Kailua Vacation Rentals

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Check prices for these dates

In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Vacation Rentals in Kailua

Suite, 2 Bedrooms | Living area | TV
Maui Beach Vacation Club

Aparthotel in North Kihei

2.5 star property
8.2 out of 10, Very Good, (816)
"A excelent service in the office. Nice and clean room y all the hotel. I recommend this hotel."
United States
Blanca I
Maui Beach Vacation Club
Garden
Yonegan Maui Getaways - Haiku

Vacation Home in Haiku

3.0 star property
9.2 out of 10, Wonderful, (9)
"Loved having the hot tub to come home to!!"
United States
Pedro
$222 nightly
The price is $244
Nov 27 - Nov 28
Total with taxes and fees
Yonegan Maui Getaways - Haiku
Premium Condo, 2 Bedrooms, Kitchen, Ocean View | Terrace/patio
Maui Sunset

Aparthotel in Central Kihei

3.5 star property
8.8 out of 10, Excellent, (477)
"Good place to spend your vacation "
United States
Tomasz
Maui Sunset
BBQ/picnic area
Maui Schooner Resort

Aparthotel in Central Kihei

3.5 star property
9.2 out of 10, Wonderful, (496)
"Nice amenities and huge space. Nice pool and spa."
United States
Danyang
Maui Schooner Resort
Outdoor pool
Sugar Beach Resort

Aparthotel in North Kihei

3.0 star property
8.6 out of 10, Excellent, (1099)
"We loved it there! "
United States
Babatunde
Sugar Beach Resort
Exterior
Wonderful South Maui Beach Condos

Condo in South Kihei

3.5 star property
9.4 out of 10, Exceptional, (28)
"Direct beach access walkable access to everything you could need "
United States
Scott
Wonderful South Maui Beach Condos
On the beach, sun loungers, beach towels
Time Beach @ Grand Van Kleef

Condo in South Kihei

9.4 out of 10, Exceptional, (89)
"AC could have been more effective but worked OK when we ran the fans. Good view of the mountains from the balcony..."
United States
Jeffrey
Time Beach @ Grand Van Kleef
Beach nearby, white sand, beach towels
Kihei Ali'i Kai Condos with Free Parking

Apartment in South Kihei

4.0 star property
9.0 out of 10, Wonderful, (20)
"I loved that it was a short walk to the beach and there were grocery stores nearby. Lots of options of places to eat and shop and explore the island!"
United States
Emma
$366 nightly
The price is $388
Nov 29 - Nov 30
Total with taxes and fees
Kihei Ali'i Kai Condos with Free Parking
Exterior detail
Gated 2-story beach house with big yard

Villa in South Kihei

10.0 out of 10, Exceptional, (67)
"This was an amazing place in a great location. Slept 6 adults very comfortably. Would definitely recommend this place to others. "
United States
Denis B.
Gated 2-story beach house with big yard
On the beach, sun loungers, beach towels
Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view

Vacation Home in North Kihei

9.8 out of 10, Exceptional, (207)
"Perfect home for a large group. Beach is across the street the back to the pool when the waves got to be to much for our little ones. Great property manager! Great location! "
United States
sandy C.
Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view
Outdoor dining
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores

Condo in South Kihei

9.8 out of 10, Exceptional, (192)
"Had a wonderful experience staying here! A sweet, cozy and comfortable little getaway for our family and little one!"
United States
Misty
$390 nightly
The price is $454
Nov 29 - Nov 30
Total with taxes and fees
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores
On the beach, white sand, beach towels
Waiohuli Beach Hale Ocean View Condos with Parking

Apartment in Central Kihei

3.0 star property
10.0 out of 10, Exceptional, (3)
"We had a wonderful stay in this condo. It had everything we needed for a fun Hawaiian beach vacation. They stocked it with beach chairs, a cooler, and even a boogie board. The kitchen had everything we needed, although we didn't cook that much. Management was super responsive whenever we had any issues. It was just enough space for our family of four. The beach was just steps away and the pool was also very nice. "
United States
Anthony
$414 nightly
The price is $444
Dec 4 - Dec 5
Total with taxes and fees
Waiohuli Beach Hale Ocean View Condos with Parking
Exterior
Private lush 2 Acre Mountain Home Maui w/ many amenities

Vacation Home in Makawao

10.0 out of 10, Exceptional, (231)
"I absolutely love staying here! It’s a new yearly tradition and great location! "
United States
Courtney P.
Private lush 2 Acre Mountain Home Maui w/ many amenities
Beach nearby
Kaiholo Hale

Vacation Home in Paia

3.0 star property
9.4 out of 10, Exceptional, (201)
"Area was quiet but close to amenities. We could drive anywhere on Maui easily. There was a lovely beach less than a block from the suite with good snorkeling and friendly locals. Bed in the suite was very comfortable, and it had everything we needed for a relaxing vacation."
United States
Carley
Kaiholo Hale
Property grounds
Kihei Maui Beach house - On the water

Vacation Home in Central Kihei

9.8 out of 10, Exceptional, (58)
"Mark was wonderful to work with. Some things could use some updates but overall it was a great location and we had a great stay."
United States
Tiffany S.
Kihei Maui Beach house - On the water
Outdoor pool
Sugar Beach Resort - Maui Condo & Home

Aparthotel in North Kihei

3.0 star property
8.4 out of 10, Very Good, (516)
"Love this location, great beach, quiet."
United States
Nataliya
Sugar Beach Resort - Maui Condo & Home
Beach
Tropical Oasis! Beaches, Shopping and Comfort Pacific Shores A212

Condo in South Kihei

2.5 star property
10.0 out of 10, Exceptional, (6)
"Such a great location. Close to several walkable restaurants, shops and beautiful beaches! We felt at home!"
United States
Lorna R.
Tropical Oasis! Beaches, Shopping and Comfort Pacific Shores A212
On the beach, sun loungers, beach towels
BEACHFRONT FAMILY ESTATE: Sleeps 15 - 4 separate Units with optional cottage.

Vacation Home in Central Kihei

10.0 out of 10, Exceptional, (152)
"Could not have been better!! This was our third time renting this house, and Michael has always been the perfect host. We are definitely going back, God willing!"
United States
John C.
BEACHFRONT FAMILY ESTATE: Sleeps 15 - 4 separate Units with optional cottage.
3 outdoor pools
Maui Vista – Maui Condo & Home

Condo in South Kihei

4.0 star property
8.4 out of 10, Very Good, (53)
"Great for working trip. "
United States
Andrew
Maui Vista – Maui Condo & Home
On the beach
2B2B Oceanfront Condo, Oceanview in masterbed and living RM ^summer 2025 on sale

Condo in South Kihei

9.4 out of 10, Exceptional, (163)
"Terrific location in a spotlessly clean condo with everything you could ask for. Right next to the amazing Food Park Oasis. Would happily stay here again. "
United States
John W.
2B2B Oceanfront Condo, Oceanview in masterbed and living RM ^summer 2025 on sale
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 Beach Hotel

Maui Beach Hotel

10/10 Excellent
"The staff was very kind and helpful. During check in the staff was very informative of where things were. "
Gabryella 1-night trip
Posted 4 days ago
Maui Beach Hotel

Find out more about Kailua

Everything you need to know about Kailua vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kailua vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kailua vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kailua vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kailua. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Kailua in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $244 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Kailua rentals

At Expedia, we put the best Kailua vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Kailua rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kailua vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kailua. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.