Search Cottages in Kailua

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 42 Cottages in Kailua with updated reviews, rates, and availability.

Secluded cottage on Tropical flower farm
Outdoor dining

Secluded cottage on Tropical flower farm

9.6 out of 10, Exceptional, (256)
"We stayed 2 nights. Beautiful stay if you want to be off the grid. "
The price is AED 1,084
AED 2,050 total
includes taxes & fees
7 Jun - 8 Jun
Secluded cottage on Tropical flower farm
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Sun loungers, beach towels

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

10.0 out of 10, Exceptional, (72)
"Just can’t say enough good about this place. Absolutely incredible location and everything else was perfect as well!"
The price is AED 1,139
AED 2,003 total
includes taxes & fees
2 Jun - 3 Jun
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Evergreen Cottage @ Maui Adventure Villa
Property grounds

Evergreen Cottage @ Maui Adventure Villa

9.8 out of 10, Exceptional, (164)
"Beautiful property "
Evergreen Cottage @ Maui Adventure Villa
Plantation Style cottage short walk to beach and town Permit STPH2013/0004
Sun loungers, beach towels

Plantation Style cottage short walk to beach and town Permit STPH2013/0004

9.8 out of 10, Exceptional, (107)
"Short walks to the market, to a wonderful breakfast spot just up the hill, to Old Paia, to the beach. Central location made doing the Hana Road, going up Haleakala, getting to Kihei/Wailea, and 'I ao Valley, all very convenient.Quiet, set back from a semi-main road which has little traffic at night. Thanks for the high chair and port-a-crib, very helpful."
Plantation Style cottage short walk to beach and town Permit STPH2013/0004
Luxury Upcountry retreat with breathtaking views!
Outdoor pool

Luxury Upcountry retreat with breathtaking views!

10.0 out of 10, Exceptional, (84)
"We loved staying at this great home up on the mountain. David Met us when we arrived and showed us around the property. It is a gorgeous place with amazing views, a must stay. "
Luxury Upcountry retreat with breathtaking views!
Ocean View Cabin located on Organic Coffee Farm with Hiking Trails
Pool

Ocean View Cabin located on Organic Coffee Farm with Hiking Trails

10.0 out of 10, Exceptional, (85)
"Enjoyed the property. More rustic than I am used to. "
Ocean View Cabin located on Organic Coffee Farm with Hiking Trails
Bamboo Bliss: Ocean Views & Waterfalls Await!
2 bedrooms, free WiFi, bed sheets

Bamboo Bliss: Ocean Views & Waterfalls Await!

Bamboo Bliss: Ocean Views & Waterfalls Await!
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Beach

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

9.6 out of 10, Exceptional, (184)
"We loved this cottage with a great porch and lovely breezes coming off the ocean. The bed was super comfortable and the location was perfect for our visit to the National Park. "
The price is AED 973
AED 2,123 total
includes taxes & fees
16 Jun - 17 Jun
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Great location between Hana Town and Hamoa Beach, private, family-friendly
Beach nearby, sun loungers, beach towels

Great location between Hana Town and Hamoa Beach, private, family-friendly

9.8 out of 10, Exceptional, (226)
"Clean property at a convenient location and reasonable priced. There are many food options nearby and key Hana locations are easily accessible."
The price is AED 992
AED 1,905 total
includes taxes & fees
9 Jun - 10 Jun
Great location between Hana Town and Hamoa Beach, private, family-friendly
Cute Plantation Cottage; Walk into Wailuku Town; Central Location!
Fridge, microwave, oven, stovetop

Cute Plantation Cottage; Walk into Wailuku Town; Central Location!

9.6 out of 10, Exceptional, (24)
"Had a great stay visiting friends on Maui. The cottage is very clean, kitchen has all you need, and it is located within walking distance to several restaurants and cafes. Also location is great if you want to venture to both, the South of Maui, incl Hana as well as to the West/North (Napili etc)Communication with host was easy and prompt."
Cute Plantation Cottage; Walk into Wailuku Town; Central Location!
HOOKIPA BAYVIEW COTTAGE Private, Romantic Maui Cottage, in Haiku

HOOKIPA BAYVIEW COTTAGE Private, Romantic Maui Cottage, in Haiku

10.0 out of 10, Exceptional, (190)
"Enjoyed the privacy and beautiful decor. "
HOOKIPA BAYVIEW COTTAGE Private, Romantic Maui Cottage, in Haiku
Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01
Beach towels

Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01

9.8 out of 10, Exceptional, (185)
"An excellent place if you want to stay in Hana, cosy house, fully equipped, near to all sights, quiet, would have liked stay longer"
Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
Outdoor dining

Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops

10.0 out of 10, Exceptional, (71)
"We came here for a week and it was amazing. Great location and the outdoor space is perfect. Great spot for two people, highly recommend!"
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
Charming. permitted cottage, short walk to Paia town & beach. STPH 2013/0004
Beach nearby

Charming. permitted cottage, short walk to Paia town & beach. STPH 2013/0004

10.0 out of 10, Exceptional, (113)
"Quiet, comfortable, and a short walk to town. No complaints."
Charming. permitted cottage, short walk to Paia town & beach. STPH 2013/0004
Charming Country Cottage with WiFi and Smart TV in Kula!!!
Sun loungers, beach towels

Charming Country Cottage with WiFi and Smart TV in Kula!!!

Charming Country Cottage with WiFi and Smart TV in Kula!!!
Hawaiian Dream Temple
Outdoor pool

Hawaiian Dream Temple

4.0 star property
Hawaiian Dream Temple
HAWAIIAN DREAM TEMPLE - w/Private Hot Tub and Shared Pool - Permit#BBPH2012-0004
Outdoor pool

HAWAIIAN DREAM TEMPLE - w/Private Hot Tub and Shared Pool - Permit#BBPH2012-0004

10.0 out of 10, Exceptional, (83)
"The most beautiful and peaceful tropical getaway! We will be coming back for sure!"
HAWAIIAN DREAM TEMPLE - w/Private Hot Tub and Shared Pool - Permit#BBPH2012-0004
Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach
Sun loungers, beach towels

Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach

9.6 out of 10, Exceptional, (60)
"This unit is very well equipped with everything you need. The space is comfortable and spacious for two. Has a nice private patio area. It is easy to get to from the airport by car, has grocery options within a few miles, and is within walking distance of the beach and several restaurants. The owner is very responsive to needs. We'd be happy to stay her again if in Maui."
Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach
1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!
Fridge, microwave, oven, stovetop

1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!

9.2 out of 10, Wonderful, (36)
"I was traveling for work and the house was convenient for my meetings and very spacious to work in and rest in. I found my stay lovely. "
1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!
Newly Renovated Modern Cottage: Walk into Historic Wailuku Town!
Interior

Newly Renovated Modern Cottage: Walk into Historic Wailuku Town!

9.8 out of 10, Exceptional, (11)
"Beautiful place to stay. Very welcoming touch with the goodie basket. We have family on Maui and for us, the location was perfect. We will definitely stay there again."
Newly Renovated Modern Cottage: Walk into Historic Wailuku Town!
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
Sign in
Sign up, it's free

Frequently asked questions

Why book your cottage in Kailua with Expedia?
We think that a vacay should be a piece of cake, so if you’re seeking cottages in Kailua at a great price, Expedia delivers. Keep costs down and pick an economical option far from the rush of the city, or book a 5-star cottage to spoil your loved ones.
How can I find cheap cottages in Kailua?
The best way to compare cheap cottages in Kailua is with Expedia’s handy filter tool. Narrow down your search results by budget, amenities and star rating to discover awesome rates in just a few keystrokes.