Holiday houses in Osceola County

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Top-rated holiday rentals in Osceola County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A spacious living area features light-colored sofas arranged around a glass coffee table atop a patterned rug. Natural light floods the room through large windows, highlighting the high vaulted ceiling. An archway leads to another room, while greenery adds a touch of nature.
Villa in Kissimmee
4.92 out of 5 average rating, 168 reviews

Relax & Play :Luxury Villa Near Disney w/ Pool&Spa

Enjoy a stay at our luxurious fully equipped lakefront vacation pool Villa. All the creature comforts you enjoy at home, plus a few extras! • Beautifully maintained, quiet & safe resort-like neighborhood • Screened in Lanai enclosing private pool & hot tub • Extra privacy as this Villa has no neighbors in the back plus tropical hedges surrounding Lanai. • Only 3 miles to Disney and only 18 miles to Universal • Onsite Washer & Dryer • Fiber Gigabit WiFi 940Mbps • Easy Self checkin • Pet Friendly

Guest favourite
Home in Kissimmee
4.88 out of 5 average rating, 17 reviews

Comfort Home with BBQ, Private Pool & Hot tub

Step into our inviting single home where coziness eagerly awaits you! This beautiful Villa is nestled in the prestigious, award-winning Terra Verde Resort, a guard-gated community in Kissimmee, just 30 feet from the clubhouse and a mere 10 minutes from Disney. BBQ grill & Pool Heating are optional and must be requested at least one day before arrival. Terra Verde Resort HOA requirement: Upon check-in, guests must purchase a $25 non-refundable gate card for each vehicle entering the community.

Top Guest favourite
A bright living area features a light-colored sofa complemented by colorful accent chairs. A patterned area rug adds warmth to the space, which includes a ceiling fan and large windows allowing natural light. A blend of greenery and decorative items enhance the inviting atmosphere.
Home in St. Cloud
4.95 out of 5 average rating, 86 reviews

Lakefront home near Disney/Beach

Relax after a long day visiting the beaches, Disney, or springs in this peaceful lakefront home. Enjoy your morning coffee on the front patio overlooking the lake or wind down with a glass of wine underneath the pergola soaked with tropical flora. A paved walking path is just a few steps from the front door with quick access to the local marina. Downtown St Cloud is minutes away where you can enjoy local eats, drinks, shopping and other amenities! 30 minutes from Disney, an hour to the beaches.

Top Guest favourite
A private heated pool is surrounded by a screened enclosure, featuring a brightly colored tiled edge. Sun loungers are positioned nearby, offering a relaxing space to unwind. A covered BBQ grill is accessible on the patio, creating an inviting setting for outdoor gatherings.
Home in Kissimmee
4.93 out of 5 average rating, 112 reviews

3BR / 2BR Heated Pool Home 7 Min to Disney |

✨ Experience comfort, style, and a private heated pool 💦 (optional) just 7 minutes from Disney World! This 3BR/2BA Kissimmee home is perfectly located near theme parks, shopping, and dining — and designed for families looking to unwind in a sparkling-clean, beautifully curated space. 📍Prime Kissimmee Location ⭐7 Min– Walt Disney World ⭐5 min–Orlando Premium Outlets ⭐15 min – Universal Studios, SeaWorld, Epic Universe 🎢 ⭐ 25 min – MCO Airport ✈️ ⭐ Walk to Walmart, Publix & Starbucks ☕️

Top Guest favourite
An inviting outdoor area showcases a private pool and spa, surrounded by lounge chairs and colorful beach balls. A dining table and large gas grill offer options for outdoor meals. Lush greenery lines the fence, providing privacy and a vibrant backdrop against a sunny sky.
Home in Four Corners
5 out of 5 average rating, 59 reviews

Gorgeous 5BR @ Encore Next to Disney - 305

Modern 3,000sf luxury home, with 5 bedrooms, at world's renowned Encore Resort at Reunion. Featuring 5 bedrooms, 5 1/2 bathrooms, a game room, a beautiful backyard, a private pool and spa. 6 Minutes away from Super Walmart and Publix supermarket 15 Minutes away from Disney Parks 15 minutes away from Disney Springs 15 Minutes away from Premium Outlets 20 Minutes away from Universal Studios 20 Minutes away from International Drive attractions *PLEASE MAKE SURE TO READ THE HOUSE RULES*

Top Guest favourite
The exterior of a large, two-story home is displayed, featuring a light-colored facade and a covered front porch. Lush landscaping surrounds the driveway, which is paved with stone. A garage door is positioned on the right side, complemented by decorative lanterns and palm trees.
Home in Osceola County
4.98 out of 5 average rating, 81 reviews

Large Private Home on Golf course by Disney

Bring the whole family to this great place with lots of room for fun. With fantastic views of the 4th hole on the Tom Watson golf course and your own private pool and hot tub everyone will enjoy this stylish and modern vacation home. Located in premier Reunion Resort and only 10 minutes to Disney you can have it all! This home boats over 4000sq feet, two very large masters suites, 2 additional bedrooms and plenty of space throughout the home. There are 6 tvs! Pets are welcome too!

Top Guest favourite
A treehouse is illuminated by warm string lights, nestled among large branches under a deep blue sky. The structure features large windows allowing views of the surrounding greenery, with a cozy seating area visible inside. A wooden walkway leads to the entrance.
Treehouse in St. Cloud
4.97 out of 5 average rating, 1,097 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

Superhost
Villa in Kissimmee
4.75 out of 5 average rating, 4 reviews

Modern Luxury Themed 7 Bed Pool Villa near Disney

There is only one word that truly describes this spacious luxury Villa and that is STUNNING! The Owners of this fabulous 7 Bedroom 5.5 Bath home have lovingly renovated every room in the Villa to provide the perfect modern location for your Floridian vacation. Not only is the property equipped with everything you could possibly need for your vacation, but it is located on the Emerald Island Resort, which has a host of amenities available for your stay.

Top Guest favourite
Villa in Kissimmee
5 out of 5 average rating, 7 reviews

4BR Jungle Cruise Villa w/Pool & Spa Near Disney

Welcome to your dream getaway just minutes from Disney! Luxury family retreat – Sleeps 8! Private pool, bubbling spa and jungle-themed theater. • 🛏️ 4 Disney-themed bedrooms with en-suite baths • 🏰 Under 5 miles to Disney parks, shops and dining • 🏝️ Adventureland décor • 👨‍🍳 Gourmet kitchen + washer/dryer & baby gear • 🅿️ Free parking • 📞 24/7 response Book now and let the adventure begin.

Top Guest favourite
A sunset scene captures two shipping containers framed against a colorful sky. The foreground features green plants and shrubs among mulched earth, while a rainbow arched above enhances the natural ambiance of the retreat. The surrounding area is open and spacious.
Shipping container in Osceola County
4.97 out of 5 average rating, 88 reviews

Beautiful off-grid tiny home cottage #1

Retreat to the food covered grounds of this off-grid oasis in Central Florida, reconnect to the beauty and vibrancy of nature, and experience the magnitude of freedom and abundance it has to offer on your sustainable getaway. Your shipping container has a full kitchen, mini-split cooler and spacious shower with an on-demand water heater fed by pristine well water... you would never know you’re off-grid!

Guest favourite
An open living area features a modern kitchen with a large island and granite countertops, seamlessly connecting to the dining and lounging spaces. Natural light floods the room through expansive sliding glass doors leading to the terrace, accented by comfortable seating and contemporary decor.
Townhouse in Kissimmee
5 out of 5 average rating, 9 reviews

8005 Elegant Villa Near to Disney Magic

Formosa Valley Resort - 4 Bedrooms in Orlando offers an outdoor pool, free WiFi, and private parking. The vacation home is conveniently located near popular Disney attractions such as Disney's Boardwalk, Hollywood Studios, and Animal Kingdom. Units include a private bathroom. The nearest airport is Orlando International Airport, 22 miles away. Couples rated the location 9.0 for a two-person trip.

Superhost
A modern kitchen features a large, light granite countertop with seating for four at a stylish island. The space includes stainless steel appliances, ample cabinetry, and is well-lit by pendant lighting above. A door leads to an adjoining room, enhancing the open layout.
Townhouse in Kissimmee
4.81 out of 5 average rating, 59 reviews

BRAND NEW 4 bedroom near Disney and Universal

BRAND NEW house with 4 bedrooms, 4.5 bathrooms, large living room Integrated kitchen, outdoor area overlooking the preservation area. Excellent location, next to Walmart and 17 minutes from Disney parks. Condominium with Clubhouse, magnificent structure with swimming pool, and gym. All the best at your fingertips and that of your family. Space for up to 2 cars parked in front of the house.

Popular amenities for Osceola County holiday rentals

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