Cabin vacation rentals in Osceola County

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Top-rated cabin rentals in Osceola County

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Cabin in River Ranch

New place to stay

New Years Eve! Westgate River Ranch Resort & Rodeo

Rockin New Year's Eve! Available Fri. 12/27 - Fri. 1/3/25 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+

Guest favorite

Cabin in St. Cloud

5 out of 5 average rating, 40 reviews

“Tailypo” - Charming Studio Cabin

Welcome to what we affectionately call “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 some modern amenities.

Cabin in Dripping Springs

New place to stay

Upstay - Dreamland Cabin with Loft

Come visit Texas without breaking the bank by staying in this cabin at Dreamland! This home is designed to maximize space and optimize functionality. Featuring a full sized bedroom, and an additional bedroom loft, there's enough space for up to 4 guests to stay here. Located at the Dreamland entertainment venue, which offers fun for the whole family (pay-to-play services but kids under 5 play free). Enjoy pickleball, mini golf, live entertainment, a family friendly beer garden and more.

Cabin in Babson Park

4.9 out of 5 average rating, 21 reviews

Sunrise on the Lake

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 Kissimmee

New place to stay

Mouse House Cabin / Near Disney

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!

Guest favorite

Cabin in Davenport

4.93 out of 5 average rating, 201 reviews

$69! Cozy Cabin- Disney 20 Miles Away!

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

Cabin in Lake Wales

New place to stay

Freedom Cabin

***MUST HAVE ACCESS TO GET YOURSELF INTO RIVER RANCH POA AND MUST BRING FUEL FOR GENERATOR*** Bring your own towels and queen bed sheets. There are 4 pillows provided. 24x24 cabin. 2 12x8 rooms and a 16x24 living room detached bathhouse. Amnesties: 2 queen beds 2 couches. Hot water, outside sink, hot plate, pots and pans, paper plates plastic silverware. Propane Flattop and Outdoor sink. Fridge Freezer.