Cabin holiday rentals in Osceola County

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Top-rated cabin rentals in Osceola County

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Guest favourite

Cabin in St. Cloud

4.96 out of 5 average rating, 75 reviews

“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

Top Guest favourite

Cabin in Kissimmee

5 out of 5 average rating, 9 reviews

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.

Cabin in Kissimmee

Authentic Disney Fort Wilderness Cabin near WDW

Authentic Fort Wilderness cabin from Walt Disney World upgraded with extra classic Disney style. Welcome to our family vacation home in Kissimmee next to Celebration. 9 minutes to WDW arch 18 min. from Magic Kingdom (no I-4 traffic) Sea World & Universal also nearby. Beaches 1 hr. drive Shop, dining & bus service to WDW all walking distance Accommodates a large family: Full bathroom Full kitchen Queen bed 2 bunk beds Pull out double bed sofa Fold up cot All Disney quality Not Disney affiliated

Top Guest favourite

Cabin in Kissimmee

5 out of 5 average rating, 29 reviews

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!

Cabin in River Ranch

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!

Cabin in Babson Park

4.86 out of 5 average rating, 22 reviews

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.

Cabin in River Ranch

Cabin in Westgate River Ranch

Forget your worries in this spacious and serene space. Rent a cabin in westgate river ranch for the holidays. We have availability for 1 or 2 bedroom. Please contact us for availability and what you are looking for. This resort has cabins that are being remodeled as well, although they all look amazing!! We will check for availability once we are contacted. Please send us a message for final pricing as it will depend on date of booking (Holidays, summer, etc) We will then confirm.

Cabin in Davenport

5 out of 5 average rating, 4 reviews

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!

Cabin in Lake Wales

Lake Rosalie Retreat

Welcome to Oakasa Nestled beneath majestic oaks on three peaceful acres, Oakasa is a charming lakefront cabin where time slows down and memories come easy. Whether you're sipping coffee, casting a line off the dock, or watching the sun rise over Lake Rosalie, this is the kind of place that helps you breathe a little deeper. Our cozy 2-bedroom, 2-bath cabin is perfect for couples, families, or friends looking to unplug and unwind. Book your escape today, the lake is calling.

Top Guest favourite

Cabin in Davenport

5 out of 5 average rating, 9 reviews

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!

Top Guest favourite