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Top Holiday Rentals in Kailua

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very good, (790)
"Just a great stay! "
Maui Beach Vacation Club

Maui Sunset

3.5 star property
8.8 out of 10, Excellent, (463)
"Located on the beach with beautiful sunsets and large pool and hot tub."
Maui Sunset

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 £192
includes taxes & fees
24 Aug - 25 Aug
Yonegan Maui Getaways - Haiku

Maui Schooner Resort

3.5 star property
9.2 out of 10, Wonderful, (485)
"Room setup is very convenient for a group of 6 with 2 full baths. Landscape looks nice."
Maui Schooner Resort

Sugar Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1083)
"Good location, easy access to beach"
Sugar Beach Resort

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

9.2 out of 10, Wonderful, (104)
"An idyllic setting where we could see the bay, hear the waves, with a short walk to the beach (black rocky sands). Neighbors a bit loud, but still one of the best spots in Hāna. Easy drive to the 7 sacred pools. Good food trucks nearby. "
The price is £350
includes taxes & fees
24 Aug - 25 Aug
Oceanview Condo in Hana-Let the ocean lull you to sleep

Dazzling Ocean View, Modern, Whole house AC. Upgraded Glass for a quiet setting

10.0 out of 10, Exceptional, (261)
"Completely remodeled and location is excellent! Host were great!"
Dazzling Ocean View, Modern, Whole house AC. Upgraded Glass for a quiet setting

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 £2,283
includes taxes & fees
10 Sept - 11 Sept
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

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

Maui Sunset B123 Beachfront, Ocean View, Ground Floor Families! Pool! 3 Bedrooms

9.8 out of 10, Exceptional, (55)
"We’ve been going there since about 1985. Love the location and the grounds. We like a ground unit so we can just flow to the outside "
Maui Sunset B123 Beachfront, Ocean View, Ground Floor Families! Pool! 3 Bedrooms

OCEAN FRONT: spacious, remodeled 4th floor condo

9.4 out of 10, Exceptional, (72)
"The corner ocean view 3 bedroom condo was perfect for my family. The condo was accessible with the elevator for my mom as well."
OCEAN FRONT: spacious, remodeled 4th floor condo

Sugar Beach Resort - Maui Condo & Home

3.0 star property
8.4 out of 10, Very good, (513)
"Love this location, great beach, quiet."
Sugar Beach Resort - Maui Condo & Home

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

Maui Sunset B120 Beachfront, Ground Floor, Ocean-View, Families! Amenities! Pool

10.0 out of 10, Exceptional, (71)
"Great condo. Great location. Could not have asked for a better place to stay with my family (two kids under 5). The grounds are well kept and staff are friendly. "
Maui Sunset B120 Beachfront, Ground Floor, Ocean-View, Families! Amenities! Pool

Awesome Maui Vista Beach Suite

4.0 star property
9.0 out of 10, Wonderful, (17)
"Accommodations were great..would stay again! "
The price is £376
includes taxes & fees
30 Aug - 31 Aug
Awesome Maui Vista Beach Suite

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

10.0 out of 10, Exceptional, (228)
"Lovely property and very enjoyable place to stay. Great location."
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

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

9.8 out of 10, Exceptional, (203)
"We enjoyed our time at this beautiful piece of property. The yard was amazing and the lanai was definitely the hang out spot. "
Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view

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

Chic & Elegant Oceanfront Vistas

4.0 star property
9.8 out of 10, Exceptional, (25)
"Pretty standard condos. Nice beaches and restaurants nearby. "
Chic & Elegant Oceanfront Vistas

MAUI OCEAN VIEW 2 bed 2 bath with Air Conditioning

9.6 out of 10, Exceptional, (200)
"Very comfortable and perfect location for food, surf and fun! Condo was great and had what we needed to enjoy our stay. Thank you!!"
MAUI OCEAN VIEW 2 bed 2 bath with Air Conditioning
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

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?

Yonegan Maui Getaways - Haiku : This holiday home rental outside of Kailua is located near the beach, and has 1 hot tub, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a microwave, a coffee maker and kitchenware.

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.