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.
The Galleon Resort
Key West, Florida- Jun 15, 2024 - Jun 22, 2024 (7 nights)
- 1 bed/1 bath, sleeps 2
- $2,800 ($400/night)
The Galleon Resort
Key West, Florida- Jun 15, 2024 - Jun 22, 2024 (7 nights)
- Studio/1 bath, sleeps 2
- $2,100 ($300/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 16, 2024 - Jun 23, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,450 ($350/night)
Verified
Hyatt Windward Pointe Resort
Key West, Florida- Jun 22, 2024 - Jun 29, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,500 ($357/night)
Verified
Hyatt Beach House Resort
Key West, Florida- Jun 23, 2024 - Jun 29, 2024 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,300 ($217/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 23, 2024 - Jun 30, 2024 (7 nights)
- Studio/1 bath, sleeps 2
- $1,750 ($250/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 23, 2024 - Jun 30, 2024 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,900 ($271/night)
Hyatt Beach House Resort
Key West, Florida- Jun 27, 2024 - Jun 30, 2024 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,399 ($466/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jun 29, 2024 - Jul 6, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,042 ($264/night)
The Galleon Resort
Key West, Florida- Jun 29, 2024 - Jul 6, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,132 ($407/night)
The Galleon Resort
Key West, Florida- Jun 29, 2024 - Jul 6, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,500 ($500/night)
Hyatt Windward Pointe Resort
Key West, Florida- Jun 29, 2024 - Jul 6, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,500 ($214/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jun 29, 2024 - Jul 6, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,200 ($285/night)
Hyatt Beach House Resort
Key West, Florida- Jun 30, 2024 - Jul 7, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,100 ($300/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jun 30, 2024 - Jul 7, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,205 ($286/night)
Hyatt Beach House Resort
Key West, Florida- Jun 30, 2024 - Jul 4, 2024 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,500 ($375/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jul 1, 2024 - Jul 5, 2024 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,605 ($362/night)
The Galleon Resort
Key West, Florida- Jul 6, 2024 - Jul 13, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,500 ($357/night)
The Galleon Resort
Key West, Florida- Jul 6, 2024 - Jul 13, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,132 ($407/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jul 7, 2024 - Jul 14, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($300/night)
The Galleon Resort
Key West, Florida- Jul 13, 2024 - Jul 17, 2024 (4 nights)
- 1 bed/1 bath, sleeps 2
- $700 ($175/night)
Verified
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 14, 2024 - Jul 21, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,650 ($379/night)
Hyatt Beach House Resort
Key West, Florida- Jul 14, 2024 - Jul 18, 2024 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,098 ($274/night)
Hyatt Beach House Resort
Key West, Florida- Jul 14, 2024 - Jul 18, 2024 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,098 ($274/night)
The Galleon Resort
Key West, Florida- Jul 20, 2024 - Jul 27, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,350 ($621/night)
Verified
The Galleon Resort
Key West, Florida- Jul 20, 2024 - Jul 27, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,300 ($471/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jul 21, 2024 - Jul 28, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,769 ($229/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jul 21, 2024 - Jul 28, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,986 ($257/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 21, 2024 - Jul 28, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,112 ($536/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 21, 2024 - Jul 28, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,186 ($414/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 21, 2024 - Jul 27, 2024 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($583/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 21, 2024 - Jul 28, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,500 ($786/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 21, 2024 - Jul 28, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,493 ($499/night)
The Galleon Resort
Key West, Florida- Jul 27, 2024 - Aug 3, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,731 ($486/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jul 27, 2024 - Aug 3, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($571/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jul 28, 2024 - Aug 3, 2024 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,660 ($250/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jul 28, 2024 - Aug 4, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($371/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 28, 2024 - Aug 1, 2024 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,324 ($299/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 28, 2024 - Aug 1, 2024 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,104 ($249/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Aug 1, 2024 - Aug 4, 2024 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,255 ($418/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Aug 3, 2024 - Aug 10, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($471/night)
The Galleon Resort
Key West, Florida- Aug 3, 2024 - Aug 10, 2024 (7 nights)
- 2 bed/3 bath, sleeps 8
- $2,800 ($400/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Aug 3, 2024 - Aug 10, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,200 ($285/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Aug 3, 2024 - Aug 10, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($357/night)
Verified & Protected
Coconut Beach Resort
Key West, Florida- Aug 3, 2024 - Aug 10, 2024 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,750 ($357/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Aug 4, 2024 - Aug 11, 2024 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,900 ($414/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Aug 4, 2024 - Aug 11, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,711 ($352/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Aug 4, 2024 - Aug 8, 2024 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,550 ($350/night)