
Ski-in/Ski-out holiday rentals in Kissimmee
Find and book unique ski-in/out homes on Airbnb
Quick stats about holiday rentals that are ski-in/out in Kissimmee

Total holiday rentals
Explore 10 holiday rentals in Kissimmee

Nightly prices starting at
Kissimmee holiday rentals start at $90 SGD per night before taxes and fees

Verified guest reviews
Over 350 verified reviews to help you choose

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

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Kissimmee holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Kissimmee rentals
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.

510 BS - 5BD Cozy Family Haven with Pool
510 BS - 5BD Elegant Escape: Private Haven 🏠 Entire Place – 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. 🔐 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

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

ideal para estancias cortas o prolongadas
Disfruta de la sencillez de este alojamiento tranquilo y céntrico.📍 Excelente ubicación: A solo 5 minutos del Aeropuerto Internacional de Orlando (MCO) y con fácil acceso a las principales autopistas. A pocos minutos encontrarás restaurantes, tiendas, supermercados y atracciones como Lake Nona, el Florida Mall y los parques temáticos de Disney y Universal a corta distancia. 🌟 Perfecto para estancias cortas, viajes de trabajo o una escapada relajante antes de tu vuelo

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.

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

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 Orlando’s top attractions. Book now for an unforgettable stay!

Brand-new home with Reunion Village amenities
This home features 3 bedrooms and 2 bathrooms with an open-concept layout, including a fully equipped kitchen, dining area, and spacious living room perfect for family gatherings. Enjoy the ping pong table and kids' play area for added fun. The community offers a variety of amenities, including seven pools, a fitness center, playgrounds, gift shop and access to resort restaurants. Just a few minutes from Disney.

25% Off 8BR Villa. Private Pool/Spa/ Game Room
You won't regret to choose this house for your Orlando vacation, this well equipped home is just 15 min away from all the Disney parks and a few miles away from most convenient restaurants, markets and fun areas of Kissimmee and Orlando. Our private pool and spa adds to the whole fun in this gated neighborhood. A property like this is rare to find. Speak Portuguese, Spanish, Turkish and English.

Great Value 3BR Villa w/ Private Pool & Game Room
Elegant 3BR Villa with Private Pool & Game Room in Emerald Island Resort Welcome to your dream vacation home! This luxurious 3-bedroom, 2-bathroom villa is located in the prestigious Emerald Island Resort in Kissimmee. Perfect for families and large groups, this spacious home offers top-notch amenities and a prime location just minutes from Disney World and other top attractions.
Popular amenities for Kissimmee ski-in/out rentals
Ski-in/out house rentals

Encantada Resort:Pool Gym Clubhouse 10mi to Disney

Spacious Pool Home w/ 2 Masters, Games Room

alojamiento

Cozy 2-Bed Studio with Pool & A/C

Windsor Hills Home w/Arcade Game Room|Near Disney

Luxury Storey Lake 10 Bedroom HM

8848 BC - 8Bds Windsor At Westside

Resort home, Lakeview, private pool (4417AC)
Family-friendly, ski-in/out home rentals

Stunning Townhome with Private Pool

Exclusive 8BR Themed Villa • Private Pool Retreat

Luxurious Retreat near Disney: Pool & Game Room

Luxury 3-Bed Condo in Storey Lake Resort

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

Cozy 3BR Condo in Gated Resort with Pool

Family Home w/ Pool & Resort Perks Near Disney

5BR Villa Near Disney | Windsor Westside
Ski-in/out apartment rentals

MARBELLA beautiful residential complex

Penthouse Level! Disney! Ensuite king-bed/bathroom

Tuscana Resort,Disney a 17 minutos

25% Off Stylish Disney Condo Near Parks! Pool/Arca

Club Wyndham Cypress Palms Resort (Deluxe)
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $172 SGD | $180 SGD | $179 SGD | $168 SGD | $130 SGD | $152 SGD | $172 SGD | $150 SGD | $126 SGD | $143 SGD | $176 SGD | $217 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 |
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Key West Holiday rentals
- Tampa Bay Holiday rentals
- Rentals with beach access Kissimmee
- Rentals with a fireplace Kissimmee
- Cottage rentals Kissimmee
- Lakehouse rentals Kissimmee
- Apartment rentals Kissimmee
- Resort rentals Kissimmee
- Rentals with a washing machine and dryer Kissimmee
- Rentals with an accessible-height bed Kissimmee
- Fitness-friendly rentals Kissimmee
- Rentals with pools Kissimmee
- Rentals with outdoor seating Kissimmee
- Rentals with a hot tub Kissimmee
- Rentals with an EV charger Kissimmee
- Family-friendly rentals Kissimmee
- Flat rentals Kissimmee
- Rentals with a cinema Kissimmee
- Holiday home rentals Kissimmee
- Rentals with lake access Kissimmee
- Mansion rentals Kissimmee
- Villa rentals Kissimmee
- Pet-friendly rentals Kissimmee
- Private suite rentals Kissimmee
- Rentals with breakfast Kissimmee
- Waterfront rentals Kissimmee
- Cabin rentals Kissimmee
- Beachfront rentals Kissimmee
- Serviced apartment rentals Kissimmee
- Hotel rooms Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Guest house rentals Kissimmee
- Beach house rentals Kissimmee
- Rentals with an accessible-height toilet Kissimmee
- Rentals with a kayak Kissimmee
- Rentals with a sauna Kissimmee
- House rentals Kissimmee
- Tiny house rentals Kissimmee
- Rentals with a firepit Kissimmee
- Townhouse rentals Kissimmee
- Ski-in/ski-out rentals Osceola County
- Ski-in/ski-out rentals Florida
- Ski-in/ski-out rentals United States
- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Camping World Stadium
- Reunion Resort Golf Courses - Palmer & Watson
- Aquatica
- University of Central Florida
- ICON Park
- Disney's Hollywood Studios
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- ESPN Wide World of Sports







