Hyatt Windward Pointe Resort
Key West, Florida
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Hyatt Windward Pointe Resort Timeshare rentals
« Back to resort20 rentals from $299/night
Nov 29 – Dec 6, 2025
7 Nights
RedWeek Verified
2 Bedroom Condominium
Sleeps: 6
$371/night
$2,600 before tax
Dec 20–27, 2025
7 Nights
Verified & Protected
Sleeps: 6
$271/night
$2,095 before tax
Dec 20–27, 2025
7 Nights
Verified & Protected
Sleeps: 6
$300/night
$2,314 before tax
Dec 20–27, 2025
7 Nights
Verified & Protected
$279/night
$2,150 before tax
Dec 20–27, 2025
7 Nights
RedWeek Verified
2 Bedroom Condominium, Ocean view
Sleeps: 6
$200/night
$1,400 before tax
Dec 21–28, 2025
7 Nights
Verified & Protected
$329/night
$2,532 before tax
Dec 21–28, 2025
7 Nights
RedWeek Verified
2 Bedroom Condominium
Sleeps: 6
$370/night
$2,590 before tax
Dec 21–28, 2025
7 Nights
RedWeek Verified
2 Bedroom Condominium, Partial ocean view
Sleeps: 6
$329/night
$2,300 before tax
Dec 23–27, 2025
4 Nights
Verified & Protected
New!
Sleeps: 6
$388/night
$1,714 before tax
Dec 27, 2025 – Jan 3, 2026
7 Nights
RedWeek Verified
2 Bedroom Condominium, Ocean view
Sleeps: 6
$500/night
$3,500 before tax
Dec 27, 2025 – Jan 3, 2026
7 Nights
RedWeek Verified
2 Bedroom Condominium, Partial ocean view
Sleeps: 6
$543/night
$3,800 before tax
Dec 28, 2025 – Jan 4, 2026
7 Nights
RedWeek Verified
2 Bedroom Condominium, Ocean view
Sleeps: 6
$564/night
$3,949 before tax
Dec 28, 2025 – Jan 4, 2026
7 Nights
RedWeek Verified
2 Bedroom Condominium, Partial ocean view
Sleeps: 6
$429/night
$3,000 before tax
Jan 3–10, 2026
7 Nights
Verified & Protected
Sleeps: 6
$429/night
$3,295 before tax
Jan 4–10, 2026
6 Nights
Verified & Protected
$333/night
$2,204 before tax
Jan 8–15, 2026
7 Nights
RedWeek Verified
2 Bedroom Condominium
Sleeps: 6
$328/night
$2,299 before tax
Jan 17–24, 2026
7 Nights
Verified & Protected
$475/night
$3,649 before tax
Jan 18–24, 2026
6 Nights
Verified & Protected
Sleeps: 6
$450/night
$2,968 before tax
Jan 25 – Feb 1, 2026
7 Nights
RedWeek Verified
2 Bedroom Condominium
Sleeps: 6
$400/night
$2,800 before tax
Feb 7–14, 2026
7 Nights
Verified & Protected
Sleeps: 6
$395/night
$3,039 before tax
Feb 8–15, 2026
7 Nights
RedWeek Verified
2 Bedroom Condominium, Ocean view
Sleeps: 6
$429/night
$3,000 before tax
Feb 14–21, 2026
7 Nights
Verified & Protected
New!
Sleeps: 6
$429/night
$3,298 before tax
Feb 14–21, 2026
7 Nights
Verified & Protected
$500/night
$3,840 before tax
Feb 21–28, 2026
7 Nights
Verified & Protected
New!
Sleeps: 6
$550/night
$4,222 before tax
Feb 21–28, 2026
7 Nights
Verified & Protected
$470/night
$3,611 before tax
Feb 28 – Mar 7, 2026
7 Nights
RedWeek Verified
2 Bedroom Condominium, Partial ocean view
Sleeps: 6
$486/night
$3,400 before tax
Mar 8–12, 2026
4 Nights
2 Bedroom Condominium
Sleeps: 6
$388/night
$1,550 before tax
Mar 8–15, 2026
7 Nights
RedWeek Verified
2 Bedroom Condominium, Partial ocean view
Sleeps: 6
$414/night
$2,900 before tax
Mar 8–12, 2026
4 Nights
2 Bedroom Condominium
Sleeps: 6
$400/night
$1,600 before tax
Mar 10–14, 2026
4 Nights
New!
Sleeps: 6
$350/night
$1,550 before tax
Mar 15–19, 2026
4 Nights
New!
Sleeps: 6
$425/night
$1,878 before tax
Mar 21–28, 2026
7 Nights
Verified & Protected
$471/night
$3,622 before tax
Mar 22–29, 2026
7 Nights
Verified & Protected
New!
$514/night
$3,949 before tax
Apr 18–25, 2026
7 Nights
Verified & Protected
$286/night
$2,205 before tax
May 31 – Jun 7, 2026
7 Nights
New!
Sleeps: 6
$375/night
$2,886 before tax
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