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.
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 30 – Apr 6, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,599 ($514/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Mar 30 – Apr 6, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($571/night)
Hyatt Windward Pointe Resort
Key West, Florida- Apr 4–5, 2025 (1 night)
- 2 bed/2 bath, sleeps 6
- $788 ($788/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Apr 6–13, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,330 ($564/night)
Hyatt Windward Pointe Resort
Key West, Florida- Apr 6–13, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,500 ($500/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Apr 6–13, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $1,800 ($257/night)
The Galleon Resort
Key West, Florida- Apr 12–19, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,550 ($650/night)
Hyatt Windward Pointe Resort
Key West, Florida- Apr 12–19, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,500 ($500/night)
Hyatt Windward Pointe Resort
Key West, Florida- Apr 12–19, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,165 ($595/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Apr 13–20, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($643/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Apr 13–20, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $1,750 ($250/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Apr 13–20, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,500 ($500/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Apr 13–20, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($471/night)
Coconut Beach Resort
Key West, Florida- Apr 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,200 ($457/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Apr 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($357/night)
Hyatt Beach House Resort
Key West, Florida- Apr 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,488 ($498/night)
Hyatt Windward Pointe Resort
Key West, Florida- Apr 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,788 ($541/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Apr 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($557/night)
The Galleon Resort
Key West, Florida- Apr 26 – May 10, 2025 (14 nights)
- 2 bed/2 bath, sleeps 6
- $9,600 ($686/night)
Hyatt Windward Pointe Resort
Key West, Florida- Apr 26 – May 3, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,998 ($428/night)
The Galleon Resort
Key West, Florida- Apr 26 – May 3, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,000 ($571/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Apr 27 – May 1, 2025 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,200 ($300/night)
Verified & Protected
Coconut Mallory Marina & Resort
Key West, Florida- May 3–10, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($357/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 3–10, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($643/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 3–10, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($571/night)
Verified & Protected
Coconut Mallory Marina & Resort
Key West, Florida- May 3–10, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($400/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 4–11, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($500/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 4–10, 2025 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,769 ($267/night)
Hyatt Sunset Harbor Resort
Key West, Florida- May 18–22, 2025 (4 nights)
- Studio/1 bath, sleeps 2
- $950 ($238/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 25 – Jun 1, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($386/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 25 – Jun 1, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($500/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 31 – Jun 7, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($429/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 8–15, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($500/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 12–15, 2025 (3 nights)
- Studio/1 bath, sleeps 2
- $733 ($220/night)
The Galleon Resort
Key West, Florida- Jun 21–28, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,000 ($429/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 22–29, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($471/night)
The Galleon Resort
Key West, Florida- Jun 28 – Jul 5, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,950 ($564/night)
The Galleon Resort
Key West, Florida- Jun 28 – Jul 5, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $2,050 ($293/night)
The Galleon Resort
Key West, Florida- Jun 28 – Jul 5, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,200 ($457/night)
The Galleon Resort
Key West, Florida- Jun 28 – Jul 5, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,100 ($443/night)
The Galleon Resort
Key West, Florida- Jul 26 – Aug 2, 2025 (7 nights)
- 2 bed/3 bath, sleeps 6
- $4,850 ($693/night)
The Galleon Resort
Key West, Florida- Jul 26 – Aug 2, 2025 (7 nights)
- 2 bed/2 bath, sleeps 2
- $4,950 ($707/night)
The Galleon Resort
Key West, Florida- Jul 26 – Aug 2, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,000 ($571/night)
The Galleon Resort
Key West, Florida- Aug 2–9, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,150 ($593/night)
The Galleon Resort
Key West, Florida- Aug 2–9, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,300 ($471/night)
The Galleon Resort
Key West, Florida- Aug 2–9, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,150 ($593/night)
Hyatt Windward Pointe Resort
Key West, Florida- Aug 30 – Sep 6, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,950 ($279/night)