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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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,641 ($377/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 3–8, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,932 ($386/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- May 3–8, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,769 ($354/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,493 ($642/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 3–10, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,467 ($352/night)
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Club Wyndham Ka 'Eo Kai
Princeville, Hawaii- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,878 ($268/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 3–8, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,363 ($473/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 3–8, 2026 (5 nights)
- Studio/1 bath, sleeps 2
- $1,426 ($285/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 3–10, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,276 ($611/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,548 ($650/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- May 3–9, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $3,802 ($634/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,167 ($595/night)
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,786 ($541/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 3–10, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- May 4–7, 2026 (3 nights)
- Studio/1 bath, sleeps 4
- $1,931 ($644/night)
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The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- May 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- May 4–12, 2026 (8 nights)
- 1 bed/2 bath, sleeps 4
- $4,385 ($548/night)
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Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- May 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,745 ($1,249/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- May 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 6–12, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $2,596 ($433/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 7–12, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($768/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 7–14, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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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)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,679 ($668/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,474 ($782/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- May 8–15, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 8–16, 2026 (8 nights)
- 2 bed/3 bath, sleeps 8
- $6,020 ($752/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,256 ($751/night)
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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)
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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
- $3,077 ($440/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,132 ($447/night)
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- May 8–14, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,186 ($531/night)
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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)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,602 ($657/night)
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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)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/night)
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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)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,712 ($673/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,756 ($679/night)
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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
- $3,077 ($440/night)
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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
- $4,658 ($665/night)
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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)
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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)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,186 ($455/night)