Bargain Timeshare Rentals in Kissimmee

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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

Jan 19–24, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,370 ($274/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,378 ($276/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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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 - River Island

Kissimmee, Florida

Mar 13–20, 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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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Nov 25–30, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,385 ($277/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
$1,932 ($276/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 - 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 - East Village

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

Dec 20–27, 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

Nov 24–29, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,385 ($277/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,956 ($280/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Feb 13–19, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,682 ($280/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
$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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Silver Lake Resort

Kissimmee, Florida

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

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26–31, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,436 ($287/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,436 ($287/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,004 ($286/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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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22, 2026 – Jan 2, 2027 (11 nights)
2 bed/2 bath, sleeps 8
$3,230 ($294/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,118 ($303/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 - North Village

Kissimmee, Florida

Jun 12–19, 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 - East Village

Kissimmee, Florida

Sep 3–10, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,205 ($315/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 26, 2026 – Jan 9, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$4,385 ($313/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

May 1–8, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,205 ($315/night)

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Westgate Town Center

Kissimmee, Florida

Sep 25 – Oct 2, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,205 ($315/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
$2,205 ($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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Westgate Town Center

Kissimmee, Florida

Dec 18–25, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,205 ($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 - West Village

Kissimmee, Florida

Dec 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,605 ($321/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Aug 15–22, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,238 ($320/night)

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Westgate Town Center

Kissimmee, Florida

Oct 4–11, 2026 (7 nights)
4 bed/4 bath, sleeps 16
$2,257 ($322/night)

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Westgate Town Center

Kissimmee, Florida

Oct 2–9, 2026 (7 nights)
4 bed/4 bath, sleeps 16
$2,257 ($322/night)

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Westgate Town Center

Kissimmee, Florida

Oct 9–16, 2026 (7 nights)
4 bed/4 bath, sleeps 16
$2,257 ($322/night)

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Westgate Town Center

Kissimmee, Florida

Oct 2–9, 2026 (7 nights)
4 bed/4 bath, sleeps 16
$2,257 ($322/night)

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Westgate Town Center

Kissimmee, Florida

Aug 8–15, 2026 (7 nights)
4 bed/4 bath, sleeps 16
$2,257 ($322/night)

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Westgate Town Center

Kissimmee, Florida

Sep 20–27, 2026 (7 nights)
4 bed/4 bath, sleeps 16
$2,257 ($322/night)

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Westgate Town Center

Kissimmee, Florida

Oct 4–11, 2026 (7 nights)
4 bed/4 bath, sleeps 16
$2,257 ($322/night)

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Westgate Town Center

Kissimmee, Florida

Oct 9–16, 2026 (7 nights)
4 bed/4 bath, sleeps 16
$2,257 ($322/night)

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Westgate Town Center

Kissimmee, Florida

Jul 17–24, 2026 (7 nights)
4 bed/4 bath, sleeps 16
$2,257 ($322/night)