A lake with a wooden bridge and a gazebo.

Osceola County Vacation Rentals

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Top Cities in Osceola County

Our top choices for Osceola County vacation rentals

1. Hotel-Style Room Pool, Disney Shuttle

Hotel-Style Room Pool, Disney Shuttle
3.0 star property
Kissimmee
The price is CA $56
CA $167 total
includes taxes & fees
Nov 18 - Nov 19
Hotel-Style Room Pool, Disney Shuttle

2. Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (5,309 reviews)
"Great stay"
United States
Jonatan
The price is CA $90
CA $138 total
includes taxes & fees
Dec 6 - Dec 7
Vacation Village Orlando, Celebration

3. Villas at Fortune Place

Villas at Fortune Place
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (285 reviews)
"Love it nice place to stay"
United States
iris
The price is CA $119
CA $148 total
includes taxes & fees
Dec 6 - Dec 7
Villas at Fortune Place

4. Lyrios Vacation Rentals - The Palms

Lyrios Vacation Rentals - The Palms
4.0 star property
Kissimmee
The price is CA $126
CA $271 total
includes taxes & fees
Nov 15 - Nov 16
Lyrios Vacation Rentals - The Palms

5. Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (388 reviews)
"My favorite place to stay in Kissimmee"
United States
James
The price is CA $123
CA $157 total
includes taxes & fees
Dec 13 - Dec 14
Barefoot'n Resort Kissimmee Orlando

6. Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,947 reviews)
"Our favorite hotel to book in Orlando!"
United States
Mary
The price is CA $124
CA $169 total
includes taxes & fees
Nov 15 - Nov 16
Barefoot Suites

7. 129 Seneca Point Trl

129 Seneca Point Trl
4.0 star property
Indian Point
The price is CA $154
CA $563 total
includes taxes & fees
Nov 18 - Nov 19
129 Seneca Point Trl

8. 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, (3,276 reviews)
"Nice property friendly place"
United States
Tina
The price is CA $102
CA $397 total
includes taxes & fees
Nov 16 - Nov 17
Regal Oaks Resort Vacation Townhomes by IDILIQ

9. 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, (2,373 reviews)
"Great stay!"
United States
Haley
The price is CA $269
CA $688 total
includes taxes & fees
Nov 16 - Nov 17
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

10. Lifetime of Vacations Resort

Lifetime of Vacations Resort
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (188 reviews)
"Enjoyed stay"
United States
Shanequa
The price is CA $104
CA $143 total
includes taxes & fees
Nov 29 - Nov 30
Lifetime of Vacations Resort

11. Grand Lake Resort

Grand Lake Resort
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (291 reviews)
"Clean rooms and great parking."
United States
Rose
The price is CA $101
CA $127 total
includes taxes & fees
Nov 30 - Dec 1
Grand Lake Resort

12. 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 CA $112
CA $184 total
includes taxes & fees
Nov 18 - Nov 19
Garden in the Cloud- Cottage St. Cloud with WiFi, AC, Free parking

13. Sunset Bliss Retreat Condo - Near Disney

Sunset Bliss Retreat Condo - Near Disney
Kissimmee
9.6 out of 10, Exceptional, (64 reviews)
"Will stay again ! Amazing place . Host was very responsive to our needs"
United States
marie c.
The price is CA $77
CA $206 total
includes taxes & fees
Nov 16 - Nov 17
Sunset Bliss Retreat Condo - Near Disney

14. 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, (1,484 reviews)
"Nice stay"
United States
Pamela
The price is CA $103
CA $397 total
includes taxes & fees
Dec 7 - Dec 8
Vacation Townhomes by IDILIQ at Encantada Resort

15. 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 CA $84
CA $95 total
includes taxes & fees
Nov 17 - Nov 18
Maple Leaf Inn & Suites

16. Sophisticated Retreat

Sophisticated Retreat
Kissimmee
9.4 out of 10, Exceptional, (13 reviews)
"It was a nice place, would stay again"
United States
chaynna s.
The price is CA $118
CA $265 total
includes taxes & fees
Nov 13 - Nov 14
Sophisticated Retreat

17. 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 CA $156
CA $364 total
includes taxes & fees
Nov 16 - Nov 17
Charming 1-bedroom house in pleasant St. Cloud within close distance to Parks

18. Orlando Emerald Dream House

Orlando Emerald Dream House
3.0 star property
Kissimmee
The price is CA $272
CA $309 total
includes taxes & fees
Nov 15 - Nov 16
Orlando Emerald Dream House

19. 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 CA $155
CA $432 total
includes taxes & fees
Nov 29 - Nov 30
LOVELY LUXURY APARTMENT CLOSE DISNEY

20. Fantastic Award Winning Newly Renovated Condo 4 miles to Disney 2+2

Fantastic Award Winning Newly Renovated Condo 4 miles to Disney 2+2
Kissimmee
9.6 out of 10, Exceptional, (220 reviews)
"Great property."
United States
Paula M.
The price is CA $114
CA $354 total
includes taxes & fees
Dec 7 - Dec 8
Fantastic Award Winning Newly Renovated Condo 4 miles to Disney 2+2
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osceola County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Osceola County vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osceola County vacation rentals we have selected for you start as low as CA $127 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 vacation 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 vacation.

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.