Osceola County Holiday Homes with Staff

We selected the 235 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

Siesta Shade

Siesta Shade

  • 15 guests

  • 5 bedrooms

Loughman, Polk County

This luxurious new single-family home boasts six bedrooms, six bathrooms, and a game room complete with air hockey, pool table, and ping pong. The first floor features one suite while the second floor has two suites and a spacious loft.

Orlando Sunshine

Orlando Sunshine

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

This family home offers plenty of space and style for your dream Florida getaway. The kitchen is fully equipped, perfect for whipping up meals to enjoy outside by the screened private pool and spa.

The Entertainment Enclave

The Entertainment Enclave

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Welcome to a haven of fun for the whole family. Home entertainment of every type is available here, for both children and adults – kids will love the dedicated arcade room, themed bedrooms including integrated bunk beds, and a video games room complete with karaoke.

Family Adventure Base

Family Adventure Base

  • 12 guests

  • 5 bedrooms

Four Corners, Osceola County

A private pool, resort access, and just twenty minutes from Walt Disney World – this villa is a dream for families. Inside, it’s bright and airy, with plenty of space to gather or unwind.


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

Explore the 235 most perfect homes in our collection

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Most popular homes in Osceola County

Fun-Filled Getaway

Fun-Filled Getaway

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Orange Vista

Orange Vista

  • 18 guests

  • 6 bedrooms

Polk County, Florida

Sunshine Ranch

Sunshine Ranch

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

Strawberry Sunrise

Strawberry Sunrise

  • 18 guests

  • 6 bedrooms

Polk County, Florida

Sunshine on the Lake

Sunshine on the Lake

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

Sunflower Sun

Sunflower Sun

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

The Starlight Sky

The Starlight Sky

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Sugar Sky

Sugar Sky

  • 24 guests

  • 10 bedrooms

Polk 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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