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 Beach House Resort
Key West, Florida- Mar 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,132 ($447/night)
Hyatt Windward Pointe Resort
Key West, Florida- Mar 3–7, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,769 ($442/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Mar 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
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The Galleon Resort
Key West, Florida- Mar 7–14, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,276 ($325/night)
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The Galleon Resort
Key West, Florida- Mar 7–14, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,641 ($377/night)
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The Galleon Resort
Key West, Florida- Mar 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($595/night)
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The Galleon Resort
Key West, Florida- Mar 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/night)
Hyatt Beach House Resort
Key West, Florida- Mar 8–12, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,769 ($442/night)
Hyatt Windward Pointe Resort
Key West, Florida- Mar 8–12, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,714 ($429/night)
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Hyatt Beach House Resort
Key West, Florida- Mar 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Mar 10–14, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($388/night)
The Galleon Resort
Key West, Florida- Mar 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Mar 15–19, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,878 ($470/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Mar 19–22, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $2,586 ($862/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Mar 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)
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Hyatt Beach House Resort
Key West, Florida- Mar 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,290 ($470/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Mar 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,412 ($630/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Mar 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($564/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Mar 22–26, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $2,749 ($687/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Mar 22–28, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,786 ($631/night)
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The Galleon Resort
Key West, Florida- Mar 28 – Apr 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,802 ($829/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Mar 29 – Apr 2, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $1,220 ($305/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Apr 5–12, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $4,112 ($588/night)
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The Galleon Resort
Key West, Florida- Apr 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,312 ($759/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Apr 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,205 ($315/night)
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Hyatt Beach House Resort
Key West, Florida- Apr 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Apr 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Apr 26 – May 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,366 ($767/night)
Hyatt Windward Pointe Resort
Key West, Florida- Apr 27 – May 2, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($386/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Hyatt Beach House Resort
Key West, Florida- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,649 ($521/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 3–10, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 10–14, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $1,220 ($305/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- May 17–21, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $722 ($180/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- May 17–21, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,330 ($332/night)
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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)
Hyatt Windward Pointe Resort
Key West, Florida- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- May 24–28, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,330 ($332/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 31 – Jun 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,914 ($416/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- May 31 – Jun 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,886 ($412/night)
Verified & Protected
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)
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 21–25, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $777 ($194/night)
Hyatt Beach House Resort
Key West, Florida- Jun 28 – Jul 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($510/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jul 4–11, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $4,603 ($658/night)