Fall Rentals
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Oct 3–10, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,451 ($493/night)
Verified & Protected
Kona Coast Resort
Kailua-Kona, Hawaii- Oct 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,963 ($423/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Oct 4–11, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,412 ($630/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Oct 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,993 ($428/night)
Verified & Protected
Club Wyndham Mauna Loa Village
Kailua-Kona, Hawaii- Oct 4–11, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $1,780 ($254/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Oct 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,344 ($478/night)
Verified & Protected
WorldMark Kona Resort
Kailua-Kona, Hawaii- Oct 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,022 ($432/night)
Verified & Protected
Club Wyndham at Waikiki Beach Walk
Honolulu, Hawaii- Oct 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
Verified & Protected
Club Wyndham Kona Hawaiian Resort
Kailua-Kona, Hawaii- Oct 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
Club Wyndham Royal Sea Cliff
Kailua-Kona, Hawaii- Oct 4–12, 2026 (8 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($330/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Oct 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,954 ($565/night)
Verified & Protected
Club Wyndham Kona Hawaiian Resort
Kailua-Kona, Hawaii- Oct 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,069 ($438/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,200 ($1,171/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Oct 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,260 ($609/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,908 ($701/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Oct 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,282 ($755/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,366 ($767/night)
Verified & Protected
Club Wyndham Royal Sea Cliff
Kailua-Kona, Hawaii- Oct 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,505 ($358/night)
Verified & Protected
Club Wyndham Mauna Loa Village
Kailua-Kona, Hawaii- Oct 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
Verified & Protected
The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Oct 5–11, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($386/night)
Verified & Protected
Club Wyndham Kona Hawaiian Resort
Kailua-Kona, Hawaii- Oct 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,665 ($238/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,679 ($668/night)
Verified & Protected
Club Wyndham Royal Sea Cliff
Kailua-Kona, Hawaii- Oct 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,505 ($358/night)
Verified & Protected
Club Wyndham Kona Hawaiian Resort
Kailua-Kona, Hawaii- Oct 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Verified & Protected
Club Wyndham Kona Hawaiian Resort
Kailua-Kona, Hawaii- Oct 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,821 ($689/night)
Verified & Protected
Club Wyndham Royal Sea Cliff
Kailua-Kona, Hawaii- Oct 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,665 ($238/night)
Verified & Protected
Club Wyndham Kona Hawaiian Resort
Kailua-Kona, Hawaii- Oct 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,505 ($358/night)
Verified & Protected
Club Wyndham Holua Resort at the Mauna Loa Village
Kailua-Kona, Hawaii- Oct 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Oct 6–11, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $2,205 ($441/night)
Verified & Protected
Club Wyndham Kona Hawaiian Resort
Kailua-Kona, Hawaii- Oct 6–12, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($604/night)
Verified & Protected
Club Wyndham Royal Sea Cliff
Kailua-Kona, Hawaii- Oct 6–12, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($731/night)
Verified & Protected
WorldMark Kapaa Shore
Kapaa, Hawaii- Oct 6–15, 2026 (9 nights)
- 1 bed/1 bath, sleeps 4
- $2,232 ($248/night)
Verified & Protected
WorldMark Kona Resort
Kailua-Kona, Hawaii- Oct 7–14, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,428 ($347/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Oct 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Oct 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,382 ($626/night)
Verified & Protected
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Oct 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Verified & Protected
Club Wyndham Royal Sea Cliff
Kailua-Kona, Hawaii- Oct 8–11, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,314 ($438/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,473 ($782/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
Verified & Protected
Kona Coast Resort
Kailua-Kona, Hawaii- Oct 9–12, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,330 ($443/night)
Verified & Protected
Club Wyndham Mauna Loa Village
Kailua-Kona, Hawaii- Oct 9–12, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $1,165 ($388/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 9–16, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,390 ($341/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Oct 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,802 ($543/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,977 ($711/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,726 ($532/night)
Verified & Protected
Wyndham Kauai Coast Resort at the Beachboy
Kapaa, Hawaii- Oct 9–19, 2026 (10 nights)
- 1 bed/1 bath, sleeps 4
- $2,368 ($237/night)