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 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,993 ($570/night)
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The Point at Poipu
Koloa, Hawaii- May 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,745 ($392/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,688 ($384/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,543 ($935/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,467 ($352/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,211 ($602/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,876 ($696/night)
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Kahana Villa Resort
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,550 ($221/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,584 ($798/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,894 ($556/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- May 22–29, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,641 ($377/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 22–27, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,641 ($528/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,147 ($735/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,458 ($494/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,148 ($735/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 22–28, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,804 ($467/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Pono Kai
Kapaa, Hawaii- May 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $1,412 ($202/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 23–29, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,655 ($609/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,450 ($350/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
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Lawai Beach Resort
Koloa, Hawaii- May 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($315/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,257 ($751/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,306 ($472/night)
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,658 ($665/night)
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Pono Kai
Kapaa, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,096 ($299/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,129 ($876/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 23–29, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,813 ($635/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,458 ($780/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($517/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,658 ($665/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,123 ($303/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,886 ($412/night)
Hanalei Bay Resort
Princeville, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,619 ($374/night)
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Sands of Kahana Vacation Club
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $3,077 ($440/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,787 ($541/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 23–30, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,705 ($386/night)