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.
Verified & Protected
The Galleon Resort
Key West, Florida- Mar 7–14, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,641 ($377/night)
Verified & Protected
Coconut Mallory Marina & Resort
Key West, Florida- Mar 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,726 ($389/night)
The Galleon Resort
Key West, Florida- Mar 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
Verified & Protected
Marathon Key Beach Club
Marathon, Florida- Mar 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,714 ($245/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Mar 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Tranquility Bay Resort
Marathon, Florida- Mar 27 – Apr 3, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Tranquility Bay Resort
Marathon, Florida- Mar 27 – Apr 3, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $5,693 ($813/night)
Verified & Protected
Florida Bay Club
Key Largo, Florida- Mar 28 – Apr 4, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $2,205 ($315/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 29 – Apr 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,731 ($533/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Mar 29 – Apr 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,731 ($533/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Apr 1–5, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($497/night)
The Galleon Resort
Key West, Florida- Apr 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,112 ($588/night)
Verified & Protected
Coconut Beach Resort
Key West, Florida- Apr 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Apr 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,704 ($529/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Apr 5–12, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $3,840 ($549/night)
The Galleon Resort
Key West, Florida- Apr 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,202 ($743/night)
Hyatt Windward Pointe Resort
Key West, Florida- Apr 12–16, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($660/night)
Hyatt Beach House Resort
Key West, Florida- Apr 19–23, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($388/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Apr 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,963 ($423/night)
Hyatt Beach House Resort
Key West, Florida- Apr 19–23, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,440 ($360/night)
Hyatt Beach House Resort
Key West, Florida- Apr 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Apr 25 – May 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,214 ($602/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
- $4,930 ($704/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
Verified & Protected
The Galleon Resort
Key West, Florida- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 10–14, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $1,220 ($305/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
Tranquility Bay Resort
Marathon, Florida- May 15–22, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $2,859 ($408/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- May 17–21, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,110 ($278/night)
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 Windward Pointe Resort
Key West, Florida- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,422 ($346/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
Hyatt Beach House Resort
Key West, Florida- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,066 ($438/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,532 ($362/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 24–29, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $2,205 ($441/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)
- 2 bed/2.5 bath, sleeps 6
- $3,077 ($440/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 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 Windward Pointe Resort
Key West, Florida- May 31 – Jun 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
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
- $3,513 ($502/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/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 Sunset Harbor Resort
Key West, Florida- Jun 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/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)