The 30 Best Holiday Rentals in Hawaii

Ranked 1 out of 3,377 in the Hawaii region, as well as being 1 of 25 for holiday rentals in Volcano.

• “Very cute and cozy.”
• “Thanks Bill for your warm welcome and recommandations.”
• “Immaculate, cozy and clean”
• See more reviews of Volcano Teapot Cottage

Ranked 2 out of 3,377 in the Hawaii region, as well as being 1 of 65 for holiday rentals in Kapaa.

• “Absolutely the best stay ever.”
• “”
• “Tranquil, peaceful and amazing room, just not perfect.”
• See more reviews of The Secret Garden Room

Ranked 3 out of 3,377 in the Hawaii region, as well as being 1 of 38 for holiday rentals in Wailuku.

• “Amazing location, very easy to reach several beaches, plus...”
• “It was a great rental that was full stocked, had great views, would definitely book again”
• “”
• See more reviews of This place is different!! Award winning! Oceanfront, View View!

Ranked 4 out of 3,377 in the Hawaii region, as well as being 1 of 395 for holiday rentals in Honolulu.

• “”
• “Great condo close to everything!”
• “Fantastic!”
• See more reviews of Amazing waikiki Beach condo 2Bed2Bath+free Parking

Ranked 5 out of 3,377 in the Hawaii region, as well as being 1 of 1 for holiday rentals in Holualoa.

• “Good kitchen and living space.”
• “We enjoyed our comfortable cottage which was very nicely decorated with all the comforts of home along with the fresh av”
• “Perfect stay.”
• See more reviews of Hawaii Getaway

Ranked 6 out of 3,377 in the Hawaii region, as well as being 1 of 29 for holiday rentals in Keaau.

• “A tropical paradise”
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• “Great, quiet”
• See more reviews of Hale O Malu at Kaloli Point

Ranked 7 out of 3,377 in the Hawaii region, as well as being 3 of 395 for holiday rentals in Honolulu.

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• See more reviews of Aston Waikiki Beach Tower

Ranked 8 out of 3,377 in the Hawaii region, as well as being 1 of 164 for holiday rentals in Kailua-Kona.

• “Great affordable condo!”
• “So enjoyed our stay”
• “Comfortable, & welcoming Ohana!”
• See more reviews of ZERO FEES Aloha Lani Condo #A208 at Casa De Emdeko

Ranked 9 out of 3,377 in the Hawaii region, as well as being 1 of 24 for holiday rentals in Hilo.

• “Wonderful place;”
• “”
• “This stay made me wish I could live in such a spotless and beautifully designed home.”
• See more reviews of NEW Paddler's Inn- 3BR Hilo Downtown

Ranked 10 out of 3,377 in the Hawaii region, as well as being 1 of 44 for holiday rentals in Waikoloa.

• “”
• “Absolutely fantastic!”
• “Ocean breezes and sunsets, warm pool relaxing!”
• See more reviews of Coconut at Shores - Waikoloa Beach Resort

Ranked 11 out of 3,377 in the Hawaii region, as well as being 2 of 78 for holiday rentals in Wailea.

• “Excellent service, great location, carefully crafted space.”
• “It was an awesome place to stay and felt very inviting.”
• “Nice set up, pool was great, BBQ grills helped with meals.”
• See more reviews of Tiki Tiki - Gorgeous Boho Beach Hideaway!

Ranked 12 out of 3,377 in the Hawaii region, as well as being 1 of 2 for holiday rentals in Kipu.

• “Perfect stay in Kauai”
• “Comfortable and relax place”
• “Wondering”
• See more reviews of Pili Mai

Ranked 13 out of 3,377 in the Hawaii region, as well as being 2 of 164 for holiday rentals in Kailua-Kona.

• “The condo was spacious and perfect for our family with...”
• “Roomy.”
• “Gary was an exceptional host - incredibly responsive and...”
• See more reviews of Winter Getaway - Prime Location - at Magic Sands Beach

Ranked 14 out of 3,377 in the Hawaii region, as well as being 1 of 2 for holiday rentals in Papa Bay Estates.

• “Peaceful stay in a tiny house with lots of amenities”
• “Adorable little house with nicely-finished interior.”
• “Cute, well and efficiently equipped cottage with amazing views.”
• See more reviews of Country Cottage in Papa Bay

Ranked 15 out of 3,377 in the Hawaii region, as well as being 1 of 145 for holiday rentals in Kihei.

• “I give it a 9 out of 10”
• “Excellent get away”
• “Great service good communication”
• See more reviews of Nona Lani Cottages

Ranked 16 out of 3,377 in the Hawaii region, as well as being 3 of 78 for holiday rentals in Wailea.

• “We had a great trip.”
• “”
• “Lovely Hawaiien appartment”
• See more reviews of Beautiful 2 Bedroom Oceanview Condo at Maui Kamaole Located at South End of Kihei Adjacent to Wailea Traditional Hawaiian Style

Ranked 17 out of 3,377 in the Hawaii region, as well as being 4 of 29 for holiday rentals in Keaau.

• “A little bit of paradise!”
• “”
• “Super clean and elegant bungalow style retreat, where you can pamper yourself and experience nature.”
• See more reviews of The Red Cottage and Hawaiian Pond Garden Paradise!

Ranked 18 out of 3,377 in the Hawaii region, as well as being 2 of 145 for holiday rentals in Kihei.

• “We were very comfortable.”
• “Great stay!”
• “Location”
• See more reviews of 3mins Walk to Beach! Laundry, Pool, Hot Tub & More

Ranked 19 out of 3,377 in the Hawaii region, as well as being 3 of 164 for holiday rentals in Kailua-Kona.

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• “Do not stay here”
• See more reviews of Holualoa Gardens 101

Ranked 20 out of 3,377 in the Hawaii region, as well as being 4 of 78 for holiday rentals in Wailea.

• “A perfect vacation getaway”
• “Peaceful, luxurious, and the ultimate Maui experience.”
• “Super hosts; fabulous condo with many upscale touches!”
• See more reviews of Aloha Moon - A Chic and Dreamy Modern Tropical Hideaway!

Ranked 21 out of 3,377 in the Hawaii region, as well as being 1 of 9 for holiday rentals in Laie.

• “”
• “Excellent property for a perfect stay near the beautiful beaches of the North Shore.”
• “The amenities of home.”
• See more reviews of Laie Hawaii Studio

Ranked 22 out of 3,377 in the Hawaii region, as well as being 1 of 11 for holiday rentals in Pahoa.

• “”
• “Cozy apartment and lovely hosts”
• “Perfect isolated place great for exploring the south of Big Island”
• See more reviews of Hale “Hā Hā”

Ranked 23 out of 3,377 in the Hawaii region, as well as being 4 of 164 for holiday rentals in Kailua-Kona.

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• “Nice Apartment, Nature Experience, Nice Host.”
• See more reviews of The Great Kona Escape

Ranked 24 out of 3,377 in the Hawaii region, as well as being 5 of 164 for holiday rentals in Kailua-Kona.

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• See more reviews of Newly Renovated Condo with SUP Paddle Boards and Golf Clubs Included

Ranked 25 out of 3,377 in the Hawaii region, as well as being 2 of 65 for holiday rentals in Kapaa.

• “They keys were available on time.”
• “We absolutely loved everything about our stay here!”
• “Would recommend if you’re staying in Kauai”
• See more reviews of Fern Grotto Inn

Ranked 26 out of 3,377 in the Hawaii region, as well as being 2 of 11 for holiday rentals in Pahoa.

• “Beautiful location and vibe.”
• “Just the perfect place”
• “Magical!”
• See more reviews of Tropical Zen Bungalow

Ranked 27 out of 3,377 in the Hawaii region, as well as being 6 of 164 for holiday rentals in Kailua-Kona.

• “Very nice location , clean , beautiful.”
• “Wonderful studio, a home away from home”
• “Very pleasant- had all the extra touches like coffee, toothpaste and other amenities.”
• See more reviews of The Ohia at The Koi House

Ranked 28 out of 3,377 in the Hawaii region, as well as being 3 of 145 for holiday rentals in Kihei.

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• See more reviews of Unrivaled S Kihei Maui location! Walk to it all!

Ranked 29 out of 3,377 in the Hawaii region, as well as being 7 of 164 for holiday rentals in Kailua-Kona.

• “Very well-kept property. Exceptionally nice host.”
• “Everything you could possibly need for a relaxing and fun-filled stay!”
• “Top-notch appointments all around, great kitchen & bathroom, appliances appear brand new.”
• See more reviews of "Makani Moana" at Keauhou Resort #104, Entire townhome close to Kona

Ranked 30 out of 3,377 in the Hawaii region, as well as being 1 of 55 for holiday rentals in Koloa.

• “Excellent views, excellent accommodations and excellent...”
• “We had a magical family holiday”
• “Highly recommend , and we would gladly return here for our next stay.”
• See more reviews of Whalers Cove in Poipu