
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

โCasa Del Solโ
"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 waterโperfect for couples. Outlets shopping just few mins, restaurants groups surrounded give you perfect romantic dinners, unforgettable experiences.

Luxury home with 4Bd Heated Pool near Disney
Nuestro espacio en Airbnb es รบnico y especial por varias razones. En primer lugar, nuestra ubicaciรณn es excepcional. Estamos situados en un tranquilo vecindario, lejos del bullicio de la ciudad, pero lo suficientemente cerca como para acceder fรกcilmente a todas las atracciones principales. Ademรกs, ofrecemos vistas impresionantes de la naturaleza circundante, lo que brinda a nuestros huรฉspedes una sensaciรณn de paz y tranquilidad. En cuanto al diseรฑo, 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.

510 BS - 5BD Cozy Family Haven with Pool
510 BS - 5BD Elegant Escape: Private Haven ๐ Entire Place โ Experience the ultimate in comfort and privacy in our spacious 5-bedroom, 5-bathroom home, accommodating up to 14 guests. Your dream vacation starts here. ๐ Self Check-In โ Enjoy a seamless arrival with our keyless entry system. You'll receive a personalized door code for convenient, stress-free access. ๐ House Rules โ Check-in: 4:00 PM โ Check-out: 10:00 AM ๐ซ No pets, parties, or smoking ๐ค Minimum booking age: 21 years old

Encantada Resort:Pool Gym Clubhouse 10mi to Disney
Welcome to your vacation haven at Encantada Resort, a secure and gated community just minutes from Disney! This 3-bedroom villa comfortably sleeps up to 7 guests and features a private pool, spacious living and dining areas, and a fully-equipped kitchen with modern amenities. Relax in this stylish retreat with convenient parking and access to resort amenities like a clubhouse, gym, and heated pools. Perfect for a memorable family getaway close to all the excitement Orlando has to offer!

MARBELLA beautiful residential complex
Diviรฉrtete 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

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.

Luxurious house near Disney
Our space on Airbnb is unique and special for several reasons. First of all, our location is exceptional. We are located in a quiet neighborhood, away from the hustle and bustle of the city, but close enough to easily access all the main attractions. In addition, we offer stunning views of the surrounding nature, which gives our guests a feeling of peace and tranquility. As for the design, we have created a cozy and elegant space

Ideal for short or long stays
Enjoy the simplicity of this quiet and centrally located accommodation.๐ Excellent location: Just 5 minutes from Orlando International Airport (MCO) and with easy access to the main highways. Restaurants, shops, supermarkets, and attractions such as Lake Nona, the Florida Mall, and Disney and Universal theme parks are just a few minutes away. ๐ Perfect for short stays, business trips, or a relaxing getaway before your flight

Storey Lake Home:Pool, Gym, Lazy River&near Disney
Escape to this beautiful home in the secure Storey Lake Resort, just minutes from Disney. Enjoy a private pool, modern kitchen, spacious living and dining areas, and stylish decor. Resort amenities include a clubhouse, heated pool, lazy river, waterslides, gym, and more. Perfect for families or groups, this home offers comfort, convenience, and easy access to Orlandoโs top attractions. Book now for an unforgettable stay!
Popular amenities for Kissimmee ski-in/out rentals
Ski-in/out house rentals

Spacious Pool Home w/ 2 Masters, Games Room

Pet-Friendly Home w/Pool near Disney&ChampionsGate

*Luxury Orlando Oasis | Private Community Gate

Windsor Hills Home w/Arcade Game Room|Near Disney

Luxury Storey Lake 10 Bedroom HM

Family Home w/ Pool & Resort Perks Near Disney

1589Pool House 4bd Villa with game room

8848 BC - 8Bds Windsor At Westside
Family-friendly, ski-in/out home rentals

4 Bed Villa Ultimate Family Adventure Awaits

Stunning Townhome with Private Pool

Exclusive 8BR Themed Villa โข Private Pool Retreat

Disney Dreams: 5BR Luxury Retreat, Poolside Paradi

Luxury Oasis: 5BR/5BA Home, Private Pool

Luxury 3-Bed Condo in Storey Lake Resort

5-BR Luxury Villa with Pool - Disney Delight

4-Bed Luxury: Private Pool, Disney Suites Await!
Ski-in/out apartment rentals

MARBELLA beautiful residential complex

8102 Vacation getaway at Windsor

Club Wyndham Cypress Palms Resort (Deluxe)

Tuscana Resort,Disney a 17 minutos
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 | $143 SGD | $176 SGD | $217 SGD |
| Avg. temp | 16ยฐC | 18ยฐC | 20ยฐC | 22ยฐC | 25ยฐC | 27ยฐC | 28ยฐC | 28ยฐC | 27ยฐC | 24ยฐC | 20ยฐC | 17ยฐC |
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 $90ย SGD per night before taxes and fees

Verified guest reviews
Over 370 verified reviews to help you choose

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

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
10 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
Destinations to explore
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- Ski-in/ski-out rentalsย United States
- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Magic Kingdom Park
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Give Kids the World Village
- Southern Dunes Golf and Country Club






