Cabin holiday rentals in Kissimmee

“Tailypo” - Charming Newly Remodeled Studio Cabin

Welcome to our little cabin affectionately called “Tailypo”. What was once the original homestead shack over time had become a rundown ransacked shed that we jokingly called Tailypo reminiscent of the shack in the spooky classic tale. We didn’t have the heart to see it rot away so little by little we have restored the one room shack including reusing the original cypress cladding, refinishing the old wood floor, skinning an interior wall with the original tin roofing, mixed with modern amenities

VIP safe haven

This beautiful cabin is located in one of the best areas, privileged by its proximity to Disney parks (10-15 minutes), supermarkets, pharmacies, and restaurants (less than 1 mile). This spectacular cabin, small but cozy, gives you the tranquility you are looking for to rest or spend a few days relaxing. It has a pool to enjoy the beautiful Florida sun. Our guests have always been satisfied with the maintenance of our cabin. Visiting our cabin is like repeating the experience of having been here.

Mouse House Cabin / Disney Fort Wilderness Cabin

Book July & August = Free Gift! Welcome to our cozy cabin, straight from Disney’s Fort Wilderness! This one-bedroom retreat sleeps six comfortably, featuring a queen bed, bunk beds, and a pull-out sofa. Enjoy the charm of original Disney furnishings alongside updated smart TVs for modern convenience. Relax on the spacious front deck with a picnic table, or take advantage of the resort amenities: pool, hot tub, game room, and fitness area. Perfect for a magical getaway with family and friends!

Lakefront Cabin in Private Woods - Central Florida

Located in the "Heart of Florida." Halfway between Tampa & Orlando. Beaches are only 75-90 miles to either coast. Previous guests describe: Breathtaking sunrises. Wide-open views. A cozy and comfortable space. Perfect for relaxing & recharging. An oasis of serenity on a quiet lake—total privacy. Immaculate. Squeaky-clean. Frequent wildlife sightings. Thoughtfully stocked with amenities. Truly a home away from home… a little piece of heaven. *Please read additional house rules before booking*

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.

Entire Cabin at peaceful Retreat in Christmas, FL

Welcome to your getaway paradise away from the hustle and bustle of everyday life! Relax, unwind and enjoy the tranquility that nature has to offer, nestled in acres of Tosohatchee Wildlife Area, this oasis offers families and friends a true unique experience. Enjoy taking a nap in the hammock or have a coffee sitting on the rustic rocking chairs, bathe in the beautiful sunshine Florida provides. At night tell stories around the outdoor fireplace and look at the beautiful night sky!

Hidden Disney Cabin- Close to parks!

Escape to our peaceful, gated retreat just 20 minutes from the theme parks. Nestled in nature, this unique retreat features three vintage cabins originally used by Disney, offering a magical and cozy stay. Enjoy the outdoor pavilion with yard games, picnic tables, a fire pit, and a barbecue grill—perfect for relaxing after a day of adventure. Whether you're a Disney fan, a tourist, or a local seeking a getaway, this one-of-a-kind experience is waiting for you!

Woodsy cabin close to major theme parks

This is a woodsy getaway in a small town. Take it easy at this unique and tranquil getaway and relax on your screened porch and watch the birds in all the surrounding old oak trees. All the major theme parks are less than an hour away. St Pete beach is just 90 minutes away, or just relax in the woods! We are renting with a 7 day minimum, so come and stay for a while. There is a 20% discount for 7 days or more and 45% for 28 days or more.

Serene Cabin Escape- Lakeside Romantic Getaway

Lakeside Cabin Near Legoland + Golf! Your perfect Winter Haven escape awaits in this 3BR/2BA retreat. Just minutes from Legoland & top golf courses, this spacious woodsy cabin blends rustic charm with modern comfort. Relax on the porch, enjoy lake views, or unwind in spacious living areas. Ideal for families, couples, or golf getaways—create unforgettable memories in this serene Florida haven! Come experience the hype for yourselves!

Cabin Near Disney & Beach | Spa, Firepit & More!

Experience the charm of a Unique 3BR/2BA log cabin retreat on a 3.7-acre oasis! Enjoy a jacuzzi, firepit, outdoor kitchen, ping pong, soccer area, and hammock under the trees. The huge paver deck is perfect for gathering. Feel secluded yet be minutes from markets & dining. Go fishing, horseback riding, or hiking nearby. Whether for family fun, a romantic escape, or a remote work retreat, adventure & relaxation await!

Modern log cabin between the beach and Disney

Relax in this calm, stylish cabin tucked away on over a half acre. 3 bedroom, 2 bath modern space. Take in views of the horses next door while sitting on the front porch. Conveniently located between the beach and Disney. 9.5 miles to UCF, 6.5 miles to Boombah Sports Complex, 13 miles to historic Sanford. Plenty of parking. Bring your boat and go fishing in the nearby St. Johns River.

Jungle in Orlando: Glamp Life the Experience

Williams Estates is back! This time bringing an amazing "Glamping type Experience" through a jungle vibes atmosphere... but don't worry, you'll actually be right in the middle of town! Yes, nature and wildlife meets Urbana here!! No Pets, No kids, 2 guest Max!!