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!
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,214 ($602/night)
Hyatt Beach House Resort
Key West, Florida- Mar 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
Hyatt Beach House Resort
Key West, Florida- Nov 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
Hyatt Beach House Resort
Key West, Florida- Mar 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
Hyatt Beach House Resort
Key West, Florida- Mar 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
Hyatt Windward Pointe Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,298 ($614/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 24–27, 2026 (3 nights)
- 2 bed/2.5 bath, sleeps 6
- $1,878 ($626/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 27 – Jul 4, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $4,385 ($626/night)
Hyatt Beach House Resort
Key West, Florida- Oct 22–25, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,922 ($641/night)
The Galleon Resort
Key West, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,450 ($636/night)
Coconut Beach Resort
Key West, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,595 ($656/night)
The Galleon Resort
Key West, Florida- Dec 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Oct 15–18, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($662/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Oct 15–18, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($662/night)
Hyatt Sunset Harbor Resort
Key West, Florida- May 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
Hyatt Windward Pointe Resort
Key West, Florida- Oct 22–25, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $2,020 ($673/night)
The Galleon Resort
Key West, Florida- Apr 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,794 ($685/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 28 – Apr 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 28 – Apr 4, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $4,984 ($712/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Feb 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
The Banyan Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/1 bath, sleeps 6
- $5,175 ($739/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 14–21, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $5,175 ($739/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,557 ($794/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $5,693 ($813/night)
The Galleon Resort
Key West, Florida- Mar 27 – Apr 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
The Galleon Resort
Key West, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
The Galleon Resort
Key West, Florida- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
The Galleon Resort
Key West, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,938 ($848/night)
The Galleon Resort
Key West, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,976 ($854/night)
The Galleon Resort
Key West, Florida- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,053 ($865/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/night)
The Galleon Resort
Key West, Florida- Mar 20–27, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,129 ($876/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jan 24–31, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $6,565 ($938/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Feb 18–21, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $2,965 ($988/night)
The Galleon Resort
Key West, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,464 ($1,066/night)