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Osceola County Holiday Rentals

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Featured Osceola County Holiday Rentals

Interior
Margaritaville Cottages Orlando by Rentyl

Margaritaville Cottages Orlando by Rentyl

4.0 star property
Kissimmee
8.8 out of 10, Excellent, (1742)
"Amazing accommodations "
Canada
Marina
The price is S$537
includes taxes & fees
9 Dec - 10 Dec
Margaritaville Cottages Orlando by Rentyl
Billiards
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, (3020)
" Clean room and a great staff"
United States
Victor
The price is S$480
includes taxes & fees
5 Jan - 6 Jan, 2026
Regal Oaks Resort Vacation Townhomes by IDILIQ
Dock
Barefoot Suites

Barefoot Suites

3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1796)
"We love to go to Old town and this is the perfect spot for walking distance and room is always clean. We always come here with our kids. It has a full kitchen that i love to use to make quick meals for my family and i love the pool and the hot tube . I love the porch is has a screen which is great to have breakfast and coffee and a lil wine in the afternoon. Very relaxing atmosphere 😌 "
United States
Isabel
Barefoot Suites
Water park
Reunion Resort & Golf Club

Reunion Resort & Golf Club

5.0 star property
Reunion
8.8 out of 10, Excellent, (1436)
"Family Friendly"
United States
Janaya
The price is S$405
includes taxes & fees
9 Dec - 10 Dec
Reunion Resort & Golf Club
Exterior
Magical Dreams

Magical Dreams

4.0 star property
Kissimmee
6.0 out of 10, (5)
"Parking can be an issue but as long as you communicate with the others, you’ll be alright. "
United States
Shana
The price is S$170
includes taxes & fees
9 Dec - 10 Dec
Magical Dreams
Exterior
voco Kissimmee Orlando by IHG

voco Kissimmee Orlando by IHG

4.0 star property
Kissimmee
7.4 out of 10, Good, (1004)
"Place was clean, staff great, cozy very nice area swimming pool"
United States
KRYSTLE
The price is S$97
includes taxes & fees
10 Dec - 11 Dec
voco Kissimmee Orlando by IHG
Exterior
Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando

2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (165)
"Fully equipped kitchen was decent, staff was warm and welcoming."
United States
Karunya Bharadwaja
The price is S$155
includes taxes & fees
4 Jan - 5 Jan, 2026
Barefoot'n Resort Kissimmee Orlando
Aerial view
Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3089)
"Great place to stay"
United States
Jose
The price is S$180
includes taxes & fees
9 Dec - 10 Dec
Vacation Village Orlando, Celebration
Sauna
Harmony Haven

Harmony Haven

2.5 star property
Kissimmee
The price is S$160
includes taxes & fees
9 Dec - 10 Dec
Harmony Haven
5 bedrooms
Super Cool- Sleeps 17 Newly Built Near Parks

Super Cool- Sleeps 17 Newly Built Near Parks

2.0 star property
Kissimmee
The price is S$471
includes taxes & fees
11 Dec - 12 Dec
Super Cool- Sleeps 17 Newly Built Near Parks
Private pool
Formosa Valley Resort by UNE Homes

Formosa Valley Resort by UNE Homes

4.0 star property
Kissimmee
9.4 out of 10, Exceptional, (193)
"Loved our stay here. Would highly recommend "
United States
Walter
The price is S$658
includes taxes & fees
9 Dec - 10 Dec
Formosa Valley Resort by UNE Homes
2 outdoor pools
Storey Lake condos by UNE Homes

Storey Lake condos by UNE Homes

3.5 star property
Kissimmee
Storey Lake condos by UNE Homes
Full-sized fridge, microwave, oven, stovetop
Enchanted Dreams

Enchanted Dreams

3.5 star property
Kissimmee
7.4 out of 10, Good, (6)
"Clean, comfortable home. Everything was excellent from the security to amenities. I will book again, share with friends and family. "
United States
Gregory
The price is S$189
includes taxes & fees
9 Dec - 10 Dec
Enchanted Dreams
Blackout curtains, iron/ironing board, free WiFi
The Irlo

The Irlo

3.0 star property
Kissimmee
The price is S$284
includes taxes & fees
9 Dec - 10 Dec
The Irlo
2 outdoor pools, pool umbrellas, pool loungers
Encantada Resort Vacation Townhomes by IDILIQ

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
Kissimmee
8.4 out of 10, Very good, (1400)
"2nd time staying here safe to say this is our second home "
United States
Melanie
The price is S$417
includes taxes & fees
14 Dec - 15 Dec
Encantada Resort Vacation Townhomes by IDILIQ
Private kitchen
Modern 3 Bed Villa, Newly Renovated, Prime Location

Modern 3 Bed Villa, Newly Renovated, Prime Location

3.0 star property
Kissimmee
The price is S$374
includes taxes & fees
9 Dec - 10 Dec
Modern 3 Bed Villa, Newly Renovated, Prime Location
In-room dining
LOVELY LUXURY APARTMENT CLOSE DISNEY

LOVELY LUXURY APARTMENT CLOSE DISNEY

3.5 star property
Kissimmee
8.0 out of 10, Very good, (4)
"We liked the friendliness of the folks around us. Once we got used to the the streets and how they changed names we were able to navigate around without trouble. At first though we got lost quite often. There weren't enough towels and wash cloths and the kitchen faucet had a broken faucet nut which we had to fix ourselves a couple of times. Other than that it was a most comfortable abode and we are glad that we rented it. "
United States
Edward
LOVELY LUXURY APARTMENT CLOSE DISNEY
Waterslide
Champions Gate Resort Home w BBQ Pool

Champions Gate Resort Home w BBQ Pool

2.0 star property
Champions Gate
9.2 out of 10, Wonderful, (7)
"Very relaxing and my property assistant was great over the phone "
United States
Robert
Champions Gate Resort Home w BBQ Pool
2 outdoor pools
Champions Gate condos by UNE

Champions Gate condos by UNE

4.0 star property
Champions Gate
9.0 out of 10, Wonderful, (52)
"Home and owners were amazing. We would definitely stay again if need. Great for soccer families as there is a little field right across the street. "
United States
Melissa
The price is S$397
includes taxes & fees
9 Dec - 10 Dec
Champions Gate condos by UNE
4 bedrooms
Super Liked - 4BD 3 5b 6 Miles To Disney Springs

Super Liked - 4BD 3 5b 6 Miles To Disney Springs

2.0 star property
Kissimmee
Super Liked - 4BD 3 5b 6 Miles To Disney Springs
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

Red Lion Hotel Orlando Lake Buena Vista South

Red Lion Hotel Orlando Lake Buena Vista South

10/10 Excellent
"Room was very clean and the whole staff was A+ will gladly recommend this hotel. Thank you for a great stay and thank you to the entire staff from the 2nd floor will come back and ask to be in that floor."
Virmary 1-night trip
Posted 3 days ago
Red Lion Hotel Orlando Lake Buena Vista South