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 Windward Pointe Resort
Key West, Florida- Mar 1–8, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,031 ($525/night)
The Galleon Resort
Key West, Florida- Mar 1–8, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,900 ($700/night)
The Galleon Resort
Key West, Florida- Mar 1–8, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,400 ($629/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 2–9, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($557/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 2–9, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,500 ($500/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Mar 2–9, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($571/night)
The Galleon Resort
Key West, Florida- Mar 8–15, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,800 ($686/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Mar 8–15, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $10,925 ($1,429/night)
Coconut Mallory Marina & Resort
Key West, Florida- Mar 8–15, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,500 ($357/night)
Hyatt Windward Pointe Resort
Key West, Florida- Mar 8–15, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($543/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Mar 8–15, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,420 ($707/night)
The Galleon Resort
Key West, Florida- Mar 8–15, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $2,600 ($371/night)
The Galleon Resort
Key West, Florida- Mar 8–15, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,800 ($543/night)
The Galleon Resort
Key West, Florida- Mar 8–29, 2025 (21 nights)
- 2 bed/2 bath, sleeps 6
- $14,850 ($707/night)
The Galleon Resort
Key West, Florida- Mar 8–15, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,200 ($600/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 9–15, 2025 (6 nights)
- 2 bed/2 bath, sleeps 6
- $4,650 ($775/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 9–16, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,900 ($700/night)
The Galleon Resort
Key West, Florida- Mar 15–22, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,725 ($675/night)
Hyatt Windward Pointe Resort
Key West, Florida- Mar 15–22, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,058 ($529/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Mar 15–22, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($600/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 16–22, 2025 (6 nights)
- Studio/1 bath, sleeps 2
- $2,250 ($375/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 16–23, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $1,750 ($250/night)
Hyatt Windward Pointe Resort
Key West, Florida- Mar 16–20, 2025 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,800 ($450/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Mar 22–29, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($457/night)
The Galleon Resort
Key West, Florida- Mar 22–29, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,725 ($675/night)
The Galleon Resort
Key West, Florida- Mar 22–29, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,600 ($514/night)
The Galleon Resort
Key West, Florida- Mar 22–29, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,950 ($707/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Mar 22–29, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($600/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 23–30, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $1,749 ($250/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 23–30, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $1,750 ($250/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 23–29, 2025 (6 nights)
- Studio/1 bath, sleeps 2
- $2,250 ($375/night)
The Galleon Resort
Key West, Florida- Mar 29 – Apr 5, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,200 ($600/night)
The Galleon Resort
Key West, Florida- Mar 29 – Apr 5, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,725 ($675/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 30 – Apr 6, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $1,899 ($271/night)
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)
Port Largo Villas
Key Largo, Florida- Apr 4–11, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,800 ($257/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Apr 6–13, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,565 ($595/night)
Port Largo Villas
Key Largo, Florida- Apr 11–18, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,800 ($257/night)
Hyatt Windward Pointe Resort
Key West, Florida- Apr 12–19, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,865 ($695/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)
Hyatt Sunset Harbor Resort
Key West, Florida- Apr 13–20, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $1,750 ($250/night)
The Galleon Resort
Key West, Florida- Apr 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,900 ($557/night)
Hyatt Beach House Resort
Key West, Florida- Apr 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,988 ($570/night)
Hyatt Windward Pointe Resort
Key West, Florida- Apr 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,488 ($498/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Apr 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($571/night)
Verified & Protected
The Hammocks at Marathon
Marathon, Florida- Apr 21–25, 2025 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($375/night)
Hyatt Windward Pointe Resort
Key West, Florida- Apr 26 – May 3, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,488 ($498/night)