Discounted Timeshare Rentals in Kissimmee

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Jul 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,220 $1,110 ($159/night) 50% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 13–18, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$809 $526 ($105/night) 35% off

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jul 4–11, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,301 $1,932 ($276/night) 16% off

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Barefoot Suites

Kissimmee, Florida

Jul 26 – Aug 2, 2026 (7 nights)
2 bed/1 bath, sleeps 6
$1,164 $722 ($103/night) 38% off

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Barefoot Suites

Kissimmee, Florida

Jul 26 – Aug 2, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,164 $722 ($103/night) 38% off

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jun 28 – Jul 5, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,947 $1,110 ($159/night) 43% off

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Aug 8–16, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$2,138 $1,625 ($203/night) 24% off

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Jun 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,930 $888 ($127/night) 54% off

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Westgate Town Center

Kissimmee, Florida

Jul 17–24, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,110 $555 ($79/night) 50% off

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Westgate Town Center

Kissimmee, Florida

Jun 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,770 $1,385 ($198/night) 50% off

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Westgate Town Center

Kissimmee, Florida

Nov 28 – Dec 5, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,543 $1,358 ($194/night) 12% off

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Westgate Town Center

Kissimmee, Florida

Nov 28 – Dec 5, 2026 (7 nights)
Studio/1 bath, sleeps 2
$1,116 $971 ($139/night) 13% off

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$3,306 $2,612 ($373/night) 21% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 23–28, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,025 $666 ($133/night) 35% off

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jul 21–27, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,790 $1,110 ($185/night) 38% off

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jul 5–11, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,998 $999 ($166/night) 50% off

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Aug 15–22, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,543 $2,238 ($320/night) 12% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,304 $848 ($121/night) 35% off

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Jul 1–8, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,135 $1,110 ($159/night) 48% off

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Westgate Vacation Villas

Kissimmee, Florida

Jul 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,890 $1,550 ($221/night) 18% off

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WorldMark Orlando – Reunion

Kissimmee, Florida

Jul 31 – Aug 3, 2026 (3 nights)
3 bed/3 bath, sleeps 8
$1,661 $1,495 ($498/night) 10% off

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WorldMark Orlando – Reunion

Kissimmee, Florida

Jul 31 – Aug 3, 2026 (3 nights)
3 bed/3 bath, sleeps 8
$1,661 $1,495 ($498/night) 10% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 20–26, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,058 $687 ($115/night) 35% off

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jun 19–26, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,722 $1,932 ($276/night) 29% off

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jul 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,852 $2,042 ($292/night) 47% off

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Jul 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,985 $1,330 ($190/night) 33% off

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Westgate Town Center

Kissimmee, Florida

Jul 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,477 $2,886 ($412/night) 17% off

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Jul 3–10, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,510 $1,932 ($276/night) 23% off

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Jun 20–27, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,937 $1,220 ($174/night) 37% off

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Silver Lake Resort

Kissimmee, Florida

Jul 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,287 $2,696 ($385/night) 18% off

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Westgate Town Center

Kissimmee, Florida

Jun 27 – Jul 4, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,310 $1,987 ($284/night) 14% off

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Westgate Town Center

Kissimmee, Florida

Jun 27 – Jul 4, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,207 $1,986 ($284/night) 10% off

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jul 25 – Aug 1, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,000 $1,440 ($206/night) 28% off

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jul 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,823 $1,440 ($206/night) 21% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 17–20, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$745 $484 ($161/night) 35% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,304 $848 ($121/night) 35% off

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Westgate Towers

Kissimmee, Florida

Jul 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,951 $1,385 ($198/night) 29% off

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,669 $1,385 ($198/night) 17% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 10–19, 2026 (9 nights)
1 bed/1 bath, sleeps 4
$1,792 $1,165 ($129/night) 35% off

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Westgate Vacation Villas

Kissimmee, Florida

Jun 28 – Jul 5, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,662 $1,330 ($190/night) 20% off

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jul 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,218 $1,220 ($174/night) 45% off

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jul 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,313 $1,550 ($221/night) 33% off

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Jun 21–28, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,323 $1,440 ($206/night) 38% off

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Westgate Vacation Villas

Kissimmee, Florida

Jun 27 – Jul 4, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,665 $666 ($95/night) 60% off

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Jun 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,656 $1,275 ($182/night) 23% off

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jul 4–11, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,870 $1,627 ($232/night) 13% off

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Mystic Dunes Resort & Golf Club

Kissimmee, Florida

Nov 22–28, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,512 $1,119 ($186/night) 26% off

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Jul 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,543 $1,358 ($194/night) 12% off