Cabin holiday rentals in Kissimmee

4.97 out of 5 average rating, 63 reviews

Cabin in St. Cloud

“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

4.92 out of 5 average rating, 201 reviews

Cabin in Orlando

Peaceful wooden bungalow w private yard

NOTHING IS SHARED, very private with your own entrance, Take it easy at this unique and tranquil getaway. A wooden cabin with a private back yard perfect for a couple. Centrally located 15 minutes from MCO airport + downtown Orlando, 30 minutes to Disney, Universal, Sea World. Kitchenette with all amenities, free parking, fresh sheets, towels, coffee! WiFi + Smart TV Netflix, Prime, Hulu, etc. This Bungalow in the city sleeps 2 people on a luxurious queen bed. We live close by should you need us

4.75 out of 5 average rating, 156 reviews

Cabin in Christmas

Clear Landing /Cabin in the Forest

This is 2 acres nestled in 53,000 acres of forest, yet just 1 min. Tosohatchee Wildlife Mangt Area, 5 min. to Ft. Christmas Historical Park, 20 min. to Orlando Airport, 20 min. to Kennedy Space Center, 30 min. to Jetty Park Beach (Atlantic Ocean), 10 min. Lone Cabbage Air-boat rides on the St. Johns River, 45 min. Disney World & many other attractions.. You’ll love my peaceful place, because of the Diverse change of environment w/in min. & gives you a variety of pleasures w/in just mins.

5 out of 5 average rating, 32 reviews

Cabin in Lake Alfred

Lakefront Cabin in Private Woods - Central Florida

Located in the "Heart of Florida." Halfway between Tampa & Orlando. Previous guests describe: Breathtaking sunrises. Wide-open views. A cozy and comfortable space. Perfect for relaxing and recharging. An oasis of serenity nestled on a quiet lake—with total privacy. Immaculate. Squeaky-clean. Frequent wildlife sightings. Thoughtfully stocked with amenities. Truly a home away from home… a little piece of heaven. Beaches are only 75-90 miles to either coast. Check in/out 1:00pm.

4.9 out of 5 average rating, 96 reviews

Cabin in Orlando

Private cabin 15 min to downtown, Valencia or MCO

Located in a safe area (3 min walk to bus 15), this cozy cabin (8x12ft.) in my private yard has a queen bed, mini fridge, microwave, Roku TV, window A/C (space heather available). The kitchen, bathroom and shower are NOT inside the cabin. They are about 20ft away and shared with other guests. This cabin is mostly enjoyed by outdoor lovers. Downtown is 6.5mi away, Florida Hospital East -1,5 mile, MCO airport -8.5mi, Valencia College -4mi. Free street parking for one car.

Cabin in Lake Panasoffkee

4.84 out of 5 average rating, 189 reviews

Lake Pan Cabin #2

This quaint one room cabin provides a tranquil lake view with a front porch swing for your ultimate relaxation. Restroom located within a few feet and a larger bath house (with shower) located less than 300 feet from cabin. Charcoal grills and a fire pit located near the cabin for your use. Complimentary use of our single kayaks or canoe. The boats are available after 9am (office opens) and must be returned by 3:30pm. They are not available when the office is closed.

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!

5 out of 5 average rating, 22 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!

5 out of 5 average rating, 14 reviews

Cabin in Geneva

Cabin Near Disney & Beach | Spa, Firepit & More!

Experience the charm of a Unique 3BR/2BA log cabin retreat on a 3.7-acre oasis! Enjoy a jacuzzi, firepit, outdoor kitchen, ping pong, soccer area, and hammock under the trees. The huge paver deck is perfect for gathering. Feel secluded yet be minutes from markets & dining. Go fishing, horseback riding, or hiking nearby. Whether for family fun, a romantic escape, or a remote work retreat, adventure & relaxation await!

4.9 out of 5 average rating, 59 reviews

Cabin in Christmas

Cozy Cabin in Orlando

Forget your worries in this spacious and serene space. Enjoy your stay in this completely remodeled cozy, clean home siting on one half acre lot surrounded by big oak trees and providing a feeling of calmness and a connection with nature. Perfect place to relax after enjoying Orlando's attractions all or a long day at the beach. SNOW BIRD PARADISE Featuring a spacious lot to park recreational toys 🚤🚐

5 out of 5 average rating, 76 reviews

Cabin in Geneva

Modern log cabin between the beach and Disney

Relax in this calm, stylish cabin tucked away on over a half acre. 3 bedroom, 2 bath modern space. Take in views of the horses next door while sitting on the front porch. Conveniently located between the beach and Disney. 9.5 miles to UCF, 6.5 miles to Boombah Sports Complex, 13 miles to historic Sanford. Plenty of parking. Bring your boat and go fishing in the nearby St. Johns River.

4.98 out of 5 average rating, 45 reviews

Cabin in Center Hill

Woodsy cabin close to major theme parks

This is a woodsy getaway in a small town. Take it easy at this unique and tranquil getaway, or play all day at the theme parks then come home to relax on your screened porch and watch the birds in all the surrounding old oak trees. All the major theme parks are less than an hour away. Head to Tampa/St Pete to the beach just 90 minutes away, or just relax in the woods!

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Popular amenities for cabin rentals in Kissimmee

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cabin rentals with a hot tub

CherylRating, 5 stars1 week ago

Authentic Disney Fort Wilderness Cabin near WDW

It is very nice . Just as described if not more than. Felt like a home. Loved the swimming pools. I would go back there anytime I need a vacation! Victor is very accommodating and very nice to deal with!

4.68 out of 5 average rating, 120 reviews

Romantic Cabin w/ Balcony + Tub + Hammock + Grill

SkyeRating, 5 stars1 week ago

Wonderful place to stay, Angelica, Sebastian, and Joseph were very quick to respond and attentive. Would 100% stay over again

RichardRating, 5 stars14 months ago

Relax & Reboot - Fantastic Margaritaville Cottage

The place was amazing and clean. Check in instructions were a little unclear and I would like them to be delivered earlier. The hot tub was low on water and dirty and not private at all. There is no privacy

Cabin in St. Cloud

Economic studio Lake nona.

zenRating, 5 stars3 months ago

their the best hosts I've ever had. they were super flexible about the check in time and very accommodating to a flexible lifestyle. would definitely recommend this place to singles or new couples nice cozy private clean cold ASF ac!!! what's not to love the neighborhood always feels like home when I drive thru it. fell in love with the trees around right away! overall 9/10

Cabin in Four Corners

Sunny Margaritaville Cottage - Private Pool, Full

Cabin in Clermont

The Caddie Shack

Private room in Orlando

Westgate Lakes Resorts & Spa 3 bedroom-Orlando FL

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Pet-friendly cabin rentals

Cabin in Lake Panasoffkee

4.88 out of 5 average rating, 145 reviews

Lake Pan Cabin #1

GabeRating, 5 stars9 months ago

Had a great weekend! Kayaking the lake was a plus!

DeborahRating, 5 stars1 month ago

Studio vacacional cerca de legoland/disney

Nos encanto. Todo muy hermoso y limpio. Perfecto para relajarse

MarinaRating, 5 stars2 months ago

Great cabin for a couple at lakeside retreat

I absolutely loved this place and so did my pup. Mrs. Cheryl and her husband are the best, the cabin was so clean and beautiful. I definitely recommend coming to this beautiful relaxing paradise. we will definitely be back

Superhost

Private room in Groveland

4.88 out of 5 average rating, 8 reviews

Florida’s country living retreat

ShauntaeaRating, 5 stars3 months ago

Felt very homey , definitely a change of scenery love that the cows were out said good morning. It was overall a great experience.

KristaRating, 5 stars3 months ago

Cozy two bedroom cabin at lakeside retreat

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Cute 2 Bedroom cabin at lakeside retreat

Adorable cabin at lakeside retreat

Amazing views from Lake House

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Private cabin rentals

5 out of 5 average rating, 6 reviews

Cabin in Geneva

Cabin 52

CathieRating, 5 stars5 months ago

Cabin 52 is a peaceful retreat! Excellent Communications. Immaculate. Well stocked kitchen. The most comfortable beds! This location exceeded our expectations! We will definitely be back.

Cabin in Apopka

KyleRating, 5 stars4 days ago

Charming Hidden Cabin

⭐️⭐️⭐️⭐️⭐️ Cozy, Peaceful, Perfect This hidden cabin is an absolute gem! Tucked away in nature, it’s cozy, clean, and full of thoughtful touches — from comfy blankets to twinkling lights and fresh coffee. We loved sitting on the porch in the morning just listening to the nature around us. It’s the perfect escape to relax and recharge. The host was kind and responsive. We didn’t want to leave and can’t wait to come back.

5 out of 5 average rating, 13 reviews

Cabin in Christmas

Entire Cabin at peaceful Retreat in Christmas, FL

AlonaRating, 5 stars1 week ago

My family and I were looking for a quiet and cozy place to relax and get away, and we found it. The accommodation is clean and spacious. The kitchen is equipped with everything down to the smallest details. We will definitely come back here again. ☺️☺️👍🏻

Superhost

5 out of 5 average rating, 4 reviews

Vintage Disney Cabin -Close to parks!

DavideRating, 5 stars2 weeks ago

A great stay. Really. The entire property is very well planned and maintained. A definite “cabin in the woods” atmosphere. Location is also a huge plus; it’s not in the middle of Orlando/Disney crowd, but not too far away from town. Already looking forward to another stay.

Superhost