Search Vacation Homes in Kailua

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Vacation Homes in Kailua

Yonegan Maui Getaways - Haiku

3.0 star property
9.4 out of 10, Exceptional, (6)
"Loved having the hot tub to come home to!!"
The price is AED 414
AED 852 total
includes taxes & fees
5 Oct - 6 Oct
Yonegan Maui Getaways - Haiku

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

9.6 out of 10, Exceptional, (402)
"The property was excellent, highly recommend. "
The price is AED 639
AED 1,308 total
includes taxes & fees
8 Oct - 9 Oct
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher's Hana Bay Hale, Across from Hana Bay

9.4 out of 10, Exceptional, (406)
"Wonderful property and a great place to stay in Hana"
The price is AED 716
AED 1,458 total
includes taxes & fees
8 Oct - 9 Oct
Fisher's Hana Bay Hale, Across from Hana Bay

Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!

9.6 out of 10, Exceptional, (20)
"Great place, very convenient and amazing settings! "
Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!

Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC

10.0 out of 10, Exceptional, (129)
"Plenty of room. Great kitchen for lots of cooks."
Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC

Menuhene Shores 604, Oceanfront Bliss with Incredible Whale Watching Views

Menuhene Shores 604, Oceanfront Bliss with Incredible Whale Watching Views

Kaiholo Hale

3.0 star property
9.4 out of 10, Exceptional, (201)
"Area was quiet but close to amenities. We could drive anywhere on Maui easily. There was a lovely beach less than a block from the suite with good snorkeling and friendly locals. Bed in the suite was very comfortable, and it had everything we needed for a relaxing vacation."
Kaiholo Hale

Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view

9.8 out of 10, Exceptional, (205)
"Perfect home for a large group. Beach is across the street the back to the pool when the waves got to be to much for our little ones. Great property manager! Great location! "
Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view

Exceptional Upcountry Villa with breathtaking views

10.0 out of 10, Exceptional, (44)
"Beautiful views and beautiful accommodations! We loved being in the up country and this house was perfect for my family of five. "
Exceptional Upcountry Villa with breathtaking views

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

10.0 out of 10, Exceptional, (228)
"I absolutely love staying here! It’s a new yearly tradition and great location! "
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

Oceanfront Hideaway on the Beach

10.0 out of 10, Exceptional, (1)
"We really enjoyed this house! It had everything we needed and more! They provided beach chairs and umbrellas, all the kitchen necessities, and even a high chair and port-a-crib for the baby! It was clean and spacious. Host was been very efficient and friendly. "
The price is AED 3,684
AED 8,530 total
includes taxes & fees
19 Oct - 20 Oct
Oceanfront Hideaway on the Beach

3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

9.8 out of 10, Exceptional, (76)
"Phenomenal property for your stay in Hana - especially for a large group "
The price is AED 2,645
AED 4,248 total
includes taxes & fees
2 Oct - 3 Oct
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

Hale Kai O Kihei Condo w/ Shared Pool, Ocean View-Beaches Await

9.4 out of 10, Exceptional, (49)
"We had a great time "
Hale Kai O Kihei Condo w/ Shared Pool, Ocean View-Beaches Await

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

10.0 out of 10, Exceptional, (174)
"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

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

10.0 out of 10, Exceptional, (35)
"Lovely place. The pool is awesome as is the home itself. So nice it was hard to leave to explore other parts of the island. "
Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!

Mountain to Ocean Views Pole House @ Maui Adventure Villa

9.8 out of 10, Exceptional, (230)
"Will certainly be returning"
Mountain to Ocean Views Pole House @ Maui Adventure Villa

PRIVATE HOME-NEWLY REMODELED-AC-HOT TUB-METICULOUS CLEANING

10.0 out of 10, Exceptional, (65)
"This property is fantastic! It is set in a quiet neighborhood and the home itself is very quiet. The layout of the home was perfect for our family of 6. The kitchen was well laid out, the living room was a great place for us to hang out, and the back yard was incredible. The provided beach gear came in very handy. Check in was a breeze and our entire stay was absolutely flawless. "
PRIVATE HOME-NEWLY REMODELED-AC-HOT TUB-METICULOUS CLEANING

2 Private Homes for 1! Pool and Waterslide at Cove Hale

10.0 out of 10, Exceptional, (26)
"Amazing place. Amazing pool and the host was just awesome"
2 Private Homes for 1! Pool and Waterslide at Cove Hale

Island Surf with Ocean View - Across from popular Surf spot, Beach, and Shops

9.8 out of 10, Exceptional, (80)
"Centrally located on S Kihei Rd with lots of food options within walking distance. Kamala Park across the street and beaches close. Condo was nice and has a beautiful view. "
Island Surf with Ocean View - Across from popular Surf spot, Beach, and Shops

Gingerbread House-Less than a mile from Paia town and all North Shore beaches

9.8 out of 10, Exceptional, (54)
"We loved our stay in Paia! The house was wonderful, clean, comfortable and a great location. Really close to a couple nice beaches and a short drive to town. Pro tip… have coffee on the balcony up stairs in the morning. There are a bunch of little geckos hanging out in the morning sunshine. 10/10 could come back!"
Gingerbread House-Less than a mile from Paia town and all North Shore beaches
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Kailua Hotel Reviews