Kailua Vacation Rentals

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Check prices for these dates

Tonight
Aug 8 - Aug 9
Tomorrow
Aug 9 - Aug 10
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Vacation Rentals in Kailua

Maui Beach Vacation Club
Enjoy ocean views from the balcony, featuring a comfortable sofa and a wicker cabinet.

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very Good, (775)
"Overall very nice place to stay with family. "
Maui Beach Vacation Club
Maui Sunset
Relax by the pool surrounded by lush palm trees and enjoy scenic views of the lake and mountains.

Maui Sunset

3.5 star property
8.8 out of 10, Excellent, (460)
"Very beautiful with lovely grounds. Easy check in and out…and right on the beach!"
Maui Sunset
Maui Schooner Resort
Relax by the pool surrounded by lush gardens and comfortable lounge chairs.

Maui Schooner Resort

3.5 star property
9.2 out of 10, Wonderful, (483)
"Room setup is very convenient for a group of 6 with 2 full baths. Landscape looks nice."
Maui Schooner Resort
Sugar Beach Resort
Relax by the pool with a view of the ocean.

Sugar Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1079)
"Loved the fully stocked kitchen and amenities available. It was a delightful stay! We would stay here again."
Sugar Beach Resort
Yonegan Maui Getaways - Haiku
Garden

Yonegan Maui Getaways - Haiku

3.0 star property
9.4 out of 10, Exceptional, (3)
"It was a last minute stay and it had what we needed. "
The price is ￥19,940
￥38,070 total
includes taxes & fees
Aug 10 - Aug 11
Yonegan Maui Getaways - Haiku
Oceanview Condo in Hana-Let the ocean lull you to sleep
Relax in a tranquil outdoor seating area with two comfortable chairs and a round table, surrounded by a wooden railing and a serene view.

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

9.2 out of 10, Wonderful, (103)
"Perfect spot, comfy bed, clean and relaxing. An absolute dream thank you!"
The price is ￥35,706
￥66,224 total
includes taxes & fees
Aug 26 - Aug 27
Oceanview Condo in Hana-Let the ocean lull you to sleep
Awesome Maui Vista Beach Suite
Walking along the wide, sandy beach is a serene experience.

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 ￥34,164
￥74,792 total
includes taxes & fees
Aug 10 - Aug 11
Awesome Maui Vista Beach Suite
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! "
Beautiful 3-bedroom townhome in Kihei
Wonderful South Maui Beach Condos
Enjoy a serene beach experience with turquoise waters and palm trees.

Wonderful South Maui Beach Condos

3.5 star property
9.4 out of 10, Exceptional, (22)
"Exactly what we needed with beach access right across the street"
The price is ￥34,164
￥74,792 total
includes taxes & fees
Aug 10 - Aug 11
Wonderful South Maui Beach Condos
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
Completely remodeled 2 bedroom King bed AC Kauhale Makai on the top floor
Enjoy the tranquil ocean views and tropical surroundings.

Completely remodeled 2 bedroom King bed AC Kauhale Makai on the top floor

10.0 out of 10, Exceptional, (82)
"Great location and the A/C was a must compared to other places we have stayed in Maui. "
Completely remodeled 2 bedroom King bed AC Kauhale Makai on the top floor
25% off Sep-Dec Tropical Gated Oceanfront Estate, Pool, Privacy, huge ocean view
Enjoy stunning ocean views from your balcony amidst lush greenery and palm trees.

25% off Sep-Dec Tropical Gated Oceanfront Estate, Pool, Privacy, huge 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. "
25% off Sep-Dec Tropical Gated Oceanfront Estate, Pool, Privacy, huge ocean view
Beach Front Ocean View Penthouse Kealia Resort Condo - Sugar Beach
Escape to a tranquil beach paradise with crystal-clear waters and a serene mountain backdrop.

Beach Front Ocean View Penthouse Kealia Resort Condo - Sugar Beach

10.0 out of 10, Exceptional, (134)
"It was great, would come back and stay again!"
Beach Front Ocean View Penthouse Kealia Resort Condo - Sugar Beach
Beautiful 1 bedroom ocean front condo with a/c in Menehune Shores ,Kihei
Enjoy breathtaking ocean views from this balcony with a palm tree and seating for two.

Beautiful 1 bedroom ocean front condo with a/c in Menehune Shores ,Kihei

8.6 out of 10, Excellent, (131)
"The location is perfect and So is the property that is recently renovated. Steve is a great host and was always available to answer any questions or concerns. My wife and I had great time here and we will certainly book it again. "
Beautiful 1 bedroom ocean front condo with a/c in Menehune Shores ,Kihei
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 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, (227)
"Lovely property and very enjoyable place to stay. Great location."
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores
Outdoor dining

2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores

9.8 out of 10, Exceptional, (183)
"Had a wonderful experience staying here! A sweet, cozy and comfortable little getaway for our family and little one!"
The price is ￥28,885
￥73,658 total
includes taxes & fees
Aug 15 - Aug 16
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores
MAUI OCEAN VIEW 2 bed 2 bath with Air Conditioning
Enjoy breathtaking views of the ocean from this serene beachside location.

MAUI OCEAN VIEW 2 bed 2 bath with Air Conditioning

9.6 out of 10, Exceptional, (199)
"The location was perfect. The condo had everything you could need for a short-term stay.The pool and grill area are convenient (although they were closed for 2 days of our stay for maintenance of the tile)."
MAUI OCEAN VIEW 2 bed 2 bath with Air Conditioning
Maui Sunset #B-417 Spacious, Renovated Unit, Oceanfront Complex, Full A/C
Enjoy breathtaking ocean views and serene surroundings from this beachfront haven.

Maui Sunset #B-417 Spacious, Renovated Unit, Oceanfront Complex, Full A/C

9.8 out of 10, Exceptional, (74)
"My wife, I and our 3 young kids stayed here. It was a great location with an unbeatable view. The place worked out great for us and would rent again. "
Maui Sunset #B-417 Spacious, Renovated Unit, Oceanfront Complex, Full A/C
The Maui Moon Oceanfront Condo- Perfect for couples!
Enjoy breathtaking ocean views from this serene beachside retreat.

The Maui Moon Oceanfront Condo- Perfect for couples!

10.0 out of 10, Exceptional, (120)
"This condo is spectacular. The views are amazing and they have made sure to have everything you could possibly need for any day trips or excursions you take. Highly recommend staying here and hope to be back someday. "
The Maui Moon Oceanfront Condo- Perfect for couples!
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 Sunset

Maui Sunset

10/10 Excellent
"The unit was updated and clean. The best part for me was the stunning views of the ocean and you can walk to the ocean just over the grass. Would definitely stay there again. "
Michelle 7-night trip
Posted 2 days ago
Maui Sunset

Frequently asked questions

Can I find a vacation rental in Kailua?

Yes, there are vacation rentals near top sights in Kailua, or you can select a more secluded option if you're looking for relaxation.

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

Yonegan Maui Getaways - Haiku : This vacation home rental near Kailua is located near the beach and has a hot tub, a barbecue grill, 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 larger area, you’ll find Garden of Eden Arboretum and Maui Garden Of Eden - Botanical Gardens & Arboretum.

What’s a vacation rental in Kailua like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Kailua. Vacation rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a small group gathering.