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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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 10–22, 2026 (12 nights)
- 1 bed/1 bath, sleeps 4
- $6,347 ($529/night)
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Voted Top Pick 2025
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)
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WorldMark Kihei Resort
Kihei, Hawaii- May 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,932 ($276/night)
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Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 12–16, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($578/night)
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The Point at Poipu
Koloa, Hawaii- May 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,298 ($471/night)
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Kahana Beach Resort
Lahaina, Hawaii- May 13–20, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,818 ($260/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
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Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 14–21, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $9,780 ($1,397/night)
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Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 14–21, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $9,835 ($1,405/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- May 15–17, 2026 (2 nights)
- Studio/1 bath, sleeps 4
- $1,389 ($695/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 15–22, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 15–22, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 15–22, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,641 ($377/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- May 15–22, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,148 ($735/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 15–22, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/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)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- May 15–21, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $3,916 ($653/night)
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Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,581 ($654/night)
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Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/night)
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Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 16–21, 2026 (5 nights)
- 2 bed/3 bath, sleeps 8
- $3,404 ($681/night)
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Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- May 16–30, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $8,745 ($625/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,183 ($598/night)
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Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $11,466 ($1,638/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,938 ($848/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 16–23, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,058 ($580/night)
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 16–23, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,696 ($385/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,385 ($626/night)
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Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,802 ($829/night)
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Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,510 ($930/night)
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Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($595/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,083 ($1,012/night)
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Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,911 ($844/night)
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Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- May 16–23, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,093 ($299/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,966 ($852/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,474 ($782/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 17–24, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,578 ($511/night)