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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Hyatt Sunset Harbor Resort
Key West, Florida- May 18–21, 2026 (3 nights)
- Studio/1 bath, sleeps 2
- $666 ($222/night)
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Hyatt Beach House Resort
Key West, Florida- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,066 ($438/night)
The Galleon Resort
Key West, Florida- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,412 ($630/night)
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Hyatt Windward Pointe Resort
Key West, Florida- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- May 24–28, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,110 ($278/night)
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Hyatt Beach House Resort
Key West, Florida- May 24–29, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($528/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- May 29–31, 2026 (2 nights)
- Studio/1 bath, sleeps 2
- $610 ($305/night)
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Hyatt Windward Pointe Resort
Key West, Florida- May 31 – Jun 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,886 ($412/night)
Hyatt Sunset Harbor Resort
Key West, Florida- May 31 – Jun 4, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($497/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- May 31 – Jun 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- May 31 – Jun 7, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $3,295 ($471/night)
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The Galleon Resort
Key West, Florida- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
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The Galleon Resort
Key West, Florida- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Jun 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,186 ($455/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Jun 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Jun 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,512 ($502/night)
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The Galleon Resort
Key West, Florida- Jun 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,412 ($630/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 14–20, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($658/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Jun 27 – Jul 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,512 ($502/night)
Hyatt Windward Pointe Resort
Key West, Florida- Jun 27 – Jul 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,486 ($498/night)
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Hyatt Beach House Resort
Key West, Florida- Jun 28 – Jul 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($510/night)
Hyatt Windward Pointe Resort
Key West, Florida- Jun 28 – Jul 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Jul 1–5, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,987 ($497/night)
The Galleon Resort
Key West, Florida- Jul 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
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Hyatt Beach House Resort
Key West, Florida- Jul 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($377/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,839 ($548/night)
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The Galleon Resort
Key West, Florida- Jul 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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The Galleon Resort
Key West, Florida- Jul 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,314 ($331/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Hyatt Beach House Resort
Key West, Florida- Jul 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($564/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Jul 26 – Aug 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,886 ($412/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Jul 26 – Aug 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Jul 26 – Aug 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,914 ($416/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Jul 26 – Aug 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,112 ($588/night)
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Hyatt Beach House Resort
Key West, Florida- Aug 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($424/night)
The Galleon Resort
Key West, Florida- Aug 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,112 ($588/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Aug 9–13, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $1,220 ($305/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Aug 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)