Bargain Timeshare Rentals
Timeshare rentals by-owner are almost always a bargain when compared to resort rack rates. Here are the best deals on your next timeshare rental vacation.
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 2–9, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($571/night)
The Galleon Resort
Key West, Florida- May 3–10, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($571/night)
The Galleon Resort
Key West, Florida- Aug 2–9, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,150 ($593/night)
The Galleon Resort
Key West, Florida- Aug 2–9, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,150 ($593/night)
Hyatt Windward Pointe Resort
Key West, Florida- Apr 12–19, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,165 ($595/night)
The Galleon Resort
Key West, Florida- Mar 8–9, 2025 (1 night)
- 1 bed/1 bath, sleeps 4
- $595 ($595/night)
The Galleon Resort
Key West, Florida- Nov 8–15, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,200 ($600/night)
The Galleon Resort
Key West, Florida- Feb 15–18, 2025 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,800 ($600/night)
Hyatt Beach House Resort
Key West, Florida- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,200 ($600/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Mar 22–29, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($600/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Mar 15–22, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($600/night)
The Galleon Resort
Key West, Florida- Mar 29 – Apr 5, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,200 ($600/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Feb 16–23, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,658 ($607/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Feb 9–16, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,250 ($607/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Feb 8–15, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,756 ($620/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Feb 1–8, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,756 ($620/night)
The Galleon Resort
Key West, Florida- Jan 18–25, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,425 ($632/night)
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The Galleon Resort
Key West, Florida- Dec 13–20, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($643/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 22–29, 2024 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,500 ($643/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Dec 6–13, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($643/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Dec 13–20, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($643/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Apr 13–20, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($643/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Nov 29 – Dec 6, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($643/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 3–10, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($643/night)
The Galleon Resort
Key West, Florida- Apr 12–19, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,550 ($650/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Mar 22–29, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($657/night)
The Galleon Resort
Key West, Florida- Mar 8–15, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,600 ($657/night)
The Galleon Resort
Key West, Florida- Feb 22 – Mar 1, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,700 ($671/night)
The Galleon Resort
Key West, Florida- Mar 15–22, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,725 ($675/night)
The Galleon Resort
Key West, Florida- Mar 22–29, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,725 ($675/night)
The Galleon Resort
Key West, Florida- Mar 29 – Apr 5, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,725 ($675/night)
Hyatt Beach House Resort
Key West, Florida- Dec 29, 2024 – Jan 5, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,800 ($686/night)
The Galleon Resort
Key West, Florida- Jul 26 – Aug 2, 2025 (7 nights)
- 2 bed/3 bath, sleeps 6
- $4,850 ($693/night)
The Galleon Resort
Key West, Florida- Mar 1–8, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,900 ($700/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Feb 1–8, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,366 ($700/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 9–16, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,900 ($700/night)
Hyatt Beach House Resort
Key West, Florida- Dec 29, 2024 – Jan 5, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,900 ($700/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Mar 8–15, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,420 ($707/night)
The Galleon Resort
Key West, Florida- Mar 8–29, 2025 (21 nights)
- 2 bed/2 bath, sleeps 6
- $14,850 ($707/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 27 – Aug 3, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,420 ($707/night)
The Galleon Resort
Key West, Florida- Jul 26 – Aug 2, 2025 (7 nights)
- 2 bed/2 bath, sleeps 2
- $4,950 ($707/night)
The Galleon Resort
Key West, Florida- Mar 8–15, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,950 ($707/night)
The Galleon Resort
Key West, Florida- Mar 15–22, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,950 ($707/night)
The Galleon Resort
Key West, Florida- Mar 22–29, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,950 ($707/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Feb 16–23, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,000 ($714/night)
The Galleon Resort
Key West, Florida- Oct 25 – Nov 1, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,000 ($714/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Feb 1–8, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,911 ($771/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 9–15, 2025 (6 nights)
- 2 bed/2 bath, sleeps 6
- $4,650 ($775/night)