Spring & Summer Rentals in Kissimmee

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Mar 1–8, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,878 ($268/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Mar 7–14, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Mar 7–14, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,385 ($198/night)

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Calypso Cay Vacation Villas

Kissimmee, Florida

Mar 8–15, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,330 ($190/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Mar 8–15, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,091 ($299/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Mar 8–15, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,696 ($242/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Mar 8–15, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,987 ($284/night)

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Calypso Cay Vacation Villas

Kissimmee, Florida

Mar 8–15, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,330 ($190/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Mar 14–21, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,769 ($253/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Mar 14–21, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,358 ($194/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Mar 14–21, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,660 ($237/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Mar 14–21, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,565 ($224/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Mar 14–21, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,932 ($276/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Mar 14–21, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,878 ($268/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Mar 14–21, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,660 ($237/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Mar 14–21, 2026 (7 nights)
2 bed/1.5 bath, sleeps 8
$1,769 ($253/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Mar 14–21, 2026 (7 nights)
2 bed/1.5 bath, sleeps 8
$1,769 ($253/night)

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Westgate Town Center

Kissimmee, Florida

Mar 14–21, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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Westgate Town Center

Kissimmee, Florida

Mar 14–21, 2026 (7 nights)
4 bed/4 bath, sleeps 16
$1,660 ($237/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Mar 14–21, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,091 ($299/night)

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Westgate Town Center

Kissimmee, Florida

Mar 15–22, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$855 ($122/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Mar 15–22, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,314 ($331/night)

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Calypso Cay Vacation Villas

Kissimmee, Florida

Mar 15–22, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,330 ($190/night)

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Silver Lake Resort

Kissimmee, Florida

Mar 15–22, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Mar 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Westgate Vacation Villas

Kissimmee, Florida

Mar 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 10
$1,495 ($214/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Mar 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,769 ($253/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Mar 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,796 ($257/night)

Westgate Town Center

Kissimmee, Florida

Mar 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,878 ($268/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Mar 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,200 ($314/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Mar 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,769 ($253/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Mar 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,204 ($315/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Mar 21–28, 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

Mar 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,714 ($245/night)

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WorldMark Orlando – Reunion

Kissimmee, Florida

Mar 21–29, 2026 (8 nights)
3 bed/3 bath, sleeps 8
$3,295 ($412/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Mar 21–28, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,804 ($401/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Mar 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

Mar 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,096 ($299/night)

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Westgate Vacation Villas

Kissimmee, Florida

Mar 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 10
$1,440 ($206/night)

Westgate Vacation Villas

Kissimmee, Florida

Mar 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 10
$1,987 ($284/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Mar 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,742 ($249/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Mar 23–28, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$944 ($189/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Mar 27 – Apr 3, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,878 ($268/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Mar 28 – Apr 4, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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Vacation Village at Parkway

Kissimmee, Florida

Mar 29 – Apr 5, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,440 ($206/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Apr 1–8, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,423 ($346/night)

Club Wyndham Cypress Palms

Kissimmee, Florida

Apr 3–10, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,434 ($205/night)

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Westgate Town Center

Kissimmee, Florida

Apr 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,742 ($249/night)