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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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 23–29, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($640/night)
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Sands of Kahana Vacation Club
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($377/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,473 ($639/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,745 ($1,249/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,911 ($844/night)
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Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 23–30, 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
Lahaina, Hawaii- May 23–29, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $2,804 ($467/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,945 ($992/night)
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Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- May 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,352 ($336/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 23 – Jun 6, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $8,200 ($586/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,886 ($412/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,504 ($358/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
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Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,835 ($548/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
- $5,202 ($743/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)
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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
The Westin Kaanapali Ocean Resort Villas North
Lahaina, 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
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,993 ($570/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
- $5,693 ($813/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
- $2,859 ($408/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, 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
- $2,487 ($355/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,167 ($595/night)
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Voted Top Pick 2025
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 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,031 ($576/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 24–31, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,892 ($985/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 24–30, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($749/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,112 ($588/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 24–30, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $5,420 ($903/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 24–31, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,200 ($1,171/night)
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Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,328 ($1,047/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 24–31, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,128 ($875/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- May 24–31, 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 25–30, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($550/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 25–30, 2026 (5 nights)
- 1 bed/2 bath, sleeps 4
- $2,750 ($550/night)
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Voted Top Pick 2025
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 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 26 – Jun 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 26 – Jun 2, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,412 ($630/night)
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The Point at Poipu
Koloa, Hawaii- May 27 – Jun 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,112 ($588/night)