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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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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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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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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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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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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Pono Kai
Kapaa, Hawaii- May 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $1,932 ($276/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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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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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)
- 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
- $5,693 ($813/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 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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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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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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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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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 31 – Jun 7, 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 31 – Jun 7, 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- Jun 1–7, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($731/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jun 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
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Hanalei Bay Resort
Princeville, Hawaii- Jun 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Jun 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,229 ($318/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jun 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Jun 6–12, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,498 ($416/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Jun 6–13, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,031 ($576/night)
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,301 ($757/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jun 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,382 ($1,055/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Jun 7–14, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,968 ($424/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jun 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Jun 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,494 ($642/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jun 8–13, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($703/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Jun 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,494 ($642/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jun 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jun 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jun 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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The Cliffs at Princeville
Princeville, Hawaii- Jun 13–20, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jun 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- Jun 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jun 13–20, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,183 ($598/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jun 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)