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.
Verified
Hyatt Windward Pointe Resort
Key West, Florida- May 19, 2024 - May 26, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,850 ($264/night)
Hyatt Windward Pointe Resort
Key West, Florida- May 18, 2024 - May 25, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,390 ($199/night)
Hyatt Sunset Harbor Resort
Key West, Florida- May 19, 2024 - May 26, 2024 (7 nights)
- Studio/1 bath, sleeps 2
- $1,750 ($250/night)
The Galleon Resort
Key West, Florida- May 25, 2024 - Jun 1, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,500 ($357/night)
Verified
Hyatt Sunset Harbor Resort
Key West, Florida- May 26, 2024 - Jun 2, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,850 ($407/night)
Verified
Hyatt Windward Pointe Resort
Key West, Florida- May 26, 2024 - May 30, 2024 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,000 ($250/night)
Verified
Hyatt Windward Pointe Resort
Key West, Florida- May 29, 2024 - Jun 1, 2024 (3 nights)
- 2 bed/2 bath, sleeps 6
- $750 ($250/night)
The Galleon Resort
Key West, Florida- Jun 1, 2024 - Jun 8, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,800 ($400/night)
Verified
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 2, 2024 - Jun 6, 2024 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,000 ($250/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jun 8, 2024 - Jun 15, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,200 ($314/night)
The Galleon Resort
Key West, Florida- Jun 8, 2024 - Jun 15, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,500 ($357/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 9, 2024 - Jun 13, 2024 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,500 ($375/night)
Hyatt Beach House Resort
Key West, Florida- Jun 9, 2024 - Jun 13, 2024 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,100 ($275/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 9, 2024 - Jun 13, 2024 (4 nights)
- Studio/1 bath, sleeps 2
- $700 ($175/night)
The Galleon Resort
Key West, Florida- Jun 15, 2024 - Jun 22, 2024 (7 nights)
- Studio/1 bath, sleeps 2
- $2,100 ($300/night)
The Galleon Resort
Key West, Florida- Jun 15, 2024 - Jun 22, 2024 (7 nights)
- 1 bed/1 bath, sleeps 2
- $2,800 ($400/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 & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 16, 2024 - Jun 22, 2024 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,700 ($283/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jun 22, 2024 - Jun 29, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,700 ($386/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 23, 2024 - Jun 30, 2024 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,900 ($414/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 23, 2024 - Jun 30, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,793 ($399/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 23, 2024 - Jun 30, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,793 ($399/night)
Hyatt Beach House Resort
Key West, Florida- Jun 27, 2024 - Jun 30, 2024 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,450 ($483/night)
Verified
Hyatt Windward Pointe Resort
Key West, Florida- Jun 29, 2024 - Jul 6, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,300 ($329/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 29, 2024 - Jul 6, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,199 ($314/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jun 29, 2024 - Jul 6, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,199 ($314/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jun 29, 2024 - Jul 6, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,599 ($371/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jun 29, 2024 - Jul 6, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,199 ($314/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)
Verified
Hyatt Beach House Resort
Key West, Florida- Jun 30, 2024 - Jul 7, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,500 ($500/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jun 30, 2024 - Jul 7, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,415 ($345/night)
Hyatt Windward Pointe Resort
Key West, Florida- Jun 30, 2024 - Jul 7, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,150 ($307/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jun 30, 2024 - Jul 7, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,800 ($400/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jul 1, 2024 - Jul 5, 2024 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,800 ($450/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jul 1, 2024 - Jul 7, 2024 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,900 ($317/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jul 2, 2024 - Jul 6, 2024 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,280 ($320/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)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jul 7, 2024 - Jul 14, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,100 ($300/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jul 7, 2024 - Jul 14, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,999 ($286/night)
Hyatt Beach House Resort
Key West, Florida- Jul 7, 2024 - Jul 14, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,450 ($350/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jul 7, 2024 - Jul 14, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,100 ($300/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jul 13, 2024 - Jul 20, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,900 ($414/night)
Verified
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 14, 2024 - Jul 21, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,950 ($421/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 & Protected
The Galleon Resort
Key West, Florida- Jul 20, 2024 - Jul 27, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,600 ($514/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jul 21, 2024 - Jul 28, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,100 ($300/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 21, 2024 - Jul 28, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,750 ($536/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jul 21, 2024 - Jul 28, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,999 ($286/night)