Guesthouse holiday rentals in Seminole County

A charming pathway made of light-colored bricks leads to the entrance of a compact guest studio. Lush greenery, including tropical plants and palm trees, surrounds the area, enhancing the inviting atmosphere. Natural sunlight brightens the facade, complemented by textured wooden accents on the side.

4.94 out of 5 average rating, 268 reviews

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

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4.94 out of 5 average rating, 224 reviews

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

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4.95 out of 5 average rating, 129 reviews

The living area features a comfortable blue chair and a gray sofa, with a flat-screen TV mounted on the wall. A standing lamp provides soft lighting. Natural light enters through the window, complemented by light curtains and green walls.

Guesthouse in Oviedo

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!

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4.98 out of 5 average rating, 142 reviews

A refreshing pool with stone borders is surrounded by lush greenery and shaded by a blue canopy. Comfortable seating for two is visible, along with a hammock, creating a serene outdoor space ideal for relaxation.

Guesthouse in Longwood

"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.

FamilyLocationDecor

4.9 out of 5 average rating, 145 reviews

A well-manicured pathway leads to the studio, surrounded by lush greenery and colorful plants. Visible are large windows framed by white curtains, providing a view of the scenic lake. A patio with a red umbrella and a picnic table is accessible for outdoor relaxation.

Guesthouse in Lake Mary

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.

ValueFamilyOutdoor spaces

5.0 out of 5 average rating, 22 reviews

LaLa's Carriage House

Nestled along the charming cobblestone streets of the historic district, this beautifully updated carriage house is a rare find. Just minutes from downtown’s vibrant dining, entertainment, and serene lakefront paths. This oversized 1-bed, 1-bath home features a spacious, airy layout and is completely separate from the main property. Enjoy a peaceful backyard oasis—perfect for morning coffee, unwinding by the small pool, or soaking up the sun. Shared laundry facilities for convenience.

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4.97 out of 5 average rating, 154 reviews

A serene view of Lake Mary is framed by a large tree and a white post. The sky transitions into vibrant hues as the sun sets, reflecting softly on the water's surface. A lamp illuminates the foreground, enhancing the peaceful lakeside atmosphere.

Guesthouse in Lake Mary

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.

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The spacious room features a queen bed dressed in crisp white linens, flanked by two blue accent chairs. A large area rug adds comfort underfoot. Natural light streams in through a nearby window, and a ceiling fan provides a cooling breeze. A small dining area is also visible.

4.93 out of 5 average rating, 147 reviews

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!

LocationValueQuiet

4.87 out of 5 average rating, 147 reviews

A cozy living area is furnished with a sofa adorned in blue and neutral tones, accompanied by a woven chair. A wooden coffee table is placed in front of the sofa. A wall-mounted television is visible, with a light fixture illuminating the space.

Guesthouse in Deltona

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.

LocationFamilyPets

4.96 out of 5 average rating, 81 reviews

A calm body of clear blue-green water reflects surrounding lush greenery. A wooden bridge crosses over the water, leading to a natural area that showcases vibrant foliage and tranquil scenery.

Guesthouse in Lake Mary

Labor Day Weekend Lake Mary Boutique Guest Suite

Welcome to the beautiful city of Lake Mary! Sit back and relax in this calm, stylish space. Located in Central Florida and with easy access to all your vacation needs-beaches, Disney, Universal, Sea World and so much more! Our cottage is equipped and ready for your getaway and has everything you'll need for the most relaxing vacation. This cottage includes washer, dryer and WIFI. Enjoy our covered lanai for some quiet time.

ValueFamilyDecor

4.88 out of 5 average rating, 444 reviews

Guesthouse in Maitland

Chez Bienvenu

Close proximity to Park Avenue in Winter Park! Sunny and Adorable Vintage Guest House ...entire spacious guest house; with private entrance and driveway* Just a couple of blocks off Park Avenue to enjoy Shopping! Cafes! Museums! Nestled in quiet family community* •Smart TV •Stackable washer and dryer included in the unit. •Grill, Beach Chairs, Fishing Poles available •750 square feet of living space

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