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 Beach House Resort

Key West, Florida
  • Apr 13–20, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,622 ($471/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
  • Apr 13–20, 2025 (7 nights)
  • Studio/1 bath, sleeps 2
  • $1,750 ($250/night)

Coconut Beach Resort

Key West, Florida
  • Apr 19–26, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,200 ($457/night)

Hyatt Sunset Harbor Resort

Key West, Florida
  • Apr 20–24, 2025 (4 nights)
  • Studio/1 bath, sleeps 2
  • $925 ($231/night)

Hyatt Windward Pointe Resort

Key West, Florida
  • Apr 20–27, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,488 ($498/night)

Hyatt Beach House Resort

Key West, Florida
  • Apr 20–27, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,988 ($570/night)
Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida
  • Apr 20–27, 2025 (7 nights)
  • 1 bed/1 bath, sleeps 4
  • $3,295 ($429/night)
Verified & Protected

The Hammocks at Marathon

Marathon, Florida
  • Apr 21–25, 2025 (4 nights)
  • 1 bed/1 bath, sleeps 4
  • $1,138 ($256/night)

Hyatt Windward Pointe Resort

Key West, Florida
  • Apr 26 – May 3, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,488 ($498/night)

Port Largo Villas

Key Largo, Florida
  • May 2–9, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $1,800 ($257/night)
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The Galleon Resort

Key West, Florida
  • May 3–10, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $4,930 ($643/night)
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Coconut Mallory Marina & Resort

Key West, Florida
  • May 3–10, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,077 ($400/night)

Hyatt Sunset Harbor Resort

Key West, Florida
  • May 4–8, 2025 (4 nights)
  • Studio/1 bath, sleeps 2
  • $950 ($238/night)
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Hyatt Sunset Harbor Resort

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

Hyatt Sunset Harbor Resort

Key West, Florida
  • May 18–22, 2025 (4 nights)
  • Studio/1 bath, sleeps 2
  • $950 ($238/night)
Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida
  • May 25 – Jun 1, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $2,968 ($386/night)
Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida
  • May 25 – Jun 1, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,840 ($500/night)
Verified & Protected

The Galleon Resort

Key West, Florida
  • May 31 – Jun 7, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,295 ($429/night)
Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida
  • Jun 8–15, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,840 ($500/night)
Verified & Protected

Hyatt Sunset Harbor Resort

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

The Galleon Resort

Key West, Florida
  • Jun 21–28, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,100 ($443/night)
Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida
  • Jun 22–29, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $4,380 ($571/night)

The Galleon Resort

Key West, Florida
  • Jun 28 – Jul 5, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,950 ($564/night)

The Galleon Resort

Key West, Florida
  • Jun 28 – Jul 5, 2025 (7 nights)
  • Studio/1 bath, sleeps 2
  • $2,050 ($293/night)

The Galleon Resort

Key West, Florida
  • Jun 28 – Jul 5, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,200 ($457/night)

The Galleon Resort

Key West, Florida
  • Jul 26 – Aug 2, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $4,000 ($571/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
  • Jul 26 – Aug 2, 2025 (7 nights)
  • 2 bed/3 bath, sleeps 6
  • $4,850 ($693/night)
Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida
  • Jul 27 – Aug 3, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $5,420 ($707/night)

The Galleon Resort

Key West, Florida
  • Aug 2–9, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $4,150 ($593/night)

The Galleon Resort

Key West, Florida
  • Aug 2–9, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,300 ($471/night)

The Galleon Resort

Key West, Florida
  • Aug 2–9, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $4,150 ($593/night)

The Galleon Resort

Key West, Florida
  • Aug 16–23, 2025 (7 nights)
  • 3 bed/3 bath, sleeps 8
  • $3,400 ($486/night)
Verified & Protected

The Hammocks at Marathon

Marathon, Florida
  • Aug 20–25, 2025 (5 nights)
  • 2 bed/2 bath, sleeps 6
  • $2,096 ($380/night)

The Galleon Resort

Key West, Florida
  • Aug 23–30, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $2,900 ($414/night)

Hyatt Windward Pointe Resort

Key West, Florida
  • Aug 30 – Sep 6, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $1,950 ($279/night)