Villas and Vacation Homes in Anna Maria Island, FL

This Old Florida oasis in Cortez offers a private retreat, conveniently located just a short drive from Anna Maria Island beaches and IMG Academy.
This welcoming 2400 sq ft villa, featuring 3 bedrooms and 4 bathrooms, accommodates up to 10 guests with a heated pool, outdoor kitchen with TV, fire pit, and a fully fenced backyard, perfect for families and groups seeking a memorable holiday home experience.

Just 3 minutes on foot from the Gulf's sugar-white sands, this Key West-style cottage is perfectly situated in Bradenton Beach, offering convenient access to Bridge Street's dining and shopping.
This welcoming 550 sq ft beach house, ideal for up to 4 guests, features 1 bedroom and 1 bathroom, air conditioning, a full kitchen, and access to a seasonally heated community pool with Bay views, making it an excellent villa for your next holiday home escape.

House to rent. You will stay in Cortez.
Services and facilities include a kitchen, a fitness center and a washing machine. Enjoy a swimming pool in this house in Cortez!

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.

Accommodation. You will stay in West Bradenton.
Facilities and services include a dish washer, a terrace and free parking.

Directly on Palma Sola Bay, this villa offers unmatched kayaking and fishing with stunning sunset views over Anna Maria Island, adjacent to the Palma Sola Bay Nature Preserve.
This family-friendly holiday home, accommodating up to 6 guests, features a private heated pool, a game room, and a dedicated home office, providing a unique combination of bay access and luxury amenities.

Tropical waterfront living awaits at this Bradenton villa, offering breathtaking water views and private dock access, just a short distance from the sugar-white beaches of Anna Maria Island.
This welcoming 2020 sq ft holiday home features 4 bedrooms, 3 bathrooms, and accommodates up to 10 guests, boasting a heated swimming pool, a garden, and ample parking on a peaceful ⅓-acre lot for an exceptional family and pet-friendly stay.

This custom tiny home, a unique cabin, is located in a quiet waterfront neighborhood in West Bradenton, Florida, offering convenient access to local amenities, just 6 miles from the beautiful beaches of Anna Maria Island.
Enjoy a private, fenced-off tropical oasis with a hot tub, king-sized bed, and high-end interior finishes, perfect for romantic getaways and peaceful retreats, making this an ideal holiday home.

Offering a new heated saltwater pool and hot tub, this 3-bedroom villa is located in Bradenton, approximately 6 miles from Anna Maria Island beaches and conveniently close to IMG, dining, golf, parks, and fishing.
This welcoming holiday home accommodates up to 8 guests with a fully stocked kitchen, dedicated workspace, screened-in porch, and provided beach chairs, ensuring a comfortable stay.

This welcoming villa in Bradenton offers a prime location, situated just 500 feet from the stunning beaches of Anna Maria Island and providing convenient access to historical sites like DeSoto National Memorial, Manatee Village Historical Park, and the South Florida Museum.
Boasting 4 bedrooms and 2 bathrooms to accommodate up to 10 guests, this family-friendly holiday home features a Florida-style backyard with a private pool and putting green, an upscale coffee bar, and a dedicated garage game room with a dart board and ping pong table for endless entertainment.

Just a 7-minute stroll from Anna Maria Island's beautiful beaches, this welcoming villa is perfectly situated, placing you 0.7 miles from the historic Anna Maria City Pier and an 8-minute walk from Anna Maria Bayfront Park.
This 790 square feet holiday home accommodates up to 16 guests with 2 bedrooms and 1 bathroom, featuring a fully equipped kitchen, air conditioning, a swimming pool, spa, fitness center, and complimentary WiFi.

Just steps from Anna Maria City Beach, this second-floor cottage at Anna Maria Beach Cottages offers an authentic 'Old Florida' beach house experience on the island's north end, a short walk or trolley ride to Pine Avenue's shops and restaurants.
This welcoming family-friendly cottage accommodates up to six guests with two bedrooms and two bathrooms, featuring a private deck, air conditioning, a swimming pool, jacuzzi, and on-site laundry, providing resort-style service for a perfect holiday home getaway.

Located within the exclusive gated Perico Bay Club, this villa offers a prime position just under 2 miles from the renowned white sand beaches of Anna Maria Island.
This welcoming 1130 sq ft holiday home comfortably accommodates up to 6 guests with 2 bedrooms and 2 bathrooms, boasting a private enclosed courtyard patio, screened-in lanai with mangrove views, and access to community amenities like 2 heated pools, a hot tub, fitness center, and tennis courts.

Located just 2 minutes on foot from the beach, this beach house in Bradenton Beach offers a prime location with excellent ratings for its setting, cleanliness, and overall guest experience.
This welcoming villa accommodates up to 4 guests and features a private front porch, a heated swimming pool, and is conveniently situated near restaurants, shops, and a free island trolley stop, making it an ideal holiday home.

Located in South Bradenton, this spacious holiday home is conveniently situated 1.5 miles from Legend Fishing Charters and 2.7 miles from Greens Of Manatee Golf Club.
This welcoming villa offers 1600 square feet of living space, accommodating up to 15 guests with 3 bedrooms and 3 bathrooms, and features a heated saltwater swimming pool for year-round enjoyment.

Located in Cortez, this welcoming villa offers direct access to the beach, just 1,000 feet away, and is a short distance to local seafood restaurants.
This spacious 1500 sq ft holiday home features 3 bedrooms, sleeps up to 11 guests, and boasts a heated outdoor pool, hot tub, BBQ grill, fire pit, outdoor TV, pickleball, ping pong, and cornhole for year-round enjoyment.