Some info has been automatically translated. Show original language

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.

%{current} / %{total}1 / 1
Home in Kissimmee
4.33 out of 5 average rating, 3 reviews

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

Top guest favorite
The exterior of the single-family home is illuminated at night, highlighting the garage and front entrance. Soft lighting accentuates the landscaped garden and driveway, creating a welcoming entrance. The home's design features a combination of stone and stucco, framed by a well-maintained lawn.
Home in Kissimmee
4.96 out of 5 average rating, 84 reviews

“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

Superhost
Apartment in Orlando

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.

Home in Davenport
4.58 out of 5 average rating, 12 reviews

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.

Condo in Orlando
4.87 out of 5 average rating, 30 reviews

!! 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

Superhost
A swimming pool and a spa are shown, surrounded by a paved area with lounge chairs. Lush greenery and colorful buildings are visible in the background, adding to the inviting atmosphere. The pool features clear blue water, with a gentle gradient from shallow to deep.
Condo in Kissimmee
4.77 out of 5 average rating, 30 reviews

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

Guest favorite
A whimsical bedroom features a bunk bed with a top twin and bottom double sleeping arrangement. The walls are decorated with colorful Toy Story characters, and plush bedding includes playful designs. A light blue theme and bright white trim create a cheerful atmosphere.
Home in Kissimmee
4.85 out of 5 average rating, 54 reviews

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

Guest favorite
A cozy living area features a comfortable sofa with light cushions and a coffee table at its center. A ceiling fan is positioned above, while a television is mounted on the wall. Natural light enters through glass doors that lead to a balcony with greenery visible outside.
Condo in Davenport
4.83 out of 5 average rating, 24 reviews

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.

A serene pool area is showcased, featuring a crystal-clear oval pool and a connected spa. Comfortable lounge chairs are positioned around the pool, all set under a protective screen enclosure. A grassy retention area is visible in the background, enhancing the tranquil atmosphere.
Home in Davenport
4.42 out of 5 average rating, 19 reviews

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.

A vibrant game room features a Super Mario theme, with colorful murals of Mario characters on blue walls. An air hockey table occupies the foreground, while a large screen television is mounted on the wall. Bright red pendant lights hang from the ceiling, enhancing the playful atmosphere.
Home in Kissimmee

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

Superhost
Home in Davenport
4.58 out of 5 average rating, 12 reviews

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

A single-story home is presented with a neatly landscaped front, featuring a two-car garage and a welcoming entrance. An updated kitchen displays stainless steel appliances and a large island. The private pool area, enclosed by a screen, features a clear blue pool and outdoor seating.
Home in Kissimmee
4.5 out of 5 average rating, 4 reviews

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

When is the best time to visit Kissimmee?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$28,034 GYDG$24,896 GYDG$29,290 GYDG$27,407 GYDG$21,130 GYDG$24,687 GYDG$25,105 GYDG$20,712 GYDG$23,432 GYDG$22,595 GYDG$24,478 GYDG$30,545 GYD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Quick stats about vacation rentals that are ski-in ski-out in Kissimmee

  • Total vacation rentals

    Explore 20 vacation rentals in Kissimmee

  • Nightly prices starting at

    Kissimmee vacation rentals start at G$10,461 GYD per night before taxes and fees

  • Verified guest reviews

    Over 460 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Kissimmee vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Kissimmee rentals

Destinations to explore