Spring & Summer Rentals in Kissimmee

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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)

Westgate Town Center

Kissimmee, Florida

Mar 21–28, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,696 ($385/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
$1,769 ($253/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
$1,660 ($237/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 - East Village

Kissimmee, Florida

Mar 22–27, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,110 ($222/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Mar 22–29, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,750 ($393/night)

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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
$1,769 ($253/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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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Mar 28 – Apr 6, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$2,762 ($307/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Mar 29 – Apr 5, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,851 ($264/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)

Club Wyndham Cypress Palms

Kissimmee, Florida

Mar 29 – Apr 1, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$944 ($314/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Mar 30 – Apr 6, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,765 ($252/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
$1,660 ($237/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Apr 3–10, 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

Apr 3–5, 2026 (2 nights)
3 bed/3 bath, sleeps 12
$555 ($278/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Apr 3–10, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,330 ($190/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Apr 4–11, 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

Apr 4–11, 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 - River Island

Kissimmee, Florida

Apr 4–11, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,205 ($315/night)

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WorldMark Orlando – Reunion

Kissimmee, Florida

Apr 4–11, 2026 (7 nights)
3 bed/3 bath, sleeps 8
$2,696 ($385/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Apr 4–11, 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

Apr 4–11, 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

Apr 4–11, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,329 ($190/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Apr 4–11, 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

Apr 4–11, 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

Apr 4–11, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,877 ($268/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Apr 4–11, 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 - East Village

Kissimmee, Florida

Apr 4–11, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$3,077 ($440/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Apr 4–11, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,329 ($190/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Apr 4–11, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,768 ($253/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Apr 5–11, 2026 (6 nights)
2 bed/2 bath, sleeps 6
$1,330 ($222/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Apr 5–11, 2026 (6 nights)
2 bed/2 bath, sleeps 6
$1,330 ($222/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Apr 5–11, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,878 ($313/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Apr 6–11, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,099 ($220/night)

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Westgate Town Center

Kissimmee, Florida

Apr 10–17, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,283 ($183/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Apr 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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Westgate Vacation Villas

Kissimmee, Florida

Apr 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,439 ($206/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Apr 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,330 ($190/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Apr 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,330 ($190/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Apr 12–18, 2026 (6 nights)
3 bed/3 bath, sleeps 12
$1,980 ($330/night)

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Westgate Vacation Villas

Kissimmee, Florida

Apr 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 10
$2,804 ($401/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Apr 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,615 ($231/night)

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Westgate Town Center

Kissimmee, Florida

Apr 17–24, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,550 ($221/night)