
Holiday houses in Osceola County
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Top-rated holiday rentals in Osceola County
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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!

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!

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!!

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

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.

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)

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.

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*

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!

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.

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.

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!
Popular amenities for Osceola County holiday rentals
Other great holiday rentals in Osceola County

Pool+Game Room 10 min to Disney sleeps 10

Luxury 4 Bedrooms, 3.5 Bathrooms with pool.

The Cozy Nook

Family Getaway Near Disney Magic - 20104

Hidden Gem - Hot Tub/ Fire pit/Hammock/Grill Area

2026 Themed New 08 Bedrooms At Solara Resort

Midcentury Lakefront Home on Crooked Lake

Premium Lake Wales Getaway!
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- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Magic Kingdom Park
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Sebastian Inlet
- Playalinda Beach
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!




