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
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/night)
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,711 ($673/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,112 ($588/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,977 ($711/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,121 ($874/night)
Verified & Protected
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- May 9–16, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,031 ($576/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,726 ($1,389/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 9–16, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 9–15, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($731/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- May 9–16, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,568 ($510/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 9–15, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,739 ($457/night)
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,743 ($1,249/night)
Verified & Protected
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,478 ($354/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Verified & Protected
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,848 ($693/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 9–15, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $2,478 ($413/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,072 ($439/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 9–15, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $6,009 ($1,002/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 9–15, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $5,094 ($849/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Verified & Protected
The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,859 ($408/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,366 ($767/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 9–16, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,886 ($412/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,175 ($739/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 10–22, 2026 (12 nights)
- 1 bed/1 bath, sleeps 4
- $5,475 ($456/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 10–17, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 10–17, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $11,470 ($1,639/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,658 ($665/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 10–17, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,464 ($781/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- May 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,314 ($331/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 10–17, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,475 ($782/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 10–17, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,257 ($751/night)
Verified & Protected
WorldMark Kihei Resort
Kihei, Hawaii- May 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,932 ($276/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,001 ($429/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)