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Osceola County Holiday Rentals

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Our top choices for Osceola County holiday rentals

Exterior

1. Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (5,041 reviews)
"Nice hotel and great location close to the Parks."
United States
Monica
The price is HK$538
HK$807 total
includes taxes & fees
20 Sept - 21 Sept
Vacation Village Orlando, Celebration
2 outdoor pools, open 8:00 AM to 11:00 PM, pool umbrellas, pool loungers

2. Villas at Fortune Place

Villas at Fortune Place
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (224 reviews)
"Great stay for the cost. Close to all the parks & the airport. Would definitely book this spot again."
United States
Joseph
The price is HK$616
HK$770 total
includes taxes & fees
21 Sept - 22 Sept
Villas at Fortune Place
Outdoor pool, pool umbrellas, pool loungers

3. Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,921 reviews)
"Great place to stay!"
United States
David
The price is HK$691
HK$939 total
includes taxes & fees
20 Sept - 21 Sept
Barefoot Suites
Water park

4. Reunion Resort & Golf Club

Reunion Resort & Golf Club
5.0 star property
Reunion
8.8 out of 10, Excellent, (1,623 reviews)
"Great stay! Will visit again."
United States
RYAN
The price is HK$1,807
HK$2,422 total
includes taxes & fees
20 Sept - 21 Sept
Reunion Resort & Golf Club
Exterior

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, (2,262 reviews)
"nice place to stay!"
United States
Victor
The price is HK$1,600
HK$3,921 total
includes taxes & fees
21 Sept - 22 Sept
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
Private pool

6. Club Wyndham Cypress Palms

Club Wyndham Cypress Palms
3.5 star property
Kissimmee
9.0 out of 10, Wonderful, (1,975 reviews)
"The place was nice clean and amazing will return in December"
United States
Natarisha
The price is HK$1,052
HK$1,194 total
includes taxes & fees
14 Oct - 15 Oct
Club Wyndham Cypress Palms
Exterior

7. Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (367 reviews)
"Nice rooms pool was great definitely will be back"
United States
Gilbert
The price is HK$667
HK$854 total
includes taxes & fees
20 Sept - 21 Sept
Barefoot'n Resort Kissimmee Orlando
Exterior

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, (3,235 reviews)
"Loved the resort"
United States
Janet
The price is HK$683
HK$2,325 total
includes taxes & fees
20 Sept - 21 Sept
Regal Oaks Resort Vacation Townhomes by IDILIQ
Outdoor pool

9. Maple Leaf Inn & Suites

Maple Leaf Inn & Suites
2.5 star property
Kissimmee
6.8 out of 10, (72 reviews)
"The room was clean and the staff was okay "
United States
Shaneka
The price is HK$463
HK$525 total
includes taxes & fees
20 Sept - 21 Sept
Maple Leaf Inn & Suites
Flat-screen TV, DVD player

10. Grand Lake Resort

Grand Lake Resort
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (250 reviews)
"I enjoyed my stay at this hotel and the pool was clean and refreshing"
United States
LeeAnna
The price is HK$559
HK$705 total
includes taxes & fees
20 Sept - 21 Sept
Grand Lake Resort
Exterior

11. Lifetime of Vacations Resort

Lifetime of Vacations Resort
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (182 reviews)
"We absolutely love coming to lifetime and grand lake resort. This is our favorite place to stay!!"
United States
Alena
The price is HK$521
HK$725 total
includes taxes & fees
20 Sept - 21 Sept
Lifetime of Vacations Resort
Lobby sitting area

12. Encantada Resort Vacation Townhomes by IDILIQ

Encantada Resort Vacation Townhomes by IDILIQ
3.0 star property
Kissimmee
8.4 out of 10, Very good, (1,471 reviews)
"Nice stay"
United States
Pamela
The price is HK$749
HK$2,399 total
includes taxes & fees
20 Sept - 21 Sept
Encantada Resort Vacation Townhomes by IDILIQ
Coffee/tea maker, fridge, microwave, oven

13. Charming 2-bedroom Florida Getaway! Sleeps 6

Charming 2-bedroom Florida Getaway! Sleeps 6
Kissimmee
9.8 out of 10, Exceptional, (21 reviews)
"Great little place. We would book it again."
United States
Jack Francis G.
The price is HK$682
HK$2,353 total
includes taxes & fees
18 Sept - 19 Sept
Charming 2-bedroom Florida Getaway! Sleeps 6
Private kitchen

14. 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 HK$820
HK$2,346 total
includes taxes & fees
18 Sept - 19 Sept
LOVELY LUXURY APARTMENT CLOSE DISNEY
Microwave, oven, stovetop, dishwasher

15. Think Pink in Kissimmee - Gorgeous 2BD with free WIFI, free parking and more!!

Think Pink in Kissimmee - Gorgeous 2BD with free WIFI, free parking and more!!
Kissimmee
9.6 out of 10, Exceptional, (13 reviews)
"This was a cute, quiet, and convenient rental location."
United States
Tabitha W.
The price is HK$847
HK$1,817 total
includes taxes & fees
22 Sept - 23 Sept
Think Pink in Kissimmee - Gorgeous 2BD with free WIFI, free parking and more!!
Exterior

16. Stunning Seaside Theme Water View Condo - no resort fees!

Stunning Seaside Theme Water View Condo - no resort fees!
Kissimmee
9.6 out of 10, Exceptional, (37 reviews)
"Everything was clean and host was available to answer any lingering questions."
United States
Monica O.
The price is HK$1,737
HK$2,924 total
includes taxes & fees
18 Sept - 19 Sept
Stunning Seaside Theme Water View Condo - no resort fees!
Pool

17. 10BR Villa Near Disney, Pool and Resort Waterpark

10BR Villa Near Disney, Pool and Resort Waterpark
Kissimmee
10.0 out of 10, Exceptional, (25 reviews)
"Great place to stay"
United States
Jefferson C.
The price is HK$1,589
HK$5,890 total
includes taxes & fees
18 Sept - 19 Sept
10BR Villa Near Disney, Pool and Resort Waterpark
Living area

18. Cozy 2BD/2BTH Condo Near Disney

Cozy 2BD/2BTH Condo Near Disney
Kissimmee
9.4 out of 10, Exceptional, (36 reviews)
"Comfy, cute, clean and affordable place to stay!"
United States
Anna W.
The price is HK$565
HK$1,510 total
includes taxes & fees
27 Sept - 28 Sept
Cozy 2BD/2BTH Condo Near Disney
Lake view

19. Willow Bend

Willow Bend
4.0 star property
Crescent Lakes
10.0 out of 10, Exceptional, (2 reviews)
"this house abuts woods and a slow river that made the property peaceful "
United States
John
The price is HK$1,823
HK$4,888 total
includes taxes & fees
17 Oct - 18 Oct
Willow Bend
Coffee/tea maker, fridge, microwave, oven

20. Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!

Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!
Buena Ventura Lakes
10.0 out of 10, Exceptional, (44 reviews)
"Comfortable & close to Orlando attractions."
United States
Bridget H.
The price is HK$981
HK$2,362 total
includes taxes & fees
27 Sept - 28 Sept
Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!
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

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

10/10 Excellent
"Pet friendly and very close to Walt Disney World"
Stephonie 7-night trip
Posted 1 hour ago
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark