Villas and Holiday homes in Anna Maria Island, FL

3777 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

3777 Villa rentals in Anna Maria Island, FL

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

Among the 3777 accommodations in Anna Maria Island, FL, here are the 4 best villas and holiday homes with a pool

'Colorful Cottage' W/ Lanai: 7 Mi To Cortez Beach! - Anna Maria Island, FL
No reviews

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

house, Bradenton
This three-bedroom house is located in Bradenton, just 11 kilometres from the beautiful beaches and 16.1 kilometres from the John and Mable Ringling Museum of Art.
The 227 square metre property boasts a private patio, a swimming pool, and a fully-equipped kitchen, perfect for families or groups of up to six people.
Beach House W/ Pool: 3 Mi To Anna Maria Island! - Anna Maria Island, FL
9.4 109 reviews

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

house, Cortez
The Canalfront Caribbean Retreat is situated in Bradenton, Florida, just a short drive from the charming fishing village of Cortez and its local attractions. This holiday home consistently receives excellent ratings for location, cleanliness, and overall user experience.
The property spans 185 square metres and comfortably accommodates up to six guests in its three bedrooms. Guests can enjoy a range of amenities including a private boat dock, heated pool, garden, terrace, and a fully equipped kitchen, perfect for self-catering.
Bridge Street Pier Beach House + Dog-friendly - Anna Maria Island, FL
9.8 33 reviews

Bridge Street Pier Beach House + Dog-friendly

cottage, Bradenton Beach
This Bridge Street Pier Beach House offers unbeatable waterfront access in Bradenton Beach, directly adjacent to the Bridge Street Pier and Anna Maria Oyster Bar, providing stunning Sarasota Bay views.
This three-bedroom, two-bathroom property boasts 80 square metres of living space, sleeping up to six guests and featuring a private swimming pool, spa, tennis court, and kayaks/paddleboards for exploring Sarasota Bay; nearby amenities include a community pool and clubhouse.
Beautiful Pool Home Minutes From Anna Maria Island - Anna Maria Island, FL
10 4 reviews

Beautiful Pool Home Minutes From Anna Maria Island

house, Bradenton
This detached house in Bradenton is located a 14-minute walk from Palma Sola Causeway Park and 17.7 kilometres from the John and Mable Ringling Museum of Art.
The property accommodates up to 11 guests in 1 bedroom and 2 bathrooms, featuring a private swimming pool, complimentary WiFi, free private parking, and a fully equipped kitchen, with Anna Maria Island just minutes away.

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

'Ocean Breeze Oasis' W/ Boat Dock & Slip On Canal! - Anna Maria Island, FL
9.4 110 reviews

'Ocean Breeze Oasis' W/ Boat Dock & Slip On Canal!

house, Bayshore Gardens
This Bayshore Gardens holiday home is situated in Bradenton, Florida, 3.1km from Sarasota Bradenton International Airport and a short drive from attractions such as the Van Wezel Performing Arts Hall and The John and Mable Ringling Museum of Art.
The 135-square-metre property boasts three bedrooms, a private boat dock, a swimming pool, Jacuzzi, fitness centre, free Wi-Fi, and bicycles for guest use, perfect for families or groups seeking a relaxing Florida getaway.
Sea Spray Private Beach Cottage - Anna Maria Island, FL
10 5 reviews

Sea Spray Private Beach Cottage

house, Holmes Beach
Sea Spray Private Beach Cottage is located in Holmes Beach, a 4-minute walk from Anna Maria Island and 4.3 kilometres from Anna Maria City Pier.
This 111 square metre holiday home offers 2 bedrooms, 2 bathrooms, air conditioning, a garden, a spa, and free WiFi, with opportunities for cycling nearby.
Shorewalk Condominium - Anna Maria Island, FL
9.5 2 reviews

Shorewalk Condominium

house, Bradenton
Shorewalk Condo, a one-bedroom apartment in Bradenton, Florida, is situated 11km from Sarasota Bradenton International Airport and 6km from the Greens of Manatee Golf Club, offering easy access to local attractions.
This self-catering property sleeps seven, boasting a fully equipped kitchen, in-unit laundry, free Wi-Fi, a swimming pool, and free private parking; nearby activities include cycling and exploring museums such as The John and Mable Ringling Museum of Art and The Dali Museum.
Anna Maria Island Tree House - Anna Maria Island, FL
9.8 313 reviews

Anna Maria Island Tree House

house, Bradenton Beach
Ami Beach Shack is located on a quiet street in Bradenton Beach, just a 2-minute walk from the beach and a 1.9 kilometre walk from Holmes Beach. The property has excellent ratings for location, cleanliness and user experience.
The holiday home is 74 square metres and has two bedrooms, a living room with a flat-screen TV, and a bathroom with a bathtub. Amenities include free parking, free Wi-Fi, a private balcony, a garden, a fully equipped kitchen with a dishwasher and oven, and air conditioning.

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

The Beach Club At Anna Maria #3 - Anna Maria Island, FL
10 1 review

The Beach Club At Anna Maria #3

house, Bradenton Beach
This beachfront property in Bradenton Beach offers direct access to the sandy shores, situated just a few steps from the water's edge and 19 kilometres from Sarasota Bradenton International Airport.
This holiday let accommodates up to seven guests and features a kitchen with a fridge, microwave, and dishwasher, a swimming pool, a Jacuzzi, a garden, a fitness centre, a tennis court, and complimentary Wi-Fi and private parking.
1 Mi To Anna Maria Island: Pet-friendly Retreat - Anna Maria Island, FL
9.4 72 reviews

1 Mi To Anna Maria Island: Pet-friendly Retreat

house, Cortez
This holiday home is situated in Cortez, Florida, just 1.8 kilometres from Bradenton Beach and 1.9 kilometres from Cortez Beach. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The property is a spacious two-bedroom house with one bathroom, covering 111 square metres and accommodating up to four guests. It offers a range of amenities, including a fully equipped kitchen, air conditioning, a garden, a spa, parking, and free Wi-Fi, making it ideal for families or groups looking for a comfortable and convenient stay.
Townhouses In The Cay - A1 - Anna Maria Island, FL
9.2 6 reviews

Townhouses In The Cay - A1

house, Bradenton
This townhouse in Bradenton, Townhouses In The Cay - A1, offers a convenient location within an 8-minute walk of Palma Sola Causeway Park and is situated 22 kilometres from the Sarasota International Convention Centre.
This air-conditioned holiday home boasts 124 square metres of living space with 2 bedrooms, 2 bathrooms, and accommodation for up to 7 guests, featuring a fully equipped kitchen with a dishwasher and oven, and an on-site restaurant.
Shorewalk 202 - By Skyrun Anna Maria - Anna Maria Island, FL
9.5 2 reviews

Shorewalk 202 - By Skyrun Anna Maria

house, Bradenton
This holiday property is located in the Anna Maria Island area of Bradenton, offering convenient access to cycling routes.
The 109 square meter villa accommodates up to 11 guests, featuring a private swimming pool, jacuzzi, tennis court, a fully equipped kitchen with a dishwasher and microwave, air conditioning, and complimentary high-speed WiFi.

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

Sunset Oasis By Skyrun Anna Maria - Anna Maria Island, FL
No reviews

Sunset Oasis By Skyrun Anna Maria

house, Bradenton
Sunset Oasis by SkyRun Anna Maria, a three-bedroom house in Bradenton, Florida, is located 1.1 km from Palma Sola Causeway Park and within a 20-23 km radius of Sarasota International Convention Center and the John and Mable Ringling Museum of Art.
This 176 square metre property boasts a fully equipped kitchen, private and communal swimming pools, a hot tub, and accommodates up to 15 guests, offering a comfortable stay with air conditioning.
Seaside Manor - Anna Maria Island, FL
10 3 reviews

Seaside Manor

house, Bradenton Beach
Seaside Manor, a detached house in Bradenton Beach, is located a 9-minute walk from Cortez Beach and 22.5 kilometres from The John and Mable Ringling Museum of Art.
This air-conditioned holiday home offers 135 square metres of living space with 3 bedrooms, 2 bathrooms, and accommodation for 13 guests, featuring a fully equipped kitchen with a dishwasher, oven, fridge, and microwave, along with a TV, private entrance, and outdoor seating on its balcony.
Fancy Retreat - Luxury-pool-bbq-karaoke - Anna Maria Island, FL
No reviews

Fancy Retreat - Luxury-pool-bbq-karaoke

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.
Luxury 5br Retreat, Pool, Spa, Mini Golf, Game Rm - Anna Maria Island, FL
10 2 reviews

Luxury 5br Retreat, Pool, Spa, Mini Golf, Game Rm

house, West Bradenton
This West Bradenton holiday villa is situated approximately 21 kilometres from the John and Mable Ringling Museum of Art and the Sarasota International Convention Centre, and 18 kilometres from Sarasota Bradenton International Airport, with the beach a mere 12-minute drive away.
This expansive holiday home, covering 232 square metres, offers accommodation for up to 16 guests across 5 bedrooms, featuring a private heated swimming pool, hot tub, billiards, and mini-golf, alongside free WiFi and parking.
©2026 cozycozy.com