A lake with a wooden bridge and a gazebo.

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Our top choices for Osceola County holiday rentals

1. Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (5,265 reviews)
"Great place to stay at a great place."
United States
Desiree
The price is £77
includes taxes & fees
29 Nov - 30 Nov
Vacation Village Orlando, Celebration

2. Hotel-Style Room Pool, Disney Shuttle

Hotel-Style Room Pool, Disney Shuttle
3.0 star property
Kissimmee
The price is £85
includes taxes & fees
9 Nov - 10 Nov
Hotel-Style Room Pool, Disney Shuttle

3. Lyrios Vacation Rentals - The Palms

Lyrios Vacation Rentals - The Palms
4.0 star property
Kissimmee
The price is £141
includes taxes & fees
10 Nov - 11 Nov
Lyrios Vacation Rentals - The Palms

4. Villas at Fortune Place

Villas at Fortune Place
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (275 reviews)
"Love it nice place to stay"
United States
iris
The price is £78
includes taxes & fees
16 Nov - 17 Nov
Villas at Fortune Place

5. Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
4.0 star property
Kissimmee
9.0 out of 10, Wonderful, (2,353 reviews)
"The cottages wonderful will book again"
United States
Cadine
The price is £342
includes taxes & fees
16 Nov - 17 Nov
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

6. 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, (3,269 reviews)
"Nice property friendly place"
United States
Tina
The price is £204
includes taxes & fees
3 Nov - 4 Nov
Regal Oaks Resort Vacation Townhomes by IDILIQ

7. Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (384 reviews)
"My favorite place to stay in Kissimmee"
United States
James
The price is £98
includes taxes & fees
8 Nov - 9 Nov
Barefoot'n Resort Kissimmee Orlando

8. Grand Lake Resort

Grand Lake Resort
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (281 reviews)
"Everyone and everything was awesome clean friendly"
United States
LaShonda
The price is £63
includes taxes & fees
16 Nov - 17 Nov
Grand Lake Resort

9. LOVELY LUXURY APARTMENT CLOSE DISNEY

LOVELY LUXURY APARTMENT CLOSE DISNEY
3.5 star property
Kissimmee
8.4 out of 10, Very good, (12 reviews)
"Good price and very comfortable"
United States
Yandra
The price is £227
includes taxes & fees
3 Nov - 4 Nov
LOVELY LUXURY APARTMENT CLOSE DISNEY

10. Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,943 reviews)
"Our favorite hotel to book in Orlando!"
United States
Mary
The price is £84
includes taxes & fees
3 Nov - 4 Nov
Barefoot Suites

11. Sunset Bliss Retreat Condo - Near Disney

Sunset Bliss Retreat Condo - Near Disney
Kissimmee
9.6 out of 10, Exceptional, (62 reviews)
"Will stay again ! Amazing place . Host was very responsive to our needs"
United States
marie c.
The price is £115
includes taxes & fees
3 Nov - 4 Nov
Sunset Bliss Retreat Condo - Near Disney

12. Maple Leaf Inn & Suites

Maple Leaf Inn & Suites
2.5 star property
Kissimmee
7.0 out of 10, Good, (73 reviews)
"Yes recomende"
United States
Alex
The price is £50
includes taxes & fees
3 Nov - 4 Nov
Maple Leaf Inn & Suites

13. Lifetime of Vacations Resort

Lifetime of Vacations Resort
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (186 reviews)
"We absolutely love coming to lifetime and grand lake resort. This is our favorite place to stay!!"
United States
Alena
The price is £80
includes taxes & fees
29 Nov - 30 Nov
Lifetime of Vacations Resort

14. Garden in the Cloud- Cottage St. Cloud with WiFi, AC, Free parking

Garden in the Cloud- Cottage St. Cloud with WiFi, AC, Free parking
St. Cloud
10.0 out of 10, Exceptional, (32 reviews)
"Great cute and clean place."
United States
Victoria T.
The price is £99
includes taxes & fees
16 Nov - 17 Nov
Garden in the Cloud- Cottage St. Cloud with WiFi, AC, Free parking

15. Vacation Townhomes by IDILIQ at Encantada Resort

Vacation Townhomes by IDILIQ at Encantada Resort
3.0 star property
Kissimmee
8.4 out of 10, Very good, (1,481 reviews)
"Nice stay"
United States
Pamela
The price is £201
includes taxes & fees
3 Nov - 4 Nov
Vacation Townhomes by IDILIQ at Encantada Resort

16. The Grand Retreat at CG with pool

The Grand Retreat at CG with pool
4.0 star property
Champions Gate
The Grand Retreat at CG with pool

17. Luxe Condo Double Bed Bliss Getaway near Disney

Luxe Condo Double Bed Bliss Getaway near Disney
Kissimmee
8.8 out of 10, Excellent, (48 reviews)
"This place is nice. Easy access and the pools are nice. Property is a bit dated but for the price you can’t beat it. I will stay here again."
United States
Jeremy
The price is £121
includes taxes & fees
3 Nov - 4 Nov
Luxe Condo Double Bed Bliss Getaway near Disney

18. It’s only 15 minutes drive to Disney World and the amazing outlets in Orlando

It’s only 15 minutes drive to Disney World and the amazing outlets in Orlando
Kissimmee
9.8 out of 10, Exceptional, (39 reviews)
"Nice view! Very quiet."
United States
Donald B.
The price is £245
includes taxes & fees
3 Nov - 4 Nov
It’s only 15 minutes drive to Disney World and the amazing outlets in Orlando

19. Charming 1-bedroom house in pleasant St. Cloud within close distance to Parks

Charming 1-bedroom house in pleasant St. Cloud within close distance to Parks
St. Cloud
9.8 out of 10, Exceptional, (9 reviews)
"The host was very responsive and helpful.The home was so clean and well equipped.We totally enjoyed our stay!"
United States
Brenda G.
The price is £187
includes taxes & fees
9 Nov - 10 Nov
Charming 1-bedroom house in pleasant St. Cloud within close distance to Parks

20. Luxe King Suite Bliss Getaway Condo Near Disney

Luxe King Suite Bliss Getaway Condo Near Disney
Kissimmee
9.2 out of 10, Wonderful, (50 reviews)
"I was very pleased and happy with my stay at this property. It was clean, convenient to where I needed to be daily and I felt very safe. I definitely would return as it was a great stay!"
United States
Sarah M.
The price is £117
includes taxes & fees
9 Nov - 10 Nov
Luxe King Suite Bliss Getaway Condo Near Disney
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.
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Top Osceola County Hotel Reviews

Find out more about Osceola County

Everything you need to know about Osceola County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osceola County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osceola County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Osceola County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osceola County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osceola County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osceola County holiday rentals we have selected for you start as low as £63 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Osceola County rentals

At Expedia, we put the best Osceola County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Osceola County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osceola County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osceola County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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