Villas and Holiday homes in Anna Maria Island, FL

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Anna Maria Island, FL holiday homes
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2864 Villa rentals in Anna Maria Island, FL

Best Anna Maria Island, FL villas and holiday homes with a pool

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

149 M² House ∙ 3 Bedrooms ∙ 6 Guests - Anna Maria Island, FL
Anna Maria Island, FL
27/06 – 28/06
£597/nightfor 1 night

149 M² House ∙ 3 Bedrooms ∙ 6 Guests

3 6
house , Holmes Beach
This Holmes Beach holiday home is situated a short 0.9-kilometre walk from the beach and close to Anna Maria Island's restaurants.
The 148-square-metre property boasts three bedrooms, three bathrooms, sleeps six guests, features a private boat dock, heated pool, Tesla EV charger, and full kitchen with stainless steel appliances.
Silver Sands #247a - Anna Maria Island, FL
Anna Maria Island, FL
28/06 – 29/06
£397/nightfor 1 night

Silver Sands #247a

1 2
house , Longboat Key
This Silver Sands #247A apartment in Longboat Key offers direct beachfront access, located 24 kilometres from the John and Mable Ringling Museum of Art.
This non-smoking apartment accommodates up to three guests and features a kitchenette, air conditioning, complimentary WiFi, private parking, and is equipped for disabled guests, with cycling opportunities nearby.
Captain America Dream - Anna Maria Island, FL
9.6 107 reviews
Anna Maria Island, FL
17/07 – 20/07
£260/nighttotal: £780 (3 )

Captain America Dream

3 2
house , Bradenton
This charming house is located in Bradenton, Florida, just a short drive from Sarasota Bradenton International Airport and the John and Mable Ringling Museum of Art. It has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The property offers three bedrooms and two bathrooms, comfortably accommodating up to six guests. Guests can enjoy a private pool, a children's playground, a fully equipped kitchen, free Wi-Fi, a garden, and the opportunity to explore the area by bike.
Blue Oasis - Anna Maria Island, FL
Anna Maria Island, FL
27/06 – 04/07
£273/nighttotal: £1911 (7 )

Blue Oasis

1 2
house , Holmes Beach
Blue Oasis, a detached house in Holmes Beach, is located a 2-minute walk from Anna Maria Island, 28.97 kilometres from The John and Mable Ringling Museum of Art, and 25.75 kilometres from Sarasota Bradenton International Airport.
This accommodation, spanning 105 square metres, offers 2 bedrooms, 2 bathrooms, sleeps up to 11 guests, and features a private swimming pool, air conditioning, and a fully equipped kitchen with high-speed WiFi and private parking, with a strict no-party policy.

Best Anna Maria Island, FL villas and holiday homes with a kitchen

Resort Style Condo By The Beach With Heated Pool At Runaway Bay - Anna Maria Island, FL
9.0 1 review
Anna Maria Island, FL
27/06 – 04/07
£195/nighttotal: £1365 (7 )

Resort Style Condo By The Beach With Heated Pool At Runaway Bay

1 2
house , Bradenton Beach
This Bradenton Beach holiday home is a short walk from Bradenton Beach and Cortez Beach, and within 8.5km of Anna Maria City Pier and 22.5km from the John and Mable Ringling Museum of Art.
The 65 square metre one-bedroom property sleeps seven, boasting a heated pool, tennis court, fully equipped kitchen and is close to Greens of Manatee Golf Club (15km).
Blue Wave Villa East - Anna Maria Island, FL
9.1 168 reviews
Anna Maria Island, FL
07/10 – 14/10
£212/nighttotal: £1484 (7 )

Blue Wave Villa East

2 4
house , Holmes Beach
Blue Wave Villa East is a short walk from Anna Maria Island, just 1.6 kilometres from Anna Maria City Pier, making it a great base for exploring this beautiful area. The property has consistently received excellent ratings from previous guests, highlighting its cleanliness, location and overall experience.
The villa is a comfortable 80 square metre property, with two bedrooms and a bathroom, comfortably sleeping up to four guests. Guests can enjoy a private pool, a fully equipped kitchen, free Wi-Fi and a terrace, as well as access to a garden and parking.
⚓New! Driftwood Dreams, Heated Pool, Game Room, Min To Ami Beaches! - Anna Maria Island, FL
10 1 review
Anna Maria Island, FL
11/07 – 25/07
£313/nighttotal: £4382 (14 )

⚓New! Driftwood Dreams, Heated Pool, Game Room, Min To Ami Beaches!

1 7
house , Bradenton
This detached house in Bradenton is situated a mere 2.7 kilometres from the shores of Anna Maria Island and 2.7 kilometres from Palma Sola Causeway Park, with Sarasota International Convention Centre and the Ringling Museums a moderate drive away.
This property offers 139 square metres of living space, featuring air conditioning, a heated swimming pool, a games room, a fully equipped kitchen, and free on-site parking, accommodating up to 19 guests with 2 bathrooms.
Lakefront 2br Bradenton Rental Near Img & Beaches - Anna Maria Island, FL
8.8 3 reviews
Anna Maria Island, FL
06/11 – 08/11
£159/nighttotal: £318 (2 )

Lakefront 2br Bradenton Rental Near Img & Beaches

2 2
house , South Bradenton
This lakefront duplex in South Bradenton is conveniently located just 3 minutes from IMG Academy, 10 minutes from Downtown Bradenton, and 15 minutes from Anna Maria Island beaches.
This property offers 93 square meters of living space with 2 bedrooms, 2 bathrooms, and can accommodate up to 6 guests, featuring a fully stocked kitchen, dedicated workspace with fast Wi-Fi, and a washer/dryer, with pet-friendly options available.

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, of course! Bean Point is a must-see for its stunning sunsets and views. 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 great spot for birdwatching and exploring the local flora and fauna. And don't forget the charming shops and restaurants along Pine Avenue in Anna Maria city.
  • What are the best holiday homes in Anna Maria Island, FL?

    Among the holiday homes in Anna Maria Island, FL, Standard 2 Bedroom B, 2nd House From The Beach With No Roads To Cross and Playa Esmeralda One Bedroom Cottages 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. Think pristine sands, turquoise waters, and gentle sea breezes, rather than mountains or forests. There are some small nature preserves, but the island's main draw is its beachfront location.
  • What are the best holiday homes with a pool in Anna Maria Island, FL?

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

    While many flock to the main beaches, exploring the quieter stretches of coastline can be a delightful surprise. The north end of the island, near Bean Point, offers more secluded areas. Also, taking a leisurely stroll along the bay side, you might discover hidden coves and charming little fishing spots. The Bridge Street historical district is also a lovely place to explore away from the main tourist areas.
  • What are the best holiday homes with a jacuzzi in Anna Maria Island, FL?

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

    Chatting with the locals at the Anna Maria Island Farmers Market is a great way to get a feel for the community. Many local artists and craftspeople sell their wares there. You can also strike up conversations with staff at local businesses – many have lived on the island for years and have fascinating stories to tell. Visiting the Anna Maria Island Historical Society Museum provides insight into the island's history and heritage.
  • What are the best holiday homes for families and kids in Anna Maria Island, FL?

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

    A long weekend (3-4 days) is enough to get a good feel for Anna Maria Island, allowing time to relax on the beach, explore the shops and restaurants, and visit some of the key attractions. However, a week would allow for a more leisurely pace and opportunities for exploring the natural surroundings more thoroughly.
  • What are the best pet friendly holiday homes in Anna Maria Island, FL?

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

    Sunscreen is essential, even on cloudy days. A reusable water bottle is also a good idea, to stay hydrated in the Florida heat. Comfortable walking shoes are a must, for exploring the island's many pathways and beaches. And don't forget insect repellent, especially if you plan on spending time outdoors in the evenings.
  • What are the best holiday homes with parking in Anna Maria Island, FL?

    Standard 2 Bedroom B, 2nd House From The Beach With No Roads To Cross and Playa Esmeralda One Bedroom Cottages are the best holiday homes with parking in Anna Maria Island, FL.

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

    Anna Maria Island doesn't have a large number of scheduled cultural workshops. However, checking local listings for art classes or events at the Island Players theatre might reveal some unique experiences. The Anna Maria Island Historical Society Museum offers insights into the island's history, which is a cultural experience in itself.
  • 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. However, many restaurants feature fresh, locally sourced seafood and produce. Checking local event listings closer to your travel dates might reveal smaller, pop-up events.
  • What seasonal natural events, such as migrations or blooming periods, occur on Anna Maria Island?

    Anna Maria Island experiences peak bird migration seasons in spring and autumn. You'll see various species of shorebirds and wading birds. The island's flora also changes with the seasons, although there isn't one specific, highly notable blooming period like some other regions.
  • What exclusive experiences are available when visiting Anna Maria Island?

    Dolphin watching tours are a popular exclusive experience. Private boat charters allow for a more personalised exploration of the coastline and surrounding waters. A sunset cruise is a romantic and unique way to experience the island's natural beauty.

Nearby regions

Best Anna Maria Island, FL villas and holiday homes with air conditioning

Pelican Paradise Villa - Anna Maria Island, FL
10 2 reviews
Anna Maria Island, FL
06/11 – 08/11
£247/nighttotal: £494 (2 )

Pelican Paradise Villa

1 2
house , Bradenton
Pelican Paradise Villa, a self-catering property in Bradenton, Florida, is located 4.8km from the Greens of Manatee Golf Club, 12.5km from the Van Wezel Performing Arts Hall, and 10km from Sarasota Bradenton International Airport.
This one-bedroom villa sleeps seven guests and boasts a fully equipped kitchen, two bathrooms, a swimming pool, fitness centre, free Wi-Fi, in-unit laundry, and free private parking; nearby activities include cycling and exploring Bradenton's attractions.
172 M² House ∙ 3 Bedrooms ∙ 8 Guests - Anna Maria Island, FL
10 2 reviews
Anna Maria Island, FL
17/07 – 24/07
£267/nighttotal: £1869 (7 )

172 M² House ∙ 3 Bedrooms ∙ 8 Guests

3 7
house , West Bradenton
Waterfall Retreat is a family-friendly holiday home situated in the Palma Sola district of West Bradenton, offering easy access to the beaches of Anna Maria Island, just 9.6 kilometres away, and within 4.8 kilometres of Palma Sola Causeway.
This spacious 171 square metre villa accommodates up to eight guests with three bedrooms and two bathrooms, featuring a screened-in heated pool and spa, a fully equipped kitchen, two living areas, and ample parking for boats and RVs.
Family & Pet Friendly Bradenton House - Heated Pool -Hot Tub -Ev Chrger-near Beaches - Anna Maria Island, FL
9.3 3 reviews
Anna Maria Island, FL
27/06 – 28/06
£772/nightfor 1 night

Family & Pet Friendly Bradenton House - Heated Pool -Hot Tub -Ev Chrger-near Beaches

4 8
house , Bradenton
This spacious four-bedroom holiday home in Bradenton, Florida, is situated approximately 23 kilometres from the John and Mable Ringling Museum of Art and 13.5 kilometres from the Greens of Manatee Golf Club.
The 204-square-metre property boasts a private heated pool, hot tub, indoor arcade, and outdoor dining area, comfortably accommodating up to 18 guests and offering numerous amenities including tennis court and free Wi-Fi.
An Island Getaway At Palm Tree Villas - Anna Maria Island, FL
9.3 324 reviews
Anna Maria Island, FL
27/06 – 28/06
£716/nightfor 1 night

An Island Getaway At Palm Tree Villas

2 6
house , Holmes Beach
This property is located in Holmes Beach, Florida, just 3.2 kilometres from Captain Mike's Fishing Charters, 6.4 kilometres from Bradenton Beach Marina, and a 7-minute drive from Anna Maria City Pier. The villa boasts a very good user rating, an excellent location rating and an excellent cleanliness rating.
The accommodation offers a private patio, a barbecue, a fully equipped kitchen and free parking. Guests can enjoy a refreshing dip in the private pool and stay connected with free Wi-Fi access.

Best Anna Maria Island, FL villas and holiday homes with jacuzzi

The Beach Club At Anna Maria #4 And #5 - Anna Maria Island, FL
10 1 review
Anna Maria Island, FL
24/09 – 27/09
£347/nighttotal: £1041 (3 )

The Beach Club At Anna Maria #4 And #5

1 8
house , Bradenton Beach
This beachfront residence in Bradenton Beach offers direct access to the sand and sea, situated 19 kilometres from Sarasota Bradenton International Airport and 22 kilometres from the Sarasota International Convention Centre and John and Mable Ringling Museum of Art.
This detached house accommodates up to 19 guests with three bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, jacuzzi, garden, fitness centre, tennis court, and private parking, plus free WiFi and an outdoor patio area ideal for cycling enthusiasts.
Funky Flamingo 3kings Beach Gear Hot Tub & Pool - Anna Maria Island, FL
8.8 16 reviews
Anna Maria Island, FL
24/09 – 27/09
£347/nighttotal: £1041 (3 )

Funky Flamingo 3kings Beach Gear Hot Tub & Pool

4 8
house , Bradenton
This Bradenton holiday home is situated 2.4 kilometres from Palma Sola Causeway Park, 10.1 kilometres from Greens of Manatee Golf Club, and 14 kilometres from Anna Maria City Pier, offering easy access to waterfront recreation and local attractions.
The 215-square-metre property boasts four bedrooms, two bathrooms, accommodates up to 27 guests, and includes a private swimming pool, hot tub, and fully equipped kitchen; free Wi-Fi and cable TV are also provided.
Bermuda Bay Club 1427 Townhouse - Anna Maria Island, FL
10 1 review
Anna Maria Island, FL
27/06 – 04/07
£541/nighttotal: £3787 (7 )

Bermuda Bay Club 1427 Townhouse

3 2
house , Bradenton Beach
Bermuda Bay Club 1427, a Bradenton Beach townhouse, offers direct beach access and is situated 8.5 km from Anna Maria City Pier, 14.6 km from Greens Of Manatee Golf Club, and 23 km from The John and Mable Ringling Museum of Art.
This three-bedroom, two-bathroom property sleeps eleven guests and boasts a heated swimming pool, free private parking, a fully equipped kitchen with a dishwasher, and air conditioning.
237 M² House ∙ 3 Bedrooms ∙ 9 Guests - Anna Maria Island, FL
9.3 5 reviews
Anna Maria Island, FL
18/07 – 25/07
£245/nighttotal: £1715 (7 )

237 M² House ∙ 3 Bedrooms ∙ 9 Guests

3 2
house , Bradenton
Sunshine Rays, a detached house in Bradenton's Palma Sola district, is a short drive from Anna Maria Island and offers easy access to downtown Bradenton's historic sites, dining, and shops.
This spacious 237 square meter property accommodates up to nine guests with three bedrooms and two bathrooms, featuring a private pool, jacuzzi, and a fully fenced garden ideal for families and pets.
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