Cabin holiday rentals in Lake 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!

New Years Eve! Westgate River Ranch Resort & Rodeo

Rockin New Year's Eve! Available Fri. 12/26 - Fri. 1/2/26 XL Grand Luxury Cabin # 1 Desirable Week! Sleeps 8+ BYO air mattresses (1 King Bed 1 Queen Bed 2 Queen Sofa Beds). Pet Friendly** Experience an unforgettable family vacation where the old-West meets modern amenities! Florida's only Authentic Dude Ranch at Westgate River Ranch Resort & Rodeo. Exclusive Privately XL Luxury Cabin on 1,700 Acres of lush land. Award-winning live Rodeo Saturday nights! Wraparound porch rocking chairs! Nature!

Sunrise on the Lake: Make Offer Winter '26

Savor gorgeous sunrises year round from our lakeside cabin. Nestled among citrus groves in a very quiet neighborhood, you'll be minutes from town & Webber Univ; only 35-60 minutes from Disney, Legoland, Orlando, Winter Haven, Lakeland & Sebring. Enjoy a spacious lakeview bedroom, living room with dinette, bathroom & kitchen. Amenities for your stay: high-speed wifi, off-street parking, private sandy beach & access to 2 patios—perfect for dining al fresco. Contact us for special rates.

Relax Away Retreat | Cozy Cabin

Book with us now and receive access to all of these amenities: •Lightning Fast Internet •Mini Golf & Plenty of Games •Private Fire Pit •Private Swinging Bench •Covered Patio •Safe Gated Location •Keypad Entry Door •Comfortable Queen Sized Bed •TV (Adjustable) •Modernized Brand New Full Bathroom •Outdoor Dining Area •Kitchen, Fridge/Freezer, & Breakfast Nook •Complimentary Coffee & Breakfast •Cooking Equipment •Nearby All Major Attractions •And Much More! Book with us now!

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!

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!

Great cabin for a couple at lakeside retreat

Cute one bedroom/one bathroom furnished cabin at lakeside retreat. Large patio out front with table and umbrella to enjoy the beautiful surroundings. Full kitchen and bathroom, linens and towels provided. Queen bedroom and leather couch and recliner in living room. Close to Bok Tower Gardens, Bella Cosa Wedding Venue and Orlando attractions. Family owned campground on beautiful Lake Pierce.