An aerial view of a coastal town with clear turquoise waters, two prominent islands, and lush green hills.

Kailua Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Kailua vacation rentals

Studio, Garden View (Haiku #6) | Terrace/patio

1. Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (36 reviews)
"Large room and bathroom. Nice little kitchen area. We had a room with two balconies so great air flow through to cool the room. Beautiful area of Hawaii to explore"
Canada
Amanda
$283 nightly
The price is $308
Aug 23 - Aug 24
Total with taxes and fees
Yonegan Maui Getaways - Haiku
House (3 Bedrooms) | Interior

2. 2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
3.0 star property
Haiku
$926 nightly
The price is $1,099
Aug 31 - Sep 1
Total with taxes and fees
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
1 bedroom, iron/ironing board, internet, bed sheets

3. Yonegan Maui Getaways - Haiku - Unit 2

Yonegan Maui Getaways - Haiku - Unit 2
Haiku-Pauwela
9.0 out of 10, Wonderful, (15 reviews)
"This place is in a great location, less than 10 minutes from downtown Paia, with nice beaches nearby as well.We didn’t end up using the kitchen, but having a refrigerator and freezer was very convenient.The bed was soft and comfortable, and the pillows were great too.For this specific unit, the toilet does work properly you just need to make sure the handle is positioned correctly so the tank refills.Overall, this was a great rental and we enjoyed our stay."
United States
Raechell F.
$335 nightly
The price is $337
Aug 18 - Aug 19
Total with taxes and fees
Yonegan Maui Getaways - Haiku - Unit 2
Property grounds

4. Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
Hana
10.0 out of 10, Exceptional, (524 reviews)
"Absolutely wonderful place in paradise. Hosts were amazing. Brough us fresh eggs and fruit. Amazing view and love the kitty too!"
United States
Diann
$337 nightly
The price is $394
Aug 16 - Aug 17
Total with taxes and fees
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
Exterior

5. Yonegan Maui Getaways - Haiku - Unit 4

Yonegan Maui Getaways - Haiku - Unit 4
Haiku
9.0 out of 10, Wonderful, (21 reviews)
"Great location for driving the Road to Hana."
United States
Lisa
$347 nightly
The price is $349
Aug 19 - Aug 20
Total with taxes and fees
Yonegan Maui Getaways - Haiku - Unit 4
Beach towels

6. A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Kuau
9.4 out of 10, Exceptional, (215 reviews)
"We had a great time! Everything was perfect. "
United States
Samantha S.
$383 nightly
The price is $448
Aug 17 - Aug 18
Total with taxes and fees
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Property grounds

7. Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Makawao
10.0 out of 10, Exceptional, (82 reviews)
"Great stay with Heleina and John! The property was spacious, very clean, and comfortable. Despite the terrible weather in Hawaii, they went above and beyond to accommodate us, even offering a complimentary extra night in case we got stuck. Truly thoughtful hosts. Would definitely stay again and I highly recommend! "
United States
Anna H.
$2,548 nightly
The price is $2,980
Aug 21 - Aug 22
Total with taxes and fees
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Beach nearby

8. North Shore retreat w/ lanai & beach access

North Shore retreat w/ lanai & beach access
Paia
9.8 out of 10, Exceptional, (44 reviews)
"Absolutely perfect accommodations! It was very well equipped, perfectly clean & a fantastic location. One thing I would note is that it is on the second floor and there isn’t an elevator so you need to be able to carry your luggage. But other than that, I would highly recommend this condo."
United States
Kristin J.
$851 nightly
The price is $996
Aug 19 - Aug 20
Total with taxes and fees
North Shore retreat w/ lanai & beach access
Coffee/tea maker, fridge, microwave, oven

9. Paia 2 Bedroom 2 Bathroom

Paia 2 Bedroom 2 Bathroom
Paia
9.2 out of 10, Wonderful, (14 reviews)
"The Condo was perfect for our stay! Two bedrooms and two bathrooms! Plenty of space and very clean and nicely furnished. The kitchen had everything we needed and more. The location was located in a great area. Our host was wonderful with tips and recommendations! We would definitely stay here again!"
United States
Sherri W.
$601 nightly
The price is $703
Aug 16 - Aug 17
Total with taxes and fees
Paia 2 Bedroom 2 Bathroom
Smart TV, books

10. Eco-Friendly Condo on Road to Hāna - Walk to Beach

Eco-Friendly Condo on Road to Hāna - Walk to Beach
Paia
10.0 out of 10, Exceptional, (18 reviews)
"We had a wonderful stay, our host was sweet"
United States
Nancy k.
$328 nightly
The price is $384
Aug 18 - Aug 19
Total with taxes and fees
Eco-Friendly Condo on Road to Hāna - Walk to Beach
Beach nearby, sun loungers, beach towels

11. Hale Nihi - Paia, Maui

Hale Nihi - Paia, Maui
Paia
9.6 out of 10, Exceptional, (64 reviews)
"Very convenient place to stay within walking distance to activities and beach. "
United States
Chameil H.
$491 nightly
The price is $574
Aug 21 - Aug 22
Total with taxes and fees
Hale Nihi - Paia, Maui
Exterior

12. Yonegan Maui Getaways - Haiku - Unit 6

Yonegan Maui Getaways - Haiku - Unit 6
Haiku-Pauwela
9.2 out of 10, Wonderful, (40 reviews)
"Everything was great."
United States
Bryan
$312 nightly
The price is $314
Aug 16 - Aug 17
Total with taxes and fees
Yonegan Maui Getaways - Haiku - Unit 6
Exterior detail

13. Yonegan Maui Getaways - Haiku - Unit 3

Yonegan Maui Getaways - Haiku - Unit 3
Haiku-Pauwela
9.0 out of 10, Wonderful, (22 reviews)
"Perfect getaway for an island vacation if your not planning on staying in just your room. Made breakfast every morning close to beaches, turtles and shops"
United States
Jeremiah J.
$311 nightly
The price is $313
Aug 23 - Aug 24
Total with taxes and fees
Yonegan Maui Getaways - Haiku - Unit 3
Beach towels

14. Maui's best Surf, wdsurf, snorkeling by secluded beach+ AC.

Maui's best Surf, wdsurf, snorkeling by secluded beach+ AC.
Paia
9.6 out of 10, Exceptional, (57 reviews)
"This was an amazing place to stay! So close to the beach and downtown Paia - we would totally recommend this place to any of our friends! "
United States
Lizzie B.
$357 nightly
The price is $418
Aug 18 - Aug 19
Total with taxes and fees
Maui's best Surf, wdsurf, snorkeling by secluded beach+ AC.
Property grounds

15. Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Kaʻeleku
9.8 out of 10, Exceptional, (249 reviews)
"Beautiful place to stay!"
United States
Mary B.
$512 nightly
The price is $598
Aug 24 - Aug 25
Total with taxes and fees
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Beach towels

16. Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Hana Town Center
9.6 out of 10, Exceptional, (461 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
$332 nightly
The price is $388
Aug 16 - Aug 17
Total with taxes and fees
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Property grounds

17. Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!

Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!
Hana Town Center
9.6 out of 10, Exceptional, (30 reviews)
"Loved the view. Property was beautiful. Great place for a couple of quiet nights in Hana."
United States
Vera G.
$340 nightly
The price is $398
Aug 15 - Aug 16
Total with taxes and fees
Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!
Property grounds

18. Oceanview #101 at Hana Kai Maui - 1 Bedroom King/Twins , Amazing View!

Oceanview #101 at Hana Kai Maui - 1 Bedroom King/Twins , Amazing View!
Hana Town Center
9.6 out of 10, Exceptional, (82 reviews)
"Great beach view lovely gardens"
United States
Dianne
$353 nightly
The price is $413
Aug 15 - Aug 16
Total with taxes and fees
Oceanview #101 at Hana Kai Maui - 1 Bedroom King/Twins , Amazing View!
Property grounds

19. Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
Hana Town Center
9.6 out of 10, Exceptional, (119 reviews)
"Beautiful place to stay in Hana and super nice people. "
United States
Tanya L.
$344 nightly
The price is $402
Aug 16 - Aug 17
Total with taxes and fees
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
Beach

20. Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Hana Town Center
9.6 out of 10, Exceptional, (201 reviews)
"Comfortable, clean, well equipped cottage in the heart of Hana. Great place, highly recommend! "
United States
Michelle S.
$503 nightly
The price is $588
Sep 11 - Sep 12
Total with taxes and fees
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
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 Coast Hotel

Maui Coast Hotel

10/10 Excellent
"The staff are the best. I needed extra pillows and blankets and they arrived super fast. We also needed a wine bottle opener and that arrived within 10 mins. Everyone is super friendly and kind. The room I stayed in was a little rundown, but it was clean. The pools were really nice. I think overall the service at this hotel is above most. We had moved from another hotel, and the same pillow request took 90 mins. I would stay again."
Jennifer 3-night trip
Posted 12 hours ago
Maui Coast 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 $308 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, kitchenware, and a coffee maker.

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 Haleakala National Park. In the larger area, you’ll find Maui Garden Of Eden - Botanical Gardens & Arboretum and Maui Spa Retreat.

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.