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

Kailua Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Kailua vacation rentals

A wooden deck with a chair, surrounded by lush tropical vegetation and a clear blue sky.

1. Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (39 reviews)
"Good location for the Road to Hana and exploring Paia, hot tub was enjoyable."
United States
Matt
$305 nightly
The price is $334
Oct 18 - Oct 19
Total with taxes and fees
Yonegan Maui Getaways - Haiku
A wooden staircase leading to a balcony of a blue building surrounded by lush greenery and flowering plants.

2. Yonegan Maui Getaways - Haiku - Unit 3

Yonegan Maui Getaways - Haiku - Unit 3
Haiku-Pauwela
9.2 out of 10, Wonderful, (24 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
Oct 29 - Oct 30
Total with taxes and fees
Yonegan Maui Getaways - Haiku - Unit 3
Room

3. Yonegan Maui Getaways - Haiku - Unit 4

Yonegan Maui Getaways - Haiku - Unit 4
Haiku
9.0 out of 10, Wonderful, (23 reviews)
"Check in instructions was bit complicated property but we were able to figure out in sometime was clean and nice AC was working fine keep house cool, Hot tub was the MVP of the stay loved and enjoyed overall stay highly recommend for future potential travelers place was quite and very close to nature perfect spot to start road to hana adventure!"
United States
NIDHI
$345 nightly
The price is $347
Oct 18 - Oct 19
Total with taxes and fees
Yonegan Maui Getaways - Haiku - Unit 4
A two-story house with a balcony, surrounded by well-maintained lawns and tropical vegetation.

4. Yonegan Maui Getaways - Haiku - Unit 6

Yonegan Maui Getaways - Haiku - Unit 6
Haiku-Pauwela
9.2 out of 10, Wonderful, (42 reviews)
"Everything was great."
United States
Bryan
$310 nightly
The price is $312
Oct 20 - Oct 21
Total with taxes and fees
Yonegan Maui Getaways - Haiku - Unit 6
A bedroom with a bed, a nightstand, a lamp, a painting, and a balcony with a view of greenery.

5. 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.
$333 nightly
The price is $335
Oct 21 - Oct 22
Total with taxes and fees
Yonegan Maui Getaways - Haiku - Unit 2
A beach with palm trees, clear blue water, and rocky shoreline.

6. Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi

Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi
Paia
9.8 out of 10, Exceptional, (99 reviews)
"Close walk to a beach. Owner took care of maintenance problem quickly."
United States
David
$364 nightly
The price is $426
Oct 18 - Oct 19
Total with taxes and fees
Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi
Beach

7. 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, (224 reviews)
"Great location for our last night. Walk to the beach and close enough to the airport for an early flight."
United States
jeff s.
$381 nightly
The price is $446
Oct 16 - Oct 17
Total with taxes and fees
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
A beach with clear blue water, rocky shore, and palm trees.

8. Condo w/ Lanai at Beginning of Road to Hana!

Condo w/ Lanai at Beginning of Road to Hana!
Paia
9.2 out of 10, Wonderful, (45 reviews)
"The property was very clean and well-appointed. It was a great location that allowed us to walk in to Mama's Fish House. The host was extremely helpful and proactive and checked to make sure we had everything we needed. If you are looking for a place to stay in Paia, this is it."
United States
Martin S.
$360 nightly
The price is $421
Oct 18 - Oct 19
Total with taxes and fees
Condo w/ Lanai at Beginning of Road to Hana!
A paved pathway leading to a gate with red pillars, surrounded by lush greenery and palm trees, with a view of the ocean in the background.

9. 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, (535 reviews)
"Beautiful scenery and hostess!"
United States
Sonja W.
$327 nightly
The price is $384
Oct 18 - Oct 19
Total with taxes and fees
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
A living room with a sofa, a coffee table, a TV, and a sliding glass door leading to a patio with a view of palm trees and a lawn.

10. Locally-Owned Eco-Friendly Condo on Road to Hana - Walk to Beach

Locally-Owned Eco-Friendly Condo on Road to Hana - Walk to Beach
Paia
10.0 out of 10, Exceptional, (21 reviews)
"Chloe was very helpful! Her place was very convenient for an early trip to go to Hana. The place was clean and furnished and had everything we needed. Clear instructions smooth check in&out. Chloe was also fast with responses when I had questions. Would recommend to stay here!"
United States
Janette
$393 nightly
The price is $460
Oct 29 - Oct 30
Total with taxes and fees
Locally-Owned Eco-Friendly Condo on Road to Hana - Walk to Beach
A beach with clear water, rocky shore, and palm trees.

11. Maui's best Surf, wdsurf, snorkeling by secluded beach+ bdAC.

Maui's best Surf, wdsurf, snorkeling by secluded beach+ bdAC.
Paia
9.6 out of 10, Exceptional, (61 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.
$436 nightly
The price is $511
Oct 19 - Oct 20
Total with taxes and fees
Maui's best Surf, wdsurf, snorkeling by secluded beach+ bdAC.
A beach with clear turquoise waters, rocky shoreline, and distant mountains under a clear sky.

12. Hale Nihi - Paia, Maui

Hale Nihi - Paia, Maui
Paia
9.6 out of 10, Exceptional, (65 reviews)
"Very convenient place to stay within walking distance to activities and beach. "
United States
Chameil H.
$402 nightly
The price is $471
Oct 16 - Oct 17
Total with taxes and fees
Hale Nihi - Paia, Maui
A tropical beach with clear water, palm trees, and rocky terrain.

13. North Shore retreat w/ lanai & beach access

North Shore retreat w/ lanai & beach access
Paia
9.8 out of 10, Exceptional, (44 reviews)
"Wonderful property."
United States
Samantha A.
$807 nightly
The price is $945
Oct 25 - Oct 26
Total with taxes and fees
North Shore retreat w/ lanai & beach access
A bamboo structure with a sloped roof, surrounded by rocks and plants.

14. 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)
"This place was perfect for our big group!"
United States
Lisa B.
$2,548 nightly
The price is $2,980
Oct 30 - Oct 31
Total with taxes and fees
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
A wooden deck with a staircase leading to a covered area, surrounded by lush greenery.

15. Stay in Hana #2

Stay in Hana #2
Hana Town Center
9.6 out of 10, Exceptional, (68 reviews)
"Everything was as described and very clean"
United States
Kathy
$318 nightly
The price is $372
Oct 18 - Oct 19
Total with taxes and fees
Stay in Hana #2
A beach with red sand, waves, and a rocky outcrop in the distance.

16. Fisher's Hana Bay Hale, Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay
Hana Town Center
9.4 out of 10, Exceptional, (466 reviews)
"We had a very nice stay at this home."
United States
Jenn / Ant S.
$369 nightly
The price is $432
Oct 17 - Oct 18
Total with taxes and fees
Fisher's Hana Bay Hale, Across from Hana Bay
A beach with red sand, scattered rocks, and a distant rocky island.

17. 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, (471 reviews)
"Super nice place and so helpful to have for a night at the end of the Road to Hana!"
United States
Tyler M.
$369 nightly
The price is $432
Oct 19 - Oct 20
Total with taxes and fees
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
A balcony with a table set for two, featuring a bottle of wine and two glasses.

18. 10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
9.8 out of 10, Exceptional, (308 reviews)
"Awesome stay, all you need around there, very quiet place, good neighbors, excellent Host and amazing commons area."
United States
pablo
$347 nightly
The price is $406
Oct 28 - Oct 29
Total with taxes and fees
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
A house with a lawn and tropical plants.

19. 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, (253 reviews)
"Beautiful place to stay!"
United States
Mary B.
$509 nightly
The price is $595
Oct 18 - Oct 19
Total with taxes and fees
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
A table with a bottle and glasses on a red mat, surrounded by red chairs on a balcony with a view of palm trees and a tennis court.

20. 10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
9.8 out of 10, Exceptional, (280 reviews)
"Absolutely perfect stay! Kevin was very kind and very communicative. I highly recommend staying here when visiting Kīhei."
United States
Sylvia
$342 nightly
The price is $399
Oct 22 - Oct 23
Total with taxes and fees
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
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 Schooner Resort

Maui Schooner Resort

10/10 Excellent
"Great everything"
Yazmin 4-night trip
Posted 1 hour ago
Maui Schooner Resort

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 $334 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.

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

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.