Fall Rentals
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Sep 24 – Oct 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,268 ($467/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Sep 24 – Oct 1, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,001 ($286/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Sep 24 – Oct 1, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Sep 24 – Oct 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,832 ($547/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Sep 25 – Oct 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Sep 25 – Oct 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Maui Schooner
Kihei, Hawaii- Sep 25 – Oct 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,396 ($199/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Sep 25 – Oct 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,832 ($547/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Sep 25 – Oct 2, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,917 ($417/night)
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Sep 25 – Oct 6, 2026 (11 nights)
- 2 bed/2 bath, sleeps 6
- $3,802 ($346/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Sep 25 – Oct 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,175 ($739/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Sep 25 – Oct 1, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,987 ($331/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Sep 25 – Oct 2, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,129 ($876/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Sep 25 – Oct 2, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $4,412 ($630/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Sep 25 – Oct 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Sep 25 – Oct 2, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Sep 25 – Oct 2, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,750 ($393/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Sep 25 – Oct 2, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,123 ($303/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Sep 25 – Oct 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Sep 25 – Oct 3, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $3,513 ($439/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Sep 26 – Oct 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,153 ($450/night)
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The Gardens at West Maui
Kapalua, Hawaii- Sep 26 – Oct 3, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,329 ($190/night)
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Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Sep 26 – Oct 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
Voted Top Pick 2026
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Sep 26 – Oct 3, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,713 ($1,388/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Sep 26 – Oct 3, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $4,412 ($630/night)
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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Sep 26 – Oct 3, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $12,010 ($1,716/night)
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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Sep 26 – Oct 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,665 ($238/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Sep 26 – Oct 3, 2026 (7 nights)
- 1 bed/2 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- Sep 26 – Oct 3, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,458 ($494/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Sep 26 – Oct 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,458 ($494/night)
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Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Sep 26 – Oct 3, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $4,222 ($603/night)
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Sep 26 – Oct 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Sep 26 – Oct 3, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $4,870 ($696/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Sep 26 – Oct 3, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Sep 26 – Oct 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Sep 26 – Oct 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Sep 26 – Oct 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Sep 26 – Oct 3, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,442 ($777/night)
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Sands of Kahana Vacation Club
Lahaina, Hawaii- Sep 26 – Oct 3, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $3,622 ($517/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Sep 26 – Oct 3, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,191 ($456/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Sep 27 – Oct 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,901 ($700/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Sep 27 – Oct 4, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $2,825 ($404/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Sep 27 – Oct 4, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $6,121 ($874/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Sep 27 – Oct 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,901 ($700/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Sep 27 – Oct 4, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,750 ($393/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Sep 27 – Oct 2, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $1,824 ($365/night)
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Club Wyndham Kona Hawaiian Resort
Kailua-Kona, Hawaii- Sep 27 – Oct 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,358 ($194/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Sep 27 – Oct 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,175 ($739/night)