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
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 24–30, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,641 ($440/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
- $6,129 ($876/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
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 24–31, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,366 ($767/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
- $3,268 ($467/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
- $5,257 ($751/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
- $3,022 ($432/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
- $5,475 ($782/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- May 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/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 25–30, 2026 (5 nights)
- 1 bed/2 bath, sleeps 4
- $2,423 ($485/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)
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)
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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 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
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
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
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
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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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
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 29 – Jun 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,658 ($665/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
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,847 ($978/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,586 ($370/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/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)
- 1 bed/2 bath, sleeps 4
- $3,295 ($471/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/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
- $5,148 ($735/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)
- 1 bed/1 bath, sleeps 4
- $3,658 ($523/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 Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $9,562 ($1,366/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
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
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $9,835 ($1,405/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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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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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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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($595/night)