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 17–24, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/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)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 17–24, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 17–24, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,462 ($352/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 17–24, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,019 ($860/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,641 ($377/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 18–23, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,014 ($403/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- May 19–21, 2026 (2 nights)
- Studio/1 bath, sleeps 4
- $1,244 ($622/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/night)
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Kahana Beach Resort
Lahaina, Hawaii- May 20–27, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,818 ($260/night)
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The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- May 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,595 ($656/night)
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Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,077 ($440/night)
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The Point at Poipu
Koloa, Hawaii- May 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,290 ($470/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,240 ($463/night)
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Pono Kai
Kapaa, Hawaii- May 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $1,932 ($276/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,219 ($1,031/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- May 22–28, 2026 (6 nights)
- 1 bed/2 bath, sleeps 4
- $3,190 ($532/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/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 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,184 ($883/night)
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Voted Top Pick 2025
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 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 22–29, 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 - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,622 ($517/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,532 ($362/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 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,148 ($735/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 22–27, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,968 ($594/night)
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Voted Top Pick 2025
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 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,197 ($742/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 23–30, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,581 ($369/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,649 ($521/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 23–30, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,487 ($355/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)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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WorldMark Kihei Resort
Kihei, Hawaii- May 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,932 ($276/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 23–30, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,619 ($374/night)
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $11,470 ($1,639/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 23–30, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,835 ($1,405/night)