Spring Summer Rentals
Did you know that 75% of travelers book their spring and summer travel at least 3 months in advance? Unlock exceptional resort deals for your upcoming seasonal getaways before they sell out. Whether you're planning a family vacation, a couple's trip, or a solo adventure, these deals offer the best opportunities to elevate your next travel experience.
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Vacation Village at Parkway
Kissimmee, Florida- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,749 ($250/night)
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Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,358 ($194/night)
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Westgate Town Center
Kissimmee, Florida- May 8–15, 2026 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,257 ($322/night)
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Westgate Vacation Villas
Kissimmee, Florida- May 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,459 ($208/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)
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Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- May 16–23, 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- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,434 ($205/night)
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Westgate Town Center
Kissimmee, Florida- May 17–24, 2026 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,257 ($322/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- May 20–25, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $813 ($162/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- May 20–25, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,172 ($234/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- May 20–25, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,554 ($311/night)
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Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- May 22–26, 2026 (4 nights)
- 3 bed/3 bath, sleeps 12
- $1,110 ($278/night)
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Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- May 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,329 ($190/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- May 22–29, 2026 (7 nights)
- 3 bed/3 bath, sleeps 11
- $1,932 ($276/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- May 22–25, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $642 ($214/night)
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Westgate Town Center
Kissimmee, Florida- May 23–30, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $1,987 ($284/night)
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Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,385 ($198/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)
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Westgate Vacation Villas
Kissimmee, Florida- May 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
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Westgate Town Center
Kissimmee, Florida- May 29 – Jun 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,536 ($219/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
- $2,310 ($330/night)
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Westgate Town Center
Kissimmee, Florida- May 31 – Jun 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,536 ($219/night)
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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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WorldMark Orlando – Reunion
Kissimmee, Florida- Jun 4–11, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $3,382 ($483/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Jun 4–8, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $999 ($250/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jun 5–8, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $852 ($284/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jun 5–8, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $599 ($200/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jun 5–8, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $1,158 ($386/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
- $1,660 ($237/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
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Westgate Town Center
Kissimmee, Florida- Jun 6–13, 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 - West Village
Kissimmee, Florida- Jun 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,605 ($229/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Jun 9–15, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $2,205 ($368/night)
Westgate Vacation Villas
Kissimmee, Florida- Jun 13–20, 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 - North Village
Kissimmee, Florida- Jun 14–21, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $2,096 ($299/night)
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Westgate Vacation Villas
Kissimmee, Florida- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,459 ($208/night)
Westgate Town Center
Kissimmee, Florida- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($393/night)
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Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,088 ($155/night)
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Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,660 ($237/night)
Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Jun 21–28, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $2,091 ($299/night)
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Jun 21–28, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $2,314 ($331/night)
Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Jun 26 – Jul 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
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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Westgate Vacation Villas
Kissimmee, Florida- Jun 27 – Jul 4, 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 - River Island
Kissimmee, Florida- Jun 28 – Jul 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,207 ($315/night)
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Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Jun 28 – Jul 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,330 ($190/night)
Westgate Vacation Villas
Kissimmee, Florida- Jun 28 – Jul 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 10
- $2,750 ($393/night)
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Westgate Town Center
Kissimmee, Florida- Jun 28 – Jul 5, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $1,862 ($266/night)