Holiday Rentals in Osceola County

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Top Cities in Osceola County

Delonix regia tree in bloom
Holiday RentalsHoliday Rentals

Poinciana

Poinciana

Our top choices for Osceola County holiday rentals

Exterior

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (4,279 reviews)
"My family and I loved our stay at this resort."
United States
April
The price is €93
includes taxes & fees
19 Jun - 20 Jun
Vacation Village Orlando, Celebration
2 outdoor pools, open 8:00 AM to 11:00 PM, pool umbrellas, pool loungers

Villas at Fortune Place

Villas at Fortune Place
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (153 reviews)
"Nice and friendly staff; it is a family friendly place."
United States
Leonel
The price is €81
includes taxes & fees
7 Jun - 8 Jun
Villas at Fortune Place
Outdoor pool

Maple Leaf Inn & Suites

Maple Leaf Inn & Suites
2.5 star property
Kissimmee
6.8 out of 10, (71 reviews)
"The room was clean and the staff was okay "
United States
Shaneka
The price is €59
includes taxes & fees
7 Jun - 8 Jun
Maple Leaf Inn & Suites
Exterior

Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (313 reviews)
"Staff were excellent."
United States
Luz
The price is €129
includes taxes & fees
7 Jun - 8 Jun
Barefoot'n Resort Kissimmee Orlando
2 outdoor pools

Value Edge

Value Edge
Kissimmee
The price is €117
includes taxes & fees
7 Jun - 8 Jun
Value Edge
Outdoor pool, pool umbrellas, pool loungers

Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,878 reviews)
"Great for families"
United States
Frank
The price is €110
includes taxes & fees
13 Jun - 14 Jun
Barefoot Suites
Outdoor pool

Harmony Ensuite Room Shared Home No Car

Harmony Ensuite Room Shared Home No Car
2.5 star property
Kissimmee
The price is €172
includes taxes & fees
8 Jun - 9 Jun
Harmony Ensuite Room Shared Home No Car
Terrace/patio

Sunset Bliss Retreat Condo - Near Disney

Sunset Bliss Retreat Condo - Near Disney
Kissimmee
9.6 out of 10, Exceptional, (47 reviews)
"Clean, nice area. "
United States
Melissa B.
The price is €121
includes taxes & fees
17 Jun - 18 Jun
Sunset Bliss Retreat Condo - Near Disney
Exterior

Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0 star property
Kissimmee
8.4 out of 10, Very good, (3,143 reviews)
"The price is reasonable and staff are really nice."
Canada
Moonyeen
The price is €250
includes taxes & fees
7 Jun - 8 Jun
Regal Oaks Resort Vacation Townhomes by IDILIQ
Exterior

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
4.0 star property
Kissimmee
8.8 out of 10, Excellent, (1,996 reviews)
"Great place for families "
United States
Luis
The price is €389
includes taxes & fees
30 Jun - 1 Jul
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
Flat-screen TV, DVD player

Grand Lake Resort

Grand Lake Resort
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (175 reviews)
"Great place to stay "
United States
Dian
The price is €79
includes taxes & fees
22 Jun - 23 Jun
Grand Lake Resort
Exterior

Lifetime of Vacations Resort

Lifetime of Vacations Resort
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (166 reviews)
"The kitchen was fully equipped and there were plenty of beds, all of which were comfortable. The grounds are gorgeous! An excellent play are for kids is provided and the pool is huge, and clean. The staff are all friendly and personable. When I return in May, this is where I will stay again. Highly recommend!"
United States
Robin
The price is €91
includes taxes & fees
12 Jun - 13 Jun
Lifetime of Vacations Resort
House, Accessible

Star Wars Pool Home - Emerald Island Resort

Star Wars Pool Home - Emerald Island Resort
2.0 star property
Kissimmee
The price is €484
includes taxes & fees
7 Jun - 8 Jun
Star Wars Pool Home - Emerald Island Resort
Apartment (2 Bedrooms) | Interior

Storey Lake Resort Condo w Patio5 Miles to Disney

Storey Lake Resort Condo w Patio5 Miles to Disney
3.0 star property
Kissimmee
The price is €239
includes taxes & fees
10 Jun - 11 Jun
Storey Lake Resort Condo w Patio5 Miles to Disney
Family Apartment | Private kitchen

LOVELY LUXURY APARTMENT CLOSE DISNEY

LOVELY LUXURY APARTMENT CLOSE DISNEY
3.5 star property
Kissimmee
8.4 out of 10, Very good, (8 reviews)
"Nice appartment, everything you needed and clean and modern"
United Kingdom
Martyn
The price is €268
includes taxes & fees
7 Jun - 8 Jun
LOVELY LUXURY APARTMENT CLOSE DISNEY
Outdoor pool

The Irlo

The Irlo
3.0 star property
Kissimmee
7.6 out of 10, Good, (27 reviews)
"Management and staff have been amazing gave me a tour the facility"
United States
Robert
The price is €176
includes taxes & fees
7 Jun - 8 Jun
The Irlo
Fridge, microwave, oven, stovetop

Luxe Condo Double Bed Bliss Getaway near Disney

Luxe Condo Double Bed Bliss Getaway near Disney
Kissimmee
8.8 out of 10, Excellent, (42 reviews)
"This was the perfect property for our stay. It was a safe location and well stocked kitchen and the pictures and write up were accurate. We enjoyed our stay!! "
Canada
Barry
The price is €157
includes taxes & fees
15 Jun - 16 Jun
Luxe Condo Double Bed Bliss Getaway near Disney
House (3 Bedrooms) | Interior

Oasis Near Disney w Golf View, Family&pet Friendly

Oasis Near Disney w Golf View, Family&pet Friendly
3.0 star property
Reunion
The price is €361
includes taxes & fees
7 Jun - 8 Jun
Oasis Near Disney w Golf View, Family&pet Friendly
Living area

Cozy 2BD/2BTH Condo Near Disney

Cozy 2BD/2BTH Condo Near Disney
Kissimmee
9.6 out of 10, Exceptional, (24 reviews)
"Great host, very cozy, close to Disney and other attractions."
United States
Jessica D.
The price is €156
includes taxes & fees
16 Jun - 17 Jun
Cozy 2BD/2BTH Condo Near Disney
2 outdoor pools

Storey Lake condos by UNE Homes

Storey Lake condos by UNE Homes
3.5 star property
Kissimmee
8.4 out of 10, Very good, (6 reviews)
"Location, location, location. It was a great location. It was clean, and everything went smoothly."
United States
Carrie
The price is €323
includes taxes & fees
9 Jun - 10 Jun
Storey Lake condos by UNE Homes
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osceola County Hotel Reviews

Comfort Suites Maingate East

Comfort Suites Maingate East

10/10 Excellent
"Clean, helpful staff, 24 hour outdoor pool was great"
Lori 1-night trip
Posted 2 hours ago
Comfort Suites Maingate East

Find out more about Osceola County

Holiday Homes in Osceola County

Search for holiday homes in Osceola County on Expedia.ie! You can easily find your home rentals, villas, holiday apartments in Osceola County using one of the methods below: 

  • View our selection of featured holiday homes in Osceola County
  • Use the map to find apartments and other holiday rentals in the Osceola County neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday homes in Osceola County while they last

Look no further and take a look at our great range of rental properties in Osceola County!