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Vacation Homes in Kailua

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Enjoy the serene ocean views and scenic beach with waves gently lapping at the shore.

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. "
$306 nightly
The price is $356
Aug 11 - Aug 12
Total includes taxes and fees
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Fisher's Hana Bay Hale, Across from Hana Bay
Enjoy a serene beach setting with a rocky outcrop in the distance, where waves gently lap against the shore.

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. "
$343 nightly
The price is $399
Aug 18 - Aug 19
Total includes taxes and fees
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! "
$396 nightly
The price is $461
Aug 2 - Aug 3
Total includes taxes and fees
Beautiful 3-bedroom townhome in Kihei
Mountain to Ocean Views Pole House @ Maui Adventure Villa
Relax in this open-plan living area with expansive views of the surrounding landscape, featuring a hammock and comfortable seating.

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
Set amidst lush greenery, this two-story building offers a serene retreat with a garage and attached structure.

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
Enjoy the ocean view from this balcony with two chairs and a small table.

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
Enjoy a serene beach experience with turquoise waters and a sandy shore lined with palm trees.

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
Surrounded by lush greenery, this charming garden structure features a sloped roof and sturdy bamboo fence.

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."
$2,568 nightly
The price is $2,992
Aug 11 - Aug 12
Total includes taxes and fees
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"
$221 nightly
The price is $243
Jul 28 - Jul 29
Total includes taxes and fees
Yonegan Maui Getaways - Haiku
BEACHFRONT MAUI KIHEI HOUSE
Relax by the ocean with a serene view of distant mountains and lush greenery.

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!
Stunning views of the outdoors are showcased through large arched windows, complemented by classical design elements.

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
Relax by the oceanfront pool surrounded by palm trees and lounge chairs.

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
Relax on the patio surrounded by lush tropical plants and enjoy a meal at the barbecue grill.

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

$2,527 nightly
The price is $2,939
Aug 16 - Aug 17
Total includes taxes and fees
Oceanfront Hideaway on the Beach
Oceanfront Penthouse Vistas
Relax by the pool surrounded by palm trees and enjoy ocean views.

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
Enjoy stunning ocean views from your balcony amidst lush greenery and palm trees.

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
Relax by the pool surrounded by lush vegetation and palm trees.

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
Relax by the ocean with unobstructed views of the sea and palm trees, surrounded by lounge chairs and a pool.

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
Overlooking the clear blue sea, this property offers stunning views of the sandy beach and lush green surroundings.

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. "
$518 nightly
The price is $602
Jul 30 - Jul 31
Total includes taxes and fees
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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Top Kailua Hotel Reviews

Maui Seaside Hotel

Maui Seaside Hotel

10/10 Excellent
"We were very pleased with this property. The rooms were renovated and excellent. Great pool and great ocean views. The only suggestion would be the outside could use a coat of paint. It under sells the property. "
Greg 1-night trip
Posted 6 hours ago
Maui Seaside Hotel