Vacation Rentals in Kailua, HI
PRICE PER NIGHT
ACCOMMODATION TYPES
Calm Oasis w/ Private Yard Just Steps from Kailua Beach: Seahorse Estate
No reviews
·
Kailua
·
2 br
·
Ceiling Fan · Workspace · Balcony ·
From
$450/nightProperty
House · 2 Beds · 2 baths
Amenities
Ceiling Fan
Dishwasher
Air Conditioning
Oven
In Unit Laundry
Furnished
Residents Lounge
Other spaces
Workspace, Balcony, Kitchen
🏝NEW LISTING🌺 Lanikai, 4 bed, 3 bath, ALL NEW🏖NO CLEANING FEE!
No reviews
·
Kailua
·
4 br
·
Sleeps 8
·
Workspace · Outdoor Space · Beach ·
From
$620/nightProperty
House · 4 Beds · 3 baths
Amenities
Beach
Dishwasher
Air Conditioning
Wifi
Oven
In Unit Laundry
Furnished
Residents Lounge
Other spaces
Workspace, Kitchen
Prime Location! Sleeps 8 next to Kailua Beach Park & Lanikai Beach
9.4
Excellent
·
Kailua
·
4 br
·
Sleeps 8
·
Mountains · Ceiling Fan · Fitness Center ·
From
$459/nightProperty
House · 4 Beds · 3 baths
Amenities
Mountains
Ceiling Fan
Fitness Center
Beach
Dishwasher
Air Conditioning
Wifi
Oven
Other spaces
Workspace, Kitchen
Bright Kailua Retreat w/hot tub, Lush Pool, Walk to Beach: Hale Ohana
10
Excellent
·
Kailua
·
4 br
·
Sleeps 10
·
Hot Tub · Pool · Private Pool ·
From
$1,033/nightProperty
House · 4 Beds · 3 baths
Amenities
Hot Tub
Pool
Private Pool
Dishwasher
Air Conditioning
Wifi
Oven
In Unit Laundry
Other spaces
Balcony, Kitchen
Charming Tropical Oasis w/Private Pool & A/C, Walk to Beach - Lanikai Cottage
9.7
Excellent
·
Kailua
·
3 br
·
Sleeps 6
·
Outdoor Space · Pool · Private Pool ·
From
$761/nightProperty
House · 3 Beds · 2 baths
Amenities
Pool
Private Pool
Dishwasher
Air Conditioning
Oven
In Unit Laundry
Furnished
Onsite Management
Other spaces
Balcony, Kitchen
Steps to Kailua Beach; Newly Remodeled, Spacious home w/heated pool.
No reviews
·
Kailua
·
6 br
·
Sleeps 12
·
Walk In Closets · Hot Tub · Pool ·
From
$647/nightProperty
House · 6 Beds · 5 baths
Amenities
Walk In Closets
Hot Tub
Pool
Private Pool
Beach
Dishwasher
Air Conditioning
Wifi
Other spaces
Kitchen
Newly REMODELED AND the best access to sandy Lanikai Beach! NUC # 90/TVU-0031
9.7
Excellent
·
Kailua
·
4 br
·
Sleeps 8
·
Ceiling Fan · Fitness Center · Ocean ·
From
$2,250/nightProperty
House · 4 Beds · 4 baths
Amenities
Ceiling Fan
Fitness Center
Ocean
Waterfront
Beach
Dishwasher
Air Conditioning
Wifi
Other spaces
Kitchen
Kakela Kai, Beachfront Kailua Home, Private, A/C
10
Excellent
·
Kailua
·
4 br
·
Sleeps 10
·
Ceiling Fan · Fitness Center · Workspace ·
From
$780/nightProperty
House · 4 Beds · 3 baths
Amenities
Ceiling Fan
Fitness Center
Beach
Dishwasher
Air Conditioning
Wifi
Oven
In Unit Laundry
Other spaces
Workspace, Kitchen
The best of Zumper, delivered
Be the first to hear about new listings matching your search.
Sunny Kailua Home w/ Covered Lanai 1 Mi to Beach!
10
Excellent
·
Kailua
·
3 br
·
Sleeps 7
·
Toiletries · Tv · Microwave ·
From
$150/nightProperty
House · 3 Beds · 2 baths
Amenities
Toiletries
Tv
Microwave
Free Parking
Walk In Closets
Ceiling Fan
Fitness Center
Dishwasher
Other spaces
Kitchen
Elegant Home w/Private Beach Access, Pool & AC: Relaxing Lokomaika'i Kailua
10
Excellent
·
Kailua
·
5 br
·
Sleeps 10
·
High Ceilings · Pool · Private Pool ·
From
$785/nightProperty
House · 5 Beds · 3 baths
Amenities
High Ceilings
Pool
Private Pool
Dishwasher
Air Conditioning
Oven
In Unit Laundry
Furnished
Other spaces
Balcony, Kitchen
Luxurious Villa w/ Private Pool, Jacuzzi & Stunning Ocean Views: Lanikai Villa
No reviews
·
Kailua
·
4 br
·
High Ceilings · Hot Tub · Ceiling Fan ·
From
$1,581/nightProperty
Apartment · 4 Beds · 5 baths
Amenities
High Ceilings
Hot Tub
Ceiling Fan
Pool
Private Pool
Dishwasher
Air Conditioning
Oven
Other spaces
Balcony, Kitchen
Hawaiian Dream - Beachfront /Oceanfront paradise. by RedAwning
No reviews
·
Kailua
·
5 br
·
Sleeps 10
·
Hot Tub · Ocean · Pool ·
From
$2,163/nightProperty
Apartment · 5 Beds · 5 baths
Amenities
Hot Tub
Ocean
Pool
Private Pool
Waterfront
Beach
Dishwasher
Air Conditioning
Other spaces
Kitchen
Oceanfront Luxury Home in Lanikai- sleeps 8
No reviews
·
Kailua
·
4 br
·
Sleeps 8
·
Fitness Center · Ocean · Workspace ·
From
$2,800/nightProperty
House · 4 Beds · 3 baths
Amenities
Fitness Center
Ocean
Pool
Private Pool
Waterfront
Beach
Dishwasher
Air Conditioning
Other spaces
Workspace, Kitchen
Kailua Beachfront w/Pool - Newly Refurbished Licensed Short Term Rental
10
Excellent
·
Kailua
·
3 br
·
Sleeps 10
·
Ocean · Pool · Private Pool ·
From
$2,743/nightProperty
House · 3 Beds · 3 baths
Amenities
Ocean
Pool
Private Pool
Waterfront
Beach
Dishwasher
Air Conditioning
Wifi
Other spaces
Kitchen
Peaceful Oceanfront Home Near Downtown Kailua w/ BBQ & AC: Kai Mele
No reviews
·
Kailua
·
3 br
·
Ceiling Fan · Ocean · Outdoor Space ·
From
$600/nightProperty
House · 3 Beds · 2 baths
Amenities
Ceiling Fan
Ocean
Waterfront
Beach
Dishwasher
Air Conditioning
Wifi
Oven
Other spaces
Balcony, Kitchen
Ocean View Villa w/Beach as Backyard, Walk to Attractions: Kailua Hale Kahakai
No reviews
·
Kailua
·
6 br
·
Fireplace · Ceiling Fan · Ocean ·
From
$639/nightProperty
Apartment · 6 Beds · 5 baths
Amenities
Fireplace
Ceiling Fan
Ocean
Waterfront
Beach
Dishwasher
Air Conditioning
Oven
Other spaces
Balcony, Kitchen
Beautiful Kailua Hale Studio Unit. Walking distance to beach and town
10
Excellent
·
Kailua
·
1 br
·
Sleeps 2
·
Workspace · Beach · Air Conditioning ·
From
$353/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Beach
Air Conditioning
Wifi
In Unit Laundry
Furnished
Other spaces
Workspace, Kitchen
Kailua Beachfront - Licensed Rental #90/TVU-0141 - LOCATION!
9.9
Excellent
·
Kailua
·
4 br
·
Sleeps 10
·
Ocean · Waterfront · Beach ·
From
$1,650/nightProperty
House · 4 Beds · 5 baths
Amenities
Ocean
Waterfront
Beach
Dishwasher
Wifi
Oven
In Unit Laundry
Furnished
Other spaces
Kitchen
Beautifully remodeled Lanikai house,spacious inside alot of green space outside
No reviews
·
Kailua
·
3 br
·
Sleeps 7
·
Workspace · Outdoor Space · Balcony ·
From
$283/nightProperty
House · 3 Beds · 2 baths
Amenities
Wifi
Oven
In Unit Laundry
Furnished
Other spaces
Workspace, Balcony, Kitchen
Makani Moana - Lanikai; w/spectacular views of the Mokulua Islands
9.9
Excellent
·
Kailua
·
4 br
·
Sleeps 8
·
High Ceilings · Hot Tub · Fitness Center ·
From
$457/nightProperty
House · 4 Beds · 4 baths
Amenities
High Ceilings
Hot Tub
Fitness Center
Beach
Dishwasher
Wifi
Oven
In Unit Laundry
Other spaces
Balcony, Kitchen
Hale Mokolea: Gem of Lanikai: Steps to Lanikai Beach
No reviews
·
Kailua
·
2 br
·
Sleeps 4
·
On Site Laundry · Mountains · Beach ·
From
$228/nightProperty
House · 2 Beds · 2 baths
Amenities
On Site Laundry
Mountains
Beach
Wifi
Oven
In Unit Laundry
Furnished
Other spaces
Kitchen
Steps to Kailua Beach-Heated Pool-Air Conditioned-Ask Owner Availability
10
Excellent
·
Kailua
·
4 br
·
Sleeps 8
·
Outdoor Space · Pool · Private Pool ·
From
$850/nightProperty
House · 4 Beds · 4 baths
Amenities
Pool
Private Pool
Dishwasher
Air Conditioning
Wifi
Oven
In Unit Laundry
Furnished
Other spaces
Kitchen
Hale Oahu Villa by AvantStay | Kailua Beachfront House! Coastal Luxury!
9.7
Excellent
·
Kailua
·
5 br
·
Sleeps 10
·
Workspace · Beach · Dishwasher ·
From
$1,000/nightProperty
House · 5 Beds · 3 baths
Amenities
Beach
Dishwasher
Air Conditioning
Wifi
Oven
In Unit Laundry
Furnished
Garage Parking
Other spaces
Workspace, Kitchen
Palione Papalani by AvantStay | Steps from Kailua Beach w/ Private Pool & Hot Tub
9.5
Excellent
·
Kailua
·
6 br
·
Sleeps 12
·
High Ceilings · Hot Tub · Workspace ·
From
$2,935/nightProperty
House · 6 Beds · 6 baths
Amenities
High Ceilings
Hot Tub
Pool
Private Pool
Beach
Dishwasher
Air Conditioning
Wifi
Other spaces
Workspace, Balcony, Kitchen
Hale Oahu Estate by AvantStay | Kailua Beachfront Estate w/ Guest House
9.3
Excellent
·
Kailua
·
6 br
·
Sleeps 12
·
Workspace · Balcony · Beach ·
From
$2,730/nightProperty
House · 6 Beds · 4 baths
Amenities
Beach
Dishwasher
Air Conditioning
Wifi
Oven
In Unit Laundry
Furnished
Other spaces
Workspace, Balcony, Kitchen
🌺NEW LISTING! 5 bedroom, 4 bath, Canal Front Home, ALL NEW!🏝NO CLEANING FEE!
10
Excellent
·
Kailua
·
5 br
·
Sleeps 10
·
Mountains · Fitness Center · Workspace ·
From
$632/nightProperty
House · 5 Beds · 4 baths
Amenities
Mountains
Fitness Center
Waterfront
Beach
Dishwasher
Air Conditioning
Wifi
Oven
Other spaces
Workspace, Balcony, Kitchen
Steps to Kailua Beach ($7,500 per month)
10
Excellent
·
Kailua
·
3 br
·
Sleeps 6
·
Fitness Center · Beach · Air Conditioning ·
From
$585/nightProperty
House · 3 Beds · 1 bath
Amenities
Fitness Center
Beach
Air Conditioning
Wifi
Oven
In Unit Laundry
Furnished
Other spaces
Kitchen
The SunWalk Villa: Stunning 3BR
10
Excellent
·
Kailua
·
3 br
·
Sleeps 7
·
Private Pool · Pool · Air Conditioning ·
From
$1,199/nightProperty
House · 3 Beds · 2 baths
Amenities
Private Pool
Pool
Air Conditioning
Furnished
Garage Parking
Swimming Pool
Come Relax on the Lake! Kayaks and SUP included!!!
9.8
Excellent
·
Kailua
·
1 br
·
Sleeps 2
·
Lake · Outdoor Space · Balcony ·
From
$175/nightProperty
House · 1 Bed · 1 bath
Amenities
Lake
Waterfront
Wifi
Oven
In Unit Laundry
Furnished
Residents Lounge
Other spaces
Balcony, Kitchen
Coconut Grove Cottage, Walk to Beach and Downtown
No reviews
·
Kailua
·
2 br
·
Sleeps 4
·
Mountains · Fitness Center · Outdoor Space ·
From
$200/nightProperty
House · 2 Beds · 1 bath
Amenities
Mountains
Fitness Center
Beach
Dishwasher
Air Conditioning
Wifi
Oven
In Unit Laundry
Other spaces
Kitchen
Mountainside Ocean View Home w/ Private Pool & soaking tub with a view
No reviews
·
Kailua
·
3 br
·
Sleeps 8
·
High Ceilings · Ceiling Fan · Pool ·
From
$2,857/nightProperty
House · 3 Beds · 4 baths
Amenities
High Ceilings
Ceiling Fan
Pool
Private Pool
Dishwasher
Air Conditioning
Oven
In Unit Laundry
Other spaces
Balcony, Kitchen
Quiet, Private, Beachy 2-bedroom, Walk to Kailua Beach, A/C
9.9
Excellent
·
Kailua
·
2 br
·
Sleeps 4
·
High Ceilings · Balcony · Dishwasher ·
From
$220/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
High Ceilings
Dishwasher
Air Conditioning
Wifi
Oven
In Unit Laundry
Furnished
Fitness Center
Other spaces
Balcony, Kitchen
3,200 sq ft House with Pool, 6 Bedrooms, walking distance to Kailua and Lanikai
10
Excellent
·
Kailua
·
6 br
·
Sleeps 18
·
Walk In Closets · High Ceilings · Workspace ·
From
$870/nightProperty
House · 6 Beds · 4 baths
Amenities
Walk In Closets
High Ceilings
Pool
Private Pool
Beach
Dishwasher
Air Conditioning
Wifi
Other spaces
Workspace, Balcony, Kitchen
Kailua Beach & Kailua Town
9.9
Excellent
·
Kailua
·
2 br
·
Sleeps 5
·
Assigned Parking · On Site Laundry · Mountains ·
From
$570/nightProperty
House · 2 Beds · 1 bath
Amenities
Assigned Parking
On Site Laundry
Mountains
Fitness Center
Beach
Dishwasher
Air Conditioning
Wifi
Other spaces
Kitchen
Charming island style Studio - D&D's B&B
No reviews
·
Kailua
·
Studio
·
Sleeps 2
·
Assigned Parking · Mountains · Beach ·
From
$92/nightProperty
Apartment · Studio · 1 bath
Amenities
Assigned Parking
Mountains
Beach
Wifi
In Unit Laundry
Furnished
Swimming Pool
Delightful & Spacious 2 bedroom, 2 bath, Apartment with full Kitchen, AC
10
Excellent
·
Kailua
·
2 br
·
Sleeps 6
·
Mountains · Ceiling Fan · Beach ·
From
$219/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Mountains
Ceiling Fan
Beach
Air Conditioning
Wifi
Oven
In Unit Laundry
Furnished
Other spaces
Kitchen
Lanikai Beach Front - Licensed Rental: #90/TVU-0042 - AMAZING!
9.8
Excellent
·
Kailua
·
5 br
·
Sleeps 14
·
Ocean · Waterfront · Beach ·
From
$1,800/nightProperty
House · 5 Beds · 4 baths
Amenities
Ocean
Waterfront
Beach
Dishwasher
Air Conditioning
Oven
In Unit Laundry
Furnished
Other spaces
Kitchen
The Perfect Lanikai Retreat With Direct Access To Secluded White Sand Beach!
10
Excellent
·
Kailua
·
3 br
·
Sleeps 6
·
Fitness Center · Ocean · Balcony ·
From
$1,778/nightProperty
House · 3 Beds · 2 baths
Amenities
Fitness Center
Ocean
Waterfront
Beach
Dishwasher
Wifi
Oven
In Unit Laundry
Other spaces
Balcony, Kitchen
Superbly Designed Home w/ Views of the Mokulua Islands & Ocean: Mokulua Sunrise
10
Excellent
·
Kailua
·
4 br
·
On Site Laundry · Walk In Closets · Mountains ·
From
$2,333/nightProperty
House · 4 Beds · 4 baths
Amenities
On Site Laundry
Walk In Closets
Mountains
Ceiling Fan
Ocean
Waterfront
Dishwasher
Air Conditioning
Other spaces
Balcony, Kitchen
Studio Walk To Beach Modern A/C King Bed
10
Excellent
·
Kailua
·
Studio
·
Sleeps 2
·
On Site Laundry · Workspace · Beach ·
From
$141/nightProperty
Apartment · Studio · 1 bath
Amenities
On Site Laundry
Beach
Air Conditioning
Wifi
In Unit Laundry
Furnished
Residents Lounge
Other spaces
Workspace, Kitchen
Lanikai 5 star luxury estate, oceanfront, pool, spa, gardens, gorgeous!
10
Excellent
·
Kailua
·
4 br
·
Sleeps 7
·
Ev Charging · Mountains · Fitness Center ·
From
$2,388/nightProperty
House · 4 Beds · 5 baths
Amenities
Ev Charging
Mountains
Fitness Center
Ocean
Pool
Private Pool
Waterfront
Beach
Other spaces
Workspace, Kitchen
Oceanfront Lanikai Home with Access to Secluded White Sand Beach
9.9
Excellent
·
Kailua
·
4 br
·
Sleeps 12
·
High Ceilings · Fitness Center · Ocean ·
From
$2,438/nightProperty
House · 4 Beds · 4 baths
Amenities
High Ceilings
Fitness Center
Ocean
Waterfront
Beach
Dishwasher
Wifi
Oven
Other spaces
Workspace, Balcony, Kitchen
Resort-like, Kailua Lanikai, 2 Min walk/Beach, AC, WiFi, Pool, Kayaks
9.8
Excellent
·
Kailua
·
3 br
·
Hardwood Floor · Fireplace · Smoking Allowed ·
From
$432/nightProperty
House · 3 Beds · 3 baths
Amenities
Hardwood Floor
Fireplace
Smoking Allowed
Hot Tub
Fitness Center
Ocean
Pool
Private Pool
Other spaces
Workspace, Kitchen
Chateau Relaxo - 2 BR Kailua w/ Mountain/Lake Views/Full Kitchen/Laundry/AC
9.7
Excellent
·
Kailua
·
2 br
·
Sleeps 4
·
Lake · Waterfront · Air Conditioning ·
From
$238/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Lake
Waterfront
Air Conditioning
Wifi
Oven
In Unit Laundry
Furnished
Fitness Center
Other spaces
Kitchen
Stunning Kailua Oceanfront Getaway - MONTHLY DISCOUNT AVAILABLE
9.9
Excellent
·
Kailua
·
3 br
·
Sleeps 6
·
Mountains · Fitness Center · Ocean ·
From
$550/nightProperty
House · 3 Beds · 4 baths
Amenities
Mountains
Fitness Center
Ocean
Pool
Private Pool
Waterfront
Beach
Dishwasher
Other spaces
Workspace, Balcony, Kitchen
Pikake Hale - Large, beautiful 5 Bedroom home steps from the beach
10
Excellent
·
Kailua
·
5 br
·
Sleeps 13
·
Hot Tub · Beach · Dishwasher ·
From
$779/nightProperty
House · 5 Beds · 5 baths
Amenities
Hot Tub
Beach
Dishwasher
Wifi
Oven
In Unit Laundry
Furnished
Residents Lounge
Other spaces
Kitchen
Private Studio with amazing view and private swimming pool!
9.7
Excellent
·
Kailua
·
1 br
·
Sleeps 2
·
Lake · Walk In Closets · Ocean ·
From
$134/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Lake
Walk In Closets
Ocean
Pool
Private Pool
Waterfront
Air Conditioning
Wifi
Other spaces
Kitchen
Beachfront spectacular Kailua beach
10
Excellent
·
Kailua
·
4 br
·
Sleeps 8
·
Smoking Allowed · Ev Charging · Fitness Center ·
From
$1,710/nightProperty
Apartment · 4 Beds · 2 baths
Amenities
Smoking Allowed
Ev Charging
Fitness Center
Ocean
Waterfront
Beach
Dishwasher
Air Conditioning
Other spaces
Kitchen
Just off the Sand-Heated Pool-Air Conditioned-Quiet/Secure-Ask Owner/rates&dates
10
Excellent
·
Kailua
·
4 br
·
Sleeps 7
·
Mountains · Ceiling Fan · Ocean ·
From
$1,008/nightProperty
House · 4 Beds · 3 baths
Amenities
Mountains
Ceiling Fan
Ocean
Pool
Private Pool
Waterfront
Beach
Dishwasher
Other spaces
Kitchen
Kailua Beach "The Pink House" 100 Yards from Ocean
9.7
Excellent
·
Kailua
·
4 br
·
Sleeps 6
·
Outdoor Space · Beach · Dishwasher ·
From
$545/nightProperty
House · 4 Beds · 2 baths
Amenities
Beach
Dishwasher
Air Conditioning
Wifi
Oven
In Unit Laundry
Furnished
Residents Lounge
Other spaces
Kitchen
Showing 1 - 50 of 182 results
Updated: March 28, 2023
Learn about vacation rentals in
Kailua
There's so much history just waiting to be discovered in Kailua-Kona, a beautiful seaside town along the Kona Coast in Hawai'i. It's where King Kamehameha spent his final years. In addition to its rich history, the area offers exciting nightlife, dining, and outdoor recreational opportunities. Just steps away from the ocean, vacationers can enjoy snorkeling, swimming, scuba diving, or fishing.
Kailua-Kona, Hawai'i: What to know before you go
The island of Hawai'i is pleasantly warm all year, but the best time to visit is between the months of March and September, when the temperatures are highest and there's less rain. We recommend getting a car to navigate the area and the rest of the Big Island.
Getting around Kailua
Walking
4/10
Fewer daily needs are within walking distance (unless you’re up for a challenge).
Car
9/10
Commuting is easy with multiple accessible routes and plenty of parking.
Transit
3/10
There are a few mass transit options within the area.
Points of interest in Kailua
Groceries
4/10
At least one grocery store within a 30-minute walk
Shopping
4/10
Some shops within walking distance
Cafes
3/10
Few or no cafés within walking distance
Restaurants
4/10
Some restaurants within walking distance
Parks
7/10
Moderate amount of park space nearby
Nightlife
2/10
Few or no bars within walking distance
Vacation Rentals in Kailua, HI FAQ
How many vacation rentals in Kailua are available?
There are currently 183 vacation rentals in Kailua available. Our vacation rentals in Kailua include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.
Are there any pet friendly vacation rentals in Kailua?
Yes, right now there are 10 pet friendly vacation rentals in Kailua. A pet friendly vacation rental in Kailua means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.
Are there any vacation rentals in Kailua with a pool?
Yes there are vacation rentals with a pool available in Kailua, HI. View more detailed vacation spots on Vacations by Zumper.
Are there any vacation rentals in Kailua with internet access?
As of March 28, 2023, there are vacation rentals with internet access available in Kailua, Hawaii. Check out more enjoyable destinations on Vacations by Zumper.
More Options
Compare over 500K vacation listings
Search in one place
Our marketplace is populated with rentals from trusted partners like Vrbo, Booking.com, and more, so you can search a wide selection on a single platform.
