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- Apr 26 – May 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,794 ($685/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Apr 26 – May 3, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Apr 26 – May 3, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,505 ($358/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Apr 26 – May 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,513 ($502/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Apr 26 – May 3, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Apr 26 – May 3, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Apr 27 – May 3, 2026 (6 nights)
- 3 bed/2 bath, sleeps 8
- $8,854 ($1,476/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Apr 27 – May 5, 2026 (8 nights)
- Studio/1 bath, sleeps 4
- $2,423 ($303/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Apr 28 – May 5, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,358 ($765/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 1–8, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,932 ($276/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 1–8, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 1–8, 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 1–8, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,294 ($471/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 1–6, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $2,205 ($441/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,492 ($1,070/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,984 ($712/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,821 ($689/night)
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,276 ($611/night)
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,821 ($689/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,072 ($439/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,017 ($717/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,238 ($891/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,731 ($533/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,595 ($799/night)
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,510 ($930/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,641 ($377/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,495 ($356/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 3–8, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,287 ($457/night)
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,548 ($650/night)
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($510/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 3–10, 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 3–10, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,202 ($743/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 3–10, 2026 (7 nights)
- Studio/1 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 7–12, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $4,276 ($855/night)
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 7–12, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($768/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 8–13, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $1,769 ($354/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)