Osceola County Holiday Homes with Staff

We selected the 266 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 Cabin

The Old Cabin

  • 10 guests

  • 4 bedrooms

Four Corners, Osceola County

This brand new vacation rental is a stunning 4-bedroom, 3-bathroom property with its own private pool. Situated in the new phase of the Champions Gate Resort, guests can enjoy the community's beautiful surrounding golf courses and tennis courts.

Pines & Greenwood

Pines & Greenwood

  • 28 guests

  • 11 bedrooms

Polk County, Florida

This villa is an extravagant mansion located in Orlando, Florida that promises to take guests on a magical journey. The great room features a stylish, contemporary design with sleek and comfy furnishings that are perfect for relaxation and conversation.

Parlour Peace

Parlour Peace

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Experience a one-of-a-kind vacation in this sprawling, luxurious villa located in a resort of Orlando. The villa boasts 12 spectacular bedrooms, each with its own en suite bath, and expertly designed for ultimate comfort.

The Magic of Disney

The Magic of Disney

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

This vacation home in The resort is perfect for families with kids who will love the Winter and Superhero-themed bedrooms, private home theater, game room/loft, and private screened-in pool and spa. The game room has a karaoke system, mini jungle gym, arcade games, and a lounge area with a smart TV.


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

Explore the 266 most perfect homes in our collection

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Most popular homes in Osceola County

A Disney Mania

A Disney Mania

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Just One Night at the Hotel

Just One Night at the Hotel

  • 24 guests

  • 10 bedrooms

Polk County, Florida

The Old Ore Mine

The Old Ore Mine

  • 6 guests

  • 2 bedrooms

Four Corners, Osceola County

The Blue Burdock

The Blue Burdock

  • 24 guests

  • 9 bedrooms

Four Corners, Osceola County

A Little Piece of Sunshine

A Little Piece of Sunshine

  • 28 guests

  • 11 bedrooms

Polk County, Florida

Grand Retreat

Grand Retreat

  • 28 guests

  • 11 bedrooms

Polk County, Florida

Summer's Insomniac Dream

Summer's Insomniac Dream

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Take Me to the Ball Game

Take Me to the Ball Game

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

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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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