Compare cheap villa rentals in Kailua, HI from 100+ sites!

149 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Kailua, HI villas
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

149 Villa rentals in Kailua, HI

Find the Best Holiday Houses with Swimming Pool in Kailua, HI

On-site pool access in Kailua, HI makes a refreshing swim to complement your beach day a wonderful part of your daily routine.

Two Amazing Views In One Spacious Condo Getaway - Kailua, HI
8.8 4 reviews
Kailua, HI
10/02 – 10/03
$491/nightfor 1 night

Two Amazing Views In One Spacious Condo Getaway

1 1
house , Urban Honolulu
This condo is located in Honolulu, an 8-minute walk from Waikiki Beach and 600 yards from Royal Hawaiian Shopping Center.
This 570-square-foot accommodation offers air conditioning, a private balcony, a hot tub, free Wi-Fi, and a kitchen with a microwave and washing machine, accommodating up to 11 guests.
Spacious Waterfront With Gorgeous View & Pool - Kailua, HI
9.9 59 reviews
Kailua, HI
08/20 – 09/19
$765/nighttotal: $22950 (30 )

Spacious Waterfront With Gorgeous View & Pool

1 2
house , Kaneohe
This waterfront residence in Kaneohe offers direct access to Kaneohe Bay, featuring panoramic views and a private backyard ideal for kayaking, with convenient proximity to local malls, theaters, restaurants, and grocery stores.
This spacious two-level custom home accommodates up to 10 guests with 5 bedrooms and 4 bathrooms, boasting amenities like a large swimming pool, covered decks, full kitchen, air conditioning, and reliable WiFi, all supported by ample parking for 3 vehicles.
Ilikai Tower 2141 - Kailua, HI
9.0 28 reviews
Kailua, HI
10/03 – 10/12
$391/nighttotal: $3519 (9 )

Ilikai Tower 2141

1 2
house , Urban Honolulu
This luxurious yacht is situated in Honolulu's Ala Wai Yacht Harbor, offering stunning views of Waikiki and the south shore surf breaks.
The 500-square-foot vessel features one bedroom, one bathroom, and accommodates up to four guests, complete with a kitchen, swimming pool, and a spacious lanai perfect for enjoying the sunset; high-speed internet and cable TV are also included.
Ilikai 1310 - Kailua, HI
Kailua, HI
12/26 – 12/28
$650/nighttotal: $1300 (2 )

Ilikai 1310

2 3
house , Urban Honolulu
This Ilikai 1310 condo in Honolulu is a 12-minute walk from Fort DeRussy and 0.6 miles from the Hawaii Convention Center, offering mountain and sea views.
This 1000 square foot vacation home accommodates up to 11 guests with 2 bedrooms, 2 bathrooms, a living room, a kitchen equipped with a fridge, microwave, and dishwasher, air conditioning, internet, a swimming pool, and a terrace.

Best Kailua, HI houses with a kitchen

Hawaii Kai Dream - Kailua, HI
Kailua, HI
08/20 – 09/19
$396/nighttotal: $11880 (30 )

Hawaii Kai Dream

4 2
house , East Honolulu
Hawaii Kai Dream, located in the Hawaii Kai district of Honolulu, is 1.5 miles from Maunalua Bay and under 9 miles from Hanauma Bay and Diamond Head.
This 2310-square-foot East Honolulu home features four bedrooms, three bathrooms, a fully equipped kitchen, in-unit laundry, and parking, comfortably accommodating families or groups and offering easy access to swimming, kayaking, snorkeling, and cycling.
Ilikai Tower 1340 - Kailua, HI
9.4 5 reviews
Kailua, HI
08/15 – 08/25
$311/nighttotal: $3110 (10 )

Ilikai Tower 1340

1 2
house , Urban Honolulu
This Waikiki apartment is located just steps away from Kahanamoku Beach, Fort DeRussy Beach, and Magic Island Lagoon Beach, putting you in the heart of the action. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience.
This one-bedroom, one-bathroom condo is perfect for a group of four and offers 500 square feet of comfortable living space. Guests can enjoy amenities like a private pool, air conditioning, cable TV, a fully equipped kitchen, free Wi-Fi, and private parking.
Ilikai Tower 1806 - Kailua, HI
9.2 18 reviews
Kailua, HI
07/09 – 07/17
$326/nighttotal: $2608 (8 )

Ilikai Tower 1806

1 2
house , Urban Honolulu
This Waikiki apartment is a short walk from Fort DeRussy and a half mile from the Hawaii Convention Center, making it easy to explore the best of Honolulu. Guests consistently rate the location, cleanliness, and overall experience as excellent.
The apartment has one bedroom, one bathroom, and can comfortably accommodate up to four guests in its 500 square feet of space. Amenities include a private pool, air conditioning, a fully equipped kitchen, free Wi-Fi, cable TV, and a terrace with views of the Ala Wai Yacht Harbor.
Kailua Beach Vacation Cottage - Kailua, HI
Kailua, HI
06/24 – 07/28
$477/nighttotal: $16218 (34 )

Kailua Beach Vacation Cottage

1 5
house , Kailua
This private garden cottage in Kailua is located just 50 steps from Kailua Beach.
This 1200 sq.ft. dwelling accommodates up to 6 guests and features a full kitchen, antique furnishings, a screened-in patio, and complimentary beach amenities.

Frequently Asked Questions about villa rentals in Kailua, HI

Destinations nearby

Best Kailua, HI houses with air conditioning

Ilikai Marina 1383 - Kailua, HI
8.4 6 reviews
Kailua, HI
10/03 – 10/12
$185/nighttotal: $1665 (9 )

Ilikai Marina 1383

1 2
house , Urban Honolulu
This studio apartment in Honolulu offers a prime location near Waikiki, situated 0.7 miles from the Ala Moana Center and a short walk to Kahanamoku Beach and Fort DeRussy.
This 450 square foot studio accommodates up to two guests and features air conditioning, complimentary WiFi, a TV, and a kitchen equipped with a fridge, microwave, and oven.
We're Booking Now - Calendar Not Up To Date. - Kailua, HI
9.6 23 reviews
Kailua, HI
07/15 – 08/15
$2010/nighttotal: $62310 (31 )

We're Booking Now - Calendar Not Up To Date.

4 2
house , East Honolulu
This exquisite East Honolulu villa is a short drive from Waikiki Beach and Hanauma Bay Nature Preserve, offering easy access to shops, supermarkets, and hiking trails.
The 4,000-square-foot property boasts four bedrooms, three and a half bathrooms, a swimming pool, spa, and parking, comfortably accommodating up to sixteen guests.
Inn On The Park #2013 - Kailua, HI
Kailua, HI
10/03 – 10/12
$153/nighttotal: $1377 (9 )

Inn On The Park #2013

1 2
house , Urban Honolulu
Inn on the Park #2013, a condo in Urban Honolulu, is located an 11-minute walk from Fort De Russy and 0.9 miles from the Royal Hawaiian Shopping Center.
This 310 square feet condo accommodates up to 3 guests and features air conditioning, a kitchenette with a fridge and microwave, a swimming pool, and a balcony with ocean views.
Ilikai Tower 1918 - Kailua, HI
8.0 2 reviews
Kailua, HI
07/09 – 07/17
$326/nighttotal: $2608 (8 )

Ilikai Tower 1918

1 2
house , Urban Honolulu
Ilikai Tower 1918 in Honolulu is located a short walk to Fort DeRussy and 0.7 miles from the Hawaii Convention Center, offering proximity to Kahanamoku Beach, Hale Koa Luau, and the US Army Museum of Hawaii. This 500 square foot, one-bedroom condo features air conditioning, a fully equipped kitchen with a fridge, microwave, and dishwasher, and a private balcony with sea views.

Neighborhoods and points of interest in Kailua, HI

Best Kailua, HI villas and beach houses with jacuzzi

5 Star 270 Degree Ocean View Waikiki Penthouse New - Kailua, HI
Kailua, HI
09/16 – 09/22
$2394/nighttotal: $14364 (6 )

5 Star 270 Degree Ocean View Waikiki Penthouse New

2 2
house , Urban Honolulu
This penthouse is located in Waikiki, just a short walk from Fort DeRussy Beach and Waikiki Beach. The area is bustling with shops, restaurants, and nightlife, making it a perfect base for exploring Honolulu.
The 1150 square foot penthouse has two bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy panoramic ocean views, a fully equipped kitchen, a hot tub, a fitness center, and free WiFi.
The Landmark #2705 - 30-night Minimum - Honolulu Hi - Kailua, HI
Kailua, HI
08/20 – 09/19
$259/nighttotal: $7770 (30 )

The Landmark #2705 - 30-night Minimum - Honolulu Hi

1 2
house , Urban Honolulu
This Honolulu vacation rental is located an 8-minute walk from the Hawaii Convention Center and 1.1 miles from Honolulu Stadium Park.
This 1300 square foot home offers 2 bedrooms, 2 bathrooms, a fully equipped kitchen, a living room, and accommodates up to 11 guests with amenities including a swimming pool, hot tub, garden, fitness center, and free Wi-Fi.
Newly Innovated Oceanview Beach Condo Sauna Pool - Kailua, HI
Kailua, HI
08/17 – 08/21
$677/nighttotal: $2708 (4 )

Newly Innovated Oceanview Beach Condo Sauna Pool

1 2
house , Urban Honolulu
This condo is located in Waikiki, Honolulu, a 3-minute walk from Waikiki Beach and 0.3 miles from Saint Augustine by the Sea.
This 500 sq ft dwelling accommodates up to 7 guests and features 1 bedroom, 1 bathroom, air conditioning, a swimming pool, a jacuzzi, a garden, a sauna, and a full kitchen with a fridge and microwave oven.
Ilikai 2127 Spectacular Ocean Harbor Views - Kailua, HI
9.1 92 reviews
Kailua, HI
12/26 – 12/28
$500/nighttotal: $1000 (2 )

Ilikai 2127 Spectacular Ocean Harbor Views

1 3
house , Urban Honolulu
This studio apartment is located in the Waikiki district of Honolulu, just a short distance from popular beaches like Kahanamoku Beach, Fort DeRussy Beach, and Magic Island Lagoon Beach. The studio has excellent user, location, and cleanliness ratings.
The studio is a one-bedroom, one-bathroom apartment with a floor area of 5380 square feet. It features a private pool, elevator access, a fully equipped kitchen, free Wi-Fi, private parking, air conditioning, and a terrace with spectacular ocean and harbor views.
©2026 cozycozy.com