Fall Rentals
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)
Verified & Protected
Kamaole Beach Club
Kihei, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,856 ($265/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Oct 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,665 ($238/night)
Verified & Protected
Voted Top Pick 2026
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,840 ($406/night)
Verified & Protected
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Oct 10–17, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $3,458 ($494/night)
Verified & Protected
Voted Top Pick 2026
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,039 ($291/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Oct 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,749 ($393/night)
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,954 ($565/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,358 ($765/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
Verified & Protected
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,375 ($482/night)
Verified & Protected
Kona Coast Resort
Kailua-Kona, Hawaii- Oct 10–14, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,220 ($305/night)
Verified & Protected
Voted Top Pick 2026
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,328 ($761/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,688 ($384/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,564 ($938/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,306 ($472/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,420 ($489/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Oct 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,932 ($276/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,764 ($538/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,649 ($521/night)
Verified & Protected
Paniolo Greens
Waikoloa Village, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,434 ($205/night)
Verified & Protected
Voted Top Pick 2026
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,677 ($1,382/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,091 ($870/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,458 ($494/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,282 ($755/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Oct 11–18, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 11–18, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,077 ($440/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Oct 11–18, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,568 ($510/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Oct 11–18, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,423 ($346/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Oct 11–18, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,467 ($352/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Oct 11–18, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,456 ($922/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Oct 11–16, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $2,478 ($496/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Oct 11–17, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,510 ($418/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 11–18, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,200 ($314/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,402 ($914/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Verified & Protected
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Oct 12–16, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,656 ($414/night)
Verified & Protected
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Oct 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,049 ($150/night)
Verified & Protected
Kalia Suites by Hilton Grand Vacations
Honolulu, Hawaii- Oct 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,150 ($307/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Oct 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,742 ($249/night)
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 13–18, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($550/night)
Verified & Protected
Kahana Villa Resort
Lahaina, Hawaii- Oct 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,658 ($237/night)