Guesthouse holiday rentals in Sanford

Private Courtyard Cottage on Canal

Enjoy a comfortable stay in this private guest cottage with its own entrance, detached from the main house—perfect for privacy and relaxation. Features an extremely comfortable king-size bed, TV, and WiFi ideal for streaming or remote work. The kitchenette includes a full-size fridge, microwave, sink, air fryer, and coffee maker for easy meals and morning coffee. Ideal for couples, solo travelers, business stays, or sports families looking for a quiet, comfortable home base close to everything

Little Hidden Cottage- Near Sanford Airport

Located in Sanford FL, our Hidden Little Cottage is a Private Studio Guest House with its own entrance, fence, 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

"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.

Nature Unique lake view Tiny Guest studio

Tiny Guest house studio with separate entrance for privacy and amazing Lake view. Unlimited rental of 2 Blue kayaks included during stay!! Walking distace from windixie supermarket, downtown lake Mary, restaurants, shopping centers, entertainment and dunking Donuts. Common areas outside studio are shared. Property is at lake Mary across Country club, close to Sanford, Boombah Sports, Orlando Fl. 30 min to Daytona Beach. Near Wekiva springs. To go to Disney, easy access to I-4 and 4-17.

No Worries Carriage House, 5 min walk to Stetson

This second-floor carriage house is all yours. Located on a quiet street amidst historic homes. Walk to Stetson in 5 min. Downtown DeLand is an easy 15 min. walk. Your two bedrooms, full kitchen, private access will be great for a get-away for you and your guests. 42" flatscreen TV with cable and Amazon Prime with no ads. Wifi. The second-story banks of windows look out over beautiful, tropical plants. Space to work or relax. We look forward to you enjoying your stay with us.

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.

Suite Retreat

Avoid blah hotels with high prices and stay in this luxe new apartment suite! It’s a perfect retreat in Central Florida. Located a short drive to activities, restaurants, & shops in Lake Mary or downtown Sanford - 45-55 min to Orlando theme parks or the beaches of New Smyrna. Ideal for a couple’s retreat or a getaway for one. Guests use office space designed for comfort & productivity. A cozy chair begs readers to curl up and read. The outdoor canopy hosts breakfast with birdsong!

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

Lake Dora Cottage!

We are located 1 house behind Lake Dora's lakefront, only a 1 mile scenic drive to Downtown Mr. Dora! We renovated this vintage lakeside cottage. It was originally a 1940's fish camp! The Cottage is detached from the main home with an enclosed private patio. The shoreline of the lake is PRIVATE PROPERTY WITH PRIVATE DOCKS. Guests have public access points. ****SERVICE ANIMALS ARE NOT ALLOWED*** We live on the property and therefore, it is not considered a public accommodation.

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.

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.

Relaxing Cottage Retreat | Walk to Downtown

Welcome to your cozy Mount Dora retreat — a bright boutique-style cottage filled with vintage Florida charm, warm wood floors, soft coastal colors, and relaxing spaces to unwind. Enjoy coffee in bed, stroll downtown for shops and dining, then return to your peaceful cottage escape beneath the trees. Perfect for couples, weekend getaways, festival visits, girls’ trips, and relaxing stays near downtown Mount Dora.