Spring Summer Rentals
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,560 ($937/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
- $5,748 ($958/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
- $4,329 ($618/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
- $5,475 ($782/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,256 ($751/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
- $6,892 ($985/night)
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Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- May 9–16, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,219 ($174/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 10–17, 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 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,764 ($538/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
- $2,749 ($393/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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WorldMark Kihei Resort
Kihei, Hawaii- May 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,440 ($206/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,022 ($432/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,508 ($501/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,167 ($595/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 10–15, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $3,022 ($604/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 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,423 ($346/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
- $4,493 ($642/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,156 ($594/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
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- May 11–16, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $5,039 ($1,008/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- May 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
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Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- May 12–16, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $2,856 ($714/night)
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The Point at Poipu
Koloa, Hawaii- May 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,764 ($395/night)
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Maui Beach Vacation Club
Kihei, Hawaii- May 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,742 ($249/night)
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Kahana Beach Resort
Lahaina, Hawaii- May 13–20, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,165 ($166/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- May 13–18, 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 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
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Hanalei Bay Resort
Princeville, Hawaii- May 15–22, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,467 ($352/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,598 ($657/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 15–21, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($495/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)
- Studio/1 bath, sleeps 4
- $2,303 ($329/night)
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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
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 15–22, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,181 ($454/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
- $3,512 ($502/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 15–22, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,640 ($377/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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Marriott's Kauai Beach Club
Lihue, Hawaii- May 15–22, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,750 ($393/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 15–20, 2026 (5 nights)
- Studio/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 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,649 ($521/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,451 ($493/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/night)