Discounted Timeshare Rentals in Kissimmee

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 22–29, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,304 $848 ($121/night) 35% off

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Nov 14–21, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,661 $1,329 ($190/night) 20% off

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Jul 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,269 $888 ($127/night) 30% off

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WorldMark Orlando – Reunion

Kissimmee, Florida

Jun 29 – Jul 3, 2026 (4 nights)
3 bed/3 bath, sleeps 8
$2,214 $1,550 ($388/night) 30% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 31 – Aug 3, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$982 $638 ($213/night) 35% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 31 – Aug 3, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$745 $484 ($161/night) 35% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 27 – Aug 3, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,304 $848 ($121/night) 35% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 8–14, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,165 $758 ($126/night) 35% off

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Westgate Town Center

Kissimmee, Florida

Jul 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,665 $832 ($119/night) 50% off

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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
$2,094 $1,654 ($236/night) 21% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 26 – Aug 2, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,304 $848 ($121/night) 35% off

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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
$2,164 $1,796 ($257/night) 17% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 5–10, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$809 $526 ($105/night) 35% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 5–11, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,058 $687 ($115/night) 35% off

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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
$2,220 $999 ($143/night) 55% off

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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
$1,675 $971 ($139/night) 42% off

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Jul 3–6, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$1,337 $1,110 ($370/night) 17% off

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Westgate Town Center

Kissimmee, Florida

Jul 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,857 $2,314 ($331/night) 19% off

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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
$1,655 $1,440 ($206/night) 13% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 25 – Aug 1, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,304 $848 ($121/night) 35% off

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Silver Lake Resort

Kissimmee, Florida

Nov 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,001 $720 ($103/night) 28% off

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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
$2,722 $1,769 ($253/night) 35% off

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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
$2,338 $1,660 ($237/night) 29% off

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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
$2,722 $1,769 ($253/night) 35% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 15–19, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$777 $505 ($126/night) 35% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 12–18, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,058 $687 ($115/night) 35% off

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Jul 5–11, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,615 $888 ($148/night) 45% off

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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
$1,709 $1,077 ($154/night) 37% off

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Jul 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,220 $1,110 ($159/night) 50% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 13–18, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$809 $526 ($105/night) 35% off

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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
$2,301 $1,932 ($276/night) 16% off

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Barefoot Suites

Kissimmee, Florida

Jul 26 – Aug 2, 2026 (7 nights)
2 bed/1 bath, sleeps 6
$1,164 $722 ($103/night) 38% off

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Barefoot Suites

Kissimmee, Florida

Jul 26 – Aug 2, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,164 $722 ($103/night) 38% off

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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
$1,947 $1,110 ($159/night) 43% off

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Aug 8–16, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$2,138 $1,625 ($203/night) 24% off

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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
$1,928 $1,330 ($190/night) 31% off

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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
$1,930 $888 ($127/night) 54% off

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Westgate Town Center

Kissimmee, Florida

Jul 17–24, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,110 $555 ($79/night) 50% off

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Westgate Town Center

Kissimmee, Florida

Jun 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,770 $1,385 ($198/night) 50% off

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Westgate Town Center

Kissimmee, Florida

Nov 28 – Dec 5, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,543 $1,358 ($194/night) 12% off

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Westgate Town Center

Kissimmee, Florida

Nov 28 – Dec 5, 2026 (7 nights)
Studio/1 bath, sleeps 2
$1,116 $971 ($139/night) 13% off

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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
$3,306 $2,612 ($373/night) 21% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 23–28, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,025 $666 ($133/night) 35% off

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jul 21–27, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,790 $1,110 ($185/night) 38% off

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Jun 18–23, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,218 $999 ($200/night) 18% off

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jul 5–11, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,998 $999 ($166/night) 50% off

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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
$2,543 $2,238 ($320/night) 12% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,304 $848 ($121/night) 35% off