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Anna Maria, FL villas
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1091 Villa rentals in Anna Maria, FL

Find the Best Holiday Houses with Swimming Pool in Anna Maria, FL

Having a pool at your Anna Maria, FL vacation home lets you enjoy a dip to complement a day by the water without extra planning.

Paradise Palms - Chic Prime Spot W Pool - Anna Maria, FL
8.5 38 reviews
Anna Maria, FL
09/10 – 09/13
$267/nighttotal: $801 (3 )

Paradise Palms - Chic Prime Spot W Pool

2 4
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.
Open For Spring Break! Dockside Oasis On The Canal - Anna Maria, FL
10 1 review
Anna Maria, FL
07/28 – 08/03
$549/nighttotal: $3294 (6 )

Open For Spring Break! Dockside Oasis On The Canal

3 11
house , Cortez
This canal-side vacation home in Bradenton, Florida, is situated 11 miles from the Sarasota International Convention Center and the John and Mable Ringling Museum of Art, offering dockside access for a waterside experience.
This pet-friendly house accommodates up to 19 guests with 2 bathrooms, featuring a full kitchen, air conditioning, a swimming pool, terrace, free Wi-Fi, and private parking, located 7 miles from the Greens of Manatee Golf Club.
Surrounded By Sea Breezes - Anna Maria, FL
9.3 93 reviews
Anna Maria, FL
10/31 – 11/10
$604/nighttotal: $6040 (10 )

Surrounded By Sea Breezes

3 2
house , Anna Maria
This Anna Maria vacation home is a short 5-minute walk from the beach, just 1.1 miles from Anna Maria City Pier, and a 19-mile drive from the John and Mable Ringling Museum of Art. It boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The 1,860 square foot house features three bedrooms and three bathrooms, accommodating families or groups comfortably. Enjoy a private terrace, fully equipped kitchen with dishwasher, air conditioning, free Wi-Fi, washer and dryer, outdoor dining area, swimming pool, spa, tennis court, and parking.
Southern Breeze 5 - Anna Maria, FL
8.5 2 reviews
Anna Maria, FL
08/15 – 08/17
$515/nighttotal: $1030 (2 )

Southern Breeze 5

2 4
house , Anna Maria
Southern Breeze 5, a beachfront Anna Maria Island rental, is a 6-minute walk from Anna Maria Island and a 12-minute walk from the Anna Maria City Pier, offering easy access to the beach and local attractions.
This 790-square-foot house features two bedrooms, one bathroom, and accommodates up to 11 guests, boasting a private pool, free Wi-Fi, and a fully equipped kitchen including a fridge and microwave.

Best Anna Maria, FL houses with a kitchen

Ocean Breeze- Amil - Anna Maria, FL
Anna Maria, FL
07/05 – 07/11
$1642/nighttotal: $9852 (6 )

Ocean Breeze- Amil

7 11
house , Bradenton Beach
Ocean Breeze (AMIL), a beachfront home in Bradenton Beach, Florida, is located 14 miles from the Ringling Museum of Art and 6.2 miles from the Anna Maria City Pier.
This 4,000-square-foot vacation rental boasts seven bedrooms, seven bathrooms, and accommodates up to 29 guests, featuring a private pool, fitness center, and free Wi-Fi.
Peach Bellini - Anna Maria, FL
10 1 review
Anna Maria, FL
06/27 – 07/04
$530/nighttotal: $3710 (7 )

Peach Bellini

2 5
apartment , Holmes Beach
Peach Bellini is a house located in Holmes Beach, a 3-minute walk from Anna Maria Island and 18 miles from The John and Mable Ringling Museum of Art.
This 980 square foot rental offers 2 bedrooms, 2 bathrooms, and can accommodate up to 11 guests with a private pool, complimentary Wi-Fi, and free parking.
Sand And Sea 113 A - Anna Maria, FL
Anna Maria, FL
06/27 – 07/04
$382/nighttotal: $2674 (7 )

Sand And Sea 113 A

2 2
apartment , Anna Maria
Sand And Sea 113A is a beachfront Anna Maria Island rental, a 12-minute walk from the Anna Maria City Pier and 19 miles from The John and Mable Ringling Museum of Art.
This 760-square-foot house features two bedrooms, one bathroom, and can accommodate up to 11 guests, offering a private entrance, free Wifi, air conditioning, a swimming pool, and a fully equipped kitchen with a fridge, microwave, and dishwasher.
Cozy Cottage Retreat At Tradewind Resort #32 In Bradenton Beach - Anna Maria, FL
9.2 19 reviews
Anna Maria, FL
08/04 – 08/06
$395/nighttotal: $790 (2 )

Cozy Cottage Retreat At Tradewind Resort #32 In Bradenton Beach

1 2
cottage , Bradenton Beach
Tradewind Resort #32, a one-bedroom cottage in Bradenton Beach, Florida, offers easy access to nearby attractions like Mote Marine Laboratory & Aquarium and Cortez Beach.
This pet-friendly vacation rental sleeps four, features a fully equipped kitchen, a private patio, and access to the resort's pool and hot tub.

Frequently Asked Questions about villa rentals in Anna Maria, FL

  • What are the must-see attractions in and around Anna Maria, FL?

    You definitely want to check out the Anna Maria Island Historical Museum, it's a great place to learn about the island's history. The City Pier is a classic spot for fishing or just enjoying the view. And if you're looking for something a little more adventurous, you can take a day trip to nearby Bradenton, which has the South Florida Museum and the Bishop Museum of Science and Nature.
  • What are the best villa rentals in Anna Maria, FL?

    Among the villa rentals in Anna Maria, FL, Standard 2 Bedroom B, Do You Love The Beach? and Bay Breeze Cottages #3 are the most popular ones.

  • What types of wildlife can travelers expect to see in the area of Anna Maria, FL?

    Anna Maria is a great place to spot dolphins, manatees, and even the occasional sea turtle. You can often see them from the beach or while kayaking or paddleboarding. Be sure to keep your distance and respect their space.
  • What are the best villa rentals with a pool in Anna Maria, 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, FL.

  • What is the best time to visit Anna Maria, FL?

    The best time to visit Anna Maria is during the spring or fall when the weather is mild and the crowds are smaller. You'll still get plenty of sunshine, but it won't be as hot and humid as during the summer months.
  • What are the best villa rentals with a jacuzzi in Anna Maria, FL?

  • When is it easiest to book a villa rental in Anna Maria, FL?

    The easiest time to book a villa rental is during the off-season, which is generally from May to October. You'll find better deals and more availability during these months.
  • What are the best villa rentals for families and kids in Anna Maria, FL?

  • What are the top hiking trails near Anna Maria, FL?

    Anna Maria itself doesn't have any hiking trails, but you can find some great trails nearby at Robinson Preserve in Bradenton. It's a beautiful place to hike, bike, or kayak, and you might even see some wildlife along the way.
  • What are the best pet friendly villa rentals in Anna Maria, FL?

  • What are the advantages of renting a house or a villa in Anna Maria, FL

    Renting a house or villa in Anna Maria gives you more space and privacy than a hotel. You can also enjoy amenities like a private pool and a fully equipped kitchen, which can save you money on dining out.
  • What are the best villa rentals with parking in Anna Maria, 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, FL.

  • Are there popular destinations near Anna Maria, FL?

    Yes, there are many popular destinations near Anna Maria. You can visit the beaches of Siesta Key or Lido Key, or explore the historic downtown of Sarasota. There are also several state parks and nature preserves within a short drive.

Destinations nearby

Best Anna Maria, FL houses with air conditioning

Buena Vista #2 - 101 - 67th Street #2 - Anna Maria, FL
10 31 reviews
Anna Maria, FL
06/27 – 07/04
$1464/nighttotal: $10248 (7 )

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

4 5
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.
New! Saltwater Serenity Less Than 500ft To Ami, Canal Front! - Anna Maria, FL
Anna Maria, FL
07/24 – 08/01
$592/nighttotal: $4736 (8 )

New! Saltwater Serenity Less Than 500ft To Ami, Canal Front!

3 7
house , Cortez
This canal-front home in Cortez, Florida, is less than 500 feet from Anna Maria Island, a 19-minute walk from Bradenton Beach, and one mile from Cortez Beach.
This 1800-square-foot vacation rental boasts three bedrooms, two bathrooms, sleeps up to 15 guests, and includes a fully equipped kitchen, spa, fitness center, free Wi-Fi, and a children's playground.
84 M² House ∙ 2 Bedrooms ∙ 5 Guests - Anna Maria, FL
10 2 reviews
Anna Maria, FL
06/27 – 07/04
$359/nighttotal: $2513 (7 )

84 M² House ∙ 2 Bedrooms ∙ 5 Guests

2 5
house , Holmes Beach
Groovy Guava, a Holmes Beach half-duplex, is located less than half a block from Anna Maria Island's beaches and within walking distance of restaurants like The Feast and Freckled Fin.
This 890-square-foot pet-friendly rental boasts two bedrooms, two bathrooms, sleeps five, includes a private heated pool, and offers a street-legal golf cart for exploring the island.
Sand And Sea 113 B - Anna Maria, FL
Anna Maria, FL
06/27 – 07/04
$399/nighttotal: $2793 (7 )

Sand And Sea 113 B

2 2
apartment , Anna Maria
Sand And Sea 113B is a beachfront Anna Maria Island rental, a 12-minute walk from the Anna Maria City Pier and 19 miles from The John and Mable Ringling Museum of Art.
This two-bedroom, one-bathroom house sleeps 11, features a fully equipped kitchen with a dishwasher and microwave, a private pool, free Wi-Fi, and air conditioning.

Neighborhoods and points of interest in Anna Maria, FL

Best Anna Maria, FL villas and beach houses with jacuzzi

Freckled Fin - Anna Maria, FL
Anna Maria, FL
10/31 – 11/10
$740/nighttotal: $7400 (10 )

Freckled Fin

1 2
house , Anna Maria
Freckled Fin, a beachfront Anna Maria Island rental, is a 7-minute walk from Anna Maria Island and a 6-minute walk from the Anna Maria City Pier, located 18 miles from Sarasota Bradenton International Airport.
This 2,810-square-foot house features four bedrooms, four bathrooms, and accommodates up to 15 guests, boasting a private pool, free Wi-Fi, and free parking, plus a fully equipped kitchen and fitness center.
Swaying Palms! Coastal Home With Amazing Pool Just A Short Drive From Anna Maria Island! - Anna Maria, FL
10 1 review
Anna Maria, FL
07/03 – 07/06
$587/nighttotal: $1761 (3 )

Swaying Palms! Coastal Home With Amazing Pool Just A Short Drive From Anna Maria Island!

4 3
house , Bradenton
This Bradenton vacation home is conveniently located near Anna Maria Island's beaches, 6.2 miles from Sarasota Bradenton International Airport, and 3.3 miles from the Greens of Manatee Golf Club.
This 2,050-square-foot house features four bedrooms, two bathrooms, sleeps up to 15 guests, and includes a private pool, Jacuzzi, spa, and fully equipped kitchen with modern appliances; free Wi-Fi and parking are also provided.
The Beach Club At Anna Maria #6 And #7 - Anna Maria, FL
Anna Maria, FL
08/15 – 08/17
$497/nighttotal: $994 (2 )

The Beach Club At Anna Maria #6 And #7

1 4
house , Bradenton Beach
This beachfront vacation home in Bradenton Beach offers immediate access to the beach and is located 12-14 miles from Sarasota International Convention Center, John and Mable Ringling Museum of Art, and Sarasota Bradenton International Airport.
This non-smoking rental accommodates up to 11 guests with 2 bathrooms, a fully equipped kitchen, air conditioning, complimentary Wi-Fi, and access to an on-site hot tub and fitness room, plus private parking.
Private Oasis W Heated Saltwater Pool & Hot Tub - Anna Maria, FL
9.0 4 reviews
Anna Maria, FL
07/28 – 08/03
$711/nighttotal: $4266 (6 )

Private Oasis W Heated Saltwater Pool & Hot Tub

4 11
house , Bradenton
This Bradenton vacation home, located nine miles from the Sarasota International Convention Center and the Ringling Museum of Art, offers convenient access to Sarasota attractions.
This 1880-square-foot property features four bedrooms, two bathrooms, sleeps up to 14 guests, and includes a heated saltwater pool, hot tub, private beach access, outdoor fireplace, and barbecue facilities.
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