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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The Cliffs at Princeville
Princeville, Hawaii- May 24–31, 2026 (7 nights)
- 4 bed/4 bath, sleeps 10
- $3,295 ($471/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- May 25–30, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $1,660 ($332/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 25–30, 2026 (5 nights)
- 1 bed/2 bath, sleeps 4
- $2,423 ($485/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 25–30, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($1,095/night)
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 26 – Jun 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 26 – Jun 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/night)
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 26 – Jun 7, 2026 (12 nights)
- 1 bed/1 bath, sleeps 4
- $6,827 ($569/night)
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Pono Kai
Kapaa, Hawaii- May 27 – Jun 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,402 ($200/night)
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The Point at Poipu
Koloa, Hawaii- May 27 – Jun 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
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Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- May 28 – Jun 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,954 ($565/night)
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Club Wyndham Kona Hawaiian Resort
Kailua-Kona, Hawaii- May 28 – Jun 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,095 ($299/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 29 – Jun 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,380 ($626/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 29 – Jun 5, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,835 ($548/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- May 29 – Jun 5, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,222 ($603/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 29 – Jun 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 29 – Jun 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 29 – Jun 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,560 ($937/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- May 29 – Jun 5, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 29 – Jun 5, 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 29 – Jun 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,451 ($922/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 29 – Jun 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,194 ($599/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 29 – Jun 5, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,531 ($362/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 29 – Jun 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,175 ($739/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 29 – Jun 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 29 – Jun 5, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 29 – Jun 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,358 ($623/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 29 – Jun 5, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 29 – Jun 5, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,422 ($346/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,257 ($751/night)
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $9,906 ($1,415/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,022 ($432/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 30 – Jun 7, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($616/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,835 ($548/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,987 ($284/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,511 ($787/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
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Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,020 ($860/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,129 ($876/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,832 ($547/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,649 ($521/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,592 ($656/night)
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Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,758 ($394/night)