Bargain Timeshare Rentals in Kissimmee

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 4–9, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,629 ($326/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
$998 ($333/night)

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Mystic Dunes Resort & Golf Club

Kissimmee, Florida

Jul 3–9, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,987 ($331/night)

Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Jul 4–11, 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

Jul 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($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)

Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Jun 28 – Jul 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 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/night)

Westgate Vacation Villas

Kissimmee, Florida

Mar 13–20, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($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 - 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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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 28 – Sep 1, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,356 ($339/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 27–31, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,356 ($339/night)

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Westgate Town Center

Kissimmee, Florida

Oct 17–24, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,368 ($338/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 5–9, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,383 ($346/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
$2,422 ($346/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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Westgate Town Center

Kissimmee, Florida

Sep 13–20, 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

May 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,532 ($362/night)

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Westgate Town Center

Kissimmee, Florida

Sep 18–25, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,581 ($369/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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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 8–11, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$1,136 ($379/night)

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Apr 3–10, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,641 ($377/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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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,641 ($377/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Aug 8–15, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,641 ($377/night)

Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Jun 28 – Jul 5, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,696 ($385/night)

Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Jun 28 – Jul 5, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,696 ($385/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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Westgate Vacation Villas

Kissimmee, Florida

Jul 26 – Aug 2, 2026 (7 nights)
2 bed/2 bath, sleeps 10
$2,750 ($393/night)

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jul 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,750 ($393/night)

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Westgate Town Center

Kissimmee, Florida

Nov 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,848 ($407/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Jul 4–11, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,859 ($408/night)

Westgate Town Center

Kissimmee, Florida

Jul 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,859 ($408/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Nov 21–28, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,886 ($412/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
$2,886 ($412/night)

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Westgate Towers

Kissimmee, Florida

Nov 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,963 ($423/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Nov 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,968 ($424/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
$3,022 ($432/night)

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Westgate Town Center

Kissimmee, Florida

Dec 4–11, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,022 ($432/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jul 1–6, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$2,205 ($441/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,186 ($455/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Nov 21–28, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$3,295 ($471/night)

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WorldMark Orlando – Reunion

Kissimmee, Florida

Jun 4–11, 2026 (7 nights)
3 bed/3 bath, sleeps 8
$3,382 ($483/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,404 ($486/night)

Westgate Town Center

Kissimmee, Florida

Jul 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,458 ($494/night)

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WorldMark Orlando – Reunion

Kissimmee, Florida

Jul 3–6, 2026 (3 nights)
3 bed/3 bath, sleeps 8
$1,769 ($590/night)