Holiday Homes in Osceola County

Find and book unique holiday homes on Airbnb

Top-rated Holiday Homes in Osceola County

Guests agree: These holiday homes are highly rated for location, cleanliness and more.

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Guest favourite

A winding lazy river glides through a tropical landscape, surrounded by palm trees and colorful plants. A wooden bridge crosses above, leading to a play area. The clear blue water sparkles under a bright sky with scattered clouds.

Holiday home in Kissimmee

4.89 out of 5 average rating, 148 reviews

Urban Hip Disney condo with FREE Water Park!

Most central LOCATION in town! GORGEOUS, Brand NEW and super hip condo in the center of it all! Tastefully furnished and fully appointed to provide your family with a truly Magic vacation. Super fast Wifi, cable channels, parking immediately in front. Elevators, gated community. The resort offers FREE WATER PARK, lazy river, Tiki bar, a gym, sand volleyball, basketball court, kayak rentals and much more. Great shopping and restaurants in the vicinity and electronic lock for self check in.

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Superhost

A themed bedroom features two twin beds dressed in black and white bedding, complemented by red accents. Mickey Mouse artwork adorns the walls, while plush Mickey toys are placed on the beds. A desk lamp and storage unit are visible, adding to the overall playful atmosphere.

Holiday home in Davenport

4.86 out of 5 average rating, 51 reviews

Mickey’s Haven 5 Bdrm/4 Bath in Solterra #2355

Luxury 5 Bedroomed property located on the beautiful Solterra Resort, in Davenport, FL. The entrance leads to beautiful well presented gathering room with open plan kitchen/dining room. Family room has an oversized 70 inch Roku TV. Game Room with air conditioner, pool table, air hokey, 65 inch television Xbox and more!! . Private Pool with a covered lanai. Stunning large Master bed and Queen bed, both with suites. Themed Mickey Mouse bedroom with two twin beds. All bedrooms have fitted TV's.

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Superhost

The exterior of a single-story house is displayed, featuring a sloped roof with solar panels. Lush green grass surrounds the home, complemented by well-maintained shrubs and trees. A driveway leads to the front entrance, enhancing accessibility.

Holiday home in Kissimmee

4.75 out of 5 average rating, 112 reviews

Awesome 3BR/2BA House, Heated Pool & Disney Theme*

Awesome three bedroom two bathroom house just 20 minutes from Disney World and more. The living room contains a couch that can fold out into a queen bed ✅ The backyard contains a private pool. Our home has WiFi and a TV. For a $30 daily extra charge I will heat the pool to 87 degrees Fahrenheit but not available in the hot summer - message me if you want this. There is a barbecue grill in the backyard and a washer/dryer, foosball table, and corn-hole set in the garage. You will love it!

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Guest favourite

Holiday home in Kissimmee

4.9 out of 5 average rating, 139 reviews

12 minutes from Disney+King bed+Free parking

Relax in this beautiful and comfortable townhouse located in Compass Bay resort, a fully gated vacation home community, located just minutes away from Disney,shops, outlets, restaurants, grocery stores, like Walmart, Target, and Publix. Our house accommodates a family or group up to 7 people. Private laundry and fully stocked kitchen, with brand new stainless steel appliances. Choosing our place will guarantee you the most joyful and memorable experience. Family friendly home

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Guest favourite

Holiday home in Kissimmee

5.0 out of 5 average rating, 33 reviews

Fun Vacation Home| Disney | Solara Resort| w/ Pool

Create unforgettable memories of a lifetime and enjoy a vacation you’ll remember for years to come. This spectacular home is ideally located within the Solara Resort and only 8 miles to Disney, and within a short drive to Universal, Disney Springs, and many beaches! With 4000sqft of luxury living space, a private pool/spa and a game room for the kids, your family can enjoy the relaxing and fun atmosphere together! House is equip with 9 bedrooms and 6.5 baths, sleeps up to 20!

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Guest favourite

The entrance of Balmoral community is marked by a stone structure with a tile roof, featuring the name 'BALMORAL' prominently displayed. Lush palm trees and landscaped greenery surround the entrance, providing a welcoming ambiance. A blue sky with scattered clouds is visible in the background.

Holiday home in Haines City

5.0 out of 5 average rating, 33 reviews

Amazing Lakeview 4 BD Home w/ Pool & More!

Escape to Your Perfect Getaway! Indulge in the ultimate retreat at our thoughtfully designed Airbnb. Blending style, comfort, and modern amenities, our space offers a peaceful escape just minutes from the area’s top attractions. Relax in a spotless, inviting haven where every detail is curated to elevate your stay. Whether you’re visiting for adventure, relaxation, or business, your unforgettable experience starts here. Book now and make your next getaway extraordinary.

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Superhost

A spacious two-story home is depicted, featuring a well-manicured front lawn with decorative plantings. Large windows and a modern entrance accentuate the clean lines of the architecture. The driveway leads to a two-car garage, providing ample parking options.

Holiday home in Four Corners

4.98 out of 5 average rating, 61 reviews

Encore Luxe 9BR, Home Theater, Private Pool & Spa

This gleaming nine-bedroom oasis, located at the Encore Resort, features an open floor plan living area, fully equipped kitchen, upper floor loft area, home theater, and a private swimming pool and spa, making it the perfect home for a Central Florida vacation with the major theme parks just minutes away! Kissimmee vacation home | Luxury vacation home in Kissimmee | Family luxury properties for a magical luxurious stay | Orlando Vacation | Real Vacation | Disney Vacation

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Top Guest favourite

A modern two-story home is showcased with a spacious driveway and a brick-paved exterior. Large windows allow natural light to flood the interior. Lush greenery surrounds the property, enhancing the inviting curb appeal.

Holiday home in Kissimmee

4.97 out of 5 average rating, 93 reviews

Beautiful 6 Bedroom Villa with pool near disney

Bring the whole family to this great place with lots of room for fun. Modern home located in Encore at Reunion. This fully furnished 6 bedroom, 6 bathrooms and your own refreshing heated pool and heated spa. The kitchen is modern This wonderful open floor plan is great for large families or guests to enjoy. Relaxation at its finest can be experienced outdoors by the pool and spa overlooking the extended brick-paved pool deck. Your very own tropical paradise

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Guest favourite

A modern living area is furnished with a spacious gray sectional sofa and complemented by stylish armchairs. A sleek coffee table rests on a soft rug, and a large flat-screen television is mounted on the wall. Natural light floods the room through floor-to-ceiling windows.

Holiday home in Four Corners

4.89 out of 5 average rating, 127 reviews

Sunny 3BDR Home at Champions Gate, Free Waterpark

Luxury 3 Bedroom, 2 bath Condo with Golf View and free waterpark access. Our beautiful home is located just 13 miles from Disney World theme parks in Champions Gate Resort with the amenities that include: 2 pools, lazy river, restaurant, gym, business center, tennis courts, and inside of the Champions Gate Country Club that is rated 4.4 in one of the best golf magazines. Sleeps 7: 1 King, 1 King, 1 Bunk Bed Twin and Double + Twin roll over bed

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Guest favourite

A balcony area features dark blue cushioned seating and a wooden coffee table. A view of a calm lake is visible beyond the railing, under a sky filled with scattered clouds.

Holiday home in Kissimmee

4.9 out of 5 average rating, 248 reviews

*Free Early Check ins / Late Check outs*

Welcome to your perfect Orlando getaway! This cozy 2-bedroom, 2-bath apartment is located in the beautiful Storey Lake Resort, just minutes from Disney, Universal, SeaWorld, shopping, and restaurants. Enjoy a fully equipped kitchen, Smart TVs, high-speed Wi-Fi, and relaxing lake views. Guests have access to pools, lazy river, water slides, fitness center, mini golf, and more. Perfect for families, couples, and vacationers!

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Guest favourite

The living area features a spacious seating arrangement with a gray sofa facing a flat-screen TV. A modern dining table set with orange and gray chairs is positioned nearby, set with dining ware. Large windows provide natural light, with access to a balcony overlooking greenery.

Holiday home in Kissimmee

4.86 out of 5 average rating, 189 reviews

Cozy 3 BR Apartment - Near Disney! Pool Onsite

Lovely 3-bedroom, 2-bathroom full apartment in gated community with beautiful pool in Kissimmee, FL. It is just 10mins away from most theme parks. Stay at our lovely, peaceful and cozy apartment while you enjoy of the beauty of Orlando, FL and the amusement of the Disney parks. Enjoy our spacious bedrooms, entertainment in each room (Netflix, Disney+, Roku included), Wi-Fi, and fully equipped kitchen.

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Guest favourite

Holiday home in Kissimmee

4.9 out of 5 average rating, 68 reviews

Disney Escape | Resort Pools & Tennis | Sleeps 6+

Welcome to your relaxing getaway in Kissimmee, Florida, USA, located inside the beautiful gated Lake Berkley Resort, just minutes from Walt Disney World®, Universal Orlando Resort™, SeaWorld®, shopping, dining, and championship golf courses. Whether you're visiting with family, friends, or working remotely, this spacious home offers the perfect balance of comfort, convenience, and resort-style amenities.

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