Discounted Timeshare Rentals in Kissimmee

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 23–29, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,300 $754 ($126/night) 42% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 23–29, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$881 $511 ($85/night) 42% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 24–29, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$973 $633 ($126/night) 35% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 24–29, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$660 $429 ($86/night) 35% off

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Aug 8–15, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,669 $1,385 ($198/night) 17% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 24–28, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$469 $305 ($76/night) 35% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 24–28, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$674 $438 ($110/night) 35% off

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WorldMark Orlando – Reunion

Kissimmee, Florida

Jul 31 – Aug 3, 2026 (3 nights)
3 bed/3 bath, sleeps 8
$1,665 $666 ($222/night) 60% off

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WorldMark Orlando – Reunion

Kissimmee, Florida

Jul 31 – Aug 3, 2026 (3 nights)
3 bed/3 bath, sleeps 8
$1,665 $666 ($222/night) 60% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Aug 2–8, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,010 $586 ($98/night) 42% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Oct 9–16, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,961 $1,765 ($252/night) 10% off

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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
$2,009 $1,165 ($194/night) 42% off

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Westgate Town Center

Kissimmee, Florida

Jul 12–19, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,542 $555 ($79/night) 64% off

Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Jul 25 – Aug 1, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,547 $1,330 ($190/night) 14% off

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Westgate Vacation Villas

Kissimmee, Florida

Aug 7–14, 2026 (7 nights)
2 bed/2 bath, sleeps 10
$1,657 $1,110 ($159/night) 33% off

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Westgate Town Center

Kissimmee, Florida

Jul 17–24, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,538 $1,769 ($253/night) 50% off

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Jul 20–24, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$914 $805 ($201/night) 12% off

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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
$3,875 $1,550 ($221/night) 60% off

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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
$2,000 $1,220 ($174/night) 39% off

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Westgate Town Center

Kissimmee, Florida

Jul 25 – Aug 1, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,980 $1,109 ($158/night) 44% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 15–17, 2026 (2 nights)
2 bed/2 bath, sleeps 8
$523 $230 ($115/night) 56% off

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jul 17–20, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$637 $554 ($185/night) 13% off

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Westgate Town Center

Kissimmee, Florida

Jul 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,324 $1,099 ($157/night) 17% off

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Aug 29 – Sep 3, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,054 $832 ($166/night) 21% off

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Westgate Town Center

Kissimmee, Florida

Jul 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,650 $610 ($87/night) 63% off

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Westgate Vacation Villas

Kissimmee, Florida

Jul 26 – Aug 2, 2026 (7 nights)
2 bed/2 bath, sleeps 10
$2,771 $1,330 ($190/night) 52% off

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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
$2,157 $1,769 ($253/night) 18% off

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Barefoot Suites

Kissimmee, Florida

Jul 26 – Aug 2, 2026 (7 nights)
2 bed/1 bath, sleeps 6
$1,156 $555 ($79/night) 52% off

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Barefoot Suites

Kissimmee, Florida

Jul 26 – Aug 2, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,156 $555 ($79/night) 52% off

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Aug 1–8, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,211 $1,769 ($253/night) 20% off

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Jul 19–26, 2026 (7 nights)
Studio/1 bath, sleeps 5
$1,736 $816 ($117/night) 53% off

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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
$3,396 $2,886 ($412/night) 15% off

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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
$2,329 $2,096 ($299/night) 10% 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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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 - 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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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 - 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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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,669 $1,385 ($198/night) 17% off

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Mystic Dunes Resort & Golf Club

Kissimmee, Florida

Nov 22–28, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,512 $1,119 ($186/night) 26% off

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Jul 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,543 $1,358 ($194/night) 12% off