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Cottages in Kaupulehu

Delightful Artful Bungalow on Historic Estate Property. Choice Holualoa!

9.8 out of 10, Exceptional, (158)
"We loved our stay at Lisa’s little place, we didn’t want to leave :)Thanks Lisa!"
Delightful Artful Bungalow on Historic Estate Property. Choice Holualoa!

Holualoa Studio Cottage - GIANT OCEAN VIEW! Cool, private, near town

10.0 out of 10, Exceptional, (143)
"Awesome place to stay. Very clean and nicely furnished. Hosts are great."
Holualoa Studio Cottage - GIANT OCEAN VIEW! Cool, private, near town

PUAKO 1940's Vintage Beach Cottage - Now with Air Conditioning

10.0 out of 10, Exceptional, (233)
"Can’t beat the location - quiet, private and close to great beaches. Owners were friendly and welcoming. Cottage was well-stocked and exceptionally clean. We loved our stay!"
PUAKO 1940's Vintage Beach Cottage - Now with Air Conditioning

Private Cottage In The Rain Forest TA065882726401

10.0 out of 10, Exceptional, (144)
"This place was so magical. We loved the privacy, quiet, and incredible nature surrounding us! "
Private Cottage In The Rain Forest TA065882726401

Breezy Kailua-kona Bungalow w/ Lanai & Ocean View!

3.0 star property
9.0 out of 10, Wonderful, (2)
Breezy Kailua-kona Bungalow w/ Lanai & Ocean View!

Craftsman Cottage on 6 forested acres

9.8 out of 10, Exceptional, (84)
"Loved this place - was quiet, secluded, and safe, and nearly 3000' above Kona. Good communication - would definitely stay here again. Looks for the signs to Ohia Rental! "
Craftsman Cottage on 6 forested acres

Charming Oceanfront Cottage in Beautiful Historic Kailua-Kona Village

9.4 out of 10, Exceptional, (40)
"The property is at a beautiful spot"
Charming Oceanfront Cottage in Beautiful Historic Kailua-Kona Village

Big Island Hale Mele Mele - Fall Special! Stay 7+ nights get 1 night FREE

10.0 out of 10, Exceptional, (55)
"Our family of 6 had a wonderful stay. Thank you!"
Big Island Hale Mele Mele - Fall Special! Stay 7+ nights get 1 night FREE

Charming Kailua-kona Apartment Near Hiking & Golf!

3.0 star property
8.6 out of 10, Excellent, (7)
"We had a wonderful stay in April. The onsite property manager is a delight to chat with, and the apartment was clean, comfortable, and has everything we could need from appliances to beach equipment. We look forward to staying again!"
Charming Kailua-kona Apartment Near Hiking & Golf!

Lovely Kailua-kona Home ~ 2 Mi to Town & Beach!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Lovely place to stay. 1 really tall bed was an adventure to jump into but was fun being so high up off of the ground. The home was really clean and it was a really nice touch with the gift pack. The balcony is really lovely spot early mornings and evenings to chill out on too. "
Lovely Kailua-kona Home ~ 2 Mi to Town & Beach!

Welcome to Mango Cottage

9.8 out of 10, Exceptional, (124)
"The Mango Cottage was the perfect place to spend our last 5 days on the island. The location is fantastic, the neighborhood is quiet and the cottage is beautifully landscaped and comfortable. Friendly and accommodating hosts made the stay even better. We hope to return soon!"
Welcome to Mango Cottage

Kailua-kona House w/ Balcony & Ocean Views!

3.0 star property
10.0 out of 10, Exceptional, (1)
Kailua-kona House w/ Balcony & Ocean Views!

Kailua-kona Coastal Refuge w/ Lanai + Ocean Views!

3.0 star property
Kailua-kona Coastal Refuge w/ Lanai + Ocean Views!

Cozy Vintage Inspired Hawaiian Guest Cottage

2.0 star property
10.0 out of 10, Exceptional, (4)
"Very neat and clean little cottage in a nice little quiet neighborhood. Close to airport and coastline of Kona. Shopping and great places to visit are within a short drive. The owner, Andrew, is nearby and always available for suggestions or questions about the area. I highly recommend staying here."
Cozy Vintage Inspired Hawaiian Guest Cottage

2 bedroom 1 bath cottage 10 minutes from beach

8.0 out of 10, Very Good, (3)
"Great communication, clean and organized home with the things needed to enjoy Hawaii."
2 bedroom 1 bath cottage 10 minutes from beach

Stunning, Romantic Cottage on Slope of Hualalai

10.0 out of 10, Exceptional, (203)
"This place is beautiful, Gale is so sweet and helpful and her property is the most relaxing place to stay. We hope to come back and definitely stay here again. "
Stunning, Romantic Cottage on Slope of Hualalai

Charming Kailua-Kona Apartment Near Hiking & Golf!

8.6 out of 10, Excellent, (16)
"Very comfortable and would stay there again."
Charming Kailua-Kona Apartment Near Hiking & Golf!

1 Mile to Magic Sands Beach: Kailua-kona Cottage

3.0 star property
1 Mile to Magic Sands Beach: Kailua-kona Cottage

Gated Tropical Retreat in Kailua Kona Hawai’i, five minutes from the ocean.

4.0 star property
Gated Tropical Retreat in Kailua Kona Hawai’i, five minutes from the ocean.

Cozy Kona Coast Apt w/ Lanai ~ 8 Miles to Beach!

9.0 out of 10, Wonderful, (11)
"Small but adequate 1br with some view of the coastline overlooking the airport."
Cozy Kona Coast Apt w/ Lanai ~ 8 Miles to Beach!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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