Fall Rentals
Hyatt Beach House Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($300/night)
Hyatt Windward Pointe Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($250/night)
Hyatt Beach House Resort
Key West, Florida- Oct 18–22, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($350/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($300/night)
Hyatt Beach House Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,619 ($340/night)
Hyatt Beach House Resort
Key West, Florida- Oct 18–22, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,110 ($250/night)
Hyatt Beach House Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,306 ($299/night)
Hyatt Windward Pointe Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($200/night)
Hyatt Beach House Resort
Key West, Florida- Oct 20–24, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,765 ($399/night)
Hyatt Beach House Resort
Key West, Florida- Oct 22–25, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,495 ($450/night)
Hyatt Windward Pointe Resort
Key West, Florida- Oct 22–25, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,594 ($480/night)
Hyatt Beach House Resort
Key West, Florida- Oct 24–27, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $999 ($300/night)
The Galleon Resort
Key West, Florida- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,886 ($375/night)
Hyatt Beach House Resort
Key West, Florida- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,204 ($155/night)
Hyatt Beach House Resort
Key West, Florida- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,196 ($154/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Oct 25 – Nov 1, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,742 ($225/night)
Hyatt Windward Pointe Resort
Key West, Florida- Oct 31 – Nov 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($450/night)
Hyatt Beach House Resort
Key West, Florida- Nov 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($400/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 1–5, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $1,400 ($316/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($800/night)
Hyatt Beach House Resort
Key West, Florida- Nov 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($550/night)
Caloosa Cove Resort
Islamorada, Florida- Nov 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($200/night)
Coconut Beach Resort
Key West, Florida- Nov 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($500/night)
Coconut Beach Resort
Key West, Florida- Nov 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($450/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 22–26, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($500/night)
Hyatt Windward Pointe Resort
Key West, Florida- Nov 22–26, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,895 ($429/night)
Hyatt Windward Pointe Resort
Key West, Florida- Nov 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,649 ($475/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,276 ($295/night)
Hyatt Beach House Resort
Key West, Florida- Nov 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,293 ($428/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 26–29, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,412 ($425/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 26–29, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $1,109 ($333/night)
Coconut Mallory Marina & Resort
Key West, Florida- Nov 27 – Dec 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($250/night)
The Banyan Resort
Key West, Florida- Nov 28 – Dec 5, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($300/night)
The Galleon Resort
Key West, Florida- Nov 28 – Dec 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,649 ($475/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 29 – Dec 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,268 ($425/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 29 – Dec 3, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $888 ($200/night)
Hyatt Windward Pointe Resort
Key West, Florida- Nov 29 – Dec 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,062 ($398/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 29 – Dec 6, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $3,420 ($445/night)