Kailua Vacation Rentals

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Check prices for these dates

Tonight
Jul 25 - Jul 26
Tomorrow
Jul 26 - Jul 27
This weekend
Jul 25 - Jul 27
Next weekend
Aug 1 - Aug 3

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, (771)
"Great place to stay. "
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, (452)
"Beautiful and centrally located. "
Maui Sunset
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, (1077)
"Loved the fully stocked kitchen and amenities available. It was a delightful stay! We would stay here again."
Sugar Beach Resort
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, (479)
"This property was a amazing and we are definitely going to stay here again in the future."
Maui Schooner Resort
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 ￥34,194
￥74,860 total
includes taxes & fees
Aug 4 - Aug 5
Awesome Maui Vista Beach Suite
Yonegan Maui Getaways - Haiku
Garden

Yonegan Maui Getaways - Haiku

3.0 star property
9.0 out of 10, Wonderful, (2)
"Nice nature"
The price is ￥17,961
￥35,747 total
includes taxes & fees
Jul 27 - Jul 28
Yonegan Maui Getaways - Haiku
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! "
The price is ￥25,149
￥67,726 total
includes taxes & fees
Aug 2 - Aug 3
Beautiful 3-bedroom townhome in Kihei
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, (133)
"It was great, would come back and stay again!"
Beach Front Ocean View Penthouse Kealia Resort Condo - Sugar Beach
Ohana Paradise w/ Ocean View, Longest beach on Maui, Sugar Beach, Sleeps 4
Enjoy ocean views from this hotel, featuring a pool, hot tub, and lounge chairs surrounded by palm trees.

Ohana Paradise w/ Ocean View, Longest beach on Maui, Sugar Beach, Sleeps 4

9.8 out of 10, Exceptional, (114)
"Great view, ocean sounds. "
Ohana Paradise w/ Ocean View, Longest beach on Maui, Sugar Beach, Sleeps 4
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, (79)
"Came for a work trip but enjoyed the brief stay. Clean, comfortable and convenient location for our job in Kihei. Will come back and stay again and recommend to friends and family! "
Completely remodeled 2 bedroom King bed AC Kauhale Makai on the top floor
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, (102)
"Perfect spot, comfy bed, clean and relaxing. An absolute dream thank you!"
The price is ￥29,414
￥58,360 total
includes taxes & fees
Jul 27 - Jul 28
Oceanview Condo in Hana-Let the ocean lull you to sleep
Exceptionally Remodeled Oceanfront, Sunsets, A/C, King bed Hale Kai O Kihei
Enjoy the ocean view from this balcony with a table and chairs, ceiling fan, and window with a grill.

Exceptionally Remodeled Oceanfront, Sunsets, A/C, King bed Hale Kai O Kihei

10.0 out of 10, Exceptional, (139)
"Well stocked in a great location. Fantastic beach location."
Exceptionally Remodeled Oceanfront, Sunsets, A/C, King bed Hale Kai O 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 ￥34,050
￥74,545 total
includes taxes & fees
Aug 9 - Aug 10
Wonderful South Maui Beach Condos
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
Enjoy stunning ocean views from your balcony amidst lush greenery and palm trees.

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

9.8 out of 10, Exceptional, (202)
"great for large groups"
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
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
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, (225)
"Stunning and immaculate country home perfect for your Maui adventure. Comfortable and beautiful accommodation centrally located to all attractions. We would stay here again 💯! "
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Best Unit/Location w/ Ocean View! Fully Renovated End-Unit!
Relax in this spacious living area with a high ceiling, featuring a comfortable sofa set, coffee table, and TV on a stand, plus a sliding glass door leading to a balcony with a view.

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

10.0 out of 10, Exceptional, (101)
"This unit was located in the perfect spot "
Best Unit/Location w/ Ocean View! Fully Renovated End-Unit!
STUDIO: Kalama Beach Park, South Maui Gardens, Food Trucks, Hula Shows, Luaus
Enjoy serene beach activities like sailing and boating in a peaceful, natural setting surrounded by a majestic mountain.

STUDIO: Kalama Beach Park, South Maui Gardens, Food Trucks, Hula Shows, Luaus

9.4 out of 10, Exceptional, (136)
"Location was amazing. Host also provided many amenities like beach equipment, coffee, kitchenware etc.Great air con, communication and WiFi too. "
The price is ￥12,839
￥45,942 total
includes taxes & fees
Jul 27 - Jul 28
STUDIO: Kalama Beach Park, South Maui Gardens, Food Trucks, Hula Shows, Luaus
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
Deluxe 4-bedroom home across from Kalepolepo Beach! Steps to the Pool & full AC!
Surrounded by lush tropical vegetation, this serene pool area features a bridge connecting its sections.

Deluxe 4-bedroom home across from Kalepolepo Beach! Steps to the Pool & full AC!

10.0 out of 10, Exceptional, (2)
"This location was perfect for our group of two families. The pool area was lovely and located close to lots of beaches. The amenities of the condo were updated and fantastic. We enjoyed our time in Maui in this location immensely. "
Deluxe 4-bedroom home across from Kalepolepo Beach! Steps to the Pool & full AC!
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 Seaside Hotel

Maui Seaside Hotel

10/10 Excellent
"Went there for work . I really enjoyed the hotel. "
Craig 2-night trip
Posted 3 days ago
Maui Seaside Hotel

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 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.