Bargain Timeshare Rentals
Looking for an exceptional vacation deal? Timeshare rentals by owner are almost always lower than resort rack rates. These postings represent some of the best bargains available, giving deal-hunters the chance to lock in serious savings on their next getaway!
Hyatt Windward Pointe Resort
Key West, Florida- Nov 22–26, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,895 ($474/night)
Hyatt Beach House Resort
Key West, Florida- Mar 7–11, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,900 ($475/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 29 – Dec 6, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $3,420 ($489/night)
Hyatt Windward Pointe Resort
Key West, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
The Galleon Resort
Key West, Florida- Dec 11–18, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/night)
Hyatt Windward Pointe Resort
Key West, Florida- Oct 31 – Nov 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Hyatt Windward Pointe Resort
Key West, Florida- Dec 11–15, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($497/night)
Hyatt Windward Pointe Resort
Key West, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Hyatt Windward Pointe Resort
Key West, Florida- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Hyatt Windward Pointe Resort
Key West, Florida- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Hyatt Windward Pointe Resort
Key West, Florida- Apr 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Hyatt Beach House Resort
Key West, Florida- Feb 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Hyatt Beach House Resort
Key West, Florida- Mar 1–4, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,495 ($498/night)
Hyatt Beach House Resort
Key West, Florida- Mar 1–5, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($497/night)
Hyatt Beach House Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,497 ($500/night)
Hyatt Beach House Resort
Key West, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
Hyatt Windward Pointe Resort
Key West, Florida- Feb 21 – Mar 6, 2027 (13 nights)
- 2 bed/2 bath, sleeps 6
- $6,543 ($503/night)
Hyatt Windward Pointe Resort
Key West, Florida- Mar 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,535 ($505/night)
Hyatt Windward Pointe Resort
Key West, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,535 ($505/night)
Hyatt Beach House Resort
Key West, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,634 ($519/night)
Hyatt Beach House Resort
Key West, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,649 ($521/night)
Hyatt Beach House Resort
Key West, Florida- Feb 28 – Mar 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,649 ($521/night)
Hyatt Windward Pointe Resort
Key West, Florida- Nov 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,649 ($521/night)
The Galleon Resort
Key West, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,802 ($543/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Feb 21–28, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,802 ($543/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,802 ($543/night)
Hyatt Beach House Resort
Key West, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,802 ($543/night)
Hyatt Beach House Resort
Key West, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,832 ($547/night)
Hyatt Beach House Resort
Key West, Florida- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,832 ($547/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jan 24–28, 2027 (4 nights)
- Studio/1 bath, sleeps 2
- $2,205 ($551/night)
The Galleon Resort
Key West, Florida- Nov 28 – Dec 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Hyatt Beach House Resort
Key West, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Hyatt Beach House Resort
Key West, Florida- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Oct 15–18, 2026 (3 nights)
- 2 bed/2.5 bath, sleeps 6
- $1,660 ($553/night)
Coconut Beach Resort
Key West, Florida- Nov 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Coconut Beach Resort
Key West, Florida- Nov 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 22–26, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($551/night)
Hyatt Windward Pointe Resort
Key West, Florida- Mar 14–20, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($549/night)
Hyatt Beach House Resort
Key West, Florida- Feb 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Coconut Mallory Marina & Resort
Key West, Florida- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 20–27, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,840 ($549/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jan 31 – Feb 4, 2027 (4 nights)
- Studio/1 bath, sleeps 2
- $2,205 ($551/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 14–18, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($578/night)
Hyatt Beach House Resort
Key West, Florida- Feb 28 – Mar 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,031 ($576/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 28 – Apr 1, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($578/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jan 3–7, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($578/night)
The Galleon Resort
Key West, Florida- Oct 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,069 ($581/night)
Hyatt Beach House Resort
Key West, Florida- Oct 24–27, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,807 ($602/night)