A vintage red truck with a side sign advertising a bike rental service.

Search 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

Osceola County Accommodation: Most Popular Cities to Stay

A dense cluster of red flowers with green foliage.
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, (4,589 reviews)
"Great stay!"
United States
Thailia
The price is 1.692.116 ₫
2.577.801 ₫ total
includes taxes & fees
26 Jul - 27 Jul
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, (180 reviews)
"I stayed for 1 night it was a very nice place I will definitely come back to this place also very clean."
United States
Barry
The price is 2.957.850 ₫
3.593.853 ₫ total
includes taxes & fees
22 Jul - 23 Jul
Villas at Fortune Place
Outdoor pool, pool umbrellas, pool loungers

Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,896 reviews)
"Our go-to place for my family to stay. Great location, cleanliness and fair pricing."
United States
Justin
The price is 2.120.713 ₫
2.926.538 ₫ total
includes taxes & fees
26 Jul - 27 Jul
Barefoot Suites
Water park

Reunion Resort & Golf Club

Reunion Resort & Golf Club
5.0 star property
Reunion
8.8 out of 10, Excellent, (1,592 reviews)
"Excellent suite…spacious, clean, and comfortable."
United States
Melissa Andrea
The price is 7.970.665 ₫
10.292.946 ₫ total
includes taxes & fees
3 Aug - 4 Aug
Reunion Resort & Golf Club
Flat-screen TV, DVD player

Grand Lake Resort

Grand Lake Resort
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (208 reviews)
"Family friendly, equipped kitchen, huge bath tubs and clean spacious rooms!"
United States
Rose
The price is 1.873.162 ₫
2.362.649 ₫ total
includes taxes & fees
2 Aug - 3 Aug
Grand Lake Resort
Exterior

Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.2 out of 10, Wonderful, (337 reviews)
"Great location and clean spacious and comfortable"
United States
Michele
The price is 2.787.408 ₫
3.491.939 ₫ total
includes taxes & fees
3 Aug - 4 Aug
Barefoot'n Resort Kissimmee Orlando
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, (3,182 reviews)
"Great rental on a beautiful property! Description was accurate, truly enjoyed the hot tub and lakeview!!"
United States
Phinnie
The price is 3.289.129 ₫
8.925.568 ₫ total
includes taxes & fees
9 Aug - 10 Aug
Regal Oaks Resort Vacation Townhomes by IDILIQ
Outdoor pool

The Irlo

The Irlo
3.0 star property
Kissimmee
7.6 out of 10, Good, (64 reviews)
"Room was nice, staff was friendly. Location was perfect for my needs"
United States
Amanda
The price is 1.498.530 ₫
2.297.616 ₫ total
includes taxes & fees
28 Jul - 29 Jul
The Irlo
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, (2,100 reviews)
"Happy with the location and area great for families"
United States
Noah
The price is 5.363.160 ₫
11.349.320 ₫ total
includes taxes & fees
19 Aug - 20 Aug
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
Lobby sitting area

Encantada Resort Vacation Townhomes by IDILIQ

Encantada Resort Vacation Townhomes by IDILIQ
3.0 star property
Kissimmee
8.4 out of 10, Very good, (1,461 reviews)
"A wonderful peaceful getaway for you and the family or just yourself and a loved one absolutely beautiful property from clean rooms, accomadating staff , a wonderful time to enjoy no worries from being secured inside a gated community to peaceful summer nights in the hot tub or pool (your choice) but we couldn't have been more pleased with our stay and will be looking forward to coming again next year"
United States
Michael
The price is 2.786.492 ₫
8.355.076 ₫ total
includes taxes & fees
9 Aug - 10 Aug
Encantada Resort Vacation Townhomes by IDILIQ
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 1.551.228 ₫
1.760.775 ₫ total
includes taxes & fees
4 Aug - 5 Aug
Maple Leaf Inn & Suites
Exterior

Lifetime of Vacations Resort

Lifetime of Vacations Resort
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (174 reviews)
"We love coming here when we visit Orlando. The rooms are amazing and perfect for our needs. The beds are comfortable too!"
United States
Alena
The price is 1.884.085 ₫
2.585.293 ₫ total
includes taxes & fees
26 Jul - 27 Jul
Lifetime of Vacations Resort
House | 2 bedrooms

Super Boho Waterfront Retreat w Fishing Views

Super Boho Waterfront Retreat w Fishing Views
2.0 star property
Historic Downtown Kissimmee
8.0 out of 10, Very good, (1 review)
The price is 3.101.390 ₫
8.282.767 ₫ total
includes taxes & fees
22 Jul - 23 Jul
Super Boho Waterfront Retreat w Fishing Views
Villa (4 Bedrooms) | Dining

Emerald Garden - Resort - 15 Min to Disney - Pets

Emerald Garden - Resort - 15 Min to Disney - Pets
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is 4.206.720 ₫
12.212.635 ₫ total
includes taxes & fees
22 Jul - 23 Jul
Emerald Garden - Resort - 15 Min to Disney - Pets
Luxury House, 4 Bedrooms | Interior

Parkside Paradise

Parkside Paradise
2.5 star property
Reunion
Parkside Paradise
Front of property

Disney Area Home | Pool · Spa · Game Room | 5BR Sleeps 14

Disney Area Home | Pool · Spa · Game Room | 5BR Sleeps 14
4.5 star property
Lindfields
The price is 5.915.700 ₫
12.533.395 ₫ total
includes taxes & fees
22 Jul - 23 Jul
Disney Area Home | Pool · Spa · Game Room | 5BR Sleeps 14
Family Apartment | Private kitchen | Espresso maker, full-sized fridge, microwave, oven

LOVELY LUXURY APARTMENT CLOSE DISNEY

LOVELY LUXURY APARTMENT CLOSE DISNEY
3.5 star property
Kissimmee
8.4 out of 10, Very good, (11 reviews)
"Nice appartment, everything you needed and clean and modern"
United Kingdom
Martyn
The price is 2.875.030 ₫
8.007.944 ₫ total
includes taxes & fees
20 Aug - 21 Aug
LOVELY LUXURY APARTMENT CLOSE DISNEY
Outdoor pool

Harmony Ensuite Room Shared Home No Car

Harmony Ensuite Room Shared Home No Car
2.5 star property
Kissimmee
The price is 1.156.848 ₫
3.401.922 ₫ total
includes taxes & fees
3 Aug - 4 Aug
Harmony Ensuite Room Shared Home No Car
2 outdoor pools

Value Edge

Value Edge
Kissimmee
The price is 1.577.520 ₫
3.580.971 ₫ total
includes taxes & fees
22 Jul - 23 Jul
Value Edge
Condo, 2 Bedrooms | Exterior

Vacation Meadows - Storey Lake By Shine Villas 710 2 Bedroom Apts

Vacation Meadows - Storey Lake By Shine Villas 710 2 Bedroom Apts
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Great communication and close to Disney and Universal. Very roomy unit "
United States
Gilbert
The price is 3.321.479 ₫
14.197.815 ₫ total
includes taxes & fees
26 Jul - 27 Jul
Vacation Meadows - Storey Lake By Shine Villas 710 2 Bedroom Apts
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

The Adventure Hotel by the parks

The Adventure Hotel by the parks

10/10 Excellent
"super close to Denny's and freeway if you have a rental car"
vivienne 8-night trip
Posted 1 hour ago
The Adventure Hotel by the parks