Holiday houses in Osceola County

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Top-rated holiday rentals in Osceola County

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Top Guest favourite
An inviting living area features a comfortable tufted chaise lounge and a cozy recliner. A flat-screen TV is mounted above a classic fireplace, surrounded by soft curtains that frame bright windows. The floor showcases warm wooden tones, contributing to a homely ambiance.
Cottage in Lake Wales
4.97 out of 5 average rating, 152 reviews

Charming, renovated 1917 Cottage

Charming, renovated 1917 cottage in beautiful neighborhood. One block from large lake with walking/running trail, 3.5 miles to Bok Tower, 12 miles to Legoland, 38 miles to Disney World, 47 miles to Universal Studios, and 63 miles to Busch Gardens. Pet friendly! King size bed in bedroom, double sofa bed in living area. Newly renovated kitchen has full size refrigerator, sink, microwave, stove top and large toaster oven. Big backyard with beautiful landscaping. Separate driveway. Lots of privacy!

Top Guest favourite
Townhouse in Osceola County
4.94 out of 5 average rating, 33 reviews

The Sun-Kissed Retreat / near Disney

Welcome to your Orlando retreat! This spacious 5-bedroom, 4.5-bathroom townhome at the exclusive Azur Resort offers everything you need for an unforgettable vacation. Designed with comfort and style in mind, this home is ideal for families, groups, and anyone looking to explore the magic of Orlando. Located just mins from Orlando's top attractions- Disney World, Universal, and world-class shopping and dining. You’re at the center of it all! Book now and start making memories at the Azur Resort!

Top Guest favourite
A themed kitchenette features a bamboo bar with high seating and colorful pendant lighting. The walls are adorned with tribal art and shelves hold various artifacts. Kitchen appliances, including a refrigerator and counter space, reflect a blend of modern convenience and cultural decor.
Cottage in Kissimmee
4.99 out of 5 average rating, 192 reviews

Tahiti Gil’s Mananui: Disney Poly & Tiki Inspired!

Aloha Adventurers! Welcome to Faré Mananui. Your passport to a far away tropical hideaway awaits, so get ready to grab your favorite Aloha shirt! Mananui was made for the Disney/Tiki ADULT in mind! Imagined by artist @TahitiGil & designed by @TyphoonTommy (Former Disney/Universal creative team & designer of the Suffering Bastard Tiki Bar in Sanford, Fl. Experience your next Adventureland/ Enchanted Tiki Room “story dwelling” adventure from the moment you step thru the door! - Kungaloosh!!

Guest favourite
Home in Lake Wales
4.94 out of 5 average rating, 119 reviews

Fishing Lakefront Paradise w/ Boat Slip & Parking!

Welcome to Florida Lakefront Paradise! ⭐️ Breathtaking Sunsets ⭐️ Bass Fishing ⭐️ Reserved Boat Slip ⭐️ Fish Cleaning Station ⭐️ Boat Wash Station ⭐️ Marina with Ice/Gas ⭐️ Large Fire Pit Area ⭐️ Located on Kissimmee Chain of Lakes ⭐️ Smart TV's ⭐️ Screened Lakefront Back Patio ⭐️ High Speed Internet ⭐️ Spacious ⭐️ Balcony Facing the Lake ⭐️ 30 minutes to Lego Land ⭐️ 20 minutes to Bok Tower Gardens ⭐️ 1 hour to Disney World ⭐️ 18 minutes to Spook Hill ⭐️ 18 minutes to Kissimmee State Park

Guest favourite
An outdoor area showcases a private pool surrounded by sun loungers, with views of a golf course in the background. The pool's rippling water reflects the clear sky, complementing the serene atmosphere.
Villa in Four Corners
4.89 out of 5 average rating, 18 reviews

Amazing New Villa! Well Maintained! Fun for all!

My name is Mike and I’m the proud owner of Castle Pines Cove. This 6 bedroom Villa was completed and furnished in the spring of 2022. I love this house. I spend a lot of time here with my family. I have a 5 and 8 year-old and this is their favorite place to visit. It’s extremely important to me to ensure not only the house is clean but also maintained to the highest standard. Just like with my family, I want everyone who stays here to feel the exact same love for the house that we do.

Guest favourite
An aerial view showcases a large pool surrounded by lounge chairs and palm trees. The pool area is defined by well-maintained landscaping, with a hot tub and a nearby shaded structure visible in the background, creating an inviting atmosphere.
Condo in Osceola County
4.89 out of 5 average rating, 120 reviews

Stunning Orlando Condo 3 BR/2 bath, pets OK

This resort community is amazing to drive around in, let alone stay in. Just 20 to 25 minutes away from Disney World and Universal Studios and everything Orlando has to offer. Convenience stores (7-11), Dunkin' Donuts, CVS pharmacy, restaurants and grocery stores within walking distance. Three gorgeous pools and hot tub Jacuzzis, and world-class gym in the resort in this gated community with security. 5 minute drive to Champions Gate and I-4 highway. Up to 2 dogs/cats ($25/day/animal)

Guest favourite
Aerial view showcasing a serene water body surrounded by lush greenery. A boat leaves a gentle wake, while the expansive shorelines and distant trees create a peaceful ambiance. Two smaller images in the corners highlight nearby homes and waterways.
Home in Lake Wales
4.99 out of 5 average rating, 68 reviews

Crooked Lake Gem, Lake Access, on a Wide Canal

Charming home on a canal leading to beautiful Crooked Lake, near Lake Wales, Florida. This home is located on a quiet neighborhood street. The back yard faces a canal that leads to one of the cleanest and most beautiful lakes in Central Florida, Crooked Lake. Great view! Crooked Lake is listed as one of Florida’s Outstanding waters and is a large lake, over 4,000+ acres and is a great lake for swimming, water skiing, kayaking, paddle boarding....just about anything to do with water.

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!

Superhost
Home in Kissimmee
5 out of 5 average rating, 9 reviews

Themed 6BR | Game Room | Private Pool & Spa w/View

Stay at Time-Out Corner, Too @ Windsor Hills for an incredible vacation filled! Enjoy a game room, themed bedrooms, a private pool and spa w/gorgeous sunset view, and more. Plus, free access to the resort’s clubhouse and water park. Just 5 mins from Disney! 🎮Toy Story Game Room. Play Air Hockey, Skee-Ball, Arcades, Xbox, PlayStation, and more. 🏊 Private West-Facing Heated Pool/Spa. 🛏️ 6 BR & 4 BA. 3 Themed Bedrooms (UP, Alice in Wonderland, and Orange Bird). Sleeps 14.

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, 1,105 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
Home in Kissimmee
4.87 out of 5 average rating, 159 reviews

Fantasy World Enchanted Harry Potter Wizard Villa

Dive into magic at our villa in Fantasy World Villas, near Disney, Universal & Sea World. Be spellbound by the Hogwarts-themed double bedroom, king-size master, modern kitchen, and private patio. Resort: pools, slides, lazy river, kids' activities, gym, sports courts & more. Walk to shops & restaurants. Free WiFi, parking & resort access. Immerse yourself in enchantment and excitement, steps from theme parks & resort fun! Book now!

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