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
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,647 ($664/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)
- 2 bed/2 bath, sleeps 6
- $4,412 ($630/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
- $3,786 ($541/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)
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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
- $4,603 ($658/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 3–8, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,932 ($386/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
- $2,467 ($352/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
- $4,276 ($611/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
- $2,363 ($473/night)
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 7–14, 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 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 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 - Lahaina Tower
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,256 ($751/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,679 ($668/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,132 ($447/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)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 8–16, 2026 (8 nights)
- 2 bed/3 bath, sleeps 8
- $6,020 ($752/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,112 ($588/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,602 ($657/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,175 ($739/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,072 ($439/night)
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,743 ($1,249/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,674 ($953/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,816 ($688/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 9–16, 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 - Lahaina Tower
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $9,726 ($1,389/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,756 ($679/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 9–15, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $6,009 ($1,002/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,712 ($673/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 9–16, 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 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,977 ($711/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $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 10–17, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,077 ($440/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 10–17, 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 10–17, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 10–22, 2026 (12 nights)
- 1 bed/1 bath, sleeps 4
- $5,244 ($437/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,513 ($502/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 10–17, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,548 ($650/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($315/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,711 ($673/night)
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Kahana Beach Resort
Lahaina, Hawaii- May 13–20, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,434 ($205/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 14–21, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $9,835 ($1,405/night)