Holiday Rentals in Kailua

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Kailua

Maui Sunset

3.5 star property
8.8 out of 10, Excellent, (415)
"We enjoyed our stay. Grounds and pool are very well tended. Our unit was very tired and needed a deep clean. But the beds, pillows, linens and towels were very good. The A/C wall unit in the living room struggles to keep the space comfortable. I informed the property and hopefully they will replace it. The dedicated lap swimming in the morning is wonderful otherwise it’s overrun with kids even during the non-spring break time window. Good location and very close to Azeka Shopping Center with...
Maui Sunset

Maui Schooner Resort

3.5 star property
9.2 out of 10, Wonderful, (443)
"Love it!"
Maui Schooner Resort

Sugar Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1044)
"It was so great and so pretty! Loved it !"
Sugar Beach Resort

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very good, (727)
"The property was in good location in between Lahaina and the airport. The room was great despite it was not what was showed in the pictures and as listed. It appeared that we were in first floor verses the second floor also there is absolutely no air conditioning just fans. The listing should have at least stated that there wasn’t any or that it had standing floor fans. Overall, the property was great for the price and location. "
Maui Beach Vacation Club

Fisher's Hana Bay Hale, Across from Hana Bay

9.4 out of 10, Exceptional, (356)
"We are grateful to the host for renting their beautiful home to us. The kitchen was well equipped with everything we needed to cook meals. The home is well ventilated with lots of windows and screens to prevent bugs from entering. Great location near the beach and the grocery store was a few minutes away. "
Fisher's Hana Bay Hale, Across from Hana Bay

Oceanview Condo in Hana-Let the ocean lull you to sleep

9.0 out of 10, Wonderful, (75)
"Wish we could stay longer!"
The price is €390
includes taxes & fees
3 Mar - 4 Mar
Oceanview Condo in Hana-Let the ocean lull you to sleep

Amazing Ocean Views - Steps To Beach - Newly Remodeled

9.8 out of 10, Exceptional, (210)
"Nice little condo I could live here ! Had the best time in Maui The only thing was the beach at this time was a little choppy but really good beaches near by and close to wailea "
Amazing Ocean Views - Steps To Beach - Newly Remodeled

180° Oceanfront View!! Completely Remodeled - Luxury Condo!

9.8 out of 10, Exceptional, (172)
"The property is beautiful, clean and spacious. "
180° Oceanfront View!! Completely Remodeled - Luxury Condo!

Awesome Maui Vista Beach Suite

4.0 star property
8.8 out of 10, Excellent, (11)
"Clean, nice, very close to the beach. Had washer and dryer which was perfect! Easy to communicate with the property manager. "
Awesome Maui Vista Beach Suite

Oceanfront 2/2, Outstanding View, Perfect Maui Getaway!

10.0 out of 10, Exceptional, (210)
"The condo was perfect for us, and Katie was wonderful to communicate with. We enjoyed every day of our stay."
Oceanfront 2/2, Outstanding View, Perfect Maui Getaway!

Oceanside condo, full kitchen, ocean view. Fully renovated 2023

9.4 out of 10, Exceptional, (31)
"Great location , close to ocean and restaurants and easy access to Kahului and airport. Comfortable bedding and nice that beach towels, boogie boards and cooler provided. During our stay we were hit with a very bad storm that closed the road and inundated the road and resort parking lot with mud and debris. The resort staff worked tirelessly for days to clear the mess. They did a great job. Would stay here again."
The price is €345
includes taxes & fees
25 Mar - 26 Mar
Oceanside condo, full kitchen, ocean view. Fully renovated 2023

Best Unit/Location w/ Ocean View! Fully Renovated End-Unit!

10.0 out of 10, Exceptional, (92)
"excellent property close to the beach and restaurants. Nice view and finishing. Pictures were accurate. Would recommend and stay again. "
Best Unit/Location w/ Ocean View! Fully Renovated End-Unit!

The Maui Moon Oceanfront Condo- Perfect for couples!

10.0 out of 10, Exceptional, (98)
"My husband and I stayed here for a week for our 20th wedding anniversary. We enjoyed every minute of it! The condo was very nice and cozy, and had everything we needed for our stay. The view from the lanai is stunning! We spent a lot of time out there relaxing and listening to the waves! We were able to whale watch every day. The location is perfectly centralized and near every restaurant, store, beaches, and airport! Our host, Pamela, was available for any last-minute questions we had and...
The Maui Moon Oceanfront Condo- Perfect for couples!

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

9.8 out of 10, Exceptional, (192)
"We were a family of eight adults and six children ages seven and under. The pool and yard were amazing. We used all of the open areas inside and out but really loved the huge covered lanai. We also rented the Ohana unit for one of our little families. They appreciated the quiet down there. Note that you must go outside to reach it, but we didn’t mind. House was very well stocked with beach towels/regular towels and paper products. The beach is so convenient and undeveloped. We rented wagons and...
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

Spectacular Ocean Maui Sunset View

9.8 out of 10, Exceptional, (111)
"Had visited 13yrs ago, we stayed first near Lahaina, then to Kihei. The unit was just right, very comfy for our family. Loved the patio & table, pool was close & great, location was nice. Thank you for all the details you had in place, we hope to visit again soon."
Spectacular Ocean Maui Sunset View

Sugar Beach Resort - Maui Condo & Home

3.0 star property
8.4 out of 10, Very good, (512)
"Very nice. They need more help in the bar and sandwich shop"
Sugar Beach Resort - Maui Condo & Home

Secluded cottage on Tropical flower farm

9.6 out of 10, Exceptional, (247)
"We enjoyed our stay in this special part of Hana. Quiet setting and peaceful surroundings. Great for a family getaway. "
The price is €595
includes taxes & fees
7 Mar - 8 Mar
Secluded cottage on Tropical flower farm

Evergreen Cottage @ Maui Adventure Villa

9.8 out of 10, Exceptional, (157)
"John very hands-on manager. Met me when I arrived and left. Very quiet and out of the bustle of Kaanpali and Wailua."
Evergreen Cottage @ Maui Adventure Villa

Clean Comfortable Condo that is Steps to the Beach, Affordable w/Free Parking

9.6 out of 10, Exceptional, (154)
"Nice place very accommodating"
The price is €504
includes taxes & fees
24 Feb - 25 Feb
Clean Comfortable Condo that is Steps to the Beach, Affordable w/Free Parking

Oceanfront 2BD/2BA Sugar Beach Tranquility at Koa Lagoon

9.4 out of 10, Exceptional, (109)
"Amazing views from the lanai, easy access to everything in Kihei "
Oceanfront 2BD/2BA Sugar Beach Tranquility at Koa Lagoon
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.
Don't see what you're looking for?
See all available properties in Kailua
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Kailua you may be interested in

Maui Seaside Hotel

3.0 star property
8.8 out of 10, Excellent, (1248)
"Nice place"
The price is €315
includes taxes & fees
11 Mar - 12 Mar
Maui Seaside Hotel

Maui Beach Hotel

3.0 star property
7.2 out of 10, Good, (1010)
"I liked the location. I wish the was fully operational. 2hours in the morning and 2 at night feels limiting. "
The price is €280
includes taxes & fees
16 Mar - 17 Mar
Maui Beach Hotel

Kohea Kai Hotel Maui

3.0 star property
8.6 out of 10, Excellent, (733)
"Front staff was excellent. Easy check in/out. Staff kept us updated on road closures to the hotel and gave us excellent directions to the hotel. I was a little nervous about staying at the hotel due to the resent storms knowing they were close to the damage but rooms were fantastic and staff was wonderful. We will be back! "
The price is €254
includes taxes & fees
24 Feb - 25 Feb
Kohea Kai Hotel Maui
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.

Frequently asked questions

Can I find a holiday rental in Kailua?

Yes, there are holiday rentals close to the most popular sights in Kailua, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Kailua has to offer?

Fisher's Hana Bay Hale, Across from Hana Bay: This holiday home rental outside of Kailua is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Kailua?

While exploring the area, visit family-friendly sights like Waikamoi Preserve, or get outside and enjoy nature at Twin Falls. In the wider area, you’ll find Garden of Eden Arboretum and Maui Garden Of Eden - Botanical Gardens & Arboretum.

What’s a holiday rental in Kailua like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kailua. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a small group gathering.