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.

—

More Filters

Clear Filters

With Booking Protection Sort by:

The Galleon Resort

Key West, Florida

Mar 1–8, 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)

Verified & Protected

Hyatt Beach House Resort

Key West, Florida

Feb 16–23, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$4,603 ($600/night)

Verified & Protected

The Galleon Resort

Key West, Florida

Nov 24–29, 2025 (5 nights)
1 bed/1 bath, sleeps 4
$3,508 ($639/night)

The Galleon Resort

Key West, Florida

Mar 15–22, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$4,500 ($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)

Verified & Protected

Tranquility Bay Resort

Marathon, Florida

Mar 28 – Apr 4, 2025 (7 nights)
2 bed/2.5 bath, sleeps 5
$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)

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

Feb 1–8, 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)

The Galleon Resort

Key West, Florida

Feb 1–8, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$4,500 ($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

Dec 6–13, 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)

The Galleon Resort

Key West, Florida

Mar 8–15, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$4,600 ($657/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

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

Apr 26 – May 10, 2025 (14 nights)
2 bed/2 bath, sleeps 6
$9,600 ($686/night)

The Galleon Resort

Key West, Florida

Mar 1–8, 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)

Verified & Protected

The Galleon Resort

Key West, Florida

Dec 13–20, 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)

Verified & Protected

The Galleon Resort

Key West, Florida

Feb 1–8, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$5,420 ($707/night)

The Galleon Resort

Key West, Florida

Mar 22–29, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$4,950 ($707/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)

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)

Verified & Protected

The Galleon Resort

Key West, Florida

Mar 29 – Apr 5, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$5,420 ($707/night)

Verified & Protected

The Galleon Resort

Key West, Florida

Feb 8–15, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$5,475 ($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)

The Galleon Resort

Key West, Florida

Jan 11–18, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$5,000 ($714/night)

Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

Jan 26 – Feb 2, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$5,475 ($714/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

Feb 22 – Mar 1, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$5,475 ($714/night)

Verified & Protected

The Galleon Resort

Key West, Florida

Feb 8–15, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$5,584 ($729/night)

The Galleon Resort

Key West, Florida

Jan 18–25, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$5,250 ($750/night)

Hyatt Sunset Harbor Resort

Key West, Florida

Mar 9–15, 2025 (6 nights)
2 bed/2 bath, sleeps 6
$4,650 ($775/night)

Hyatt Windward Pointe Resort

Key West, Florida

Apr 4–5, 2025 (1 night)
2 bed/2 bath, sleeps 6
$788 ($788/night)

Verified & Protected

The Galleon Resort

Key West, Florida

Feb 15–22, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$6,129 ($800/night)

The Galleon Resort

Key West, Florida

Dec 28, 2024 – Jan 4, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$5,995 ($856/night)