Kailua Vacation Rentals

    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

Next weekend
In two weeks
In one month
In two months

Browse Select Kailua Vacation Homes

Yonegan Maui Getaways - Haiku

3.0 star property
9.0 out of 10, Wonderful, (4)
"It was a last minute stay and it had what we needed. "
The price is CA $187
CA $356 total
includes taxes & fees
Sep 15 - Sep 16
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, (388)
"The property was excellent, highly recommend. "
The price is CA $240
CA $492 total
includes taxes & fees
Aug 20 - Aug 21
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, (394)
"Property was in a great location, very clean. We enjoyed our stay!"
The price is CA $268
CA $549 total
includes taxes & fees
Aug 20 - Aug 21
Fisher's Hana Bay Hale, Across from Hana Bay

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! "
Beautiful 3-bedroom townhome in Kihei

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

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

10.0 out of 10, Exceptional, (19)
"Excellent all around property"
Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!

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

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

10.0 out of 10, Exceptional, (227)
"Lovely property and very enjoyable place to stay. Great location."
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

Stunning Beach Front Townhouse

10.0 out of 10, Exceptional, (94)
"Great location to spend a week to enjoy Maui "
Stunning Beach Front Townhouse

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

10.0 out of 10, Exceptional, (172)
"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

Modern 3 Bedroom Family Friendly Kihei Home Near Beach

9.8 out of 10, Exceptional, (146)
"Perfect location and great place to stay to enjoy Kihei and Wailea. Highly recommend "
Modern 3 Bedroom Family Friendly Kihei Home Near Beach

BEACHFRONT MAUI KIHEI HOUSE

9.8 out of 10, Exceptional, (165)
"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

Oceanfront Hideaway on the Beach

The price is CA $1,286
CA $2,848 total
includes taxes & fees
Sep 14 - Sep 15
Oceanfront Hideaway on the Beach

Beautiful Home in paradise!

9.6 out of 10, Exceptional, (170)
"Ticked all the boxes of what we were looking for. We would recommend to others "
Beautiful Home in paradise!

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

9.8 out of 10, Exceptional, (229)
"Wonderful location!"
The price is CA $404
CA $849 total
includes taxes & fees
Aug 17 - Aug 18
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

North Shore Ocean View Cottage

10.0 out of 10, Exceptional, (140)
"This is our third visit to this lovely cottage. If you want serenity and comfort while enjoying the North shore you can’t beat this beautiful place. The hosts are lovely and the cottage is wonderfully equipped with everything you need for a great stay. "
North Shore Ocean View Cottage

BEACHFRONT FAMILY ESTATE: Sleeps 15 - 4 separate Units with optional cottage.

10.0 out of 10, Exceptional, (149)
"Super Backyard on the beach. Lots of room for activities and relaxing. Great views and sunsets. Michael is a fantastic host."
BEACHFRONT FAMILY ESTATE: Sleeps 15 - 4 separate Units with optional cottage.

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

10.0 out of 10, Exceptional, (67)
"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 CA $1,974
CA $3,732 total
includes taxes & fees
Aug 28 - Aug 29
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

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

BEACHFRONT HOUSE KIHEI, MAUI..TRUE HAWAIIAN HOME 1960's

9.8 out of 10, Exceptional, (105)
"The view from this home is what it is all about...Huge Banyan tree, perfectly manicured yard, and a view of the ocean, across the large yard. Nice large lanai to sit and enjoy it all. The croquet set was a fun addition.... The home worked for the 5 of us. It may be better suited for 4 people, as you need to move furniture to drop the murphy bed in the living room each day. (not a complaint, just thought others might want to consider this) The location on the island is perfect. Very easy to...
BEACHFRONT HOUSE KIHEI, MAUI..TRUE HAWAIIAN HOME 1960's
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