Spring Summer Rentals
Verified & Protected
The Galleon Resort
Key West, Florida- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($424/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- May 17–23, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,660 ($277/night)
Hyatt Sunset Harbor Resort
Key West, Florida- May 17–24, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,220 ($174/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- May 19–22, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $777 ($259/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,544 ($221/night)
Verified & Protected
Coconut Beach Resort
Key West, Florida- May 23–30, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,769 ($253/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,963 ($423/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,205 ($315/night)
Hyatt Sunset Harbor Resort
Key West, Florida- May 24–31, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,220 ($174/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
Verified & Protected
Coconut Beach Resort
Key West, Florida- May 30 – Jun 6, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,932 ($276/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 31 – Jun 7, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $2,859 ($408/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 31 – Jun 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- May 31 – Jun 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,205 ($315/night)
Hyatt Sunset Harbor Resort
Key West, Florida- May 31 – Jun 4, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,066 ($266/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jun 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,404 ($486/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jun 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,543 ($363/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jun 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,512 ($502/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jun 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,478 ($354/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jun 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,173 ($453/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jun 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 14–20, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($549/night)
The Galleon Resort
Key West, Florida- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($510/night)
Verified & Protected
Coconut Beach Resort
Key West, Florida- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,505 ($358/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jun 21–25, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,769 ($442/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jun 27 – Jul 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($510/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jun 27 – Jul 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,486 ($498/night)
Verified & Protected
Coconut Beach Resort
Key West, Florida- Jun 27 – Jul 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jun 27 – Jul 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,745 ($392/night)
The Galleon Resort
Key West, Florida- Jun 27 – Jul 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($510/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jun 27 – Jul 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,512 ($502/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jun 28 – Jul 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($510/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 28 – Jul 2, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,165 ($291/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jun 29 – Jul 3, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,440 ($360/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jun 30 – Jul 4, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $888 ($222/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 1–5, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,987 ($497/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 3–6, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($553/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jul 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jul 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,731 ($533/night)
Verified & Protected
Coconut Beach Resort
Key West, Florida- Jul 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,191 ($456/night)
The Galleon Resort
Key West, Florida- Jul 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Coconut Beach Resort
Key West, Florida- Jul 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,123 ($303/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jul 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,186 ($455/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 12–16, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,752 ($438/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,839 ($548/night)
Verified & Protected
The Hammocks at Marathon
Marathon, Florida- Jul 12–17, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,054 ($211/night)