Vacation rentals with outdoor seating in Winter Park

Cozy Cottage 3 blocks from town

Come as guests, leave as friends. This super-clean 1 bed, 1 bath cottage sleeps up to 4 adults. "Cozy Cottage" is pet friendly and laid back with a super-fast internet connection. Historic Mount Dora is only steps away. Enjoy the many quaint shops, restaurants and regional festivals. The rolling hills and lakeside views give this town its New England seaside charm. Orlando theme parks are only 1 hour away. We are the perfect place to retreat after the hustle and bustle of the theme parks.

⁕ 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.

Orlando Disney new House at Resort with lake view!

Renewed house in Resort with fantastic lake view and an Amazing Clubhouse. (NO resort fees) | 1 min | Old Town Kissimmee | 3 min | Publix® | 3 min | McDonald's®, Wendy's®, Miller's Ale House® and much more | 6 min | Walmart® & Target® | 7 min | Celebration | 9 min | Premium Outlet® I-4 | 9 min | DISNEY® AREA (All Parks) | 10 min | ESPN Sports | 10 min | Convention Center | 14 min | UNIVERSAL® STUDIOS | 26 min | Orlando Airport | 60 min | Bush Garden's® | 95 min | Sarasota & Clearwater

*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.

Southern Dunes / Legoland / Golf / Disney

Welcome to your charming Florida retreat! This golf course front 4-bedroom, 3-bathroom home features a private pool and patio, spacious living areas, and a fully equipped kitchen. Enjoy comfort with cozy bedrooms and family-friendly amenities. Located minutes from local attractions, golf courses, and just a short drive from Disney World and Legoland, this home offers the perfect blend of relaxation and convenience. Book your stay today for an unforgettable Florida getaway!

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.

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