Osceola County Holiday Homes with Staff

We selected the 283 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Osceola County

The Old Ore Mine

The Old Ore Mine

  • 6 guests

  • 2 bedrooms

Four Corners, Osceola County

This beautiful brand new vacation rental condo is perfect for a family or group of friends looking for an amazing vacation. Located in Champions Gate Resort, guests will be just a stone's throw away from Disney, restaurants, and shopping.

A Little Piece of Sunshine

A Little Piece of Sunshine

  • 28 guests

  • 11 bedrooms

Polk County, Florida

This villa is a luxurious and spacious 7,200-square-foot mansion in Orlando, Florida. This stunning property boasts a chef's kitchen with black marble countertops and upgraded appliances, an adjacent versatile dining room, and a beautiful great room with modern couches and chairs.

The Time Traveler's Daughter

The Time Traveler's Daughter

  • 20 guests

  • 9 bedrooms

Four Corners, Osceola County

This vacation home is perfect for families looking to have a fun-filled retreat. The kids will love the jungle-themed bedroom with tree trunk bunk beds and the toy-themed bedroom with floor-to-ceiling wall art of their favorite toys.

Taller Than Life

Taller Than Life

  • 13 guests

  • 4 bedrooms

Osceola County, Florida

This brand new single-family home is perfect for those looking for a luxurious stay in the heart of Orlando. The cozy house features five bedrooms and five bathrooms, with two bedrooms conveniently located on the ground floor.


We selected the top 3% holiday homes in Osceola County Holiday Homes with Staff

Explore the 283 most perfect homes in our collection

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Most popular homes in Osceola County

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

The Oceanaire

The Oceanaire

  • 8 guests

  • 3 bedrooms

Osceola County, Florida

The Old Cabin

The Old Cabin

  • 10 guests

  • 4 bedrooms

Four Corners, Osceola County

Bulletproof Blue

Bulletproof Blue

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

Moon Over Lake

Moon Over Lake

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Bonsai & Blue Sky

Bonsai & Blue Sky

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Pineapple Peach

Pineapple Peach

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Black & White Paradise

Black & White Paradise

  • 4 guests

  • 2 bedrooms

Osceola County, Florida

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Check upcoming rates & availability for Osceola County Holiday Homes with Staff


Frequently asked questions

Are you hoping for a stay in one of the best holiday homes with staff in Osceola County, Florida, United States? If so, you've definitely come to the right place. Reach out to our expert team who will happily arrange for staff to be present at your home in Osceola County, Florida, United States as an addition to your booking. Our Plum Guide homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short extended stay. Should you need anything, our friendly team is on hand 24/7, so just ask.

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