Book Luxury Holiday Rentals in Osceola County

Award-winning homes from £98

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Home spotlights in Osceola County

Citrus Garden Breeze

Citrus Garden Breeze

  • 9 guests

  • 3 bedrooms

Osceola County, Florida

Wake up in your Orlando hideaway and decide what the day will bring: a family adventure at Disney, just minutes away, or a lazy morning floating down a winding river under the Florida sun. Return to the perfect spot for a coffee or an evening wine, the the balcony overlooking the garden.

 King of the Green

King of the Green

  • 10 guests

  • 4 bedrooms

Four Corners, Osceola County

Ideally located for visiting Orlando’s theme parks, this four-bedroom home is a great base for exploring Walt Disney World and beyond. There’s a private pool and covered patio for lazy days, plus a modern kitchen for making your favourite food.

Family Funhouse

Family Funhouse

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Just twenty minutes from Disney World and close to Orlando’s top attractions, this sprawling villa is a playground for the whole family. Enjoy the private pool with built-in jacuzzi, zoom down the mini waterslide, shoot hoops, or play ping-pong and foosball, then fire up the summer kitchen for alfresco feasts.

Lake Escapes

Lake Escapes

  • 4 guests

  • 2 bedrooms

Osceola County, Florida

This Orlando resort condo was made for both relaxation and excitement. Wake up to lake views from the private balcony, then dive into the fun with access to resort amenities including pools, a lazy river, golf course, gym, clubhouse, restaurant, and cinema.


We selected the top 3% holiday homes in Osceola County Holiday Rentals

Explore the 236 most perfect homes in our collection

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Most popular homes in Osceola County

Sugar Sky

Sugar Sky

  • 24 guests

  • 10 bedrooms

Polk County, Florida

Friends, Family & Fun

Friends, Family & Fun

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

Pineview Villa

Pineview Villa

  • 34 guests

  • 12 bedrooms

Polk County, Florida

The Blue Ledge

The Blue Ledge

  • 18 guests

  • 6 bedrooms

Polk County, Florida

Mickey's Melody

Mickey's Melody

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

Magic Retreat

Magic Retreat

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Harmony's Place

Harmony's Place

  • 12 guests

  • 5 bedrooms

Four Corners, Osceola County

Fun-Filled Hideaway

Fun-Filled Hideaway

  • 24 guests

  • 10 bedrooms

Polk County, Florida

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Osceola County, Florida, United States. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Osceola County, Florida, United States has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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