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Kissimmee timeshare rentals and resales

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida
219 reviews
60 rentals available $143 - $386/night
Rental availability
2025
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
2026
Jan
Feb
Mar
Apr
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Dec
20 resales available $0 - $3,000

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida
78 reviews
40 rentals available $143 - $514/night
Rental availability
2025
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
2026
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
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Dec
8 resales available $850 - $5,499

Westgate Town Center

Kissimmee, Florida
108 reviews
39 rentals available $78 - $357/night
Rental availability
2025
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
2026
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
10 resales available $0 - $10,000

Westgate Vacation Villas

Kissimmee, Florida
80 reviews
29 rentals available $78 - $357/night
Rental availability
2025
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
2026
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
12 resales available $1 - $3,500

Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida
86 reviews
11 rentals available $115 - $286/night
Rental availability
2025
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
6 resales available $500 - $5,000

Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida
46 reviews
11 rentals available $200 - $457/night
Rental availability
2025
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
2026
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
4 resales available $425 - $5,000

Star Island Resort

Kissimmee, Florida
51 reviews
7 rentals available $86 - $429/night
Rental availability
2025
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
6 resales available $1,000 - $5,000

Vacation Village at Parkway

Kissimmee, Florida
84 reviews
6 rentals available $105 - $357/night
Rental availability
2025
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
2026
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
34 resales available $0 - $3,000

Silver Lake Resort

Kissimmee, Florida
28 reviews
4 rentals available $86 - $175/night
Rental availability
2025
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
6 resales available $1 - $500

Calypso Cay Vacation Villas

Kissimmee, Florida
18 reviews
4 rentals available $71 - $200/night
Rental availability
2025
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
No resales available
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Mystic Dunes Resort & Golf Club

Kissimmee, Florida
57 reviews
3 rentals available $71 - $314/night
Rental availability
2025
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
6 resales available $1 - $9,999

Hilton Vacation Club Aqua Sol Orlando West

Kissimmee, Florida
34 reviews
3 rentals available $150 - $221/night
Rental availability
2025
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
No resales available
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Vacation Villas at Fantasy World

Kissimmee, Florida
11 reviews
3 rentals available $100 - $400/night
Rental availability
2025
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
No resales available
Sign up to be notified

Westgate Towers

Kissimmee, Florida
13 reviews
2 rentals available $170 - $207/night
Rental availability
2025
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
1 resale available $1

Club Wyndham Reunion

Kissimmee, Florida
4 reviews
2 rentals available $114 - $143/night
Rental availability
2025
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
No resales available
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WorldMark Orlando – Reunion

Kissimmee, Florida
7 reviews
2 rentals available $200 - $286/night
Rental availability
2025
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
No resales available
Sign up to be notified

Grand Lake Resort

Kissimmee, Florida
8 reviews
1 rental available $121/night
Rental availability
2025
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
1 resale available $700

Legacy Vacation Club Orlando - Resort World

Kissimmee, Florida
12 reviews
1 rental available $78/night
Rental availability
2025
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
1 resale available $0

Aptly nicknamed the Sunshine State, the shores of Florida boast hundreds of miles of sunny beaches throughout every season of the year. Palm Beach Shores, Marco Island, and The Keys are famed for their Latin-American culture and exciting nightlife, while Orlando offers family-friendly adventures via theme park resorts such as Disney World, Universal Orlando, and SeaWorld.

Home to some of the most luxurious rentals and theme park resorts in the states, you are sure to find vacation bliss at one of Florida’s exciting retreats:

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