Bargain Timeshare Rentals in Kissimmee

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Club Wyndham Cypress Palms

Kissimmee, Florida

Nov 4–8, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$888 ($222/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Sep 4–11, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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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
$1,550 ($221/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Oct 9–16, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Sep 18–20, 2026 (2 nights)
3 bed/3 bath, sleeps 12
$455 ($228/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Sep 18–20, 2026 (2 nights)
3 bed/3 bath, sleeps 12
$455 ($228/night)

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WorldMark Orlando – Reunion

Kissimmee, Florida

Jul 31 – Aug 3, 2026 (3 nights)
3 bed/3 bath, sleeps 8
$666 ($222/night)

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Westgate Town Center

Kissimmee, Florida

Feb 14–21, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$1,563 ($223/night)

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Westgate Town Center

Kissimmee, Florida

Feb 12–19, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$1,563 ($223/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Mar 21–28, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,605 ($229/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Nov 14–21, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,627 ($232/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Mar 13–20, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,660 ($237/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Nov 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,660 ($237/night)

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Vacation Village at Parkway

Kissimmee, Florida

Sep 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,660 ($237/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Mar 20–27, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,660 ($237/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 25, 2027 – Jan 1, 2028 (7 nights)
3 bed/3 bath, sleeps 12
$1,660 ($237/night)

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Nov 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,696 ($242/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Aug 16–23, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,704 ($243/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Aug 16–23, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,704 ($243/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Aug 16–23, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,704 ($243/night)

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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
$1,704 ($243/night)

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Vacation Village at Parkway

Kissimmee, Florida

Sep 26 – Oct 3, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,725 ($246/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 1, 2027 (4 nights)
2 bed/2 bath, sleeps 8
$995 ($249/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 23–27, 2026 (4 nights)
Studio/1 bath, sleeps 5
$999 ($250/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 30 – Feb 6, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,765 ($252/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Oct 9–16, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,765 ($252/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 19–26, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,765 ($252/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,768 ($253/night)

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Westgate Town Center

Kissimmee, Florida

Jul 17–24, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,769 ($253/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Aug 1–8, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,769 ($253/night)

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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
$1,769 ($253/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Nov 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,769 ($253/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Nov 22–29, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,769 ($253/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Nov 8–15, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,780 ($254/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Nov 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,818 ($260/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Aug 8–15, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,824 ($260/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 22–26, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$1,054 ($264/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Feb 15–22, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,840 ($263/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Aug 16–21, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,324 ($265/night)

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Westgate Town Center

Kissimmee, Florida

Aug 21–28, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,862 ($266/night)

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Westgate Town Center

Kissimmee, Florida

Jul 17–24, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,862 ($266/night)

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Westgate Town Center

Kissimmee, Florida

Jul 17–24, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,862 ($266/night)

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Westgate Town Center

Kissimmee, Florida

Oct 4–11, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,862 ($266/night)

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Westgate Town Center

Kissimmee, Florida

Oct 3–10, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,862 ($266/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,878 ($268/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Feb 20–28, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$2,144 ($268/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 22, 2026 – Jan 3, 2027 (12 nights)
2 bed/2 bath, sleeps 8
$3,256 ($271/night)