Holiday rentals with outdoor seating in Winter Park

⁕ Disney parks! Luxury resort villa • Private pool

This sunny single-story home has 4 beautiful bedrooms, 2 full bathrooms, new AC system, fully stocked kitchen, and a private screened heated pool. Perfect for families or groups, it accommodates up to 8 guests. Just minutes from DisneyWorld, Universal Studios, SeaWorld, Legoland, and Orlando’s top attractions. Conveniently located close to restaurants and shopping, this non-smoking house is nestled in a peaceful and secure resort, offering all the comforts of a "home away from home" vacation.

Lux Tiny Home/RV on Private 1 acre

Experience affordable private luxury in this newer destination-style RV, permanently placed on our quiet, tree-filled 1-acre estate in Apopka/Longwood. Tucked away behind a private gate, it’s a serene hideaway that still puts you close to everything. Just 35 minutes from MCO, 25 from Disney & Universal, and under 10 to Wekiva Springs State Park—this spot is perfect for guests looking to explore both natural wonders and world-class attractions. Grill and beach chairs available upon request.

The Beehive Treehouse

This one of a kind treehouse will quickly become one of the most booked tree houses on the planet. Unique in every possible way. It started as an art of love during Covid and it quickly became a project that has fought the attention of superstar singers looking to disconnect from everything but being close to everything. Queen bedroom, drawer space, full bathroom, Nespresso coffee maker, 80-inch tv, private balcony overlooking the main wedding venue, outdoor claw tub and custom chandelier.

*Sunset Perch: Views, Reunion Resort, XBox, 2Pools

This modern 3-bedroom luxury condo (with an ELEVATOR right to the door) has one of the most PICTURESQUE VIEWS in the Reunion Resort of the Arnold Palmer PGA golf course. Combining STYLISH DESIGN and LUXURIOUS COMFORT, there are 2 KING bedrooms and a playful STAR WARS themed bedroom with a classic Arcade machine & Xbox. 4 TVs with DirecTV, free high-speed wifi, your own washer & dryer, access to 6 resort pools, 2 of which are only a 3 minute walk away, and only a short drive to Disney.

Slice of paradise ranch and outdoor quality time.

A quiet country retreat., pet the horses & goats, enjoy the sunken large fire pit surrounded by nature. See wild deer, turkey, black bear, racoons, eagles and more. Majestic live oaks and of space to let the kids or pets run free. Enjoy the covered picnic area and swing near the fire or have a BBQ at our resort style outdoor entertaining area. No city lights here, see the stars in their full glory while relaxing at fire pit and swing for 2. Springs, canoeing 5 mins away.

PuraVida Lakehouse+Bungalow - Full Property

Welcome to our Pura Vida jungle-inspired urban lake house, nestled in the heart of Orlando! Combining tropical tranquility with modern luxury, this unique retreat offers the perfect escape for travelers seeking a serene atmosphere just minutes from the city's attractions. **NO PARTY OF ANY KIND OR EVENT ALLOWED** Circular driveway makes for free and easy parking. Located 15 min from the airport, 15 min to Universal, 30 min to Disney, and 50 min to Cocoa Beach.

Fresh Air Camper Van/RV

How would you like to have front row seats to a working sustainable farm, learn about the sustainable pillars and work the farm for crop share compensation? Bring your own RV/Camper Trailer/Van (under 25 feet) to the Farm! Plug into 30/50 amp three-prong electrical hookup and/or 110 watt receptacles. Available 30-foot rock driveway pad for your home on wheels, potable rainwater hookup, two outdoor showers and plenty of room to roam.

Sanford's Haven

Welcome to Sanford's Haven a charming downtown 1925 cottage with modern charms nestled in the heart of Historic Downtown Sanford! Perfectly located within walking distance of Sanford’s lively First Street, this home offers the ideal blend of modern comfort and historic charm, making it the perfect retreat for families, couples, or friends looking to explore Central Florida’s best-kept secret.

The Cherry Blossom

Premier location, steps away from historic downtown • 1 Queen Bed • Our goal is to exceed your expectations, provide a comfortable, personal experience, and give you the feeling that you are at home. • Lounge on the back porch, take a walk to the restaurant and bar district at Sanford Ave right out your door