
Ski-in/Ski-out holiday rentals in Kissimmee
Find and book unique ski-in/out homes on Airbnb
Top-rated ski-in/out rentals in Kissimmee
Guests agree: these ski-in/out homes are highly rated for location, cleanliness and more.

Stylish Family Villa with Game Room & Pool
Escape to our luxurious villa, perfect for families and groups. Enjoy modern amenities, a spacious living room, a fully equipped kitchen, and themed bedrooms. Relax by the private pool or have fun in the game room. Conveniently located near Disney, Universal, and other top attractions, it's your ideal vacation home. A maximum of five vehicles is permitted for this property. Resort features include a state-of-the-art clubhouse, heated pool, lazy river, splash park, gym, and more. Book now for an

“Casa Del Sol”
"Casa Del Sol" is an exquisitely clean stay. We have all NEW furniture. And never forgetting our four legged friends,we have some toys and a comfortable and clean yard. "Casa Del Sol" has security cameras, although it is peacefully quiet to rest.PLUS there is what you like near you.Located minutes from the attractions.*Disney Springs -2.4 Miles *Magic Kingdom -7.4 *Animal Kingdom *Hollywood Studios -4.2 *Epcot -4.1 *Universal Studios and Universal CityWalk -9*SeaWorld Orlando-4.8 *Walmart 1 min

UniqueStay w Lakeview/DisneyFireworks/WaterSports
Romantic lakefront escape with sunset views, nightly Disney fireworks, and a private oversized balcony. Unwind in the jacuzzi after a day at the parks, sip cocktails by the pool, or stroll hand in hand along the lakeside boardwalk. Starbucks and dining steps away, Disney Springs and theme parks minutes away. A serene retreat where magic meets the water—perfect for couples. Outlets shopping just few mins, restaurants groups surrounded give you perfect romantic dinners, unforgettable experiences.

4-Bed Luxury: Private Pool, Disney Suites Await!
Storey Lake Getaway: Stylish 4-Bedroom Pool Home 🏠 Entire Place – Experience the ultimate in comfort and privacy in our spacious 4-bedroom, 3-bathroom home, accommodating up to 8 guests. Your dream vacation starts here. 🔐 Self Check-In – Enjoy a seamless arrival with our keyless entry system. You'll receive a personalized door code for convenient, stress-free access. 📌 House Rules ✅ Check-in: 4:00 PM ✅ Check-out: 10:00 AM 🚫 No pets, parties, or smoking 👤 Minimum booking age: 21 years old

Luxury home with Heated Pool near Disney!#2
Nuestro espacio en Airbnb es único y especial por varias razones. En primer lugar, nuestra ubicación es excepcional. Estamos situados en un tranquilo vecindario, lejos del bullicio de la ciudad, pero lo suficientemente cerca como para acceder fácilmente a todas las atracciones principales. Además, ofrecemos vistas impresionantes de la naturaleza circundante, lo que brinda a nuestros huéspedes una sensación de paz y tranquilidad. En cuanto al diseño, hemos creado un espacio acogedor y elegante.

8102 Vacation getaway at Windsor
Introducing your dream Disney vacation rental at Winsdor Palms Resort, fully furnished and beautifully remodeled for your ultimate comfort and enjoyment. Step inside to discover a newly renovated kitchen featuring sleek cabinets, modern appliances, and stunning quartz countertops, perfect for preparing delicious meals and snacks with family. The bathrooms have undergone a complete transformation with stylish vanities and quartz countertops, offering a touch of luxury and elegance. No Carpets.

MARBELLA beautiful residential complex
Diviértete con toda la familia en este alojamiento Have fun with the whole family in this accommodation with style and a lot of comfort for your vacations, located in the center of kissimme just 15 minutes from the most fun parks of Disney world, restaurants, shops, recreational parks and much more in one place, the community has a swimming pool, picnic area, Gin, lake, free parking, 24 hour security and much more you will not regret choosing this beautiful quiet and crowded place

Near Disney, comfortable house,10 min to the parks
Stay just 10 minutes from Disney, Epcot, and Hollywood Studios at our "Near Disney Wonderful House Spa Pool Resort." Relax in your private spa and pool, and enjoy 3 cozy bedrooms (1 king, 1 queen, and 2 twins), each with a TV, plus 2.5 bathrooms. The fully equipped kitchen and in-home laundry make your stay hassle-free. Close to SeaWorld, outlets, and restaurants, our home is the perfect retreat for family fun and relaxation. Book now and create magical memories!

Tuscana Resort,Disney a 17 minutos
Welcome to Disney's Tuscana Resort at the exclusive Champion Gate Resort.Modern apartment offerings Luxury & Comfort enjoy a refreshing pool,Relax in the hot tub,stay fit in the gym,sip delicious cocktails and beverages at the Tiki bar,enjoy some delicious and flavorful dining at the restaurant open late! shops and attractions within walking distance! Attractions like Disney World are only 7 miles away! The perfect family getaway unforgettable memories and fun.

Spacious Pool Home w/ 2 Masters, Games Room
Mickey’s Holiday Home has everything you could want in a vacation rental home. You'll love the feeling of spaciousness in this home, the two master suites, the pool and spa, the privacy, the quiet neighborhood, and the wonderful view from the pool deck. It's also close to Disney and other Orlando attractions, restaurants and shops. As you enter the home, you find yourself in the spacious living room which features comfortable seating and a large flat screen TV.

8848 BC - 8Bds Windsor At Westside
🏠 Entire Place – Experience the ultimate in comfort and privacy in our spacious 8-bedroom, 6-bathroom home, accommodating up to 18 guests. Your dream vacation starts here. 🔐 Self Check-In – Enjoy a seamless arrival with our keyless entry system. You'll receive a personalized door code for convenient, stress-free access. 📌 House Rules ✅ Check-in: 4:00 PM ✅ Check-out: 10:00 AM 🚫 No pets, parties, or smoking 👤 Minimum booking age: 21 years old

ideal for short or long stays
Enjoy the simplicity of this quiet and central accommodation.📍 Excellent location: Just 5 minutes from Orlando International Airport (MCO) and with easy access to major highways. A few minutes away you will find restaurants, shops, supermarkets and attractions such as Lake Nona, the Florida Mall and the Disney and Universal theme parks within walking distance. 🌟 Perfect for short stays, business trips, or a relaxing getaway before your flight
Popular amenities for Kissimmee ski-in/out rentals
Ski-in/out house rentals

Modern 4BR Villa with Private Pool & Spa

Encantada Resort:Pool Gym Clubhouse 10mi to Disney

Pet-Friendly Home w/Pool near Disney&ChampionsGate

Budget & Pet Friendly Charming Family Suite

Windsor Hills Home w/Arcade Game Room|Near Disney

Luxury Storey Lake 10 Bedroom HM

Cozy 3BR Condo in Gated Resort with Pool

Family Home w/ Pool & Resort Perks Near Disney
Family-friendly, ski-in/out home rentals

510 BS - 5BD Cozy Family Haven with Pool

Stunning Townhome with Private Pool

Exclusive 8BR Themed Villa • Private Pool Retreat

4840 One-of-a-kind luxury 4 BD at VistaCay #107

Disney Dreams: 5BR Luxury Retreat, Poolside Paradi

7462 Themed Villa 6BD - Pool & Spa-Game room

2605 A Skyborne Retreat, The Enclave, Orlando

Windsor at Westside - Amazing 5bd Villa
Ski-in/out apartment rentals

Penthouse Level! Disney! Ensuite king-bed/bathroom

8102 Vacation getaway at Windsor

1802 Cozy Condo 3 min Universal

2701 Enclave Condo near Univesal-Lakeview

Club Wyndham Cypress Palms Resort (Deluxe)
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $172 SGD | $153 SGD | $180 SGD | $168 SGD | $130 SGD | $152 SGD | $172 SGD | $150 SGD | $126 SGD | $137 SGD | $150 SGD | $188 SGD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Quick stats about holiday rentals that are ski-in/out in Kissimmee

Total holiday rentals
Explore 20 holiday rentals in Kissimmee

Nightly prices starting at
Kissimmee holiday rentals start at $64 SGD per night before taxes and fees

Verified guest reviews
Over 460 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
20 of Kissimmee holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Kissimmee rentals
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- Ski-in/ski-out rentals Osceola County
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- Ski-in/ski-out rentals United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Walt Disney World Resort Golf
- Magic Kingdom Park
- Disney's Animal Kingdom Theme Park
- Old Town
- Epcot
- ESPN Wide World of Sports
- Kia Center
- Reunion Resort Golf Courses - Palmer & Watson
- Universal's Volcano Bay
- Discovery Cove
- Aquatica
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Universal's Islands of Adventure
- Ventura Country Club
- Shingle Creek Golf Club






