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!
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The Galleon Resort
Key West, Florida- May 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Hyatt Windward Pointe Resort
Key West, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,191 ($456/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Nov 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,191 ($456/night)
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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)
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Hyatt Windward Pointe Resort
Key West, Florida- Dec 20–24, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,878 ($470/night)
Hyatt Windward Pointe Resort
Key West, Florida- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,268 ($467/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Dec 6–13, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/night)
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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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The Galleon Resort
Key West, Florida- Aug 29 – Sep 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,268 ($467/night)
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Hyatt Beach House Resort
Key West, Florida- Mar 28 – Apr 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Hyatt Beach House Resort
Key West, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/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)
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Hyatt Beach House Resort
Key West, Florida- Nov 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,378 ($483/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,420 ($489/night)
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The Galleon Resort
Key West, Florida- Dec 11–18, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/night)
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Hyatt Windward Pointe Resort
Key West, Florida- May 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Hyatt Windward Pointe Resort
Key West, Florida- Dec 13–19, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($495/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Feb 13–20, 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)
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Hyatt Sunset Harbor Resort
Key West, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
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The Galleon Resort
Key West, Florida- Sep 26 – Oct 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Feb 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 15–19, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($497/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Dec 20–26, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($495/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Apr 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
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Hyatt Beach House Resort
Key West, Florida- Feb 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
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The Banyan Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,497 ($500/night)
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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 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,535 ($505/night)
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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- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,626 ($518/night)
Hyatt Beach House Resort
Key West, Florida- Jan 25 – Feb 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,634 ($519/night)
Hyatt Beach House Resort
Key West, Florida- Jan 18–25, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,634 ($519/night)
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Hyatt Beach House Resort
Key West, Florida- Feb 28 – Mar 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,649 ($521/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Nov 29 – Dec 6, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $3,649 ($521/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Nov 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,649 ($521/night)
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Hyatt Beach House Resort
Key West, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $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)
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Hyatt Beach House Resort
Key West, Florida- Oct 20–24, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $2,201 ($550/night)
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Hyatt Beach House Resort
Key West, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,832 ($547/night)
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Hyatt Beach House Resort
Key West, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Dec 20–27, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,840 ($549/night)
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Coconut Beach Resort
Key West, Florida- Nov 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Nov 22–26, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($551/night)
Hyatt Beach House Resort
Key West, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)