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
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,709 ($816/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 16–23, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,977 ($1,140/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 16–23, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,705 ($386/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 16–23, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,260 ($609/night)
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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
- $8,800 ($1,257/night)
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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)
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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
- $4,167 ($595/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $3,840 ($549/night)
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Voted Top Pick 2026
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 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,886 ($412/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
- $7,083 ($1,012/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,094 ($728/night)
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Aston Paki Maui
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/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
- $5,938 ($848/night)
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 16–22, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $4,548 ($758/night)
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Club Wyndham Kona Hawaiian Resort
Kailua-Kona, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,123 ($303/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/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
- $6,129 ($438/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
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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
- $3,835 ($548/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
- $5,361 ($766/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,175 ($739/night)
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The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,183 ($312/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
- $2,423 ($346/night)
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($564/night)
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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
- $8,418 ($1,203/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
- $3,840 ($549/night)
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Voted Top Pick 2026
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 2026
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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Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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Voted Top Pick 2026
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 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,591 ($656/night)
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Voted Top Pick 2026
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 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,730 ($533/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 17–24, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 17–26, 2026 (9 nights)
- Studio/1 bath, sleeps 4
- $3,164 ($352/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 17–25, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $3,164 ($396/night)
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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,602 ($657/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,314 ($331/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Kahana Beach Resort
Lahaina, Hawaii- May 20–27, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,434 ($205/night)
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Maui Beach Vacation Club
Kihei, Hawaii- May 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
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Sea Mountain
Punalu'u, Hawaii- May 20–27, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $998 ($143/night)
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Sands of Kahana Vacation Club
Lahaina, Hawaii- May 20–27, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $2,581 ($369/night)