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

The Blue Dunes

The Blue Dunes

  • 24 guests

  • 10 bedrooms

Polk County, Florida

With a private pool and Jacuzzi, a game loft, and even a twelve-seat cinema, this villa delivers on every front. Calling out for a multi-generational family stay, expect ten en-suite bedrooms – including two themed bunk rooms for little ones – and banquet-worthy dining spaces in the free-flowing living spaces downstairs to gather together.

Sunset Haze

Sunset Haze

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

Visiting Orlando's hotspots like Disney World and Universal Studios? Here's the perfect base for just that.

A True Joy

A True Joy

  • 28 guests

  • 11 bedrooms

Polk County, Florida

With a private pool, arcade room and movie theatre, this home sets the stage for a fun-filled stay in Florida. You can enjoy long soaks in the spa and there’s an outdoor kitchen for magical evening meals.

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

This is the perfect vacation home for families looking for a fun-filled getaway. Kids will love the superhero and Fashionista-themed bedrooms, complete with over-the-top bunk beds and decor.

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

Explore the 235 most perfect homes in our collection

View on map

Most popular homes in Osceola County

Harmony's Place

Harmony's Place

  • 12 guests

  • 5 bedrooms

Four Corners, Osceola County

Mickey's Melody

Mickey's Melody

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

The Blue Ledge

The Blue Ledge

  • 18 guests

  • 6 bedrooms

Polk County, Florida

Friends, Family & Fun

Friends, Family & Fun

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

The Fairy Godmother

The Fairy Godmother

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Sounds of Fun

Sounds of Fun

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Wondrous Villa

Wondrous Villa

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Lake Escapes

Lake Escapes

  • 4 guests

  • 2 bedrooms

Osceola County, Florida

View all

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.

Search Our Collection

  1. Plum Guide

  2. United States

  3. Florida

  4. Osceola County

  5. Holiday Homes with Staff