Bargain Timeshare Rentals in Kissimmee

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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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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

Jun 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 - River Island

Kissimmee, Florida

Jul 11–18, 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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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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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 25, 2027 – Jan 1, 2028 (7 nights)
3 bed/3 bath, sleeps 12
$1,932 ($276/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 20–27, 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

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

Aug 23–30, 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

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

Aug 9–14, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,436 ($287/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jun 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,009 ($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

Sep 3–8, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,444 ($289/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 23–31, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$2,327 ($291/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)

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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

Aug 22 – Sep 1, 2026 (10 nights)
2 bed/2 bath, sleeps 8
$2,903 ($290/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
$2,042 ($292/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 3–10, 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

Jun 9–15, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,758 ($293/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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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

Aug 22–25, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$906 ($302/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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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Jul 4–11, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,123 ($303/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Jul 1–8, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,123 ($303/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
$2,150 ($307/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 - East Village

Kissimmee, Florida

May 31 – Jun 7, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,157 ($308/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 10–13, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$932 ($311/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 24–27, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$932 ($311/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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Westgate Town Center

Kissimmee, Florida

May 15–22, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,204 ($315/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

May 31 – Jun 7, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,205 ($315/night)