Bargain Timeshare Rentals in Kissimmee

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Club Wyndham Cypress Palms

Kissimmee, Florida

Mar 24–29, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,629 ($326/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 1–11, 2027 (10 nights)
2 bed/2 bath, sleeps 8
$3,234 ($323/night)

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Westgate Town Center

Kissimmee, Florida

Feb 19–26, 2027 (7 nights)
4 bed/4 bath, sleeps 16
$2,283 ($326/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

May 29 – Jun 5, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,291 ($327/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
$2,306 ($329/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Feb 6–13, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,306 ($329/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
$2,309 ($330/night)

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Club Wyndham Reunion

Kissimmee, Florida

Nov 21–27, 2026 (6 nights)
3 bed/3 bath, sleeps 8
$1,986 ($331/night)

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Polynesian Isles Resort

Kissimmee, Florida

Nov 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,314 ($331/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Oct 18–24, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,987 ($331/night)

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Westgate Town Center

Kissimmee, Florida

Dec 12–19, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,314 ($331/night)

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Silver Lake Resort

Kissimmee, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,314 ($331/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 26, 2026 – Jan 3, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$2,641 ($330/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
$2,314 ($331/night)

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Westgate Vacation Villas

Kissimmee, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 10
$2,314 ($331/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Mar 13–20, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/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
$2,314 ($331/night)

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Westgate Town Center

Kissimmee, Florida

Nov 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Aug 29 – Sep 5, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/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
$2,315 ($331/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Feb 11–15, 2027 (4 nights)
2 bed/2 bath, sleeps 8
$1,334 ($334/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Mar 11–15, 2027 (4 nights)
2 bed/2 bath, sleeps 8
$1,334 ($334/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jun 10–13, 2027 (3 nights)
2 bed/2 bath, sleeps 8
$1,021 ($340/night)

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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
$2,383 ($340/night)

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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
$2,390 ($341/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–27, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,383 ($346/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Apr 7–11, 2027 (4 nights)
2 bed/2 bath, sleeps 8
$1,383 ($346/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 17–20, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$1,039 ($346/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,423 ($346/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,423 ($346/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
$2,428 ($347/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
$2,428 ($347/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jun 10–13, 2027 (3 nights)
2 bed/2 bath, sleeps 8
$1,088 ($363/night)

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Westgate Town Center

Kissimmee, Florida

Oct 9–16, 2026 (7 nights)
5 bed/5 bath, sleeps 20
$2,531 ($362/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
$2,532 ($362/night)

Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Oct 28 – Nov 1, 2026 (4 nights)
3 bed/3 bath, sleeps 12
$1,466 ($367/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Oct 28 – Nov 1, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,466 ($367/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,586 ($370/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,612 ($373/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Feb 12–15, 2027 (3 nights)
2 bed/2 bath, sleeps 8
$1,136 ($379/night)

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WorldMark Orlando – Reunion

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
3 bed/3 bath, sleeps 8
$2,641 ($377/night)

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Westgate Vacation Villas

Kissimmee, Florida

Sep 21–25, 2026 (4 nights)
2 bed/2 bath, sleeps 10
$1,544 ($386/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
$2,696 ($385/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,750 ($393/night)

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Westgate Vacation Villas

Kissimmee, Florida

Nov 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,750 ($393/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Aug 22–29, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,750 ($393/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
$2,772 ($396/night)