Kailua holiday rentals

We found 5,040 holiday rentals — enter your dates for availability
Select from 141 houses, 38 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:13 Nov - 20 Nov

View from the top of The Ilikai  - Diamond Head in the backgroud.
View from the lanai (balcony) of the unit on the 11th floor looking to the right
Entrance to The Illiai.
View looking to the left from the lanai toward the Hilton Hawaiian Village.
Exceptional
(125 reviews)

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

Honolulu

7% off
S$3,283
for 7 nights, 1 apartment
S$469 per night
includes taxes & fees
Resort Style with Hula Show, Fireworks and even Tiki Torches!
The perfect way to start the day in 'Pure Paradise'
Dukes for Fish Taco's and Catamaran ride
Views of the Yacht Harbor and Hilton Hawaiian Village Lagoon and best surf spot!
Wonderful Waikiki come play in Paradise
Exceptional
(205 reviews)

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

Honolulu

7% off
S$2,718
for 7 nights, 1 apartment
S$388 per night
includes taxes & fees
New Decor! Oceanfront, Yacht Harbor, Luxury, Friday Fireworks front row, FAB!
Room
Exterior
Swimming
Exterior detail
Exceptional
(6 reviews)

Family/Friends Hotel in Terrific Honolulu Room, AC

Honolulu

6% off
S$1,003
for 7 nights, 1 room
S$143 per night
includes taxes & fees
Family/Friends Hotel in Terrific Honolulu Room, AC
Room
Private kitchen
Living area
Property grounds
Wonderful
(16 reviews)

Ocean View Mid Waikiki 1 Block to the Beach

Honolulu

7% off
S$6,256
for 7 nights, 1 apartment
S$894 per night
includes taxes & fees
Ocean View Mid Waikiki 1 Block to the Beach
Dining
Pool
Lobby
Property grounds
Exceptional
(9 reviews)

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

Honolulu

7% off
S$2,147
for 7 nights, 1 apartment
S$307 per night
includes taxes & fees
Glam Condo Located in Central Waikiki, Panoramic Ocean View, & Full Kitchen!
Pool
Exterior
Fitness facility
Room
Very good
(17 reviews)

Beautiful Remodeled Studio with canal, city and mountain views

Honolulu

7% off
S$1,467
for 7 nights, 1 apartment
S$210 per night
includes taxes & fees
Beautiful Remodeled Studio with canal, city and mountain views
Property grounds
Plenty of comfortable seating in the lobby
Fitness equipment for guest use is Free
Pool, Sauna, bathrooms, BBQ Grill and Recreation Area!
Exceptional
(126 reviews)

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

Honolulu

7% off
S$1,951
for 7 nights, 1 apartment
S$279 per night
includes taxes & fees
In the Heart of Waikiki - Premium Studio Condo - Rated 9.6 of 10 - Walk to Beach
Enjoy the View
Grand lobby furnished with European luxury.
Grand entry of Italian marble.
ATM in lobby.
Wonderful
(39 reviews)

Affordable Luxury in Waikiki

Honolulu

7% off
S$1,588
for 7 nights, 1 apartment
S$227 per night
includes taxes & fees
Affordable Luxury in Waikiki
Room
Interior
Interior
Dining
Very good
(9 reviews)

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

Honolulu

7% off
S$2,911
for 7 nights, 1 apartment
S$416 per night
includes taxes & fees
Entire condo in Waikiki - Ocean View 2 BR & 4 bed
Property grounds
Living area
Private kitchen
Living area
Exceptional
(96 reviews)

NEW LISTING 2023 Modern Renovated Condo - 1 block to beach, free parking!

Honolulu

7% off
S$3,468
for 7 nights, 1 apartment
S$495 per night
includes taxes & fees
NEW LISTING 2023 Modern Renovated Condo - 1 block to beach, free parking!
Lobby
Jacuzzi and Gazebos
Unit 407 (2 lanais) on outer corner
Living area
Exceptional
(38 reviews)

Rare 1 Bedroom Condo in at the Heart of Waikiki 2 blocks from the beach

Honolulu

7% off
S$3,427
for 7 nights, 1 apartment
S$490 per night
includes taxes & fees
Rare 1 Bedroom Condo in at the Heart of Waikiki 2 blocks from the beach
Pineapple Cottage # 1
Pineapple Cottage # 2
Cottage Waikiki. Central AC .
On-site Swimming pool!
Exceptional
(5 reviews)

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

Honolulu

7% off
S$2,629
for 7 nights, 1 apartment
S$376 per night
includes taxes & fees
Queen beds, oceanview, 2 min walk to beach, central AC, Parking is available
Marina
Private kitchen
Dining
Interior
Wonderful
(21 reviews)

Magical Ocean View Oasis 3 Bedroom 3 Bathroom

Honolulu

7% off
S$8,436
for 7 nights, 1 apartment
S$1,205 per night
includes taxes & fees
Magical Ocean View Oasis 3 Bedroom 3 Bathroom
Room
Living area
Living area
Pool
Exceptional
(65 reviews)

Newly Renovated Sweeping Ocean and Diamond Head View Waikiki Condo.

Honolulu

7% off
S$2,761
for 7 nights, 1 apartment
S$394 per night
includes taxes & fees
Newly Renovated Sweeping Ocean and Diamond Head View Waikiki Condo.
Living area
Pool
Private kitchen
Outdoor dining
Exceptional
(45 reviews)

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

Honolulu

7% off
S$2,913
for 7 nights, 1 apartment
S$416 per night
includes taxes & fees
Newly Renovated Waikiki Condo 2 blocks to the Beach! Free parking.
Newly updated lobby
Newly updated lobby
Living room has it's own lanai and an armoire that can be used to hang clothes.
Pool
Exceptional
(57 reviews)

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

Honolulu

7% off
S$6,071
for 7 nights, 1 apartment
S$867 per night
includes taxes & fees
2 SIDE BY SIDE CONDOS 2 BLOCKS FROM THE BEACH! LOTS OF SLEEPING SPACE!
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

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)
  • Ala Wai Golf Course (10 mi / 16.2 km)
  • Honolulu Zoo (10.4 mi / 16.8 km)
  • Waialae Country Club (9.4 mi / 15.1 km)
  • Waikele Golf Club (17.1 mi / 27.6 km)
  • Ewa Beach Golf Club (17.3 mi / 27.9 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.

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