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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Hyatt Sunset Harbor Resort
Key West, Florida- Aug 9–13, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $555 ($139/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Sep 6–12, 2026 (6 nights)
- Studio/1 bath, sleeps 2
- $1,110 ($185/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- May 30 – Jun 3, 2027 (4 nights)
- Studio/1 bath, sleeps 2
- $888 ($222/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Nov 29 – Dec 3, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $888 ($222/night)
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The Banyan Resort
Key West, Florida- Aug 22–29, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,742 ($249/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Aug 28–31, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $766 ($255/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Sep 13–19, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,660 ($277/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Dec 13–17, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $1,110 ($278/night)
The Galleon Resort
Key West, Florida- Sep 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,932 ($276/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Sep 6–10, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,110 ($278/night)
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Coconut Beach Resort
Key West, Florida- Aug 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,986 ($284/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Aug 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,039 ($291/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Sep 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,161 ($309/night)
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Coconut Mallory Marina & Resort
Key West, Florida- Oct 17–24, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($315/night)
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Hyatt Beach House Resort
Key West, Florida- Sep 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,230 ($319/night)
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Hyatt Beach House Resort
Key West, Florida- Nov 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,306 ($329/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Oct 25 – Nov 1, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
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The Banyan Resort
Key West, Florida- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,423 ($346/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Sep 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,505 ($358/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,532 ($362/night)
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The Galleon Resort
Key West, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,636 ($377/night)
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The Galleon Resort
Key West, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,636 ($377/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Dec 20–27, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,641 ($377/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,641 ($377/night)
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Hyatt Beach House Resort
Key West, Florida- Nov 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,688 ($384/night)
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The Galleon Resort
Key West, Florida- Nov 14–16, 2026 (2 nights)
- 1 bed/1 bath, sleeps 4
- $775 ($387/night)
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Hyatt Beach House Resort
Key West, Florida- Oct 18–22, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($388/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Oct 11–15, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($388/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Sep 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,734 ($391/night)
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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
The Galleon Resort
Key West, Florida- Nov 28 – Dec 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,886 ($412/night)
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The Galleon Resort
Key West, Florida- Aug 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,963 ($423/night)
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The Galleon Resort
Key West, Florida- Aug 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,001 ($429/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Jan 17–21, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,764 ($441/night)
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The Galleon Resort
Key West, Florida- Aug 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
The Galleon Resort
Key West, Florida- May 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/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 Windward Pointe Resort
Key West, Florida- Mar 9–13, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,769 ($442/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/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
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 20–24, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,769 ($442/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)
Verified & Protected
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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The Galleon Resort
Key West, Florida- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,268 ($467/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)
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Hyatt Windward Pointe Resort
Key West, Florida- Oct 20–25, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $2,341 ($468/night)
The Galleon Resort
Key West, Florida- Sep 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,268 ($467/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)