
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.

Luxurious Retreat near Disney: Pool & Game Room
Welcome to our exquisite 7-bedroom villa nestled in the prestigious Windsor at Westside Resort! Ideal for large families or groups, this luxurious home boasts a private pool, expansive living room, and a fully equipped kitchen. Revel in the fun of the in-house game room with a pool table, and stay comfortable with air conditioning. A maximum of four vehicles is permitted for this property. The nearby clubhouse offers a resort-style pool with a waterslide, a lazy river, a fitness center, volleyba

“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.

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

2605 A Skyborne Retreat, The Enclave, Orlando
Not all homes are built—some are discovered, like a hidden gem shimmering between reality and dream. Welcome to The Enclave, Unit 2605, a 2-bedroom sanctuary suspended between the pulse of Orlando and the tranquility of an ethereal retreat. This isn’t just a condo—it’s a portal to an entirely new way of living. The open-concept living space is a masterpiece of motion and stillness—a place where time slows for quiet mornings yet speeds up for nights filled with energy.

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.

Luxury 3-Bed Condo in Storey Lake Resort
3131 PD - Luxury 3-Bed Condo in Storey Lake Resort 🏠 Entire Place – Experience the ultimate in comfort and privacy in our spacious 3-bedroom, 2-bathroom condo, accommodating up to 7 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

2701 Enclave Condo near Univesal-Lakeview
The 2-bedroom, 2-bathroom condo in Enclave near Universal is a modern and stylish living space designed for comfort and convenience. The open-concept layout features a spacious living room with large windows that fill the space with natural light. It is equipped with contemporary furnishings and flows seamlessly into the dining area and kitchen. The kitchen boasts stainless steel appliances, granite countertops, and ample cabinetry.

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.📍 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. 🌟 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

Spacious Pool Home w/ 2 Masters, Games Room

Pet-Friendly Home w/Pool near Disney&ChampionsGate

Windsor Hills Home w/Arcade Game Room|Near Disney

Luxury Storey Lake 10 Bedroom HM

Cozy 3BR Condo in Gated Resort with Pool

Solterra Lazy river 8004-Pool &Spa by Disney

Resort home, Lakeview, private pool (4417AC)

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

510 BS - 5BD Cozy Family Haven with Pool

Exclusive 8BR Themed Villa • Private Pool Retreat

4840 A Hidden Gem in the Heart of Orlando – 303

Disney Dreams: 5BR Luxury Retreat, Poolside Paradi

Brand New 3 Bedrooms Close to Disney

The Hub - Brand New 3 Bedrooms Close to Disney

5-BR Luxury Villa with Pool - Disney Delight

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

8102 Vacation getaway at Windsor

Penthouse Level! Disney! Ensuite king-bed/bathroom

1802 Cozy Condo 3 min Universal

2701 Enclave Condo near Univesal-Lakeview

Lake Buena Vista Condo facing Disney Fireworks

8102 Vacation getaway at Windsor

Club Wyndham Cypress Palms Resort (Deluxe)

2301 Upgraded 2BR/2Ba Enclave | Resort View
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £98 | £87 | £103 | £96 | £74 | £87 | £98 | £86 | £72 | £82 | £101 | £124 |
| 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 £51 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
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- Ski-in/ski-out rentals Osceola County
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Universal's Volcano Bay
- Give Kids the World Village
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Old Town
- Kia Center
- Reunion Resort Golf Courses - Palmer & Watson
- Aquatica
- ICON Park
- Disney's Hollywood Studios
- Island H2O Live!
- Camping World Stadium
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club






