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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Browse Select Kaupulehu Cottages

Stunning, Romantic Cottage on Slope of Hualalai
1 bedroom, in-room safe, iron/ironing board, WiFi

Stunning, Romantic Cottage on Slope of Hualalai

10.0 out of 10, Exceptional, (197)
"Gale was an amazing host and the home was outstanding! We will be back! "
Stunning, Romantic Cottage on Slope of Hualalai
Cozy Private Ohana with Sunset/Ocean Views and Private Entrance
Fridge, microwave, stovetop, coffee/tea maker

Cozy Private Ohana with Sunset/Ocean Views and Private Entrance

2.0 star property
9.8 out of 10, Exceptional, (6)
"Had everything we needed, the laundry and kitchen were very handy"
Cozy Private Ohana with Sunset/Ocean Views and Private Entrance
Private Cottage In The Rain Forest TA065882726401
Fridge, microwave, stovetop, coffee/tea maker

Private Cottage In The Rain Forest TA065882726401

10.0 out of 10, Exceptional, (130)
"This place is absolutely beautiful tucked up in the rainforest. You have a beautiful view the all the plants and friendly animals. The frogs will sing you a song each night and it's just a 15 minute drive to the ocean. "
Private Cottage In The Rain Forest TA065882726401
1 Mile to Magic Sands Beach: Kailua-Kona Cottage
Beach nearby

1 Mile to Magic Sands Beach: Kailua-Kona Cottage

10.0 out of 10, Exceptional, (65)
"A lovely cottage to spend our honeymoon. Only a few minutes walk from the lovely Magic Sands Beach. We were able to cook all our own food and were grateful for the pantry staples. All the provisions were more than expected. One minor issue that the top windows in the bedroom did not have a curtain so the room was light early in the morning which made it hard to sleep in. But we would definitely stay here again and recommend to others!"
1 Mile to Magic Sands Beach: Kailua-Kona Cottage
PUAKO 1940's Vintage Beach Cottage - Now with Air Conditioning
Outdoor dining

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

10.0 out of 10, Exceptional, (221)
"Everything about the house and hosts were just the best of the many places we've stayed. We didn't want to leave. They do a great job, and the kitchen is great for cooking, the location beautiful, and on and on. It is a special placeWe are seniors, and it was a comfortable place for us, and the ocean and wildlife were magical there. ."
PUAKO 1940's Vintage Beach Cottage - Now with Air Conditioning
Welcome to Mango Cottage
Sun loungers, beach towels

Welcome to Mango Cottage

9.8 out of 10, Exceptional, (121)
"Puako is a gem. Great host, community and nature!"
Welcome to Mango Cottage
Charming Kailua-Kona Apartment Near Hiking & Golf!
Fridge, microwave, stovetop, coffee/tea maker

Charming Kailua-Kona Apartment Near Hiking & Golf!

9.2 out of 10, Wonderful, (12)
"Very comfortable and would stay there again."
Charming Kailua-Kona Apartment Near Hiking & Golf!
Charming Oceanfront Cottage in Beautiful Historic Kailua-Kona Village
Property grounds

Charming Oceanfront Cottage in Beautiful Historic Kailua-Kona Village

9.4 out of 10, Exceptional, (39)
"the cottage was everything we hoped it would be - relaxing, amazing views, and provided a great setting to recharge our batteries!"
Charming Oceanfront Cottage in Beautiful Historic Kailua-Kona Village
Breezy Kailua-kona Bungalow w/ Lanai & Ocean View!
Outdoor dining

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!
Waimea/Kawaihae dry side with breathtaking ocean view and sunset.
Dining

Waimea/Kawaihae dry side with breathtaking ocean view and sunset.

9.6 out of 10, Exceptional, (7)
"Loved the location and the views. Between Waimea and Kawaihae just a short trip to either town. Markets in Waimea are a treat to visit, Kawaihae harbor, Spencer Beach Park, Kiholo Bay, Hawi and Pololu Valley all in easy driving distance. The house is well equipped and very comfortable and host Yumi is so helpful. Good food and fun atmosphere at the Kawaihae Seafood Bar and Grill. Saw beautiful sunsets and lots of whales."
Waimea/Kawaihae dry side with breathtaking ocean view and sunset.
Kailua-kona House w/ Balcony & Ocean Views!
House (3 Bedrooms) | Interior

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

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

10.0 out of 10, Exceptional, (133)
"Stayed 5 nights here after 5 nights on the east side. Studio was perfect - just the right amount of space for the two of us. Decorated very nice, comfortable bed, clean, had everything you needed, peaceful view of the awesome sunsets from the veranda. Wonderful hosts! Highly recommend!"
Holualoa Studio Cottage - GIANT OCEAN VIEW! Cool, private, near town
Charming Kailua-kona Apartment Near Hiking & Golf!
Cottage (1 Bedroom) | Interior

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!
House (3 Bedrooms) | Interior

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!
Craftsman Cottage on 6 forested acres
Outdoor dining

Craftsman Cottage on 6 forested acres

9.8 out of 10, Exceptional, (81)
"Exceptional in every way!"
Craftsman Cottage on 6 forested acres
BIG ISLAND BLUE MAKAI, Oceanfront 2BR in Puako! Summer Specials in Paradise!
Property grounds

BIG ISLAND BLUE MAKAI, Oceanfront 2BR in Puako! Summer Specials in Paradise!

9.8 out of 10, Exceptional, (63)
"We had a great time. It's right on the ocean, the kitchen had everything we needed for some ambitious meals, and the sliding doors were a pleasure to operate."
BIG ISLAND BLUE MAKAI, Oceanfront 2BR in Puako! Summer Specials in Paradise!
BIG ISLAND HALE MELE MELE, Lovely Cottage in Magical Puako! Summer Fun Rates!
Beach

BIG ISLAND HALE MELE MELE, Lovely Cottage in Magical Puako! Summer Fun Rates!

10.0 out of 10, Exceptional, (53)
"Our family of four had a wonderful stay here. Great house and yard. Kitchen is petite but so well stocked and cared for. The yard is amazing and we loved the stars at night. Various great shoreline accesses across the road to black lava beach Frequented by the green sea turtles. "
BIG ISLAND HALE MELE MELE, Lovely Cottage in Magical Puako! Summer Fun Rates!
$100 off the normal nightly rate of $595 for 7/2-7/16 new bookings
Pool

$100 off the normal nightly rate of $595 for 7/2-7/16 new bookings

9.8 out of 10, Exceptional, (81)
"Great communication, gorgeous location, lovely property"
$100 off the normal nightly rate of $595 for 7/2-7/16 new bookings
BIG ISLAND PLUMERIA COTTAGE New AC! Ideal Couples Getaway in Magical Puako!
Beach

BIG ISLAND PLUMERIA COTTAGE New AC! Ideal Couples Getaway in Magical Puako!

10.0 out of 10, Exceptional, (98)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Everything at Kozy's Plumeria Cottage was fabulous. Simply awesome."
BIG ISLAND PLUMERIA COTTAGE New AC! Ideal Couples Getaway in Magical Puako!
Spectacular Oceanfront Puako Cottage
Aerial view

Spectacular Oceanfront Puako Cottage

10.0 out of 10, Exceptional, (5)
"Fantastic old Hawaiian cottage right on the water. Walked to the Puako general store. Good spot for snorkeling."
Spectacular Oceanfront Puako Cottage
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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Other property types in Kaupulehu

Aston Kona by the Sea
On the beach

Aston Kona by the Sea

4.0 star property
8.8 out of 10, Excellent, (1079)
"A bit tired but convenient and reasonably priced"
The price is CA $287
CA $590 total
includes taxes & fees
Jun 1 - Jun 2
Aston Kona by the Sea
Kona Bali Kai
Beach

Kona Bali Kai

2.0 star property
8.0 out of 10, Very good, (12)
"Great place to stay, close to the Main Street of Kona and close to the ocean!"
The price is CA $360
CA $520 total
includes taxes & fees
May 11 - May 12
Kona Bali Kai
Castle Hali'i Kai at Waikoloa
Aerial view

Castle Hali'i Kai at Waikoloa

4.0 star property
9.0 out of 10, Wonderful, (682)
"Very nice property. Gated community with excellent staff. The pool area was very nice but there were no shaded areas unless you were using the dining services. Nice walking areas. Large 2- bedroom unit was a nice break from the small units we had at the large hotel chain facilities at the previous 3 islands that we stayed at. "
Castle Hali'i Kai at Waikoloa
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.