Cabin holiday rentals in Osceola County

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Top-rated cabin rentals in Osceola County

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The exterior of a rustic cabin is adorned with warm string lights, creating a welcoming ambiance. A porch with steps leads up to the entrance, flanked by lush greenery. The wooden structure features a lighted wheel decoration and bright windows, giving it a charming appearance at dusk.

Cabin in Kissimmee

5 out of 5 average rating, 4 reviews

Authentic Disney Fort Wilderness Cabin near WDW

Genuine Disney cabin purchased in 2024 from Fort Wilderness at Walt Disney World. These are authentic Disney cabins located only 2.8 miles from WDW and upgraded with extra Disney accents, style & decorative flavor. Great for families w/children for a long stay at a resort with pool, mini golf, playgrounds, dog park & wonderful amenities on site. Walking to shopping, restaurants, nature & entertainment. 10 minutes drive to Disney, 18 to MK, 16 min. To Hollywood, etc. Bus to MK through Celebration

Guest favourite

A simple cabin rests on a lush green lawn, surrounded by tall trees. A small porch extends from the front of the cabin, and the serene setting is complemented by a calm waterway in the foreground, with scattered lily pads visible.

Cabin in St. Cloud

4.96 out of 5 average rating, 79 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

Guest favourite

A single-story cabin is shown with large windows allowing ample natural light. Green lawns surround the property, with palm trees adding a tropical touch. A street sign indicating 'Mansion Ln' is positioned in the foreground, enhancing the welcoming entrance of the cabin.

Cabin in Kissimmee

4.83 out of 5 average rating, 12 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.

Top Guest favourite

A cozy cabin exterior features natural wood siding, complemented by vibrant green doors. A spacious front deck with a railing offers seating, while a picnic table sits on the grassy area nearby, surrounded by lush trees and foliage.

Cabin in Kissimmee

5 out of 5 average rating, 32 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!

A spacious cabin with a warm wooden exterior is surrounded by lush green grass. A picnic table is positioned in the foreground, while a porch with seating is visible, creating a welcoming outdoor area. The cabin features large windows allowing natural light to brighten the space.

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!

A serene lakeside view features three comfortable adirondack chairs placed on soft, sandy beach. The sun rises above the calm water, casting a gentle orange glow across the landscape. Silhouettes of trees line the horizon, enhancing the tranquil morning atmosphere.

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.

A charming cabin with a welcoming porch features ample outdoor space. The entrance is framed by well-maintained greenery and flowers, with large windows allowing natural light. The building has a mix of warm orange hues and green roofing, complementing the bright blue sky.

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.

Superhost

A cozy living area features a comfortable sectional sofa positioned next to a large window. Light wood flooring complements a dining space with a round wooden table and two chairs. A door leads to an adjoining bedroom, enhancing the home's inviting layout.

Cabin in Lake Wales

Cozy two bedroom cabin at lakeside retreat

Relax with the whole family at this peaceful lakeside retreat. This charming two bedroom, one bathroom cabin is fully furnished with a queen bed in the master, two twin beds in the spare and a small sleeper sofa in the living room. Close to Bok Tower Gardens, LEGOLAND, and across the lake from Bella Cosa Wedding venue. Full kitchen and bathroom with towels and linens provided. Consistent high reviews for cleanliness and overall experience. Family owned campground on Lake Pierce.

Guest favourite

A cozy living space features rustic sliding barn doors that open to reveal a stylish sleeping area. A queen-sized bed is neatly arranged with soft bedding, while ample natural light enters through large windows, illuminating the wooden ceiling and floor.

Cabin in Davenport

5 out of 5 average rating, 7 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!

A large, moss-draped oak tree stretches across the scene as the sun sets over Lake Rosalie. The warm colors of the sunset are visible through the tree branches, creating a serene natural backdrop. Glistening water is seen beyond the tree line.

Cabin in Lake Wales

5 out of 5 average rating, 3 reviews

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

The open living area is highlighted by wood accents and large windows allowing natural light. A comfortable sofa is paired with a rustic wooden coffee table, while a dining table complements the space. A flat-screen TV is mounted on the wall, surrounded by nature-themed decor.

Cabin in Davenport

5 out of 5 average rating, 10 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!

Guest favourite