
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.

Encantada Resort:Pool Gym Clubhouse 10mi to Disney
Welcome to your vacation haven at Encantada Resort, a secure and gated community just minutes from Disney! This 3-bedroom villa comfortably sleeps up to 7 guests and features a private pool, spacious living and dining areas, and a fully-equipped kitchen with modern amenities. Relax in this stylish retreat with convenient parking and access to resort amenities like a clubhouse, gym, and heated pools. Perfect for a memorable family getaway close to all the excitement Orlando has to offer!

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

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

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.
Popular amenities for Kissimmee ski-in/ski-out rentals
Ski-in/ski-out house rentals

Spacious Pool Home w/ 2 Masters, Games Room

lodging

Pet-Friendly Home w/Pool near Disney&ChampionsGate

Cozy 2-Bed Studio with Pool & A/C

Luxury Storey Lake 10 Bedroom HM

Spacious Townhome with Pool | Sleeps 13

8848 BC - 8Bds Windsor At Westside

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

Stunning Townhome with Private Pool

Exclusive 8BR Themed Villa • Private Pool Retreat

Disney Dreams: 5BR Luxury Retreat, Poolside Paradi

Luxurious Retreat near Disney: Pool & Game Room

Luxury 3-Bed Condo in Storey Lake Resort

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

4812 BR - Dreamscape Villa

Family Home w/ Pool & Resort Perks Near Disney
Ski-in/ski-out condo 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 | $231 NZD | $241 NZD | $240 NZD | $226 NZD | $174 NZD | $203 NZD | $231 NZD | $202 NZD | $169 NZD | $191 NZD | $236 NZD | $291 NZD |
| 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 10 holiday rentals in Kissimmee

Nightly prices starting at
Kissimmee holiday rentals start at $121 NZD 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 and kid-friendly amenities

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Kissimmee holiday 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
- 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
- University of Central Florida
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- ESPN Wide World of Sports
- Things to do Kissimmee
- Things to do Osceola County
- Things to do Florida
- Food and drink Florida
- Art and culture Florida
- Nature and outdoors Florida
- Sports activities Florida
- Tours Florida
- Wellness Florida
- Sightseeing Florida
- Entertainment Florida
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