Tiny house holiday rentals in Orange County

4.98 out of 5 average rating, 294 reviews

Private Tiny Home Retreat “Your Peaceful Escape”

🌿 Welcome to La Casita, a peaceful and private retreat in a quiet Orlando neighborhood. Perfect for couples, families, or business travelers, this cozy getaway sleeps up to 4 guests and features a queen bedroom, loft with two twin beds, full kitchen, washer/dryer, private entrance, dedicated parking, and outdoor space. Relax with your morning coffee or unwind in the rocking chairs under the warm porch lights. 🌙 Enjoy peaceful evenings on the porch and the comfort of a true home away from home.

A quaint exterior view of a small house surrounded by lush greenery. The porch is framed by a railing and features a couple of chairs, while string lights add a charming touch. Colorful flowers bloom in the foreground, enhancing the serene atmosphere.

4.95 out of 5 average rating, 470 reviews

Garden House near Orlando's cultural hub

On a quiet cobblestone street, yet close to art and culture, more than 3 dozen restaurants in walking distance, Florida Hospital and family-friendly activities. You’ll love our place because of the location, the large bathroom with jacuzzi, the skylights, window seat, porch swing. It is nestled in our back yard surrounded by trees and has its own private entrance via a rustic walk way of pavers and stones. Couples, families, most anyone will find it charming. STR 1009942 (City registration)

4.76 out of 5 average rating, 175 reviews

A welcoming wooden gate labeled 'Clear Landing' is framed by lush greenery. The area is surrounded by tall trees, creating a serene entrance. The ground is covered with gravel, leading to an open space beyond the gate, inviting guests to explore the surroundings.

Cabin in Christmas

Clear Landing /Cabin in the Forest

This is 2 acres nestled in 53,000 acres of forest, yet just 1 min. Tosohatchee Wildlife Mangt Area, 5 min. to Ft. Christmas Historical Park, 20 min. to Orlando Airport, 20 min. to Kennedy Space Center, 30 min. to Jetty Park Beach (Atlantic Ocean), 10 min. Lone Cabbage Air-boat rides on the St. Johns River, 45 min. Disney World & many other attractions.. You’ll love my peaceful place, because of the Diverse change of environment w/in min. & gives you a variety of pleasures w/in just mins.

A quaint shed is set amidst a lush green yard, featuring a stone pathway leading to a small outdoor seating area. A round, floral-patterned table is accompanied by two matching chairs. Flowering plants and delicate hanging baskets add a touch of nature to the inviting space.

4.96 out of 5 average rating, 780 reviews

Quiet Garden Cottage Downtown

Nestled behind my 1920s bungalow in Orlando’s beloved College Park neighborhood, this cozy guest cottage is close to everything, yet quiet. Enjoy coffee (French press + Keurig) or tea, and snacks before exploring downtown. The Kia Center, Orlando City Soccer Stadium, Lake Eola, AdventHealth, Camping World Stadium, Universal, and Winter Park are all short Uber away. Perfect for couples, business travelers, concertgoers, and guests looking to experience Orlando beyond the tourist corridor.

4.92 out of 5 average rating, 225 reviews

A small, white house is framed by vibrant greenery and colorful plants. The front door, painted blue, adds a pop of color, while large windows allow light to fill the space. A wooden deck leads up to the entrance, enhancing the welcoming appeal.

Home in Winter Garden

Cozy Winter Garden Home 20 MINUTES FROM DISNEY

Get the small home-town feeling and still be only 20 minutes from Disney. This little house is perfect for a couple or small family who wants to visit Orlando and all the attractions, but also get away from the traffic & stay in a desirable small town setting. Located a mile from downtown Winter Garden - home to the number 1 rated farmer's market by American Farmland Trust, & the 22-mile West Orange Trail that's home to runners, bicyclists and anyone else who wants to enjoy the sunshine.

A welcoming sign for The Green Room is displayed on the exterior wall. The sign features the name 'Green Room' in a stylish font, surrounded by a decorative circular border. The year 'EST 2022' is included, emphasizing a modern touch to the entryway.

4.92 out of 5 average rating, 103 reviews

The Green Room Orlando

Come enjoy The Green Room experience in beautiful Downtown Orlando in Thornton Park. Rub shoulders with some famous artists and performers! This stylish space is just what anyone needs before a big show or just a walk to Lake Eola. So many amenities in this hip studio! Fall asleep on our comfortable memory foam bed under the warm custom wood ceilings. You can relax on the couch watching your favorite shows, have a drink on the patio, or wash off the theme parks with a nice shower!

A bright and airy studio space is depicted, featuring a spacious bed with a light-colored blanket. A wooden tray sits on the bed with a drink. A TV is mounted on the wall opposite a casual seating area with a coffee table and a comfortable couch.

4.95 out of 5 average rating, 284 reviews

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

Superhost

A living room area features a blue couch adorned with decorative pillows and a mid-century modern chair. A round mirror reflects natural light, while a floor lamp adds warmth. A wall-mounted Smart TV is positioned nearby, providing entertainment options.

Home in Orlando

4.77 out of 5 average rating, 357 reviews

Spacious Orlando Home Near Parks & Downtown

Welcome to your comfortable, spacious 1BR guesthouse unit—perfect for families! Enjoy your own entrance with nothing shared. Comfortably sleeps 4 with a queen bed and sofa-bed. Includes a full kitchen with all essentials, fresh linens, towels, fast WiFi and a Smart TV. Conveniently located just 15 mins from the airport and downtown, and 30 mins from Disney, Universal, and SeaWorld. Driveway parking included. We’re close by and happy to help if you need anything during your stay!

A cozy space is illuminated by warm lighting and twinkling string lights. A comfortable bed with decorative pillows is framed by wooden accents. A small seating area features a television and has a view of the garden area with fire pit chairs, creating a relaxing outdoor ambiance.

4.97 out of 5 average rating, 877 reviews

The Little Treehouse 2 at Country Club of Orlando

With rustic urban charm, The Little Treehouse "2" is a perfect relaxation spot for your stay in the City Beautiful. This completely renovated 1926 carriage house downstairs unit is a 260 sq. ft. blend of cosmopolitan comfort and enchantment. Located 5 minutes from Downtown, Amway Arena, Camping World Stadium, 15 minutes to Universal Studios, 25 minutes to Disney and an hours drive to Florida's beautiful beaches! *Search "Little Tree House Orlando" in your browser for more info.

4.99 out of 5 average rating, 174 reviews

Baldwin Park Guest House

Welcome to the Baldwin Park Guesthouse! This private sanctuary features modern day comforts including a large screen SmartTV and private garden patio. It the perfect place for a romantic getaway or a solo trip to the area. Stroll over to explore Baldwin Park or visit beautiful downtown Winter Park (don’t miss the scenic boat tour). Orlando International Airport the and the area attractions are just a short drive away. We look forward to welcoming you to the guesthouse soon!

The exterior of a modern shipping container suite is displayed, featuring large windows that allow natural light to flood the interior. The surrounding landscape includes gravel and low-maintenance foliage, with a small deck leading to the entrance, emphasizing the blend of nature and contemporary design.

4.92 out of 5 average rating, 193 reviews

Luxury Shipping Container-HotTub- 30 min to Disney

Step into this unique experience: a shipping container transformed into a luxury 1 bedroom 1 bathroom suite. The space is perfect for couples, business travelers, tourists, and families. After a busy day in the parks or shopping, come back to a cozy outdoor paradise with lights strung up under a covered pergola. Lounge on the couch and enjoy a gas fireplace table, grill a meal on the Weber Spirit 2 gas grill, and soak your tired feet in the hot tub.

A serene pool area features a vibrant red pool float resting in the clear water, surrounded by lush greenery. Comfortable outdoor seating is arranged near the pool, with large umbrellas providing shade. The backdrop showcases a charming pool house with multiple glass doors, inviting natural light.