The Galleon Resort

Key West, Florida

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The Galleon Resort Timeshare rentals

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27 rentals from $276/night

Nov 29 – Dec 6, 2025 7 Nights
2 Bedroom Suite (1 Queen)
Sleeps: 6
$300/night $2,100 before tax
Rented!
Dec 20–27, 2025 7 Nights
RedWeek Verified
2 Bedroom Suite (2 Twins), Water view
Sleeps: 6
$615/night $4,305 before tax
Rented!
Dec 20–27, 2025 7 Nights
New!
$536/night $4,112 before tax
Dec 20–27, 2025 7 Nights
RedWeek Verified
2 Bedroom Suite (1 Queen), Pool
Sleeps: 6
$557/night $4,000 before tax
Rented!
Dec 27, 2025 – Jan 3, 2026 7 Nights
New!
$1,250/night $9,562 before tax
Dec 27, 2025 – Jan 3, 2026 7 Nights
2 Bedroom Penthouse (2 Twins)
Sleeps: 6
$757/night $5,300 before tax
Rented!
Jan 3–10, 2026 7 Nights
Sleeps: 2
$250/night $1,932 before tax
Jan 3–10, 2026 7 Nights
Verified & Protected
$429/night $3,295 before tax
Jan 3–10, 2026 7 Nights
Verified & Protected
New!
$829/night $6,347 before tax
View 1 More
Jan 3–10, 2026 7 Nights
2 Bedroom Suite (2 Twins)
Sleeps: 6
$925/night $6,475 before tax
Rented!
Jan 10–17, 2026 7 Nights
RedWeek Verified
2 Bedroom Suite (2 Twins), Water view
Sleeps: 6
$571/night $4,000 before tax
Rented!
Jan 17–24, 2026 7 Nights
Verified & Protected
$829/night $6,347 before tax
Jan 31 – Feb 7, 2026 7 Nights
RedWeek Verified
2 Bedroom Suite (2 Twins), Water view
Sleeps: 6
$700/night $4,900 before tax
Rented!
Feb 7–14, 2026 7 Nights
Verified & Protected
$814/night $6,238 before tax
Feb 7–14, 2026 7 Nights
Verified & Protected
$700/night $5,366 before tax
Feb 7–14, 2026 7 Nights
New!
$786/night $6,020 before tax
View 1 More
Feb 14–21, 2026 7 Nights
Verified & Protected
$714/night $5,475 before tax
Feb 14–21, 2026 7 Nights
Verified & Protected
$743/night $5,693 before tax
Feb 21–28, 2026 7 Nights
RedWeek Verified
Studio Efficiency
Sleeps: 2
$295/night $2,065 before tax
Rented!
Feb 21–28, 2026 7 Nights
RedWeek Verified
2 Bedroom Loft Penthouse, Water view
Sleeps: 8
$714/night $5,000 before tax
Rented!
Feb 28 – Mar 7, 2026 7 Nights
Verified & Protected
$714/night $5,475 before tax
Feb 28 – Mar 7, 2026 7 Nights
Verified & Protected
$714/night $5,475 before tax
Mar 7–14, 2026 7 Nights
Verified & Protected
New!
Sleeps: 2
$295/night $2,276 before tax
Mar 7–14, 2026 7 Nights
Verified & Protected
Sleeps: 2
$343/night $2,641 before tax
View 1 More
Mar 7–14, 2026 7 Nights
Verified & Protected
$557/night $4,276 before tax
Mar 21–28, 2026 7 Nights
New!
$686/night $5,257 before tax
Mar 21–28, 2026 7 Nights
RedWeek Verified
2 Bedroom Suite (1 Queen), Water view
Sleeps: 6
$657/night $4,600 before tax
Rented!
Apr 18–25, 2026 7 Nights
Verified & Protected
New!
$693/night $5,312 before tax
Apr 25 – May 2, 2026 7 Nights
New!
$543/night $4,167 before tax
Jun 6–13, 2026 7 Nights
Verified & Protected
$457/night $3,513 before tax
Jul 18–25, 2026 7 Nights
Verified & Protected
Sleeps: 2
$286/night $2,205 before tax
Jul 18–25, 2026 7 Nights
Verified & Protected
$400/night $3,077 before tax
Aug 15–22, 2026 7 Nights
Verified & Protected
$429/night $3,295 before tax
Oct 31 – Nov 7, 2026 7 Nights
New!
$929/night $7,110 before tax
Dec 12–19, 2026 7 Nights
Verified & Protected
$600/night $4,603 before tax
Dec 13, 2025 – Jan 31, 2026
Availability varies
Sleeps: 2
$300/night $2,100 before tax
Jan 10 – Apr 25, 2026
Availability varies
Sleeps: 2
$321/night $2,250 before tax
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