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!!!

Livingston Hideaway • Walk To Lake Eola • Hot Tub

Welcome to Livingston Hideaway, a charming historic duplex in downtown Orlando, just two blocks from Lake Eola. This private space offers a quiet, residential feel while being steps from dining, nightlife, and events. Perfect for couples or business travelers, it features a private entrance, fenced outdoor area with hot tub and putting green, free parking, and fast Wi-Fi. Thoughtfully updated with modern comforts, Livingston Hideaway blends historic character with walkable downtown convenience.

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.

Bungalow Near Epic, Disney and Downtown Orlando

Discover our charming cottage behind our bungalow in Downtown Orlando's College Park - located near Disney parks, Universal Studios, and Winter Park! Enjoy urban living with a small-town vibe, biking along tree-lined streets to restaurants, shops, breweries, and farmers markets. Pack and play available on request Private access, yard, and driveway and a beautiful park across the street! Winter Park (10 mins), Downtown (10 mins), Disney and Universal (15-30 mins). STR Permit # STR-1118212

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!

"Winnie's Place" A Peaceful Guesthouse with Pool.

Share the quiet yard and pool with hosts. 1 hr. from Disney & the beaches. 12 yr & older only. Single Sofa bed for 3rd guest. NOT a heated pool. Not Handicap Certified, but most wheelchair guests have not had issues. Narrowest opening 32" Ramp into unit by pool. Shower no steps. Queen bed height 29"-standard cabinets. Grab bars in bathroom. Airbnb's Accessibility Policy has exempted this listing from accepting Service & Emotional Support Animals due to owner's severe health condition.

8th Green Cottage - A relaxing oasis in the city

The 8th Green Cottage is a relaxing oasis in the heart of Orlando. Located 5 minutes from downtown. Sitting on the historic 1924 Dubsdread golf course. Enjoy the great views, pleasant and quiet neighborhood all with easy access to everything Orlando has to offer. Location is key when traveling and the 8th Green Cottage delivers! Disney, Universal, and Sea World all within a straight shot down I4. Free play Arcade with 3500 games included in spare bedroom Pets are welcome and stay Free.

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)

Private Cozy Cottage in heart of Orlando

Come stay at our Cozy quaint suite located in the historic downtown Lake Davis neighborhood with a 5 minute walk to a quiet neighborhood market, 1 mile walk to downtown Orlando with entertainment and the Downtown Farmers Market. Less than 30 minutes to the worlds greatest attractions Disney, Universal Studios, Sea World etc. The beach is a 1 hour drive. One car parking. The room is connected to a family home you’re able to hear guest next door. Not for parties . Please NO pets.

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!