Bargain Timeshare Rentals in Kissimmee

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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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Club Wyndham Cypress Palms

Kissimmee, Florida

Feb 10–15, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,330 ($266/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 3–10, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,862 ($266/night)

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Westgate Town Center

Kissimmee, Florida

Jul 10–17, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,862 ($266/night)

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Westgate Town Center

Kissimmee, Florida

Jun 28 – Jul 5, 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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Club Wyndham Cypress Palms

Kissimmee, Florida

Sep 4–14, 2026 (10 nights)
2 bed/2 bath, sleeps 8
$2,672 ($267/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

Nov 3–9, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,620 ($270/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Feb 14–20, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,634 ($272/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)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Feb 13–22, 2027 (9 nights)
2 bed/2 bath, sleeps 8
$2,454 ($273/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Mar 3–9, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,653 ($276/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Feb 12–19, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,926 ($275/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Aug 8–15, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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Westgate Town Center

Kissimmee, Florida

Nov 29 – Dec 6, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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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
$1,932 ($276/night)

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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
$1,932 ($276/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Jul 4–11, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,932 ($276/night)

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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
$1,932 ($276/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jul 18–24, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,660 ($277/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Jul 1–6, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,385 ($277/night)

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Vacation Village at Parkway

Kissimmee, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Nov 25–29, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,110 ($278/night)

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Vacation Village at Parkway

Kissimmee, Florida

Mar 26 – Apr 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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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
$1,932 ($276/night)

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Vacation Village at Parkway

Kissimmee, Florida

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Nov 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,948 ($278/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Nov 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,948 ($278/night)

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Westgate Town Center

Kissimmee, Florida

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

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Westgate Town Center

Kissimmee, Florida

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

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,987 ($284/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 2–6, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,156 ($289/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Feb 14–21, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,013 ($288/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 17–21, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,163 ($291/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Oct 7–12, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,458 ($292/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Nov 21–25, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,172 ($293/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,042 ($292/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
$2,042 ($292/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
$2,150 ($307/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jul 3–6, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$944 ($314/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Nov 6–13, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,200 ($314/night)

Westgate Vacation Villas

Kissimmee, Florida

Apr 3–10, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,204 ($315/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
$2,205 ($315/night)

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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
$2,205 ($315/night)