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- Sep 6–12, 2026 (6 nights)
- Studio/1 bath, sleeps 2
- $999 ($166/night)
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Hyatt Beach House Resort
Key West, Florida- Sep 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,311 ($187/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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Hyatt Sunset Harbor Resort
Key West, Florida- May 30 – Jun 3, 2027 (4 nights)
- Studio/1 bath, sleeps 2
- $888 ($222/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Sep 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,550 ($221/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Sep 13–19, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,330 ($222/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 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 Mallory Marina & Resort
Key West, Florida- Nov 28 – Dec 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($276/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)
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Coconut Mallory Marina & Resort
Key West, Florida- Oct 17–24, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,932 ($276/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Sep 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,123 ($303/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Oct 11–15, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,220 ($305/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- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,314 ($331/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Sep 20–24, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,330 ($332/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Dec 11–18, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,314 ($331/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Oct 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Oct 25 – Nov 1, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Nov 14–16, 2026 (2 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($333/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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Coconut Mallory Marina & Resort
Key West, Florida- Oct 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,467 ($352/night)
Hyatt Windward Pointe Resort
Key West, Florida- Oct 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,467 ($352/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Sep 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,505 ($358/night)
Hyatt Windward Pointe Resort
Key West, Florida- Oct 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,505 ($358/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Oct 18–22, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,440 ($360/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,532 ($362/night)
Verified & Protected
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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The Galleon Resort
Key West, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,636 ($377/night)
Verified & Protected
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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Hyatt Beach House Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
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Hyatt Beach House Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,848 ($407/night)
Verified & Protected
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)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 20–24, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($415/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Mar 14–20, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,478 ($413/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jan 17–21, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,764 ($441/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Dec 27–31, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,765 ($441/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Oct 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,069 ($438/night)
The Galleon Resort
Key West, Florida- Sep 27 – Oct 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,069 ($438/night)
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- 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- Oct 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/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
The Galleon Resort
Key West, Florida- May 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
Coconut Mallory Marina & Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,191 ($456/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)