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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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, (37 reviews)
"Good location for the Road to Hana and exploring Paia, hot tub was enjoyable."
United States
Matt
$283 nightly
The price is $308
Oct 4 - Oct 5
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, (23 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.
$310 nightly
The price is $312
Oct 4 - Oct 5
Total with taxes and fees
Yonegan Maui Getaways - Haiku - Unit 3
A two-story house with a balcony, surrounded by well-maintained lawns and tropical vegetation.

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
$344 nightly
The price is $346
Oct 4 - Oct 5
Total with taxes and fees
Yonegan Maui Getaways - Haiku - Unit 4
Beach

4. 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, (222 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.
$380 nightly
The price is $445
Oct 24 - Oct 25
Total with taxes and fees
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
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.

5. 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, (534 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
$335 nightly
The price is $392
Oct 18 - Oct 19
Total with taxes and fees
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
A beach with clear water, rocky shore, and palm trees.

6. 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.
$466 nightly
The price is $545
Oct 19 - Oct 20
Total with taxes and fees
Maui's best Surf, wdsurf, snorkeling by secluded beach+ bdAC.
A two-story house with a balcony, surrounded by well-maintained lawns and tropical vegetation.

7. 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 5 - Oct 6
Total with taxes and fees
Yonegan Maui Getaways - Haiku - Unit 6
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)
"This was the perfect stay to start the Road to Hana and the town of Paia is so lovely and had a lot of food options. The beaches around this area were some of our favorite. If you can, make a reservation at Mamas Fishhouse or try and walk in around lunch time-it’s worth every penny! "
United States
Kiana C.
$359 nightly
The price is $420
Oct 5 - Oct 6
Total with taxes and fees
Condo w/ Lanai at Beginning of Road to Hana!
A bedroom with a bed, a nightstand, a lamp, a painting, and a balcony with a view of greenery.

9. 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 4 - Oct 5
Total with taxes and fees
Yonegan Maui Getaways - Haiku - Unit 2
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. Eco-Friendly Condo on Road to Hāna - Walk to Beach

Eco-Friendly Condo on Road to Hāna - Walk to Beach
Paia
9.8 out of 10, Exceptional, (19 reviews)
"We had a wonderful stay, our host was sweet"
United States
Nancy k.
$364 nightly
The price is $426
Oct 5 - Oct 6
Total with taxes and fees
Eco-Friendly Condo on Road to Hāna - Walk to Beach
A beach with clear turquoise waters, rocky shoreline, and distant mountains under a clear sky.

11. 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 4 - Oct 5
Total with taxes and fees
Hale Nihi - Paia, Maui
A beach with red sand, scattered rocks, and a distant rocky island.

12. 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, (470 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
$369 nightly
The price is $432
Oct 16 - Oct 17
Total with taxes and fees
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
A beach with red sand, waves, and a rocky outcrop in the distance.

13. 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, (465 reviews)
"This property was as advertised. Not having air conditioning was uncomfortable especially in an upper apartment. Some window units would help."
United States
Jane
$369 nightly
The price is $432
Oct 5 - Oct 6
Total with taxes and fees
Fisher's Hana Bay Hale, Across from Hana Bay
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.

14. 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 4 - Oct 5
Total with taxes and fees
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
A coastal landscape with clear turquoise waters, a sandy beach, and lush greenery.

15. Beautiful Home in paradise!

Beautiful Home in paradise!
Kaʻeleku
9.6 out of 10, Exceptional, (179 reviews)
"Loved everything about it. As advertised. Will do it again."
United States
Monafou M.
$568 nightly
The price is $665
Oct 4 - Oct 5
Total with taxes and fees
Beautiful Home in paradise!
A house with a lawn and tropical plants.

16. 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 6 - Oct 7
Total with taxes and fees
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
A multi-story building with balconies, surrounded by lush greenery and a beach.

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

Oceanview Condo in Hana-Let the ocean lull you to sleep
Hana Town Center
9.2 out of 10, Wonderful, (152 reviews)
"Our stay was for one night and the condo was clean, well equipped, and the ocean waves lulled us to sleep. If doing the road to Hana an overnight stay here is recommended "
United States
Jaime C.
$384 nightly
The price is $449
Oct 4 - Oct 5
Total with taxes and fees
Oceanview Condo in Hana-Let the ocean lull you to sleep
A hotel with a pool, a lawn, and a view of the ocean.

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, (84 reviews)
"Great beach view lovely gardens"
United States
Dianne
$447 nightly
The price is $523
Oct 4 - Oct 5
Total with taxes and fees
Oceanview #101 at Hana Kai Maui - 1 Bedroom King/Twins , Amazing View!
A hotel with a pool area, beach view, and palm trees.

19. SUMMER RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.

SUMMER RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.
North Kihei
9.4 out of 10, Exceptional, (78 reviews)
"Excellent ground floor condo with easy access to the pool and beach. Clean, cozy, and comfortable with everything we needed including a washer and dryer, lots of beach chairs and beach towels and really nice staff. The grounds at the resort are beautiful and we loved the hot dry sauna and the jacuzzi! We will definitely stay here again!"
United States
Jodelle F.
$393 nightly
The price is $460
Oct 5 - Oct 6
Total with taxes and fees
SUMMER RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.
A beach with clear blue water, a sandy shore, and a distant mountain.

20. Oceanside condo, full kitchen, ocean view. Fully renovated 2023

Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Central Kihei
9.6 out of 10, Exceptional, (88 reviews)
"We loved our stay! Great location"
United States
Madison
$295 nightly
The price is $345
Oct 4 - Oct 5
Total with taxes and fees
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
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

8/10 Good
"Room was outdated but the amenities are great."
Jenna 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, 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.