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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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- May 15–22, 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 15–22, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 15–22, 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 - Lahaina Tower
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,094 ($728/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,886 ($412/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 16–22, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $3,186 ($531/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,800 ($1,257/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,493 ($642/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,999 ($714/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 16–23, 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 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/night)
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Aston Paki Maui
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,183 ($598/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,175 ($739/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 16–23, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $11,466 ($1,638/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 17–25, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $3,486 ($436/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 17–24, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 17–24, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,019 ($860/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 17–26, 2026 (9 nights)
- Studio/1 bath, sleeps 4
- $3,164 ($352/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 17–24, 2026 (7 nights)
- 2 bed/2 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 17–24, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,786 ($541/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 17–24, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,578 ($511/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 17–24, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/night)
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Kahana Beach Resort
Lahaina, Hawaii- May 20–27, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,578 ($225/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,908 ($701/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,339 ($763/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,804 ($401/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,184 ($883/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,147 ($735/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,599 ($657/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 22–29, 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 22–29, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,689 ($384/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,748 ($821/night)
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Kahana Villa Resort
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,550 ($221/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,219 ($1,031/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,295 ($471/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,894 ($556/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,004 ($572/night)
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 22–29, 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 22–29, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,622 ($517/night)