Kailua holiday rentals

We found 5,113 holiday rentals — enter your dates for availability
Select from 138 houses, 36 apartments and other holiday rentals to find the perfect place for your stay in Kailua. Holiday rentals provide the best amenities for your family, friends or furry companion, such as air conditioning and Wi-Fi. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Kailua

Showing deals for:27 Nov - 4 Dec

Room
Interior
Pool and hot tub
Entrance
Wonderful
(10 reviews)

1BR Ocean/Sunset View w/Parking

Honolulu

7% off
S$2,882
for 7 nights, 1 apartment
S$412 per night
includes taxes & fees
1BR Ocean/Sunset View w/Parking
View looking to the left from the lanai toward the Hilton Hawaiian Village.
View from the lanai (balcony) of the unit on the 11th floor looking to the right
Property grounds
View from the top of The Ilikai  - Diamond Head in the backgroud.
Exceptional
(127 reviews)

Resort Style with Hula Show, Fireworks and even Tiki Torches!

Honolulu

7% off
S$3,250
for 7 nights, 1 apartment
S$464 per night
includes taxes & fees
Resort Style with Hula Show, Fireworks and even Tiki Torches!
Views of the Yacht Harbor and Hilton Hawaiian Village Lagoon and best surf spot!
Dukes for Fish Taco's and Catamaran ride
Wonderful Waikiki come play in Paradise
Marina
Exceptional
(205 reviews)

New Decor! Oceanfront, Yacht Harbor, Luxury, Friday Fireworks front row, FAB!

Honolulu

5% off
S$2,893
for 7 nights, 1 apartment
S$413 per night
includes taxes & fees
New Decor! Oceanfront, Yacht Harbor, Luxury, Friday Fireworks front row, FAB!
Exterior detail
Exterior
Room
Swimming
Exceptional
(6 reviews)

Family/Friends Hotel in Terrific Honolulu Room, AC

Honolulu

6% off
S$1,103
for 7 nights, 1 room
S$158 per night
includes taxes & fees
Family/Friends Hotel in Terrific Honolulu Room, AC
Living area
Private kitchen
Room
Property grounds
Wonderful
(18 reviews)

Ocean View Mid Waikiki 1 Block to the Beach

Honolulu

7% off
S$7,088
for 7 nights, 1 apartment
S$1,013 per night
includes taxes & fees
Ocean View Mid Waikiki 1 Block to the Beach
Ocean view and Ala Wai canal view from balcony.
Island Colony is located at 445 Seaside Avenue.
The pool is open daily from 7:00 AM to 9:00 PM, except for one week in November.
The spacious living room includes two twin beds and a sofa bed (75x45 inches).
Exceptional
(7 reviews)

Amazing Views Waikiki Beach 28th Floor 1 Bedroom Family and Group Condo

Honolulu

7% off
S$3,993
for 7 nights, 1 apartment
S$570 per night
includes taxes & fees
Amazing Views Waikiki Beach 28th Floor 1 Bedroom Family and Group Condo
Lobby
Pool
Room
Dining
Exceptional
(9 reviews)

Glam Condo Located in Central Waikiki, Panoramic Ocean View, & Full Kitchen!

Honolulu

7% off
S$2,195
for 7 nights, 1 apartment
S$314 per night
includes taxes & fees
Glam Condo Located in Central Waikiki, Panoramic Ocean View, & Full Kitchen!
View from Bedroom / Kitchen window
Interior
Living area
Pool
Excellent
(93 reviews)

Upgraded 1BR Condo Ocean View - Kitchen, FREE parking, WiFi

Honolulu

7% off
S$2,592
for 7 nights, 1 apartment
S$370 per night
includes taxes & fees
Upgraded 1BR Condo Ocean View - Kitchen, FREE parking, WiFi
Dining
Interior
Pool
Room
Very good
(9 reviews)

Entire condo in Waikiki - Ocean View 2 BR & 4 bed

Honolulu

7% off
S$3,410
for 7 nights, 1 apartment
S$487 per night
includes taxes & fees
Entire condo in Waikiki - Ocean View 2 BR & 4 bed
Property grounds
Plenty of comfortable seating in the lobby
Pool, Sauna, bathrooms, BBQ Grill and Recreation Area!
Fitness equipment for guest use is Free
Exceptional
(126 reviews)

In the Heart of Waikiki - Premium Studio Condo - Rated 9.6 of 10 - Walk to Beach

Honolulu

7% off
S$1,828
for 7 nights, 1 apartment
S$261 per night
includes taxes & fees
In the Heart of Waikiki - Premium Studio Condo - Rated 9.6 of 10 - Walk to Beach
Fitness facility
Exterior
Private kitchen
Room
Very good
(17 reviews)

Beautiful Remodeled Studio with canal, city and mountain views

Honolulu

7% off
S$1,443
for 7 nights, 1 apartment
S$206 per night
includes taxes & fees
Beautiful Remodeled Studio with canal, city and mountain views
Pool and garden area.
Grand lobby furnished with European luxury.
Grand entry of Italian marble.
Enjoy the View
Wonderful
(39 reviews)

Affordable Luxury in Waikiki

Honolulu

7% off
S$1,563
for 7 nights, 1 apartment
S$223 per night
includes taxes & fees
Affordable Luxury in Waikiki
Pineapple Cottage # 1
Pineapple Cottage # 2
Pineapple Cottage #2
Cottage Waikiki. Central AC .
Exceptional
(6 reviews)

Queen beds, oceanview, 2 min walk to beach, central AC, Parking is available

Honolulu

7% off
S$2,602
for 7 nights, 1 apartment
S$372 per night
includes taxes & fees
Queen beds, oceanview, 2 min walk to beach, central AC, Parking is available
Pool with view
Enjoy your morning coffee
Enter into New Kitchen
Living Room with Sofa bed
Exceptional
(273 reviews)

2 Bedroom, 2 Bath Condo With Mountain And Water Views In The Heart Of Waikiki

Honolulu

7% off
S$3,480
for 7 nights, 1 apartment
S$497 per night
includes taxes & fees
2 Bedroom, 2 Bath Condo With Mountain And Water Views In The Heart Of Waikiki
Dining
Private kitchen
Interior
Interior
Wonderful
(21 reviews)

Magical Ocean View Oasis 3 Bedroom 3 Bathroom

Honolulu

7% off
S$8,364
for 7 nights, 1 apartment
S$1,195 per night
includes taxes & fees
Magical Ocean View Oasis 3 Bedroom 3 Bathroom
Room
Pool
Outdoor dining
Living area
Exceptional
(45 reviews)

Newly Renovated Waikiki Condo 2 blocks to the Beach! Free parking.

Honolulu

7% off
S$2,883
for 7 nights, 1 apartment
S$412 per night
includes taxes & fees
Newly Renovated Waikiki Condo 2 blocks to the Beach! Free parking.
Room
Newly updated lobby
Newly updated lobby
Pool
Exceptional
(57 reviews)

2 SIDE BY SIDE CONDOS 2 BLOCKS FROM THE BEACH! LOTS OF SLEEPING SPACE!

Honolulu

7% off
S$5,993
for 7 nights, 1 apartment
S$856 per night
includes taxes & fees
2 SIDE BY SIDE CONDOS 2 BLOCKS FROM THE BEACH! LOTS OF SLEEPING SPACE!
Spa
The views of coastline from your lanai.
Outdoor dining
Interior
Exceptional
(218 reviews)

Direct Oceanfront Waikiki! Parking at Waikiki Shore included!

Honolulu

7% off
S$7,015
for 7 nights, 1 apartment
S$1,002 per night
includes taxes & fees
Direct Oceanfront Waikiki! Parking at Waikiki Shore included!
Room
Exterior
Living area
Dining
Exceptional
(14 reviews)

Honolulu Central Waikiki luxury High With Views & Beach

Honolulu

7% off
S$3,097
for 7 nights, 1 apartment
S$442 per night
includes taxes & fees
Honolulu Central Waikiki luxury High With Views & Beach

Delight in the waterfront landscape of Kailua

The island views and surrounding scenery provide a peaceful ambience to your holiday home in Kailua. This city's kayaking, coral reefs and hiking draw many visitors. Ala Moana Center and Waikiki Beach Walk are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Kailua

Do you want to find attractions to visit during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Kailua a fun place to get away to. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Kaneohe Klipper Golf Course (3.4 mi / 5.5 km)
  • Honolulu Zoo (10.4 mi / 16.8 km)
  • Ko'olau Golf Club (3.6 mi / 5.8 km)
  • Waialae Country Club (9.4 mi / 15.1 km)
  • Ala Wai Golf Course (10 mi / 16.2 km)
  • Waikele Golf Club (17.1 mi / 27.6 km)

Exploring the beaches and other natural features in Kailua

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Kailua is a great place to get outside. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Waikiki Beach (10.4 mi / 16.8 km)
  • Lanikai Beach (1.7 mi / 2.7 km)
  • Honolulu Harbor (10.6 mi / 17 km)
  • Diamond Head (10.6 mi / 17 km)
  • Kalama Beach Park (0.2 mi / 0.3 km)
  • Kailua Bay Beach (0.8 mi / 1.2 km)

Seasonal weather averages in Kailua

Travellers enjoy Kailua for its snorkelling. If you're planning a holiday around warm-weather activities, September, August, October and July are the hottest months to visit, when temperatures average 26°C.

Transport to and around Kailua

The nearest airport is in Honolulu, HI (HNL-Daniel K. Inouye Intl.), located 12.6 mi (20.2 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Kapolei, HI (JRF-Kalaeloa), which is 22.2 mi (35.7 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Kailua?
Based on our research, houses are the most desirable holiday rental type in Kailua. But naturally, everyone's idea of an epic stay isn't going to be the same. Vrbo has holiday rentals of all shapes and sizes, so you're sure to discover your perfect match.
How much does it cost to rent a holiday rental in Kailua?
Different things affect what you'll pay for your holiday rental in Kailua, such as the season, length of stay and type of property. But, all of our holiday homes have something in common — incredible value. Just add your travel dates to find your perfect match.
How much does it cost to rent a beach house in Kailua?
When you travel and the size and style of the property will influence how much you'll pay for your beachside escape. Enter your Kailua travel dates to see all your options on Vrbo. Did someone just say "hot tub"? Use the filters to pick the features and amenities you want in your beach house.
What are popular rental amenities in Kailua?
Some of the most popular rental amenities people search for in Kailua are a sauna, a barbecue grill and ski-in/ski-out facilities. Whether you're holidaying with family, pals or even pets, Vrbo holiday properties feature the best amenities for fun and relaxation with the people that matter most.
What are the top attractions for families in Kailua?
There are lots of amazing things to do and see with the family in Kailua, such as:
  • Kailua Beach
  • Lanikai Beach
  • Waimanalo Beach
Can I find two-bedroom holiday rentals in Kailua?
Kailua has 28 two-bedroom holiday rentals to choose from. Discover a holiday home with all the comfort and privacy you're looking for at a price that's hard to resist on Vrbo.
Are there holiday rentals with WiFi in Kailua?
Kailua has 91 holiday rentals with WiFi, so you can stay connected while travelling. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to catching up on social media, these Vrbo homes make it a cinch to go online.
How old do you have to be to rent a holiday rental in Kailua?
The minimum age requirements can vary across properties on Vrbo, so look at the rules of the holiday rental in Kailua you want to book. But in general, it's 16, 18 or 21.
How long can I rent a holiday rental in Kailua for?
The amount of time you can stay in a Kailua holiday home for depends on the property. Simply put in your travel dates to find available options offering longer term stays. They include the things you need to make your extended getaway more enjoyable like kitchens and yards. Some Vrbo holiday homes may also offer weekly or monthly discounts, so you can stay even longer for less.

More holiday ideas