
Ski-in/out vacation 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

4 Bed Villa Ultimate Family Adventure Awaits
Modern 4-Bedroom Villa for 10 🏠 Entire Place – Experience the ultimate in comfort and privacy in our spacious 4-bedroom, 4-bathroom home, accommodating up to 10 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

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.

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 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

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

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
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

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

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

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

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

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

Remodeled Studio by Disney-Resort- New Listing

5-BR Luxury Villa with Pool - Disney Delight

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

Penthouse Level! Disney! Ensuite king-bed/bathroom

1802 Cozy Condo 3 min Universal

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 | $186 CAD | $165 CAD | $194 CAD | $182 CAD | $140 CAD | $164 CAD | $186 CAD | $162 CAD | $136 CAD | $149 CAD | $162 CAD | $203 CAD |
| 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 vacation rentals that are ski-in/out in Kissimmee

Total vacation rentals
Explore 20 vacation rentals in Kissimmee

Nightly prices starting at
Kissimmee vacation rentals start at $97 CAD per night before taxes and fees

Verified guest reviews
Over 370 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Kissimmee vacation 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
- Give Kids the World Village
- Disney Springs
- Walt Disney World Resort Golf
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- ESPN Wide World of Sports
- Disney's Animal Kingdom Theme Park
- Epcot
- Old Town
- Kia Center
- Reunion Resort Golf Courses - Palmer & Watson
- Universal's Volcano Bay
- Discovery Cove
- Aquatica
- Bluegreen Vacations Fountains, Ascend Resort Collection
- Disney's Hollywood Studios
- Island H2O Live!
- ICON Park
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club






