Spring Summer Rentals
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,058 ($580/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,186 ($455/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 10–15, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $3,022 ($604/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,976 ($854/night)
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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
- $4,385 ($626/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,493 ($642/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,423 ($346/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- May 11–16, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($615/night)
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The Point at Poipu
Koloa, Hawaii- May 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,353 ($336/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- May 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
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Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- May 12–16, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $2,856 ($714/night)
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Kahana Beach Resort
Lahaina, Hawaii- May 13–20, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,165 ($166/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- May 13–18, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $1,769 ($354/night)
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Maui Beach Vacation Club
Kihei, Hawaii- May 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,742 ($249/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- May 15–22, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,750 ($393/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 15–22, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,640 ($377/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- May 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,053 ($579/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 15–22, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,294 ($471/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 15–22, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
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Hanalei Bay Resort
Princeville, Hawaii- May 15–22, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,932 ($276/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 15–21, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($495/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 15–22, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,181 ($454/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 15–22, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,303 ($329/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,322 ($617/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,350 ($478/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,600 ($514/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,794 ($685/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/night)
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Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- May 16–23, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,329 ($190/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,579 ($797/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,294 ($471/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,283 ($469/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $6,243 ($892/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,474 ($782/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 16–22, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $3,186 ($531/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,076 ($439/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,886 ($412/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,968 ($424/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- May 16–23, 2026 (7 nights)
- 3 bed/2.5 bath, sleeps 8
- $5,584 ($798/night)