Guest house holiday rentals in Orange County

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.

NEW 1BRM Guesthouse | King Bed | Central Florida

Nestled in a private and central location, this newly constructed space offers everything needed for a relaxing stay. The space is perfect for up to four guests, featuring a king size bed, full kitchen, and smart TVs in every room. Enjoy the convenience of high-speed Wi-Fi, a spacious shower, washer / dryer, and a private driveway. Located close to Downtown, Theme Parks, the Stadiums, I-Drive, Wekiva Springs, Shopping, Dining, and More! Everything needed for your short term or long term stay.

Cozy Knight Stay

Cozy Knight Stay…minutes from UCF & much more! Welcome to our cozy and pet-friendly newly renovated condo with a full kitchen, offering sleeping space for 4 with a king-sized master suite and queen-sized pull-out sofa. A short distance from the vibrant UCF campus and the magical world of Disney, this charming retreat is perfect for solo travelers, couples, or small families looking for a comfortable stay in Orlando. Book your stay now and make unforgettable memories in the Sunshine State!

Private Guest Suite in the heart of Orlando

Cozy, artistically inspired detached guest suite with your own entrance & easy parking. Only 20-30 minutes from the theme parks. Less than 2.5 miles from the Kia Center, Camping World Stadium, Inter&Co Soccer Stadium, and the Dr. Phillips Center is 1 mile away. The suite is near major highways & toll roads making travel a breeze! Safe, quiet, beautiful historic neighborhood including many of the the lakes downtown Orlando is known for. You'll LOVE your stay, check out our reviews!

1924 Spanish Carriage House Lower

Enjoy a shared but private compound resort in the heart of downtown Orlando! Centrally located and within walking distance to major events at the Kia Center, Dr. Phillips Performing Arts Center, restaurants, and downtown nightlife. Park on site, relax and enjoy all that this historic home has to share! Besides a fresh and clean private lodging, you'll enjoy use of the tropical pool, hot tub, gas grill, covered seating and dining area. A washer and dryer are just steps away for your use.

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.

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)

Sunset Cottage in Lake Mary, Florida

Located on beautiful Lake Mary, this completely renovated studio sized guest house offers beautiful sunsets over the lake from a private patio. A comfortable queen bed, stylish sitting area and fully stocked kitchenette make for a wonderful stay in the Lake Mary- Sanford area. Minutes from the Sanford airport, close to the Sunrail station and 45 minutes to either Disney World or the beach. Our guest cottage is a perfect place to visit. Please note: The cottage is lakeview only.

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.

The Cottage A Pet Friendly Guesthouse

Welcome to The Cottage! A pet friendly, super cute, and quiet studio apartment built in 2016, located above the detached garage behind my house. Pets always stay for free, and no additional cleaning fees are charged. Private self access is provided so you come and go as you please. The unit has a full kitchen, king sized bed, 4 pillows, 100% cotton sheets and coverlet. Laundry detergent and dish soap are provided. Trash is located on the west sideof the building.