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.
Hyatt Windward Pointe Resort
Key West, Florida- Apr 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Apr 25 – May 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,031 ($576/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($595/night)
Verified & Protected
Coconut Beach Resort
Key West, Florida- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- May 3–7, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($388/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- May 3–7, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($388/night)
Hyatt Windward Pointe Resort
Key West, Florida- May 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($595/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 10–14, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $2,423 ($606/night)
Verified & Protected
The Hammocks at Marathon
Marathon, Florida- May 12–17, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,110 ($222/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
Hyatt Sunset Harbor Resort
Key West, Florida- May 17–24, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $3,513 ($502/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- May 17–23, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($386/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 18–21, 2026 (3 nights)
- Studio/1 bath, sleeps 2
- $666 ($222/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,412 ($630/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,837 ($405/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- May 24–29, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,982 ($396/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 29–31, 2026 (2 nights)
- Studio/1 bath, sleeps 2
- $610 ($305/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 31 – Jun 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- May 31 – Jun 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 31 – Jun 4, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($497/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jun 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,404 ($486/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,186 ($455/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jun 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,512 ($502/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jun 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,412 ($630/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jun 14–20, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($658/night)
The Galleon Resort
Key West, Florida- Jun 27 – Jul 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($510/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jun 27 – Jul 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,512 ($502/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jun 27 – Jul 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Hyatt Windward Pointe Resort
Key West, Florida- Jun 27 – Jul 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,486 ($498/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jun 28 – Jul 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($510/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jun 28 – Jul 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,403 ($486/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 1–5, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,987 ($497/night)
The Galleon Resort
Key West, Florida- Jul 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jul 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($377/night)
The Galleon Resort
Key West, Florida- Jul 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,839 ($548/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jul 12–16, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,873 ($468/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jul 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jul 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,314 ($331/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jul 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jul 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)