Cabin holiday rentals in Osceola County

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Top-rated cabin rentals in Osceola County

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Top Guest favourite

Cabin in St. Cloud

4.97 out of 5 average rating, 63 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

Cabin in Kissimmee

New place to stay

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 Davenport

Small Cabin - Chill Relaxing

Located In Kissimmee Florida 20 minutes to Disney, 5 minutes to shopping, Centrally located near all theme parks and event areas in Orlando. You'll love this unique, super clean escape from the hustle and bustle. Perfect for anyone who wants some peace and quiet! Professionally cleaned and prepared for each guest. Full fridge, full kitchen, full bathroom. Private Lake w/ Fish! Sit on the new porch and sip your coffee or tea! guests that stay here fall in love with it! WIFI and TV in the cabin!

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 Kissimmee

New place to stay

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 and decorative flavor. Great for families w/children for a long stay at a resort with pool, mini golf, playgrounds, dog park and wonderful amenities on site. Walking to shopping, restaurants, nature and entertainment. 10 minutes drive to Disney, 18 to MK, 16 min. To Hollywood, etc. Bus direct to MK!

Top Guest favourite

Cabin in Babson Park

5 out of 5 average rating, 5 reviews

Lakeside Crooked Lake Cottage

Rise n shine to beautiful sunrises on the lake, where you can bring your boat and poles to catch fish on one of Florida’s premium water ways. Outstanding Crooked lake is roughly 5000+ acres, offering an abundance of fish species, including largemouth bass, speck(crappie), bluegill, shellcracker, catfish, and tilapia. This lovely two-bedroom, one-and-half-bath is located on the shores of Crooked Lake and features a small private beach and includes a boat slip, depending on availability.

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 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 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.

Top Guest favourite

Cabin in Davenport

5 out of 5 average rating, 6 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

Cabin in Kissimmee

5 out of 5 average rating, 23 reviews

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!

Cabin in Davenport

Studio vacacional cerca de legoland/disney

Take a break and relax in this peaceful place surrounded by nature and warm scenery. It is a room with kitchen and bathroom so you can enjoy a comfortable vacation. There are 2 similar apartments you can attach if you have a trip with more people. There is a spacious house for 8 people and another room of 3. You can ask me about your needs.