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!
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Oct 11–15, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,824 ($456/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,186 ($455/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Aug 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,186 ($455/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,191 ($456/night)
Hyatt Windward Pointe Resort
Key West, Florida- Dec 20, 2026 – Jan 3, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $6,456 ($461/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,240 ($463/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 20–24, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,878 ($470/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 13–17, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,878 ($470/night)
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Hyatt Beach House Resort
Key West, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
The Galleon Resort
Key West, Florida- Aug 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Mar 28 – Apr 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Aug 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Nov 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,378 ($483/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,458 ($494/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- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Nov 28 – Dec 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
Verified & Protected
Coconut Beach Resort
Key West, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($510/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Oct 20–25, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $2,586 ($517/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Aug 29 – Sep 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,676 ($525/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Feb 7–14, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,802 ($543/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- Oct 25 – Nov 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,835 ($548/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Aug 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,839 ($548/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Nov 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Oct 20–24, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $2,205 ($551/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Aug 9–16, 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
Hyatt Beach House Resort
Key West, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/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
Hyatt Beach House Resort
Key West, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Aug 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Aug 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,948 ($564/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($564/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Apr 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($564/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 23–26, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,769 ($590/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Aug 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,112 ($588/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 26 – Aug 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,112 ($588/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Aug 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,166 ($595/night)
Hyatt Windward Pointe Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($595/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($595/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($595/night)
Hyatt Windward Pointe Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($595/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Mar 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)