Guesthouse holiday rentals in Seminole County

Serenity @ Court

Come check out this newly renovated luxurious 1950s guest house with spectacular ceiling height and one of a kind kitchen. Conveniently located in a golf cart area near downtown Sanford. Property is located 8 minutes away from the Sanford Airport, approximately 30 minutes from New Smyrna Beach, 40 minutes from Orlando International Airport, all major parks, and Daytona Speedway. Park your bikes in the covered breezeway to protect against rain and sun. Parking available on street and off-street.

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

Share the backyard and pool with your hosts. Half was between Disney & the beaches. 12 years & older only. Sofa extends to a single bed. Minutes from I-4 makes commuting easy. NOT a heated pool. Wheelchairs are fine. Driveway Entry gate 39"- Breezeway to Ramp entrance 32"- Slider Entrance 33"-Bedroom door 35"-Shower (no step) 35"-Laundry 32"-Closet 35"-Queen bed 29"-standard cabinets. We are not Handicap Certified but most wheelchair guests have not have issues. Grab bars in the bathroom.

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!

Little Hidden Cottage- Near Sanford Airport

Located in Sanford FL, our Hidden Little Cottage is a private studio guest house with its own entrance, features full kitchen & bath room, queen size bed, full size pull out couch & twin size travel bed, & provides flexible self check-in. We are located 7 minutes from the Sanford Airport and Boombah Sports Complex, 10 minutes to Downtown Sanford, I –4 & 4–17. We’re also central to many Central Florida attractions such as Natural Springs, Sandy Beaches, Theme Parks and Historic Districts

Palmetto Pool Retreat

The Palmetto Pool Retreat offers complete privacy - detached studio cottage, with a pull-down Queen Murphy bed. * Kitchen - refrigerator, stove, cookware, Keurig , microwave, toaster, dishes and utensils. * Studio Living area - Queen size Murphy Bed, Roku TV, WiFi Internet, AC/Heater; Closet, Iron. Please don’t put AC lower than 72. * Private Bathroom - shower, hairdryer. *Outdoors - Pool, not heated, with private double patio sitting area with 2 Fire pits Gas & Wood; BBQ gas grill

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.

Tranquil Hideaway

This serene home offers the perfect blend of comfort and convenience. Located just minutes from Green Springs State Park, you'll enjoy easy access to outdoor adventures. Inside, you'll find a spacious living area, a fully equipped kitchen, and comfortable bedrooms with queen-size beds. Ideal for remote workers, the dedicated workspace provides a quiet and productive environment. Whether you're seeking a family vacation or a romantic getaway, this home has everything you need.

Sunny Side Stay

Escape to this stylish and comfortable 1-bedroom, 1-bathroom pool house—perfect for a relaxing getaway or a weekend staycation. Enjoy indoor entertainment with pool table, and unwind outdoors in the beautifully landscaped yard featuring multiple seating areas ideal for morning coffee or evening drinks. Whether you’re here to relax or explore, this cozy guest space offers privacy, comfort, and a touch of fun.

Private full kitchen near Disney & Epic Universe!

Get ready for an Orlando escapade! Our quirky rental features a cozy futon over a twin and a full bed that sleeps up to 4. Nestled next to I-4, you're just 25 mins from Universal, Epic universe, and 35 mins from Disney, with more fun nearby. Enjoy a homey retreat with easy check-in and a fully stocked kitchen for your midnight snack raids. Book now for comfort, laughs, and unforgettable adventures!