Spring Summer Rentals
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Apr 30 – May 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,205 ($315/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,491 ($499/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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The Point at Poipu
Koloa, Hawaii- May 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($424/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 1–8, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 1–8, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,727 ($532/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,492 ($1,070/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,294 ($471/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 1–8, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,385 ($626/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,598 ($657/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,595 ($656/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,592 ($656/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $5,475 ($782/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,147 ($735/night)
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Club Wyndham Royal Sea Cliff
Kailua-Kona, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,319 ($188/night)
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Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- May 2–8, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $4,276 ($713/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,058 ($580/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 2–8, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($586/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,579 ($1,083/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,510 ($930/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,112 ($588/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,687 ($527/night)
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The Point at Poipu
Koloa, Hawaii- May 2–16, 2026 (14 nights)
- 2 bed/2 bath, sleeps 6
- $7,110 ($508/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,548 ($650/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,696 ($385/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 2–9, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,186 ($455/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- May 3–9, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $5,802 ($967/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,205 ($315/night)
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($595/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,166 ($595/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($1,094/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- May 3–8, 2026 (5 nights)
- 3 bed/3 bath, sleeps 8
- $2,979 ($596/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,493 ($642/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,949 ($564/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,404 ($486/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- May 4–12, 2026 (8 nights)
- 1 bed/2 bath, sleeps 4
- $4,385 ($548/night)
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Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- May 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,745 ($1,249/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 6–16, 2026 (10 nights)
- 3 bed/2 bath, sleeps 8
- $7,655 ($766/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 7–14, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $5,693 ($813/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 7–12, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $2,745 ($549/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- May 7–14, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,256 ($751/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- May 8–15, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,676 ($525/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/night)