Fall Rentals
The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,204 ($155/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,402 ($836/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($550/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,069 ($399/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Oct 17–24, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $10,108 ($1,321/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Oct 17–24, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,130 ($407/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,390 ($310/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,541 ($985/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,993 ($389/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($600/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,238 ($814/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Oct 18–25, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,306 ($299/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,458 ($450/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Oct 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,123 ($275/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Oct 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($500/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Oct 18–25, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $6,510 ($850/night)
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Oct 18–25, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $2,886 ($375/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,748 ($619/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,977 ($649/night)
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Oct 20–25, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($500/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Oct 20–27, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,475 ($714/night)
The Whaler
Lahaina, Hawaii- Oct 21 – Nov 4, 2026 (14 nights)
- 1 bed/2 bath, sleeps 5
- $4,527 ($295/night)
Lawai Beach Resort
Koloa, Hawaii- Oct 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,234 ($159/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Oct 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,069 ($399/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($600/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Oct 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($600/night)
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Oct 23–30, 2026 (7 nights)
- 3 bed/2.5 bath, sleeps 8
- $6,701 ($875/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,794 ($625/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Oct 23–30, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,382 ($571/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Oct 23–30, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,550 ($200/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Oct 23–30, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,603 ($600/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Oct 23–28, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $2,423 ($440/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Oct 23–30, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,077 ($400/night)
The Cliffs at Princeville
Princeville, Hawaii- Oct 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,165 ($150/night)
Club Wyndham Ka 'Eo Kai
Princeville, Hawaii- Oct 23 – Nov 1, 2026 (9 nights)
- 1 bed/1 bath, sleeps 4
- $2,840 ($287/night)
Hokulani Waikiki by Hilton Grand Vacations
Honolulu, Hawaii- Oct 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,010 ($130/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,031 ($525/night)
Hono Koa Resort
Honokowai, Hawaii- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,465 ($189/night)
Hokulani Waikiki by Hilton Grand Vacations
Honolulu, Hawaii- Oct 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,704 ($220/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,213 ($680/night)
Hokulani Waikiki by Hilton Grand Vacations
Honolulu, Hawaii- Oct 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $769 ($99/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 24–31, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,772 ($229/night)
Hokulani Waikiki by Hilton Grand Vacations
Honolulu, Hawaii- Oct 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $808 ($104/night)
Hanalei Bay Resort
Princeville, Hawaii- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,886 ($375/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Oct 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,810 ($365/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Oct 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,642 ($343/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,924 ($380/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 24–30, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $4,211 ($640/night)