Spring & Summer Rentals

Did you know that 75% of travelers book their spring and summer travel at least 3 months in advance? Unlock exceptional resort deals for your upcoming seasonal getaways before they sell out. Whether you're planning a family vacation, a couple's trip, or a solo adventure, these deals offer the best opportunities to elevate your next travel experience.

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Hyatt Sunset Harbor Resort

Key West, Florida
  • Aug 11, 2024 - Aug 18, 2024 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,295 ($429/night)
Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida
  • Aug 11, 2024 - Aug 18, 2024 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,295 ($429/night)
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The Galleon Resort

Key West, Florida
  • Aug 17, 2024 - Aug 24, 2024 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $2,968 ($386/night)

The Galleon Resort

Key West, Florida
  • Aug 17, 2024 - Aug 28, 2024 (11 nights)
  • 1 bed/1 bath, sleeps 2
  • $1,925 ($175/night)

The Galleon Resort

Key West, Florida
  • Aug 17, 2024 - Aug 24, 2024 (7 nights)
  • 3 bed/3 bath, sleeps 8
  • $4,200 ($600/night)
Verified & Protected

The Galleon Resort

Key West, Florida
  • Aug 17, 2024 - Aug 24, 2024 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,295 ($429/night)
Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida
  • Aug 18, 2024 - Aug 25, 2024 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,077 ($400/night)

Hyatt Sunset Harbor Resort

Key West, Florida
  • Aug 18, 2024 - Aug 25, 2024 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $2,800 ($400/night)

The Galleon Resort

Key West, Florida
  • Aug 24, 2024 - Aug 31, 2024 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,000 ($429/night)

The Galleon Resort

Key West, Florida
  • Aug 24, 2024 - Aug 31, 2024 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,200 ($457/night)

The Galleon Resort

Key West, Florida
  • Aug 31, 2024 - Sep 7, 2024 (7 nights)
  • 1 bed/1 bath, sleeps 2
  • $1,750 ($250/night)

The Galleon Resort

Key West, Florida
  • Aug 31, 2024 - Sep 7, 2024 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $2,800 ($400/night)
Verified & Protected

The Galleon Resort

Key West, Florida
  • Aug 31, 2024 - Sep 7, 2024 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $4,112 ($536/night)
Verified & Protected

Hyatt Beach House Resort

Key West, Florida
  • Mar 2, 2025 - Mar 9, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $4,385 ($571/night)
Verified

Hyatt Windward Pointe Resort

Key West, Florida
  • Mar 2, 2025 - Mar 6, 2025 (4 nights)
  • 2 bed/2 bath, sleeps 6
  • $1,699 ($425/night)
Verified & Protected

The Galleon Resort

Key West, Florida
  • Mar 8, 2025 - Mar 15, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $10,925 ($1,429/night)
Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida
  • Mar 9, 2025 - Mar 16, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,513 ($457/night)

Hyatt Sunset Harbor Resort

Key West, Florida
  • Mar 16, 2025 - Mar 23, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,800 ($543/night)

The Galleon Resort

Key West, Florida
  • Mar 29, 2025 - Apr 5, 2025 (7 nights)
  • 1 bed/1 bath, sleeps 2
  • $2,100 ($300/night)
Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida
  • Apr 6, 2025 - Apr 13, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $4,603 ($600/night)
Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida
  • Apr 12, 2025 - Apr 19, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,840 ($500/night)
Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida
  • Apr 24, 2025 - Apr 28, 2025 (4 nights)
  • Studio/1 bath, sleeps 2
  • $999 ($225/night)
Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida
  • May 4, 2025 - May 10, 2025 (6 nights)
  • 1 bed/1 bath, sleeps 4
  • $1,769 ($267/night)

The Galleon Resort

Key West, Florida
  • May 24, 2025 - May 31, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,000 ($429/night)

The Galleon Resort

Key West, Florida
  • Jun 7, 2025 - Jun 14, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,000 ($429/night)
Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida
  • Jun 12, 2025 - Jun 15, 2025 (3 nights)
  • Studio/1 bath, sleeps 2
  • $733 ($220/night)

Hyatt Windward Pointe Resort

Key West, Florida
  • Aug 10, 2025 - Aug 17, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $5,300 ($757/night)