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!
Coconut Mallory Marina & Resort
Key West, Florida- Oct 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,473 ($210/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 20–24, 2027 (4 nights)
- Studio/1 bath, sleeps 2
- $888 ($222/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 29 – Dec 3, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $888 ($222/night)
Caloosa Cove Resort
Islamorada, Florida- Nov 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($221/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 13–17, 2027 (4 nights)
- Studio/1 bath, sleeps 2
- $888 ($222/night)
Hyatt Windward Pointe Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($276/night)
Coconut Mallory Marina & Resort
Key West, Florida- Nov 27 – Dec 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($276/night)
Hyatt Beach House Resort
Key West, Florida- Oct 18–22, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,110 ($278/night)
Hyatt Windward Pointe Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($276/night)
The Galleon Resort
Key West, Florida- Nov 14–16, 2026 (2 nights)
- 1 bed/1 bath, sleeps 4
- $610 ($305/night)
Hyatt Windward Pointe Resort
Key West, Florida- Oct 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,123 ($303/night)
The Galleon Resort
Key West, Florida- Dec 11–18, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,314 ($331/night)
The Banyan Resort
Key West, Florida- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
Hyatt Beach House Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
The Banyan Resort
Key West, Florida- Nov 28 – Dec 5, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Oct 25 – Nov 1, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
The Banyan Resort
Key West, Florida- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,423 ($346/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jan 24–31, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,467 ($352/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Feb 7–14, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,505 ($358/night)
Hyatt Windward Pointe Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,505 ($358/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 26–29, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $1,109 ($370/night)
Hyatt Beach House Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,619 ($374/night)
The Galleon Resort
Key West, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,636 ($377/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,688 ($384/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
Hyatt Beach House Resort
Key West, Florida- Oct 18–22, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($388/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 1–5, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $1,576 ($394/night)
Coconut Mallory Marina & Resort
Key West, Florida- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,840 ($406/night)
Coconut Mallory Marina & Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,886 ($412/night)
The Galleon Resort
Key West, Florida- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,039 ($434/night)
Hyatt Windward Pointe Resort
Key West, Florida- Nov 29 – Dec 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,062 ($437/night)
Hyatt Beach House Resort
Key West, Florida- Oct 20–24, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,765 ($441/night)
Hyatt Windward Pointe Resort
Key West, Florida- Oct 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,069 ($438/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Hyatt Windward Pointe Resort
Key West, Florida- Feb 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Hyatt Windward Pointe Resort
Key West, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Hyatt Beach House Resort
Key West, Florida- Nov 1–8, 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)
Hyatt Windward Pointe Resort
Key West, Florida- Dec 13–17, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,878 ($470/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,268 ($467/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 29 – Dec 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,268 ($467/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Nov 26–29, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,412 ($471/night)
Hyatt Windward Pointe Resort
Key West, Florida- Mar 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,268 ($467/night)
Coconut Mallory Marina & Resort
Key West, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,283 ($469/night)
Hyatt Beach House Resort
Key West, Florida- Nov 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,293 ($470/night)
Hyatt Beach House Resort
Key West, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Hyatt Beach House Resort
Key West, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)