Spring Summer Rentals
Verified & Protected
Coconut Beach Resort
Key West, Florida- Apr 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)
Verified & Protected
Coconut Beach Resort
Key West, Florida- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- May 3–7, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,220 ($305/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- May 3–7, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,220 ($305/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- May 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($377/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 10–14, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $2,423 ($606/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,058 ($580/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,058 ($580/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 17–24, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- May 17–23, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($386/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 18–21, 2026 (3 nights)
- Studio/1 bath, sleeps 2
- $583 ($194/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- May 19–22, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,165 ($388/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- May 21–25, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,878 ($470/night)
Verified & Protected
Coconut Beach Resort
Key West, Florida- May 23–30, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($510/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,565 ($366/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- May 24–29, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,982 ($396/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 29–31, 2026 (2 nights)
- Studio/1 bath, sleeps 2
- $610 ($305/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 31 – Jun 4, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($497/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- May 31 – Jun 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- May 31 – Jun 6, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,313 ($385/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 31 – Jun 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/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
The Galleon Resort
Key West, Florida- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
The Galleon Resort
Key West, Florida- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,186 ($455/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jun 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,535 ($505/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)
The Galleon Resort
Key West, Florida- Jun 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jun 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($510/night)
Hyatt Beach House Resort
Key West, Florida- Jun 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Hyatt Windward Pointe Resort
Key West, Florida- Jun 14–18, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,110 ($278/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 14–20, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($658/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jun 27 – Jul 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Coconut Beach Resort
Key West, Florida- Jun 27 – Jul 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,404 ($486/night)
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
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
- $3,403 ($486/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)
Hyatt Windward Pointe Resort
Key West, Florida- Jun 30 – Jul 4, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,440 ($360/night)