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

Kailua Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Kailua vacation rentals

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
The price is AED 518
AED 1,166 total
includes taxes & fees
13 Aug - 14 Aug
Yonegan Maui Getaways - Haiku

2. 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
The price is AED 453
AED 1,138 total
includes taxes & fees
13 Aug - 14 Aug
Yonegan Maui Getaways - Haiku - Unit 6

3. 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
The price is AED 562
AED 1,263 total
includes taxes & fees
19 Aug - 20 Aug
Yonegan Maui Getaways - Haiku - Unit 4

4. 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.
The price is AED 496
AED 1,527 total
includes taxes & fees
10 Aug - 11 Aug
Maui's best Surf, wdsurf, snorkeling by secluded beach+ AC

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, (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
The price is AED 771
AED 1,440 total
includes taxes & fees
16 Aug - 17 Aug
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

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.
The price is AED 680
AED 1,626 total
includes taxes & fees
11 Aug - 12 Aug
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

7. 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.
The price is AED 701
AED 1,410 total
includes taxes & fees
18 Aug - 19 Aug
Eco-Friendly Condo on Road to Hāna - Walk to Beach

8. Yonegan Maui Getaways - Haiku - Unit 2

Yonegan Maui Getaways - Haiku - Unit 2
Haiku-Pauwela
9.0 out of 10, Wonderful, (15 reviews)
"The room is clean and the check-in instructions are pretty clear. The location is right off the route to Hana. The Google map did lead us to the wrong small side street; and since we are aware that possibility, we just U-turn back out and get back to the right street. We were there a bit there early and the room is not ready so we went to a near by sushi restaurant and had lunch. Perfect timing."
United States
Jack
The price is AED 525
AED 1,222 total
includes taxes & fees
13 Aug - 14 Aug
Yonegan Maui Getaways - Haiku - Unit 2

9. 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.
The price is AED 453
AED 1,153 total
includes taxes & fees
23 Aug - 24 Aug
Yonegan Maui Getaways - Haiku - Unit 3

10. 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, (460 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is AED 716
AED 1,418 total
includes taxes & fees
14 Aug - 15 Aug
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

11. 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, (305 reviews)
"Awesome stay, all you need around there, very quiet place, good neighbors, excellent Host and amazing commons area."
United States
pablo
The price is AED 380
AED 1,467 total
includes taxes & fees
13 Aug - 14 Aug
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

12. 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.
The price is AED 1,010
AED 2,086 total
includes taxes & fees
13 Aug - 14 Aug
Hale Nihi - Paia, Maui

13. Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly

Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly
North Kihei
9.2 out of 10, Wonderful, (11 reviews)
"Great stay, clean place. Close walk to the beach. The pool and hot tub were great and well taken care of"
United States
Danniella
The price is AED 404
AED 1,463 total
includes taxes & fees
11 Aug - 12 Aug
Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly

14. 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
The price is AED 1,653
AED 4,037 total
includes taxes & fees
31 Aug - 1 Sep
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

15. 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, (150 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.
The price is AED 826
AED 1,586 total
includes taxes & fees
6 Sep - 7 Sep
Oceanview Condo in Hana-Let the ocean lull you to sleep

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, (452 reviews)
"Great stay thanks! "
United States
Stephanie C.
The price is AED 716
AED 1,491 total
includes taxes & fees
18 Aug - 19 Aug
Fisher's Hana Bay Hale, Across from Hana Bay

17. 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.
The price is AED 559
AED 1,753 total
includes taxes & fees
21 Aug - 22 Aug
SUMMER RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.

18. Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!
Hana Town Center
9.6 out of 10, Exceptional, (82 reviews)
"Great view, excellent location. 2 -3 nights is the perfect amount of time in Hana."
United States
Jim
The price is AED 1,014
AED 1,462 total
includes taxes & fees
9 Aug - 10 Aug
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

19. 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.
The price is AED 999
AED 1,441 total
includes taxes & fees
9 Aug - 10 Aug
Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!

20. 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.
The price is AED 1,914
AED 3,960 total
includes taxes & fees
4 Sep - 5 Sep
North Shore retreat w/ lanai & beach access
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Kailua Hotel Reviews

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.