Guesthouse vacation rentals in Winter Park

Lou’s Garden Hideout

Welcome to Lou’s Garden Hideout, a private retreat tucked away in one of Orlando’s most charming neighborhoods. Just steps from Harry P. Leu Gardens, this cozy suite features a comfortable queen bed, private bathroom, Netflix, fast WiFi, coffee station, microwave, mini fridge, and free parking. Enjoy a peaceful stay while being minutes from Downtown Orlando, Winter Park, hospitals, restaurants, shopping, and world-famous attractions. Relax, recharge, and make yourself at home.**FREE WIFI NETFLIX

College Park Villa Oasis w/ Botanical Courtyard

TOP 1% ABNB PRIVATE-SAFE-QUIET Villa Oasis central to DT ORL/Eola/Winter Park. Tranquil bamboo lined Cottage provides relaxed setting in much desired COLLEGE PARK neighborhood. Former recording studio @ 2X the living space of most College Park listings. Newly renovated bathroom, kitchen, outdoor space. Guest's own separate residence, bath/laundry room, garden patio and parking. I-4 EZ access to downtown ORL, Winter Park, THEME PARKS, central Fla activities! PLEASE MESSAGE with ANY QUESTIONS!!!

The Sacred Space Downtown Orlando Milk District

This delightful hideaway embodies brightness, cleanliness, and a fragrance-free environment. Enjoy a tranquil stay with hypoallergenic bedding and experience unmatched comfort on a luxurious purple mattress for rejuvenating sleep. Conveniently located near Lake Eola, lively bars, and an abundance of dining options, this private sanctuary provides the perfect balance of convenience and serenity. Amidst the bustling surroundings, our tranquil retreat remains tucked away, offering a peaceful stay.

Oasis Garden Cottage -cozy, chic, near everything!

Our cozy cottage is located within minutes of some of the best areas, restaurants, bars, and attractions Orlando has to offer. Winter Park and College Park are 3-5 minute drives, Disney and Universal only 20 minutes, etc. The interior is chic and inviting, with a homey feel. Enjoy the fireplace, play some board games, soak in bath salts in the claw foot tub, curl up on the porch with a coffee and read one of our provided books— it’s so peaceful you’ll have a hard time leaving for the day!

Location, Location, Location!

Enjoy a stylish experience at this centrally-located Guest House. It is located in an excellent area close to the downtown Orlando, excellent restaurants, and much more. It is fully furnished and equipped with new appliances (washer and dryer included) and furniture. It is located minutes from Winter Park, Downtown Orlando and theme parks. Downtown Orlando 3 miles (6 min) Advent Health Hospital 0.6 miles (2 min) Walt Disney World 20 miles (23 min) Universal Studios 11 miles (18 min)

Bright + Modern Downtown Guesthouse near Lake Eola

Best location in Orlando. No need for a car. This beautiful, historic 1947 garage apartment is a 5-minute walk to Lake Eola, and within walking distance of many lovely cafes, restaurants, and bars. We are very proud of our little guesthouse behind our home. We would love to host you and show off our beautiful city. Driving distances to major attractions: - Dr Phillips Center || 5 min (1.2 miles) - Amway Center || 5 min (1.5 miles) - Universal Studios || 20 min - Disney || 30 min

Modern 1950s Studio • Near Downtown & Theme Parks

Fully renovated 1950s studio (2024) in a safe, quiet Orlando neighborhood! Enjoy a plush queen bed, walk-in shower, Roku TV, and full kitchen with Keurig. Includes a private driveway, separate entrance, and cozy living area with stylish modern décor. In-unit washer and dryer for your convenience. Just 3 mi to downtown, 10 mi to Universal, 8 mi to the airport, and 18 mi to Disney—perfect for couples or solo travelers seeking comfort, privacy, and modern style in a peaceful setting.

20 | Excellent | Above Average

Newly built ! Entire private garage apartment! Step into the comfort of this unique garage apartment nestled in the tranquil and picturesque Mills 50 District . This home promises a relaxing retreat close to the All Major Theme parks and biking trails Downtown Orlando , restaurants, shops, and attractions. ✔ Comfortable Queen bed sleeps "2" ✔ Full Kitchen ✔ Free designated parking spot and free street parking ✔ Smart TV ✔ Washer/Dryer "FREE" ✔ Workspace ✔ High-Speed Wi-Fi

Baldwin Park Guest House

Welcome to the Baldwin Park Guesthouse! This private sanctuary features modern day comforts including a large screen SmartTV and private garden patio. It the perfect place for a romantic getaway or a solo trip to the area. Stroll over to explore Baldwin Park or visit beautiful downtown Winter Park (don’t miss the scenic boat tour). Orlando International Airport the and the area attractions are just a short drive away. We look forward to welcoming you to the guesthouse soon!

Lovely Spacious Guesthouse in Mills 50 District

Renovated guesthouse on the same property behind our 1920's historic home in the Mills 50 District near Downtown Orlando. A large room with a comfortable queen-sized bed, a flat screen TV, two accent chairs, a kitchen corner, a/c, mini-fridge, microwave, WiFi, coffee maker and full bathroom. There is also access to a shared laundry space in the same building. Within walking distance to many bars and restaurants! A very friendly and safe neighborhood with self-check-in.

Luxe Guest House| Pool, HotTub| UCF, Rollins

This luxury guesthouse (on the same property as our main house but they are completely separate) is a hidden oasis conveniently located in the middle of downtown Winter Park (Rollins College/Full Sail) and UCF. It's roughly 10 minutes to each. Close to 417 expressway (toll road) so you can easily get around to the other areas of Orlando. Note: The guesthouse is 35 minutes to Disney, 25 minutes to Universal Studios and 20 minutes to Orlando International Airport.

Detached suite in Mills 50 food paradise

Our cozy urban-jungle retreat puts you in the heart of an impressive food district and is centrally located. You’ll be a short drive/walk from dozens of diverse restaurants and several concert venues. Our detached suite is great for both business travel (5 min from downtown) and pleasure (30 min from the theme parks). The main room of the suite has space for lounging, a wet bar, and a small desk. It connects to a room with a queen bed and ensuite bathroom.