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

Holiday Homes in Kailua

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Check prices for these dates

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

Our top choices for Kailua holiday homes

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
The price is AU$430
includes taxes & fees
4 Oct - 5 Oct
Yonegan Maui Getaways - Haiku
A hot tub on a deck with a view of palm trees and a sunset.

2. Private Hot Tub + Pool Access + AC - Star Lookout

Private Hot Tub + Pool Access + AC - Star Lookout
Haiku
9.8 out of 10, Exceptional, (18 reviews)
"This is an incredible home base for everything special Maui has to offer. On site laundry makes it homey and comfortable leg of any long vacation. Some great local food within a quick 5-15 minute drive and major cities/towns within 20-30 minutes. "
United States
Michael V.
The price is AU$1,245
includes taxes & fees
7 Oct - 8 Oct
Private Hot Tub + Pool Access + AC - Star Lookout
A beach with clear turquoise waters, rocky shoreline, and distant mountains under a clear sky.

3. 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.
The price is AU$661
includes taxes & fees
2 Oct - 3 Oct
Hale Nihi - Paia, Maui
A beach with clear turquoise waters, rocky shoreline, and distant mountains under a clear sky.

4. HALE NIHI, Paia, Maui

HALE NIHI, Paia, Maui
Paia
9.6 out of 10, Exceptional, (107 reviews)
"great location, great host"
United States
Peter M.
The price is AU$708
includes taxes & fees
2 Oct - 3 Oct
HALE NIHI, Paia, Maui
A wooden deck with outdoor furniture, a hanging lantern, and a stone fireplace.

5. Featured on Staycation TV Stunning Modern Home Surrounded by Nature

Featured on Staycation TV Stunning Modern Home Surrounded by Nature
Haiku-Pauwela
10.0 out of 10, Exceptional, (13 reviews)
"Great location and nice clean and quiet"
Canada
Greg B.
The price is AU$2,104
includes taxes & fees
8 Oct - 9 Oct
Featured on Staycation TV Stunning Modern Home Surrounded by Nature
A residential street lined with palm trees and houses.

6. Haiku Hale - 3 Bedroom Maui Getaway!

Haiku Hale - 3 Bedroom Maui Getaway!
Haiku
10.0 out of 10, Exceptional, (8 reviews)
"Clean, well lit, private, Haiku is a sweet town. Note that there are a few steep steps to master bedroom."
United States
Linda S.
The price is AU$1,176
includes taxes & fees
13 Oct - 14 Oct
Haiku Hale - 3 Bedroom Maui Getaway!
A house with a lawn and tropical plants.

7. 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.
The price is AU$851
includes taxes & fees
3 Oct - 4 Oct
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
A beach with red sand, scattered rocks, and a distant rocky island.

8. 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, (469 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is AU$608
includes taxes & fees
19 Oct - 20 Oct
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
An aerial view of a coastal area with a clear pathway leading to a beach, surrounded by lush greenery and rocky coastline.

9. 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, (110 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 AU$707
includes taxes & fees
10 Oct - 11 Oct
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
A beach with red sand, waves, and a rocky outcrop in the distance.

10. 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
The price is AU$608
includes taxes & fees
14 Oct - 15 Oct
Fisher's Hana Bay Hale, Across from Hana Bay
A coastal landscape with clear turquoise waters, a sandy beach, and lush greenery.

11. 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.
The price is AU$955
includes taxes & fees
4 Oct - 5 Oct
Beautiful Home in paradise!
A lush green lawn with a gazebo, a large rock, and a view of a forested hill under a partly cloudy sky.

12. 3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
Kaʻeleku
9.8 out of 10, Exceptional, (101 reviews)
"Beautiful property. Our second time here, it is one of our favorite places to stay. "
United States
Myra P.
The price is AU$1,215
includes taxes & fees
2 Oct - 3 Oct
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
A spacious living room with a piano, wicker furniture, and a large mirror.

13. Pikake Suite - Historic Elegance, Wailuku

Pikake Suite - Historic Elegance, Wailuku
Wailuku
10.0 out of 10, Exceptional, (9 reviews)
"Easy parking"
United States
Quinten M.
The price is AU$473
includes taxes & fees
5 Oct - 6 Oct
Pikake Suite - Historic Elegance, Wailuku
A kitchen with a large island, wooden chairs, and a view of the ocean.

14. Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!

Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!
Hana Town Center
9.6 out of 10, Exceptional, (39 reviews)
"Beautiful location!"
United States
Caroline D.
The price is AU$1,471
includes taxes & fees
3 Oct - 4 Oct
Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!
An outdoor lounge area with wooden furniture and green cushions, a pool, and a view of the surrounding greenery.

15. Villa 8

Villa 8
South Kihei
9.8 out of 10, Exceptional, (74 reviews)
"staying here was the best! perfect for our anniversary get away!"
United States
Taylor M.
The price is AU$996
includes taxes & fees
7 Oct - 8 Oct
Villa 8
A wooden fence with a sign reading "WOODSTOCK" and a peace sign.

16. Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub
North Kihei
9.6 out of 10, Exceptional, (110 reviews)
"We had a great stay! Everything was as described and perfect for our family vacation. "
United States
Kristin P.
The price is AU$1,566
includes taxes & fees
2 Oct - 3 Oct
Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub
A spacious living room with a piano, a dining area with wicker chairs, and a large window.

17. Elegant Puakenikeni Suite- Historic & Ground Floor

Elegant Puakenikeni Suite- Historic & Ground Floor
Wailuku
10.0 out of 10, Exceptional, (7 reviews)
"I liked the quaint ambiance of the property, beautiful landscape and the room was great."
United States
Wayne
The price is AU$542
includes taxes & fees
26 Oct - 27 Oct
Elegant Puakenikeni Suite- Historic & Ground Floor
An aerial view of a beachfront property with a sandy beach, a few palm trees, and a few houses.

18. Beach front Honu Cottage

Beach front Honu Cottage
South Kihei
9.4 out of 10, Exceptional, (10 reviews)
"Perfect location with a private beach a few steps outside the back door. All kitchen essentials available and a bbq included. Perfect place to relax and beautiful scenery. "
United States
JESSICA S.
Beach front Honu Cottage
A modern bedroom with a large bed, a wooden bench, and a tray with breakfast items.

19. Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub

Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub
North Kihei
9.6 out of 10, Exceptional, (7 reviews)
"Great place to stay!"
United States
Lori R.
The price is AU$2,132
includes taxes & fees
15 Oct - 16 Oct
Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub
A spacious living room with a piano, a dining area with wicker chairs, and a large window.

20. Mamane Suite - Historic charm and views

Mamane Suite - Historic charm and views
Wailuku
10.0 out of 10, Exceptional, (5 reviews)
"This was my 2nd time staying here and I love it. Super nice rooms, yummy breakfast."
United States
Jane D.
The price is AU$506
includes taxes & fees
3 Oct - 4 Oct
Mamane Suite - Historic charm and views
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 Sunset

Maui Sunset

10/10 Excellent
"I liked everything about our stay. Everything that we needed was close by. Grocery store , restaurants, and shopping. The beach, the sunset and the pool were all amazing. The property was well maintained & very clean. Will definitely come back. Even before leaving we were already discussing when we will come back."
Marius 7-night trip
Posted 1 hour ago
Maui Sunset

Find out more about Kailua

Kailua Holiday Homes information

Number of reviews
1,960
Accommodation
157 Holiday Homes
Lowest Price
AU$430
Highest Price
AU$2,132

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