Fall Rentals
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Sep 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,311 ($187/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Sep 6–12, 2026 (6 nights)
- Studio/1 bath, sleeps 2
- $999 ($166/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Sep 6–10, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,110 ($278/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Sep 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,505 ($358/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Sep 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,123 ($303/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Sep 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Sep 13–19, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,330 ($222/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Sep 19–26, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,748 ($821/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Sep 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,810 ($401/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Sep 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,550 ($221/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Sep 20–24, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,330 ($332/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Sep 26 – Oct 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
The Galleon Resort
Key West, Florida- Sep 27 – Oct 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,069 ($438/night)
Hyatt Windward Pointe Resort
Key West, Florida- Oct 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,467 ($352/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Oct 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Oct 11–15, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,220 ($305/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,532 ($362/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Oct 15–18, 2026 (3 nights)
- 2 bed/2.5 bath, sleeps 6
- $1,987 ($662/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Oct 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Oct 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,069 ($438/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Oct 17–24, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $8,418 ($1,203/night)
Verified & Protected
Coconut Mallory Marina & Resort
Key West, Florida- Oct 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,467 ($352/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Oct 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Oct 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
Coconut Mallory Marina & Resort
Key West, Florida- Oct 17–24, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,932 ($276/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Oct 18–22, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,440 ($360/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,848 ($407/night)
Hyatt Windward Pointe Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Oct 20–24, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $2,201 ($550/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Oct 24–27, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,807 ($602/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,946 ($707/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Oct 25 – Nov 1, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Oct 31 – Nov 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Nov 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Nov 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,672 ($667/night)
Verified & Protected
Coconut Beach Resort
Key West, Florida- Nov 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Coconut Beach Resort
Key West, Florida- Nov 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Nov 14–16, 2026 (2 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($333/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 15–19, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($497/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 20–24, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($415/night)
Hyatt Beach House Resort
Key West, Florida- Nov 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,827 ($547/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 22–26, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($551/night)