Bargain Timeshare Rentals in Kissimmee

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Westgate Vacation Villas

Kissimmee, Florida

Jul 4–11, 2026 (7 nights)
2 bed/2 bath, sleeps 10
$1,878 ($268/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Oct 3–12, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$2,419 ($269/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 28 – Sep 3, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,620 ($270/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Nov 15–28, 2026 (13 nights)
2 bed/2 bath, sleeps 8
$3,491 ($269/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Jun 3–8, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,385 ($277/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

Jun 28 – Jul 5, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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Westgate Towers

Kissimmee, Florida

Jul 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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
$1,932 ($276/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

Jul 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,932 ($276/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 17–29, 2026 (12 nights)
2 bed/2 bath, sleeps 8
$3,304 ($275/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Oct 9–16, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,948 ($278/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 13–17, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,119 ($280/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Nov 27 – Dec 4, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,948 ($278/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 30 – Aug 3, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,119 ($280/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

Oct 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,948 ($278/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 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 16–23, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,948 ($278/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Nov 15–22, 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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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 23–27, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,119 ($280/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Nov 8–15, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,948 ($278/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 18–23, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,405 ($281/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 16–22, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,686 ($281/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 18–22, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,132 ($283/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Sep 4–7, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$852 ($284/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Oct 9–12, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$852 ($284/night)

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Westgate Town Center

Kissimmee, Florida

Jul 25 – Aug 1, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,986 ($284/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,987 ($284/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Jun 14–21, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,987 ($284/night)

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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
$1,987 ($284/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
$1,987 ($284/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 27 – Aug 1, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,436 ($287/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Nov 4–9, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,444 ($289/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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Club Wyndham Cypress Palms

Kissimmee, Florida

Nov 18–24, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,752 ($292/night)

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 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,042 ($292/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 18–24, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,765 ($294/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

May 22–25, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$887 ($296/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Sep 18–21, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$892 ($297/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 2–6, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,189 ($297/night)

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jul 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,085 ($298/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Jun 27 – Jul 4, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,091 ($299/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Oct 8–13, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,506 ($301/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 15–22, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,100 ($300/night)