The Galleon Resort

Key West, Florida

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The Galleon Resort Timeshare rentals

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40 rentals from $221/night
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40 rentals from $221/night

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Mar 15–22, 2025 7 Nights
2 Bedroom Unit, Water view
Sleeps: 6
$4,000 ($571/night)
Rented!
Jun 7–14, 2025 7 Nights
New!
2 Bedroom Unit, Waterfront
Sleeps: 6
$2,600 ($371/night)
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Jun 7–14, 2025 7 Nights
New!
2 Bedroom Unit, Ocean view
Sleeps: 6
$2,600 ($371/night)
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Jun 7–14, 2025 7 Nights
RedWeek Verified
2 Bedroom Unit, Waterfront
Sleeps: 6
$2,700 ($386/night)
Rented!
Jun 14–21, 2025 7 Nights
New!
1 Bedroom Unit
Sleeps: 2
$1,400 ($200/night)
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Jun 14–21, 2025 7 Nights
1 Bedroom Unit, Water view
Sleeps: 2
$2,000 ($286/night)
Rented!
Jun 14–21, 2025 7 Nights
RedWeek Verified
2 Bedroom Unit, Waterfront
Sleeps: 6
$2,300 ($329/night)
Rented!
Jun 28 – Jul 5, 2025 7 Nights
Studio Unit
Sleeps: 2
$1,500 ($214/night)
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Jul 5–12, 2025 7 Nights
Verified & Protected
2 Bedroom Unit, Water view
Sleeps: 6
$2,800 ($400/night)
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Jul 19–26, 2025 7 Nights
Verified & Protected
New!
2 Bedroom Unit, Waterfront
Sleeps: 8
$3,200 ($457/night)
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Jul 19–26, 2025 7 Nights
RedWeek Verified
2 Bedroom Unit, Waterfront
Sleeps: 6
$2,700 ($386/night)
Rented!
Jul 26 – Aug 2, 2025 7 Nights
Verified & Protected
2 Bedroom Unit, Waterfront
Sleeps: 6
$3,400 ($486/night)
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Jul 26 – Aug 2, 2025 7 Nights
RedWeek Verified
2 Bedroom Unit, Waterfront
Sleeps: 8
$3,500 ($500/night)
Rented!
Aug 2–9, 2025 7 Nights
Verified & Protected
New!
2 Bedroom Unit, Waterfront
Sleeps: 8
$3,000 ($429/night)
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Aug 2–9, 2025 7 Nights
Verified & Protected
2 Bedroom Unit, Water view
Sleeps: 6
$3,750 ($536/night)
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Aug 16–23, 2025 7 Nights
3 Bedroom Unit, Oceanfront
Sleeps: 8
$3,600 ($514/night)
Rented!
Aug 23–30, 2025 7 Nights
Verified & Protected
New!
2 Bedroom Unit, Water view
Sleeps: 6
$3,500 ($500/night)
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Aug 23–30, 2025 7 Nights
Verified & Protected
New!
2 Bedroom Unit, Pool
Sleeps: 6
$3,500 ($500/night)
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Nov 1–8, 2025 7 Nights
2 Bedroom Unit, Waterfront
Sleeps: 6
$4,600 ($657/night)
Rented!
Nov 15–22, 2025 7 Nights
Verified & Protected
Studio Unit
Sleeps: 2
$1,895 ($271/night)
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Nov 24–29, 2025 5 Nights
Verified & Protected
1 Bedroom Unit, Waterfront
Sleeps: 4
$2,245 ($449/night)
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Nov 29 – Dec 6, 2025 7 Nights
RedWeek Verified
2 Bedroom Unit, Water view
Sleeps: 6
$3,150 ($450/night)
Rented!
Dec 13–20, 2025 7 Nights
Verified & Protected
Studio Unit
Sleeps: 2
$1,995 ($285/night)
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Dec 13–20, 2025 7 Nights
Verified & Protected
2 Bedroom Unit, Waterfront
Sleeps: 6
$4,900 ($700/night)
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Dec 13–20, 2025 7 Nights
RedWeek Verified
1 Bedroom Unit, Waterfront
Sleeps: 4
$2,495 ($356/night)
Rented!
Apr 19–26, 2025 7 Nights
RedWeek Verified
2 Bedroom Unit, Water view
Sleeps: 6
$4,000 ($571/night)
View posting
Apr 19–26, 2025 7 Nights
2 Bedroom Unit, Oceanfront
Sleeps: 6
$4,200 ($600/night)
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Apr 19–26, 2025 7 Nights
2 Bedroom Unit, Oceanfront
Sleeps: 6
$4,200 ($600/night)
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Apr 26 – May 3, 2025 7 Nights
2 Bedroom Unit, Water view
Sleeps: 6
$3,000 ($429/night)
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Apr 26 – May 1, 2025 5 Nights
2 Bedroom Unit, Ocean view
Sleeps: 6
$3,000 ($600/night)
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Apr 26 – May 3, 2025 7 Nights
2 Bedroom Unit, Water view
Sleeps: 6
$3,800 ($543/night)
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May 3–10, 2025 7 Nights
2 Bedroom Unit, Water view
Sleeps: 6
$3,100 ($443/night)
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Jun 7–14, 2025 7 Nights
2 Bedroom Unit, Waterfront
Sleeps: 6
$3,000 ($429/night)
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Jun 21–27, 2025 6 Nights
2 Bedroom Unit, Water view
Sleeps: 6
$2,200 ($367/night)
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Jun 21–28, 2025 7 Nights
2 Bedroom Unit, Pool
Sleeps: 6
$2,700 ($386/night)
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Jun 28 – Jul 5, 2025 7 Nights
1 Bedroom Unit, Ocean view
Sleeps: 4
$2,500 ($357/night)
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Jun 28 – Jul 5, 2025 7 Nights
2 Bedroom Unit, Water view
Sleeps: 6
$3,200 ($457/night)
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Jun 28 – Jul 5, 2025 7 Nights
2 Bedroom Unit, Ocean view
Sleeps: 6
$3,800 ($543/night)
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Jun 28 – Jul 5, 2025 7 Nights
2 Bedroom Unit, Waterfront
Sleeps: 6
$4,025 ($575/night)
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Jul 26 – Aug 2, 2025 7 Nights
2 Bedroom Unit, Water view
Sleeps: 6
$4,000 ($571/night)
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Aug 2–9, 2025 7 Nights
2 Bedroom Unit, Water view
Sleeps: 6
$3,300 ($471/night)
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Aug 9–16, 2025 7 Nights
2 Bedroom Unit, Pool
Sleeps: 6
$3,700 ($529/night)
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Aug 23–30, 2025 7 Nights
2 Bedroom Unit, Oceanfront
Sleeps: 6
$3,400 ($486/night)
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Aug 30 – Sep 6, 2025 7 Nights
2 Bedroom Unit, Water view
Sleeps: 6
$3,400 ($486/night)
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Sep 6–13, 2025 7 Nights
2 Bedroom Unit, Oceanfront
Sleeps: 6
$3,500 ($500/night)
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Sep 13–20, 2025 7 Nights
2 Bedroom Unit, Waterfront
Sleeps: 6
$2,200 ($314/night)
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Oct 11–18, 2025 7 Nights
2 Bedroom Unit, Waterfront
Sleeps: 6
$3,500 ($500/night)
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Nov 15–22, 2025 7 Nights
2 Bedroom Unit, Ocean view
Sleeps: 6
$4,400 ($629/night)
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Jan 24–31, 2026 7 Nights
2 Bedroom Unit, Ocean view
Sleeps: 6
$5,075 ($725/night)
View posting
Mar 14–21, 2026 7 Nights
2 Bedroom Unit, Water view
Sleeps: 6
$3,499 ($500/night)
View posting
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