Villas and Holiday homes in Anna Maria Island, FL

2864 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Anna Maria Island, FL holiday homes
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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

139 M² House ∙ 3 Bedrooms ∙ 10 Guests - Anna Maria Island, FL
10 2 reviews
Anna Maria Island, FL
27/07 – 29/07
£418/nighttotal: Â£836 (2 )

139 M² House ∙ 3 Bedrooms ∙ 10 Guests

3 5
house , Cortez
This waterfront property in San Remo Shores, Bradenton, Florida, offers convenient access to Anna Maria Island's beaches (a short drive away) and is close to Palma Sola Bay.
This three-bedroom, two-bathroom house, boasting 139 square metres of floor space, sleeps up to eight guests and features a private heated pool, dock suitable for a 24-foot boat, and high-speed Wi-Fi; kayaking, biking and fishing are readily available nearby.
7001 B Holmes Blvd - Anna Maria Island, FL
8.8 72 reviews
Anna Maria Island, FL
05/01 – 12/01
£269/nighttotal: Â£1883 (7 )

7001 B Holmes Blvd

3 2
house , Holmes Beach
This Holmes Beach holiday home, located in Anna Maria, is a three-minute walk from Anna Maria Island and 2.7km from Holmes Beach, offering easy access to the beach and local attractions such as Anna Maria City Pier (2.9km away).
This 130 square metre property boasts three bedrooms, a private pool, free Wi-Fi, a fully equipped kitchen with dishwasher, and parking, comfortably accommodating families or groups.
Cozy 1-bed Cottage In Adorable Tradewinds Bradenton Beach, Steps To Beach/pool - Anna Maria Island, FL
10 10 reviews
Anna Maria Island, FL
07/08 – 09/08
£341/nighttotal: Â£682 (2 )

Cozy 1-bed Cottage In Adorable Tradewinds Bradenton Beach, Steps To Beach/pool

1 2
cottage , Bradenton Beach
This recently renovated one-bedroom holiday home in Bradenton Beach is located just a few steps from Bradenton Beach and the Gulf of Mexico, placing you within 500 meters of local boutiques and dining spots such as Bridge Street Bistro.
This 65 square meter holiday home accommodates up to four guests and features a fully equipped kitchen, air conditioning, Wi-Fi, a community swimming pool, and individual televisions in each room, with the option to book a neighbouring unit for larger groups.
Bridge Street Beach House | Wi-fi | Center Of All - Anna Maria Island, FL
10 3 reviews
Anna Maria Island, FL
27/06 – 04/07
£314/nighttotal: Â£2198 (7 )

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

3 2
cottage , Bradenton Beach
This detached house is located in the Bridge Street district of Bradenton Beach, a short 500-metre walk from Bradenton Beach and the Anna Maria Sound Canal, and near amusement parks.
This 60 square metre holiday home accommodates up to six guests, offering three bedrooms, one bathroom, a kitchen with a fridge, microwave and dishwasher, air conditioning, a communal swimming pool, hot tub, garden, spa, tennis court, and on-site parking, with complimentary Wi-Fi and access to table tennis and billiards.

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

Blue Agave Villa By Beach Boutique Rentals - Anna Maria Island, FL
9.8 105 reviews
Anna Maria Island, FL
18/07 – 25/07
£221/nighttotal: Â£1547 (7 )

Blue Agave Villa By Beach Boutique Rentals

1 2
cottage , Holmes Beach
Frangipani Villa is a ground-floor holiday home in Holmes Beach, just a short walk from the beach path and within easy reach of shops and restaurants. The villa has received excellent ratings for location, cleanliness, and overall user experience.
The cottage features a private outdoor shower, a spacious porch with Adirondack chairs, and a fully equipped kitchen. Guests can enjoy a botanical courtyard with a fountain, relax on the porch, or take advantage of the beach supplies provided.
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: Â£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.
"A" Gulf Beach Bungalow - Anna Maria Island, FL
9.5 55 reviews
Anna Maria Island, FL
17/07 – 24/07
£159/nighttotal: Â£1113 (7 )

"A" Gulf Beach Bungalow

1 2
bungalow , Holmes Beach
This charming bungalow is situated on the northern end of Anna Maria Island in Holmes Beach, just a short walk from the pristine sugar-sand beaches. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The bungalow offers one bedroom and two bathrooms, comfortably accommodating up to four guests. Amenities include air conditioning, a well-equipped kitchen with a fridge and microwave, a private garden, parking, and Wi-Fi access.
121 M² House ∙ 3 Bedrooms ∙ 7 Guests - Anna Maria Island, FL
Anna Maria Island, FL
11/07 – 25/07
£213/nighttotal: Â£2982 (14 )

121 M² House ∙ 3 Bedrooms ∙ 7 Guests

3 7
house , Anna Maria
This 7th-floor apartment offers direct beachfront access on Anna Maria Island, providing panoramic Gulf of Mexico views and is a short drive from the shops and restaurants of Pine Avenue and the Anna Maria Pier.
This 120 square meter holiday home accommodates up to seven guests with three bedrooms and two bathrooms, featuring air conditioning, a swimming pool, garden, tennis court, parking, and a kitchen equipped with a fridge, microwave oven, and dishwasher.

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

Wonderful Home With Game Area - Anna Maria Island, FL
Anna Maria Island, FL
11/07 – 25/07
£302/nighttotal: Â£4228 (14 )

Wonderful Home With Game Area

3 7
house , Bradenton
This detached house in Bradenton is situated 13.68 kilometres from the Sarasota International Convention Centre and 14.16 kilometres from the John and Mable Ringling Museum of Art, offering convenient access to local attractions.
This property accommodates up to 15 guests with two bathrooms, a fully equipped kitchen, free WiFi, private parking, and a game area, with a £150 pet fee applicable for those travelling with animals.
Palma Sola Repose - Anna Maria Island, FL
9.6 15 reviews
Anna Maria Island, FL
18/07 – 25/07
£159/nighttotal: Â£1113 (7 )

Palma Sola Repose

2 2
house , Bradenton
Palma Sola Repose is situated in Bradenton, just 2.6 kilometres from Palma Sola Causeway Park and 18 kilometres from the John and Mable Ringling Museum of Art, offering a peaceful setting close to nature and local attractions. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
This two-bedroom house provides ample space for up to six guests, with a total floor area of 157 square metres. Guests can enjoy a fully equipped kitchen, a private garden, a swimming pool, and free Wi-Fi, perfect for relaxing and exploring the local area.
Bradenton Bliss - Anna Maria Island, FL
Anna Maria Island, FL
02/07 – 06/07
£210/nighttotal: Â£840 (4 )

Bradenton Bliss

1 5
house , Bradenton
Bradenton Bliss is situated approximately 13 kilometres from Sarasota's Sarasota International Convention Center and Ringling Museum of Art, offering convenient access to major attractions.
This one-bedroom house sleeps nine guests and boasts two bathrooms, a private pool, jacuzzi, free parking, a fully equipped kitchen with dishwasher, Wi-Fi, cable TV, and a washing machine; enjoy cycling nearby or explore further afield within a 48-kilometre radius of other attractions including Tropicana Field and The Dali Museum.
7 Mi To Beach Condo With Pool Access In Bradenton! - Anna Maria Island, FL
9.9 6 reviews
Anna Maria Island, FL
07/10 – 14/10
£148/nighttotal: Â£1036 (7 )

7 Mi To Beach Condo With Pool Access In Bradenton!

2 4
apartment , Bradenton
This Bradenton apartment, situated 11 kilometres from Bradenton Beach and under 13 kilometres from the Ringling Museum of Art, offers convenient access to local attractions.
The 118 square metre property boasts two bedrooms, two bathrooms, sleeps up to 11 guests, and includes a fully equipped kitchen, swimming pool, jacuzzi, tennis court, and free Wi-Fi; on-site parking is also available.

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

⚓Aqua Luxe Escape! Brand New Luxury Pool Home!⚓ - Anna Maria Island, FL
Anna Maria Island, FL
02/07 – 06/07
£1177/nighttotal: Â£4708 (4 )

⚓Aqua Luxe Escape! Brand New Luxury Pool Home!⚓

1 5
house , Bradenton
This brand new luxury pool villa in Bradenton is situated 2.1 kilometres from Palma Sola Causeway Park, with The John and Mable Ringling Museum of Art and Sarasota International Convention Centre both 17.7 kilometres away.
This spacious 232 square metre residence offers 5 bedrooms, 4 bathrooms, a fully equipped kitchen, on-site restaurant, and access to a water park, alongside a private swimming pool and hot tub, with free WiFi throughout.
Palma Sola Oasis! Cozy Tropical Home With Putting Green & Spa Minutes From Ami! - Anna Maria Island, FL
Anna Maria Island, FL
07/08 – 09/08
£354/nighttotal: Â£708 (2 )

Palma Sola Oasis! Cozy Tropical Home With Putting Green & Spa Minutes From Ami!

3 2
house , Bradenton
This Bradenton holiday home is situated near Palma Sola Causeway Park, a 10-minute walk away, and within 19 kilometres of The John and Mable Ringling Museum of Art and 48 kilometres from Tropicana Field.
The 111-square-metre, three-bedroom property sleeps six and boasts a Jacuzzi, putting green, fully equipped kitchen with dishwasher, free Wi-Fi, and is conveniently located 16 kilometres from Sarasota Bradenton International Airport.
Beach Castle Resort #23 - Anna Maria Island, FL
Anna Maria Island, FL
03/08 – 07/08
£284/nighttotal: Â£1136 (4 )

Beach Castle Resort #23

1 3
house , Longboat Key
Beach Castle Resort #23, a detached house in Longboat Key, is situated 400 metres from the beach and 22 kilometres from the John and Mable Ringling Museum of Art.
This air-conditioned accommodation offers 59 square metres of living space for up to 7 guests, featuring a fully equipped kitchen, a balcony, free WiFi, and disabled facilities.
158 M² House ∙ 3 Bedrooms ∙ 10 Guests - Anna Maria Island, FL
10 4 reviews
Anna Maria Island, FL
27/07 – 29/07
£680/nighttotal: Â£1360 (2 )

158 M² House ∙ 3 Bedrooms ∙ 10 Guests

3 5
house , Cortez
Sandys Coral Retreat, a three-bedroom house located in the Coral Shores community off Cortez Road, is 5km from Bradenton Beach and a short drive to Anna Maria Island, offering convenient access to Sarasota Bay via a private dock.
This 157 square metre property boasts a spacious open-plan layout, sleeps up to 10 guests, and includes a heated pool, hot tub, fully equipped kitchen, and multiple Smart TVs; nearby attractions include Robinson Preserve and DeSoto National Memorial Park.
©2026 cozycozy.com