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
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 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 23–30, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,649 ($521/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)
- 2 bed/3 bath, sleeps 8
- $6,238 ($891/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
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
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/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
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
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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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 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 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
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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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
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
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 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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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 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
- $2,750 ($550/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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Voted Top Pick 2025
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 2025
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 2025
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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Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,456 ($922/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,112 ($588/night)
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Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $12,996 ($1,857/night)
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Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,230 ($747/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,475 ($782/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
- $4,276 ($611/night)
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Voted Top Pick 2025
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 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,110 ($1,016/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 30 – Jun 6, 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 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2025
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 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,185 ($455/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,121 ($874/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 31 – Jun 7, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,968 ($424/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 31 – Jun 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,949 ($564/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 31 – Jun 7, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,292 ($899/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jun 1–8, 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- Jun 1–8, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,112 ($588/night)
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jun 2–6, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,704 ($426/night)