Holiday Homes in Kailua

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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Holiday Homes in Kailua

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Beach towels

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

9.6 out of 10, Exceptional, (385)
"The property was excellent, highly recommend. "
The price is AU$548
includes taxes & fees
11 Aug - 12 Aug
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Fisher's Hana Bay Hale, Across from Hana Bay
Beach towels

Fisher's Hana Bay Hale, Across from Hana Bay

9.4 out of 10, Exceptional, (391)
"Loved the location, there was even a peek-a-boo view of Hāna Bay. Lovely garden. "
The price is AU$614
includes taxes & fees
18 Aug - 19 Aug
Fisher's Hana Bay Hale, Across from Hana Bay
Beautiful 3-bedroom townhome in Kihei
Property grounds

Beautiful 3-bedroom townhome in Kihei

9.6 out of 10, Exceptional, (4)
"We loved our stay! The place had everything the family needed for visiting the beach and the place was clean and comfortable. Would stay again! "
The price is AU$709
includes taxes & fees
2 Aug - 3 Aug
Beautiful 3-bedroom townhome in Kihei
Mountain to Ocean Views Pole House @ Maui Adventure Villa
Outdoor dining

Mountain to Ocean Views Pole House @ Maui Adventure Villa

10.0 out of 10, Exceptional, (223)
"Great location with a great view. Very relaxing. "
Mountain to Ocean Views Pole House @ Maui Adventure Villa
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Exterior

Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

10.0 out of 10, Exceptional, (225)
"Stunning and immaculate country home perfect for your Maui adventure. Comfortable and beautiful accommodation centrally located to all attractions. We would stay here again 💯! "
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Stunning Beach Front Townhouse
Interior

Stunning Beach Front Townhouse

10.0 out of 10, Exceptional, (94)
"Firstly, Susan was so wonderful to deal with- thank you for being so welcoming and accommodating- we really appreciated the late checkout- with a 3 year old toddler with us…he was able to nap and that made such a wonderful difference to our last day in paradise. The view is amazing! Would love to stay there again someday soon. "
Stunning Beach Front Townhouse
Ocean View Retreat – Walk to Town and Beaches– A/C – Fast WiFi - Self Check-In
Beach nearby, sun-loungers, beach towels

Ocean View Retreat – Walk to Town and Beaches– A/C – Fast WiFi - Self Check-In

10.0 out of 10, Exceptional, (170)
"We had a great time. The house was very well organized and equipped "
Ocean View Retreat – Walk to Town and Beaches– A/C – Fast WiFi - Self Check-In
Kaiholo Hale
Beach nearby

Kaiholo Hale

3.0 star property
9.4 out of 10, Exceptional, (199)
"We stayed here 4 nights, perfect location for our activities. We did sunrise bike ride down Haleakala and Road to Hana. "
Kaiholo Hale
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Property grounds

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

10.0 out of 10, Exceptional, (65)
"16 of us stayed at this beautiful property. Two Families, 12 children total. We have nothing bad to say. All of our expectations were met. The listing is true and accurate. Communication with the property manager was always prompt and efficient.We would definitely stay her again."
The price is AU$4,600
includes taxes & fees
11 Aug - 12 Aug
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Yonegan Maui Getaways - Haiku
Garden

Yonegan Maui Getaways - Haiku

3.0 star property
9.0 out of 10, Wonderful, (2)
"Nice nature"
The price is AU$370
includes taxes & fees
28 July - 29 July
Yonegan Maui Getaways - Haiku
BEACHFRONT MAUI KIHEI HOUSE
Terrace/patio

BEACHFRONT MAUI KIHEI HOUSE

9.8 out of 10, Exceptional, (163)
"Great property with a good central location. We enjoyed the turtles every evening. The house was fully stocked with everything we needed. A great hub for a fun friend’s trip!"
BEACHFRONT MAUI KIHEI HOUSE
Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!
Interior

Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!

10.0 out of 10, Exceptional, (35)
"Loved our time and stay!"
Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!
Sugar Beach Resort condo with ocean view, AC - surf, bike & golf
Pool

Sugar Beach Resort condo with ocean view, AC - surf, bike & golf

8.8 out of 10, Excellent, (49)
"The condo is fairly old but is clean and you can't beat the location. Just steps from the water"
Sugar Beach Resort condo with ocean view, AC - surf, bike & golf
Family-friendly 4BR/2BA House🌺Close to Beach/Park,Dining & Shops | Hot Tub & AC
Outdoor dining

Family-friendly 4BR/2BA House🌺Close to Beach/Park,Dining & Shops | Hot Tub & AC

10.0 out of 10, Exceptional, (185)
"Beautiful home perfect for our group of 7 friends. Thank you!"
Family-friendly 4BR/2BA House🌺Close to Beach/Park,Dining & Shops | Hot Tub & AC
Oceanfront Hideaway on the Beach
Dining

Oceanfront Hideaway on the Beach

The price is AU$4,659
includes taxes & fees
16 Aug - 17 Aug
Oceanfront Hideaway on the Beach
Oceanfront Penthouse Vistas
Exterior

Oceanfront Penthouse Vistas

4.5 star property
10.0 out of 10, Exceptional, (5)
"I was very happy with everything. I wish I could have stayed longer. "
Oceanfront Penthouse Vistas
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
On the beach, sun-loungers, beach towels

Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

9.8 out of 10, Exceptional, (202)
"great for large groups"
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
Exceptional Upcountry Villa with breathtaking views
Outdoor pool

Exceptional Upcountry Villa with breathtaking views

10.0 out of 10, Exceptional, (44)
"We had a great time. Location is beautiful. House is comfortable, clean, and well-equipped. The view is amazing. Pool and whirlpool were a hit. Close to stores/restaurants in Makawao. Good hiking nearby. The hosts were responsive and helpful. Really can’t say enough about the views. I spent more time enjoying the views than reading my book! Didn’t even think about turning on the TV!"
Exceptional Upcountry Villa with breathtaking views
Hale Kai O Kihei Condo w/ Ocean View, Shared W/D-Waves Await
Property grounds

Hale Kai O Kihei Condo w/ Ocean View, Shared W/D-Waves Await

10.0 out of 10, Exceptional, (40)
"Everything about this place"
Hale Kai O Kihei Condo w/ Ocean View, Shared W/D-Waves Await
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
Sun-loungers, beach towels

Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

9.2 out of 10, Wonderful, (142)
"For Hana, this was a great find. AC in both bedrooms. Nice porch with a great view. Full kitchen. Modern rain shower was great after the long drive. Check and out was easy. "
The price is AU$927
includes taxes & fees
30 July - 31 July
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
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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