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

Cozy Pet-friendly Private Pool Near Beaches - Anna Maria Island, FL
9.5 4 reviews
Anna Maria Island, FL
26/06 – 30/06
£324/nighttotal: £1296 (4 )

Cozy Pet-friendly Private Pool Near Beaches

3 2
house , Bradenton
This pet-friendly holiday home in Bradenton, Florida, is situated 2.7km from Palma Sola Causeway Park and 15km from Sarasota Bradenton International Airport (SRQ).
The 128-square-metre property boasts three bedrooms, two bathrooms, sleeps eleven guests, and includes a private pool, spa, fully equipped kitchen, free Wi-Fi, and a washing machine.
Gulf Views And Pool Access Bradenton Beach Condo! - Anna Maria Island, FL
9.8 74 reviews
Anna Maria Island, FL
03/08 – 07/08
£337/nighttotal: £1348 (4 )

Gulf Views And Pool Access Bradenton Beach Condo!

2 3
apartment , Bradenton Beach
This apartment is located just steps from Cortez Beach and a short walk from Coquina Beach, offering direct access to the beautiful white sands and turquoise waters of the Gulf of Mexico. It has received excellent ratings for location, cleanliness, and user experience.
The apartment has two bedrooms and two bathrooms, providing ample space for up to six guests, and spans 93 square metres. Guests can enjoy a range of amenities, including a heated pool, a jacuzzi, a garden, a tennis court, and free Wi-Fi, as well as a fully equipped kitchen and air conditioning.
2 Mi To Riverwalk Gem With Private Pool And Yard! - Anna Maria Island, FL
Anna Maria Island, FL
26/06 – 30/06
£222/nighttotal: £888 (4 )

2 Mi To Riverwalk Gem With Private Pool And Yard!

2 2
house , Bradenton
This Bradenton holiday home is located approximately 13.7 kilometres from the Ringling Museum of Art and Sarasota International Convention Centre, and 10.9 kilometres from Sarasota Bradenton International Airport.
This 104 square metre property offers two bedrooms, two bathrooms, air conditioning, a private swimming pool, a garden, and complimentary WiFi, providing accommodation for up to 15 guests.
143 M² House ∙ 3 Bedrooms ∙ 6 Guests - Anna Maria Island, FL
Anna Maria Island, FL
27/07 – 29/07
£301/nighttotal: £602 (2 )

143 M² House ∙ 3 Bedrooms ∙ 6 Guests

3 5
house , Bradenton
This West Bradenton property is situated approximately 19km from Anna Maria Island and 18km from Bradenton Beach, offering easy access to Beachway Plaza and Sarasota Bradenton International Airport.
The 142 square metre house boasts three bedrooms, two bathrooms, sleeps six guests, and includes a private heated pool (extra charge), a fully equipped kitchen, and a screened lanai with BBQ facilities.

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

Nautical Escape! Private Pool Home With A Tropical Backyard Oasis! - Anna Maria Island, FL
10 3 reviews
Anna Maria Island, FL
10/07 – 12/07
£548/nighttotal: £1096 (2 )

Nautical Escape! Private Pool Home With A Tropical Backyard Oasis!

4 7
house , West Bradenton
This West Bradenton holiday home is situated 16 kilometres from Sarasota Bradenton International Airport and within a 48-kilometre radius of major attractions such as The Dali Museum and the Ringling Museum of Art.
This four-bedroom, two-bathroom property boasts 186 square metres of living space, a private pool, spa, and accommodates up to 15 guests, also offering free Wi-Fi and convenient access to an on-site water park.
Luxury Villa Heated Pool,  Putt-putt & Bocce - Anna Maria Island, FL
9.8 55 reviews
Anna Maria Island, FL
17/07 – 24/07
£333/nighttotal: £2331 (7 )

Luxury Villa Heated Pool, Putt-putt & Bocce

1 7
house , Bradenton
This Sunshine Coast Villa, near Bradenton, Florida, offers a luxurious four-bedroom, three-bathroom property a short drive (19-35 km) from Anna Maria Island's beaches and 8 km from Downtown Bradenton.
The self-catering villa boasts a spacious open-plan living area, a dedicated games room with arcade games and a pinball machine, a private heated pool, and sleeps up to ten guests, with beach essentials and baby gear provided.
Poolside Retreat Sleeps 8 Putt Putt Hot Tub - Anna Maria Island, FL
Anna Maria Island, FL
10/07 – 12/07
£588/nighttotal: £1176 (2 )

Poolside Retreat Sleeps 8 Putt Putt Hot Tub

1 7
house , Bradenton
This holiday home in Bradenton is situated close to a casino, offering guests convenient access to entertainment options.
This 120-square-metre villa accommodates up to 8 guests and features a private entrance, air conditioning, free Wi-Fi, a fully equipped kitchen, two bathrooms, and a garden with outdoor seating, alongside a swimming pool and hot tub.
Starfish House - 2bed/2bad - Anna Maria Island, FL
9.9 51 reviews
Anna Maria Island, FL
07/10 – 14/10
£183/nighttotal: £1281 (7 )

Starfish House - 2bed/2bad

1 4
house , Holmes Beach
Starfish Beach #4, a two-bedroom holiday home in Holmes Beach, Anna Maria Island, is located just 46 metres from Anna Maria Public Beach access.
This self-catering property sleeps six, offering a king bed, queen bed, sleeper sofa, two bathrooms, a fully equipped kitchen (including fridge, microwave, and dishwasher), air conditioning, and access to a shared pool; baby equipment is available for hire.

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

An Island Getaway At Palm Tree Villas - Anna Maria Island, FL
9.3 323 reviews
Anna Maria Island, FL
27/07 – 29/07
£542/nighttotal: £1084 (2 )

An Island Getaway At Palm Tree Villas

2 5
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.
Bradenton Retreat-pool Stunning Views & More - Anna Maria Island, FL
Anna Maria Island, FL
17/07 – 24/07
£246/nighttotal: £1722 (7 )

Bradenton Retreat-pool Stunning Views & More

3 7
house , Bradenton
This Bradenton holiday home is situated approximately 8.4 km from Anna Maria City Pier and 25 km from Sarasota's John and Mable Ringling Museum of Art and Sarasota International Convention Center.
The 155 square metre property boasts three bedrooms, three bathrooms, sleeps twelve guests, and includes a private pool, garden, free Wi-Fi, and a fully equipped kitchen with fridge and dishwasher.
Match Point Stay 6 Min To Img Academy Luxury Tennis Home - Anna Maria Island, FL
10 5 reviews
Anna Maria Island, FL
27/07 – 29/07
£230/nighttotal: £460 (2 )

Match Point Stay 6 Min To Img Academy Luxury Tennis Home

3 5
house , Bradenton
This detached house in Bradenton is situated 13.9 kilometres from the Sarasota International Convention Centre and the John and Mable Ringling Museum of Art, and 10.9 kilometres from Sarasota Bradenton International Airport, offering convenient access to the IMG Academy.
This family-friendly property boasts a floor area of 1872 square metres, accommodating up to 11 guests with 3 bedrooms and 2 bathrooms, and includes amenities such as a fully equipped kitchen, complimentary WiFi, on-site table tennis, and a private terrace with an outdoor fireplace.
Newly Renovated  Cozy Beach Cottage A1/2 Of A Duplex, 3min Walk To Beach - Anna Maria Island, FL
9.7 55 reviews
Anna Maria Island, FL
27/06 – 04/07
£272/nighttotal: £1904 (7 )

Newly Renovated Cozy Beach Cottage A1/2 Of A Duplex, 3min Walk To Beach

3 2
cottage , Holmes Beach
This charming cottage is located in Bradenton Beach, just a 15-minute walk from the beach and Island Gallery West, with Holmes Beach Beaches and Manatee Public Beach within a 3km radius. It has an excellent user rating, so you can be sure of a comfortable and enjoyable stay.
This two-bedroom property can accommodate up to six guests and includes a sofa bed, free Wi-Fi, and a fully equipped kitchen with a fridge, oven, stovetop, and microwave. Enjoy the private garden with barbecue grills for al fresco dining, and take advantage of the air conditioning and terrace/balcony.

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

The Beach Club At Anna Maria #2 - Anna Maria Island, FL
10 1 review
Anna Maria Island, FL
27/06 – 04/07
£268/nighttotal: £1876 (7 )

The Beach Club At Anna Maria #2

1 2
house , Bradenton Beach
This beachfront villa in Bradenton Beach offers direct access to the sand and is 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 property, suitable for up to seven guests, features a well-equipped kitchen with a dishwasher and microwave, air conditioning, a swimming pool, hot tub, garden, fitness centre, tennis court, and private parking, with sea views from the patio and facilities for disabled guests.
Fancy Retreat - Luxury-pool-bbq-karaoke - Anna Maria Island, FL
Anna Maria Island, FL
02/08 – 09/08
£254/nighttotal: £1778 (7 )

Fancy Retreat - Luxury-pool-bbq-karaoke

1 2
house , Bradenton
Fancy Retreat is a holiday home situated in Bradenton, 13.67 kilometres from Sarasota International Convention Centre and 10.94 kilometres from Sarasota Bradenton International Airport.
This spacious villa, covering 1700 square metres, accommodates up to 17 guests with 2 bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, jacuzzi, terrace, garden, and on-site fitness centre, with complimentary WiFi and a private entrance.
Paradise Beach House Managed By Beach Retreats - Anna Maria Island, FL
Anna Maria Island, FL
17/07 – 24/07
£1471/nighttotal: £10297 (7 )

Paradise Beach House Managed By Beach Retreats

6 7
house , Holmes Beach
Paradise Beach House, a six-bedroom holiday home in Holmes Beach, Florida, is situated 5.8km from Anna Maria City Pier and offers easy access to Anna Maria Island, Bradenton and Sarasota.
This large property sleeps 23 guests, boasts a private pool, Jacuzzi, and terrace, plus a fully equipped kitchen, free Wi-Fi, and parking; nearby opportunities for cycling and watersports are also available.
176 M² House ∙ 3 Bedrooms ∙ 8 Guests - Anna Maria Island, FL
9.9 18 reviews
Anna Maria Island, FL
07/10 – 14/10
£209/nighttotal: £1463 (7 )

176 M² House ∙ 3 Bedrooms ∙ 8 Guests

3 4
house , Bradenton
This canal-front property in Bradenton offers direct water access and views, located a short drive from local attractions.
This detached house, covering 176 square meters, features 3 bedrooms and 2 bathrooms, accommodating up to 8 guests with amenities including a private pool, hot tub, and a dock for kayaking or fishing.
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