Spring & Summer Rentals
Did you know that 75% of travelers book their spring and summer travel at least 3 months in advance? Unlock exceptional resort deals for your upcoming seasonal getaways before they sell out. Whether you're planning a family vacation, a couple's trip, or a solo adventure, these deals offer the best opportunities to elevate your next travel experience.
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Club Wyndham Ka 'Eo Kai
Princeville, Hawaii- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,205 ($315/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- May 4–13, 2026 (9 nights)
- 1 bed/2 bath, sleeps 4
- $3,949 ($439/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 4–10, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($767/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,508 ($930/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 9–16, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,932 ($276/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- May 9–16, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,568 ($510/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 10–20, 2026 (10 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($766/night)
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The Point at Poipu
Koloa, Hawaii- May 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,298 ($471/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,148 ($735/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 15–22, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,938 ($848/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 16–23, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,058 ($580/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 18–23, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,014 ($403/night)
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The Point at Poipu
Koloa, Hawaii- May 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,290 ($470/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Pono Kai
Kapaa, Hawaii- May 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $1,932 ($276/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- May 22–28, 2026 (6 nights)
- 1 bed/2 bath, sleeps 4
- $3,190 ($532/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- May 22–29, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,641 ($377/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,197 ($742/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,886 ($412/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,202 ($743/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- May 24–31, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,641 ($377/night)
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The Point at Poipu
Koloa, Hawaii- May 27 – Jun 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,112 ($588/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 29 – Jun 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- May 29 – Jun 5, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,385 ($626/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,911 ($844/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,911 ($844/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,366 ($767/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,202 ($743/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 31 – Jun 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- May 31 – Jun 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,911 ($844/night)