
Ski-in/Ski-out holiday rentals in Kissimmee
Find and book unique ski-in/ski-out homes on Airbnb
Top-rated ski-in/ski-out rentals in Kissimmee
Guests agree: These ski-in/ski-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.

Luxury home with Heated Pool near Disney!
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.

5-BR Luxury Villa with Pool - Disney Delight
3312 LW 5-BR Luxury Villa with Pool Disney Delight 🏠 Entire Place – Experience the ultimate in comfort and privacy in our spacious 5-bedroom, 6-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: 16:00 ✅ Check-out: 10:00 🚫 No pets, parties, or smoking 👤 Minimum booking age: 21 years old

!! Large/Spacious Condo over Breathtaking views!!
Come relax in paradise over breathtaking views! Only 1 mile from Disney! Wake up to a romantic sunrise from your spacious balcony. Enjoy a stroll on the boardwalk. Sip a refreshing cocktail from the Tiki Bar while relaxing poolside. Soak your sore muscles in the Jacuzzi. Covered parking, security elevators with keyed access. Watersports will deliver jet skis and pontoon or ski boats right to our dock on Lake Bryan for some aquatic fun! Shopping, dining and Mini Golf in walking distance

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

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

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

4701-Lake Berkley villa- Renovated 3 bed
This homes location is convenient to everything- just off Hwy 192 at Marker 14. Less than 10 minutes away from Disney and about 15 minutes away from Universal Studios & Sea World. 3 bedrooms and 2 bathrooms with a private pool facing a lake. What can be better? Fish at the lake in the afternoons after a long day at parks or relax at the pool and cook homemade meals in the fully equipped kitchen.
Popular amenities for Kissimmee ski-in/ski-out rentals
Ski-in/ski-out house rentals

Encantada Resort:Pool Gym Clubhouse 10mi to Disney

Storey Lake Home:Pool, Gym, Lazy River&near Disney

The Best Vacation Home & Orlando Near Disney!

lodging

Pet-Friendly Home w/Pool near Disney&ChampionsGate

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/ski-out home rentals

510 BS - 5BD Cozy Family Haven with Pool

Stunning Townhome with Private Pool

Luxury 8BR Villa-Private Pool and Themed Bedrooms

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

Luxury 3-Bed Condo in Storey Lake Resort

Brand New 3 Bedrooms Close to Disney

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

The Hub - Brand New 3 Bedrooms Close to Disney
Ski-in/ski-out condo rentals

Penthouse Level! Disney! Ensuite king-bed/bathroom

Lake Buena Vista Condo facing Disney Fireworks

8507 Retreat 3 Bedroom Condo near Disney

1802 Cozy Condo 3 min Universal

8102 Vacation getaway at Windsor

2701 Enclave Condo near Univesal-Lakeview

8102 Vacation getaway at Windsor

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 | $205 AUD | $182 AUD | $214 AUD | $200 AUD | $154 AUD | $180 AUD | $183 AUD | $151 AUD | $171 AUD | $165 AUD | $179 AUD | $223 AUD |
| 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 ski-out in Kissimmee

Total holiday rentals
Explore 20 holiday rentals in Kissimmee

Nightly prices starting at
Kissimmee holiday rentals start at $76 AUD 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 and kid-friendly amenities

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
20 of Kissimmee holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- Universal's Volcano Bay
- SeaWorld Orlando
- Disney Springs
- Discovery Cove
- Old Town Kissimmee
- Disney's Animal Kingdom Theme Park
- Magic Kingdom Park
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Walt Disney World Resort Golf
- Aquatica
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- Universal's Islands of Adventure
- Kissimmee Lakefront Park
- Ventura Country Club
- Shingle Creek Golf Club

