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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The Hammocks at Marathon
Marathon, Florida- Mar 4–18, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($196/night)
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Hyatt Beach House Resort
Key West, Florida- Mar 5–8, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,605 ($535/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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Florida Bay Club
Key Largo, Florida- Mar 7–14, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $1,768 ($253/night)
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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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Coconut Mallory Marina & Resort
Key West, Florida- Mar 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,726 ($389/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
- $3,039 ($434/night)
Hyatt Beach House Resort
Key West, Florida- Mar 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
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Hyatt Beach House Resort
Key West, Florida- Mar 22–26, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $3,022 ($756/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Mar 22–26, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $2,313 ($578/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 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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Tranquility Bay Resort
Marathon, Florida- Mar 27 – Apr 3, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 4
- $4,385 ($626/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 29 – Apr 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,687 ($527/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 29 – Apr 5, 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 31 – Apr 4, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,824 ($456/night)
Hyatt Windward Pointe Resort
Key West, Florida- Apr 1–5, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,878 ($470/night)
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The Galleon Resort
Key West, Florida- Apr 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,366 ($767/night)
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Coconut Beach Resort
Key West, Florida- Apr 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
The Galleon Resort
Key West, Florida- Apr 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($595/night)
Hyatt Beach House Resort
Key West, Florida- Apr 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,330 ($619/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Apr 5–12, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $3,840 ($549/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Apr 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($595/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Apr 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
The Galleon Resort
Key West, Florida- Apr 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,374 ($625/night)
Hyatt Windward Pointe Resort
Key West, Florida- Apr 12–16, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $3,186 ($796/night)
The Galleon Resort
Key West, Florida- Apr 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,374 ($625/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Apr 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
The Galleon Resort
Key West, Florida- Apr 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
Hyatt Beach House Resort
Key West, Florida- Apr 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Apr 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,963 ($423/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Apr 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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The Galleon Resort
Key West, Florida- Apr 25 – May 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,493 ($642/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
- $4,984 ($712/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Apr 27 – May 2, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,769 ($354/night)
The Galleon Resort
Key West, Florida- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($564/night)
The Galleon Resort
Key West, Florida- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 3–10, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $3,513 ($502/night)
The Galleon Resort
Key West, Florida- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
The Galleon Resort
Key West, Florida- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/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)
Verified & Protected
The Hammocks at Marathon
Marathon, Florida- May 12–17, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,110 ($222/night)
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Tranquility Bay Resort
Marathon, Florida- May 15–22, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $2,859 ($408/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 Windward Pointe Resort
Key West, Florida- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,749 ($393/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 17–21, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,110 ($278/night)