Villas and Vacation Homes in Anna Maria Island, FL

Just a 5-minute walk from Anna Maria City Pier and a 7-minute walk from Anna Maria Island, this Luxury Boho Beach Cottage offers a prime location in Anna Maria, 20 miles from The John and Mable Ringling Museum of Art.
This exclusive 1140 square foot holiday home features a private heated outdoor swimming pool, a garden, a spa center, and a fully equipped kitchen, providing a perfect beach house experience with on-site parking and internet.

Located 6.2 miles from Sarasota Bradenton International Airport, this Nautical Nest holiday home in Bradenton is a convenient base, offering easy access to attractions like the Sarasota International Convention Center and the John And Mable Ringling Museum Of Art.
This 910 sq ft villa accommodates up to 7 guests and features a private heated swimming pool, hot tub, garden, and tennis court, alongside a fully equipped kitchen with a fridge, microwave, and dishwasher.

Just 500 feet from the sugar-white Gulf beaches, this historic 1925 beach cottage in Anna Maria offers Old Florida character and is walkable to local boutiques, island restaurants, and attractions.
This welcoming holiday home boasts 710 square feet with 2 bedrooms and 2 bathrooms, comfortably sleeping up to 6 guests, and features a fenced tropical backyard with outdoor dining, a gas grill, and an outdoor shower, making it an ideal beach house.

Located in West Bradenton, this vacation rental is just 1.6 miles from Palma Sola Causeway Park and 9.9 miles from Sarasota Bradenton International Airport.
This 1800 sq ft villa offers 4 bedrooms, 2 bathrooms, and accommodates 19 guests with amenities including air conditioning, free WiFi, a swimming pool, and a barbecue area within the Flamingo Royale Beach Luxury Resort.

Located in Paradise Palms, Bradenton, this welcoming villa is an 8-minute walk from Palma Sola Causeway Park and 11 miles from Sarasota Bradenton International Airport.
This 950 square foot holiday home features 2 bedrooms, 2 bathrooms, and accommodates up to 11 guests with a private swimming pool, garden, and on-site parking.

Just a 2-minute walk from Bradenton Beach, this villa offers a prime location for your next holiday home experience, situated 5 miles from Anna Maria City Pier and 15 miles from the John And Mable Ringling Museum Of Art.
This 1500 square foot beach house features two bedrooms and two bathrooms, a fully equipped kitchen, air conditioning, free WiFi, a spa bath, and a barbecue area with outdoor dining, perfect for enjoying the coastal climate and proximity to scuba diving.

This welcoming villa in Cortez is located 1.5 miles from Cortez Beach, offering easy access to the coast and a short drive to Sarasota Bradenton International Airport.
This 1000 square foot holiday home features 2 bedrooms, 2 bathrooms, a fully equipped kitchen with a fridge and microwave oven, air conditioning, a terrace, garden, spa, and parking, with scuba diving opportunities nearby.

Located in Bradenton Beach, this updated duplex is just two blocks from the white sands of Anna Maria Island's beaches and one block from the bay, offering prime proximity to both the Gulf of Mexico and local island hot spots like Salt and the shops at Bridge Street.
This welcoming 4-bedroom, 2-bathroom cottage comfortably accommodates 10 guests and features a private in-law suite, a shared backyard oasis with seating and two gas grills, beach essentials, pickleball paddles, and parking for up to 4 vehicles, making it an ideal holiday home and beach house.

Vacation house. You will be located in West Bradenton.
Facilities and services: a washing machine, a fridge and a dish washer. This house also has air conditioning!

This Bradenton villa is conveniently located 6.2 miles from Sarasota Bradenton International Airport, 3.7 miles from Greens of Manatee Golf Club, and 8.7 miles from The John and Mable Ringling Museum of Art, offering tranquil lake views.
Enjoy this welcoming holiday home featuring 910 square feet, a fully equipped kitchen, air conditioning, a relaxing hot tub, and outdoor dining space perfect for exploring Bradenton.

This spacious villa in Bradenton offers a prime location, situated just 6 miles from the beautiful Bradenton beaches and 1.7 miles from Palma Sola Causeway Park.
Enjoy this welcoming holiday home featuring 2160 square feet of living space, including 3 bedrooms, 2 bathrooms, a private outdoor swimming pool, a games room, and on-site private parking.

Directly on the sand in Bradenton Beach, this exclusive beachfront villa offers unparalleled access to the shore, just a 1-minute walk from the ocean.
This expansive holiday home features 8 bedrooms, 7 bathrooms, accommodates 26 guests, and boasts an outdoor swimming pool, elevator, and is pet-friendly, with scuba diving and cycling opportunities nearby.

This recently renovated three-bedroom, two-bathroom villa in West Bradenton is located 1.7 miles from Palma Sola Causeway Park and 9.3 miles from Anna Maria City Pier.
Offering 1880 square feet of living space, this family-friendly holiday home accommodates up to 15 guests and features a saltwater swimming pool, fitness center, jacuzzi, and a fully equipped kitchen.

This Bradenton holiday home offers a prime location, situated 7.5 miles from Sarasota Bradenton International Airport, 4.3 miles from Greens of Manatee Golf Club, and 9.3 miles from the Sarasota International Convention Center.
Enjoy this spacious 1350 sq ft villa, featuring 3 bedrooms and 2 bathrooms to accommodate up to 13 guests, complete with a saltwater swimming pool, hot tub, garden, and free WiFi for a comfortable stay.

House. You will stay in Bradenton.
Facilities and services include a fridge, a washing machine and a barbecue.

Located in Bradenton, this spacious holiday home is situated 1.8 miles from Legend Fishing Charters and 3.7 miles from Greens Of Manatee Golf Club, with Sarasota International Convention Center and John and Mable Ringling Museum of Art 8.7 miles away.
This welcoming 1440 sq ft villa features 3 bedrooms, 2 bathrooms, a private outdoor swimming pool, a lush garden, barbecue facilities, and air conditioning for comfort.

Directly on Longboat Key beach, this villa offers unparalleled gulf views and immediate access to the coastline, located just 15 miles from the Ringling Museum of Art and Sarasota Bradenton International Airport.
This exceptional holiday home features a private fitness center, a lush garden with a heated pool, a spacious balcony, and accommodates up to 7 guests with complimentary WiFi and a fully equipped kitchen for a comfortable stay.

Just steps from the beautiful beaches of Bradenton Beach, this welcoming beach house offers convenient access to local boutiques, Bridge Street Bistro, and Anna Maria Oyster Bar.
This 700 square foot cottage, ideal for up to 4 guests, features 1 bedroom and 1 bathroom, a full kitchen with a dishwasher, air conditioning, and a community swimming pool, making it a perfect villa for your holiday home getaway.

Located in Bradenton, this holiday home is approximately 6.2 miles from Sarasota Bradenton International Airport, 3.7 miles from Greens of Manatee Golf Club, and 30 miles from The Pier.
This welcoming 1130 sq ft villa features two bedrooms, two bathrooms, and accommodates up to 11 guests, offering a fully equipped kitchen, air conditioning, free WiFi in public areas, a private entrance, an outdoor swimming pool, a garden, and an outdoor seating area perfect for enjoying the Florida weather, with proximity to IMG and Bradenton Beach.

Located in Cortez, this private guest cottage offers a secluded retreat just 1 mile from Anna Maria Island, providing easy access to its beaches and attractions.
This welcoming one-bedroom, one-bathroom villa comfortably accommodates two guests and features a full kitchen, air conditioning, and access to shared outdoor spaces including a garden and swimming pool.