Guesthouse vacation rentals in Hawaiian Islands
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Top-rated guesthouses in Hawaiian Islands
Guests agree: these guesthouses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Hawaiian Islands guesthouses
Family-friendly guesthouses
Guesthouse in Haiku-Pauwela
4.93 out of 5 average rating, 135 reviewsMaile Bungalow- County Licensed
Nov. 6 – 13
Guesthouse in Haiku-Pauwela
4.93 out of 5 average rating, 112 reviewsPeaceful Studio - Hobby Fruit Farm - Beach 10 min
Mar. 12 – 19
Guesthouse in Kailua
4.78 out of 5 average rating, 135 reviewsKailua Beach Cottage - 90/TVU-0287
Oct. 29 – Nov. 5
Guesthouse in Volcano
4.94 out of 5 average rating, 1247 reviewsThe Ohana at Volcanoes National Park
Oct. 2 – 9
Guesthouse in Kailua-Kona
4.96 out of 5 average rating, 167 reviewsAmazing Sunset / Ocean View, Beautiful New Home
Jan. 5 – 12
Guesthouse in Pāhoa
4.91 out of 5 average rating, 157 reviewsNEW RENTaL! Experience Aloha *Hawaiian Style Hale*
Oct. 26 – Nov. 2
Guesthouse in Kurtistown
4.91 out of 5 average rating, 485 reviewsGreat Location: Volcano to Hilo
Apr. 14 – 21
Guesthouse in Kailua-Kona
4.87 out of 5 average rating, 127 reviews180 degree ocean view, private pool
Nov. 4 – 11
Guesthouses with a patio
Guesthouse in Pāhoa
4.98 out of 5 average rating, 132 reviewsModern Jungle Cottage
Dec. 31 – Jan. 7
Guesthouse in Kailua-Kona
4.99 out of 5 average rating, 122 reviewsRomantic Cabin Treehouse in Hawaii Cloud Forest
Jul. 28 – Aug. 4
Guesthouse in Captain Cook
4.94 out of 5 average rating, 117 reviewsMongoose Manor- Modern guesthouse / amazing views
Jan. 30 – Feb. 6
Guesthouse in Holualoa
4.95 out of 5 average rating, 154 reviewsThe Light House~King
May 11 – 18
Guesthouse in Keaau
4.98 out of 5 average rating, 106 reviewsHale Hapu’u - Tropical Tiki Paradise for Couples.
Nov. 8 – 15
Guesthouse in Kailua-Kona
5.0 out of 5 average rating, 32 reviewsSunset View Modern House / Private Pool
Oct. 14 – 21
Guesthouse in Waialua
5.0 out of 5 average rating, 67 reviewsSerene Mountain Getaway with Ocean Views
Mar. 3 – 10
Guesthouse in Papaaloa
4.95 out of 5 average rating, 78 reviewsGarden Studio with Ocean View
Aug. 21 – 28
Guesthouse rentals with a washer and dryer
Guesthouse in Kihei
4.91 out of 5 average rating, 158 reviewsPrivate 1 Bedroom Guest cottage
Mar. 1 – 8
Guesthouse in Kailua
4.85 out of 5 average rating, 334 reviewsKailua Palm Studio. Walk to Beach! PERMITTED
Mar. 13 – 20
Guesthouse in Volcano
4.99 out of 5 average rating, 348 reviewsVolcano Places Laukapu Forest Cottage
Mar. 11 – 18
Guesthouse in Maui
4.93 out of 5 average rating, 158 reviewsSouth Maui Oceanview Solo Cottage
Jul. 28 – Aug. 4
Guesthouse in Kailua-Kona
4.91 out of 5 average rating, 201 reviewsKimo’s Getaway
Apr. 3 – 10
Guesthouse in Kailua-Kona
4.96 out of 5 average rating, 140 reviewsBig Lanai w/ outdoor living! Ocean view & breezes!
Jan. 17 – 24
Guesthouse in Volcano
5.0 out of 5 average rating, 240 reviewsGigi’s Volcano Cottage
Oct. 22 – 27
Guesthouse in Holualoa
4.96 out of 5 average rating, 194 reviewsHolualoa Jungle Getaway (15 min from Kona)
Aug. 25 – Sep. 1
Destinations to explore
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