to an on-site water park, restaurant, and tennis court.
Beach Castle Resort #12 - Anna Maria Island, FL
9.0 1 review
Anna Maria Island, FL
08/15 – 08/22
$345/nighttotal: $2415 (7 )

Beach Castle Resort #12

1 1
house , Longboat Key
Beach Castle Resort #12 is a house located in Longboat Key, just a 4-minute walk from Longboat Key Beach and 14 miles from the John and Mable Ringling Museum of Art.
This 910 sq ft accommodation features 2 bedrooms and 2 bathrooms, accommodates up to 11 guests, and includes a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, a patio, a balcony, and complimentary WiFi and parking.
Buena Vista #2 - 101 - 67th Street #2 - Anna Maria Island, FL
10 31 reviews
Anna Maria Island, FL
06/20 – 06/27
$1561/nighttotal: $10927 (7 )

Buena Vista #2 - 101 - 67th Street #2

4 8
house , Holmes Beach
Buena Vista #2, a Holmes Beach vacation home, is a short walk from Anna Maria Island, 1.7 miles from Holmes Beach city center, and within easy driving distance of attractions like the John and Mable Ringling Museum of Art and Greens of Manatee Golf Club.
This 2,600-square-foot property boasts a private pool, Jacuzzi, spa, fitness center, and tennis court, along with a fully equipped kitchen, cable TV, and ample parking.
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