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
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Kailua vacation rentals

Property grounds

Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens - 10% off JULY!

Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens - 10% off JULY!
Hana
10.0 out of 10, Exceptional, (515 reviews)
The price is AED 909
AED 1,627 total
includes taxes & fees
2 Jul - 3 Jul
Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens - 10% off JULY!
Beach towels

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, (455 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is AED 716
AED 1,418 total
includes taxes & fees
10 Jul - 11 Jul
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Beach towels

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, (212 reviews)
"Great location near Paia shops and short walk to Mama's Fish House, & beach. Enjoyed our stay at Kuau Plaza. The condo was just as described and pictured. Nicely furnished & decorated. Comfy bed, everything you could need in the kitchen, nice bathroom...all looked brand new! Although right next to the road, we barely heard the traffic. We would stay here again."
United States
Kimberly
The price is AED 680
AED 1,630 total
includes taxes & fees
16 Jul - 17 Jul
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Beach towels

Fisher's Hana Bay Hale, Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay
Hana Town Center
9.6 out of 10, Exceptional, (439 reviews)
"Great stay thanks! "
United States
Stephanie C.
The price is AED 716
AED 1,480 total
includes taxes & fees
10 Jul - 11 Jul
Fisher's Hana Bay Hale, Across from Hana Bay
Exterior

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, (146 reviews)
"Nice location, comfortable accommodations. We loved the view off the lanai. "
United States
Kelly J.
The price is AED 882
AED 1,644 total
includes taxes & fees
30 Jun - 1 Jul
Oceanview Condo in Hana-Let the ocean lull you to sleep
Sun loungers, beach towels

Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
Hana Town Center
9.4 out of 10, Exceptional, (158 reviews)
"The host communicated clearly and the accommodations were exactly what we were looking for. "
United States
Angie F.
The price is AED 843
AED 1,883 total
includes taxes & fees
30 Jun - 1 Jul
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
Exterior

Yonegan Maui Getaways - Haiku - Unit 6

Yonegan Maui Getaways - Haiku - Unit 6
Haiku-Pauwela
9.2 out of 10, Wonderful, (38 reviews)
"Everything was great."
United States
Bryan
The price is AED 453
AED 1,146 total
includes taxes & fees
25 Jun - 26 Jun
Yonegan Maui Getaways - Haiku - Unit 6
Smart TV

Sugar Beach 314 Front Row Ocean Views in Beautifully Upgraded Beachfront Condo

Sugar Beach 314 Front Row Ocean Views in Beautifully Upgraded Beachfront Condo
North Kihei
9.6 out of 10, Exceptional, (57 reviews)
"This is a great unit. Excellent location and easy access to everything on Maui. "
United States
scott s.
The price is AED 870
AED 2,203 total
includes taxes & fees
8 Jul - 9 Jul
Sugar Beach 314 Front Row Ocean Views in Beautifully Upgraded Beachfront Condo
Sun loungers, beach towels

Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
North Kihei
9.8 out of 10, Exceptional, (109 reviews)
"This place was in a good location in Kihei. You are within 5 mins of dozen of beaches. All the beach gear a person needs is provided(towels, chairs, snorkels, flippers, coolers and more)! Jon is super friendly and a great host!"
United States
Troy s.
The price is AED 356
AED 1,807 total
includes taxes & fees
6 Jul - 7 Jul
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
Travel crib, free WiFi, bed sheets

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

Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly
North Kihei
9.0 out of 10, Wonderful, (10 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 1,267 total
includes taxes & fees
6 Jul - 7 Jul
Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly
Smart TV, books

Locally-owned, eco-friendly condo on Road to Hāna. 2-min walk to beach & seafood

Locally-owned, eco-friendly condo on Road to Hāna. 2-min walk to beach & seafood
Paia
10.0 out of 10, Exceptional, (12 reviews)
"We had a wonderful stay, our host was sweet"
United States
Nancy k.
The price is AED 714
AED 1,438 total
includes taxes & fees
4 Jul - 5 Jul
Locally-owned, eco-friendly condo on Road to Hāna. 2-min walk to beach & seafood
Sun loungers

Ocean View 2-bedroom condo with pool and AC in wonderful Kihei

Ocean View 2-bedroom condo with pool and AC in wonderful Kihei
North Kihei
9.8 out of 10, Exceptional, (29 reviews)
"Nice place"
Canada
PC SHOP
The price is AED 559
AED 1,728 total
includes taxes & fees
24 Jun - 25 Jun
Ocean View 2-bedroom condo with pool and AC in wonderful Kihei
Elite Apartment, Balcony, Ocean View | Dining room

The Ocean View Residence

The Ocean View Residence
3.0 star property
South Kihei
10.0 out of 10, Exceptional, (1 review)
"Very nice condo for a longer-term stay. We loved being able to cook. "
United States
John
The price is AED 242
AED 2,043 total
includes taxes & fees
25 Jun - 26 Jun
The Ocean View Residence
Property grounds

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (101 reviews)
"Beautiful grounds, great location close to secluded beach."
United States
Mark S.
The price is AED 1,139
AED 2,003 total
includes taxes & fees
2 Jul - 3 Jul
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Interior

Unit 25 Waena Inn - Maui Private Suite

Unit 25 Waena Inn - Maui Private Suite
Wailuku
9.8 out of 10, Exceptional, (16 reviews)
"Had a great time, even with the rain ."
United States
Kevin M.
The price is AED 720
AED 1,056 total
includes taxes & fees
24 Jun - 25 Jun
Unit 25 Waena Inn - Maui Private Suite
Exterior

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 1,274 total
includes taxes & fees
24 Jun - 25 Jun
Yonegan Maui Getaways - Haiku - Unit 4
Property grounds

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, (247 reviews)
"I appreciated everything as advertised. Would have preferred mini splits or AC in the bedrooms, but still a nice peaceful spot."
United States
Robert
The price is AED 1,093
AED 2,186 total
includes taxes & fees
1 Jul - 2 Jul
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
On the beach, sun loungers, beach towels

Steps to the Beach, Affordable w/Free Parking

Steps to the Beach, Affordable w/Free Parking
North Kihei
9.6 out of 10, Exceptional, (171 reviews)
"Clean, across the street from beach and whale center. Great location to get to other places on the island. "
Canada
wayneiversonphotosk
The price is AED 430
AED 1,599 total
includes taxes & fees
28 Jun - 29 Jun
Steps to the Beach, Affordable w/Free Parking
Beach nearby, sun loungers, beach towels

Hale Nihi - Paia, Maui

Hale Nihi - Paia, Maui
Paia
9.6 out of 10, Exceptional, (63 reviews)
"Very convenient place to stay within walking distance to activities and beach. "
United States
Chameil H.
The price is AED 658
AED 1,634 total
includes taxes & fees
25 Jun - 26 Jun
Hale Nihi - Paia, Maui
On the beach, sun loungers, beach towels

Oceanfront, Hale Kai O Kihei, incredible sunsets, King bed, AC, remodeled 2023

Oceanfront, Hale Kai O Kihei, incredible sunsets, King bed, AC, remodeled 2023
Central Kihei
10.0 out of 10, Exceptional, (114 reviews)
"Beautiful views, lovely beach, convenient parking and good amenities nearby. "
United States
Tesha T.
The price is AED 592
AED 1,723 total
includes taxes & fees
24 Jun - 25 Jun
Oceanfront, Hale Kai O Kihei, incredible sunsets, King bed, AC, remodeled 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

Hilton Grand Vacations Club Maui Bay Villas

Hilton Grand Vacations Club Maui Bay Villas

10/10 Excellent
"I definitely will go back"
Carlos 3-night trip
Posted 2 hours ago
Hilton Grand Vacations Club Maui Bay Villas

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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 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.