
Ski-in/Ski-out vacation 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 4Bd 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.

2604 - Chic Villa, Private Pool Bliss
2604 RT - Family Paradise at Storey Lake 🏠 Entire Place – Experience the ultimate in comfort and privacy in our spacious 4-bedroom, 3-bathroom home, accommodating up to 8 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

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.

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

Stylish Disney Condo Near Parks | Pool, Arcade
Welcome to your perfect family getaway near Disney! This beautifully renovated 3-bedroom condo in the sought-after Windsor Palms Resort was designed with comfort, convenience, and fun in mind — making it the ideal home base for young families, moms traveling with kids, couples, and Disney lovers alike. Just minutes from Walt Disney World®, this bright and modern vacation home combines resort-style amenities with all the comforts of home.

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/ski-out rentals
Ski-in/ski-out house rentals

Encantada Resort:Pool Gym Clubhouse 10mi to Disney

Spacious Pool Home w/ 2 Masters, Games Room

Great Value 3BR Villa w/ Private Pool & Game Room

accommodation

Budget & Pet Friendly Charming Family Suite

Windsor Hills Home w/Arcade Game Room|Near Disney

Luxury Storey Lake 10 Bedroom HM

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

4 Bed Villa Ultimate Family Adventure Awaits

510 BS - 5BD Cozy Family Haven with Pool

Stunning Townhome with Private Pool

Exclusive 8BR Themed Villa • Private Pool Retreat

Disney Dreams: 5BR Luxury Retreat, Poolside Paradi

Luxury 3-Bed Condo in Storey Lake Resort

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

4812 BR - Dreamscape Villa
Ski-in/ski-out condo rentals

MARBELLA beautiful residential complex

Penthouse Level! Disney! Ensuite king-bed/bathroom

Tuscana Resort,Disney a 17 minutos

Stylish Disney Condo Near Parks | Pool, Arcade

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 | ﺩ.ﺇ492 | ﺩ.ﺇ514 | ﺩ.ﺇ510 | ﺩ.ﺇ481 | ﺩ.ﺇ371 | ﺩ.ﺇ433 | ﺩ.ﺇ492 | ﺩ.ﺇ430 | ﺩ.ﺇ360 | ﺩ.ﺇ408 | ﺩ.ﺇ503 | ﺩ.ﺇ621 |
| 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 ski-out in Kissimmee

Total vacation rentals
Explore 10 vacation rentals in Kissimmee

Nightly prices starting at
Kissimmee vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

Verified guest reviews
Over 350 verified reviews to help you choose

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

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Kissimmee vacation rentals include wi-fi 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
- Ski-in/ski-out rentals Florida
- Ski-in/ski-out rentals United States
- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Walt Disney World Resort Golf
- 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
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- University of Central Florida
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club






