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 - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,603 ($658/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,346 ($907/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
- $6,320 ($903/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
- $6,565 ($938/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
- $2,504 ($358/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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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
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,290 ($470/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,854 ($979/night)
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Kahana Beach Resort
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,818 ($260/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,658 ($665/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $13,105 ($1,872/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
- $3,568 ($510/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
- $3,764 ($538/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)
- 1 bed/2 bath, sleeps 4
- $3,835 ($548/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/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)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/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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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/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
- $5,748 ($821/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
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,731 ($533/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/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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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
- $8,200 ($1,171/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
- $4,222 ($603/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 24–31, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,693 ($813/night)
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Voted Top Pick 2026
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 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 24–31, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,020 ($860/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 24–31, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 24–31, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,984 ($712/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 24–30, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $3,066 ($511/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 24–31, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,750 ($393/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Voted Top Pick 2026
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 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 24–31, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,692 ($813/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,186 ($455/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 24–31, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,510 ($930/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- May 25 – Jun 1, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,039 ($434/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
- $2,750 ($550/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
- $1,824 ($365/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
- $6,358 ($908/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 27 – Jun 3, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,745 ($392/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
- $4,548 ($650/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)
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)