Guesthouse vacation 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

Family · Value · Outdoor spaces

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

Value · Family · Beach

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.

Location · Value · Air conditioning

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!

Value · Family · Hospitality

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.

Family · Location · Pool

"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.

Family · Value · View

King/Queen Quiet Vibey Bungalow Guest House

Our beautifully renovated 1950's home is nestled in a quiet neighborhood just a few blocks from everything. The ColonialTown North district of Orlando (also called Mills/50) is a vibrant, central area with exceptional walkability to grocery stores, a trendy bar scene, LOTS of coffee and boba options, foodie restaurants and casual late night eats. Families will love the playground just two streets away. When you're ready, retreat to our front deck and watch the sunset reflect off the trees!

Location · Family · Walkability

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.

Location · Family · Walkability

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.

Value · Family · Getting around

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!

Location · Family · Long stay

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.

Family · Value · Amenities

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.

Location · Family · Decor