Kailua holiday lettings

We found 5,167 holiday rentals — enter your dates for availability
Select from 137 houses, 35 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:11 Dec - 18 Dec

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

1BR Ocean/Sunset View w/Parking

Honolulu

7% off
£1,627
for 7 nights, 1 apartment
£232 per night
includes taxes & fees
1BR Ocean/Sunset View w/Parking
Interior
Private kitchen
Property grounds
Room
Wonderful
(18 reviews)

Ocean View Mid Waikiki 1 Block to the Beach

Honolulu

7% off
£4,881
for 7 nights, 1 apartment
£697 per night
includes taxes & fees
Ocean View Mid Waikiki 1 Block to the Beach
Lobby
Pool
Room
Property grounds
Exceptional
(10 reviews)

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

Honolulu

7% off
£1,860
for 7 nights, 1 apartment
£266 per night
includes taxes & fees
Glam Condo Located in Central Waikiki, Panoramic Ocean View, & Full Kitchen!
Behind the Ilikai
Second floor pool
The lobby of the Ilikai
Property grounds
Exceptional
(5 reviews)

Waikiki - Resort amenities for condo prices, just steps from the beach!

Honolulu

11% off
£1,977
for 7 nights, 1 apartment
£282 per night
includes taxes & fees
Waikiki - Resort amenities for condo prices, just steps from the beach!
Interior
Interior
Dining
Room
Very good
(9 reviews)

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

Honolulu

7% off
£1,603
for 7 nights, 1 apartment
£229 per night
includes taxes & fees
Entire condo in Waikiki - Ocean View 2 BR & 4 bed
Room
Exterior
Pool
Fitness facility
Very good
(17 reviews)

Beautiful Remodeled Studio with canal, city and mountain views

Honolulu

7% off
£835
for 7 nights, 1 apartment
£119 per night
includes taxes & fees
Beautiful Remodeled Studio with canal, city and mountain views
Pineapple Cottage # 1
Pineapple Cottage # 2
Pineapple Cottage #2
On-site Swimming pool!
Exceptional
(6 reviews)

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

Honolulu

7% off
£1,462
for 7 nights, 1 apartment
£209 per night
includes taxes & fees
Queen beds, oceanview, 2 min walk to beach, central AC, Parking is available
Lobby
Koi Pond in Lobby  Unit is in Tower 1 Makai
Property grounds
Front of the Building View
Exceptional
(102 reviews)

⛱ Ocean Escape - Your Perfect Spot! Clean, Ocean View, 5 min walk to Beach, Prkg

Honolulu

6% off
£2,214
for 7 nights, 1 apartment
£316 per night
includes taxes & fees
⛱ Ocean Escape - Your Perfect Spot! Clean, Ocean View, 5 min walk to Beach, Prkg

Why visit Kailua

  • Stunning beaches: Relax on the soft sands of Kailua Beach and Lanikai Beach, both renowned for their clear turquoise waters and idyllic settings.
  • Outdoor adventures: Hike the scenic trails of the nearby Olomana Mountains, offering breathtaking views of the coastline and lush landscapes.
  • Paddleboarding: Enjoy paddleboarding in the calm waters of Kailua Bay, perfect for both beginners and experienced enthusiasts.
  • Botanical gardens: Explore vibrant local botanical gardens that showcase Hawaii's unique flora and provide tranquil spaces for relaxation.
  • Charming local town: Experience the laid-back atmosphere of Kailua's town centre, featuring local shops, cafes, and cultural experiences.

Popular types of accommodation in Kailua

Nestled in the stunning landscapes of Honolulu County, Kailua offers a perfect blend of relaxation and adventure. Visitors can explore the beautiful beaches, such as Lanikai and Kailua Beach, renowned for their soft sands and turquoise waters. Enjoy hiking the scenic trails of the nearby Olomana Mountains or paddleboarding in the calm bay. For your stay, popular accommodation choices include condos, private holiday homes, and well-equipped apartments, ensuring a comfortable retreat after a day of exploration.

  • Condos: These modern, often spacious units are the most sought-after choice for visitors, offering stunning views and convenient amenities.
  • Houses: Ideal for families or groups, these homes provide a home-like atmosphere with added privacy and comfort.
  • Apartments: A practical option, these self-contained spaces are perfect for couples or solo travellers seeking convenience.
  • Villas: Luxurious and often expansive, villas provide an upscale retreat with beautiful surroundings.
  • Cottages: Charming and quaint, cottages offer a cosy escape with a touch of local character.**

Top attractions in and around Kailua

Kailua, located in Honolulu County, Hawaii, is a picturesque destination ideal for outdoor and family beach vacations. Visitors can enjoy the stunning Kailua Beach, known for its soft sands and clear waters, as well as explore the scenic bay and vibrant botanical gardens. This charming town offers a perfect blend of relaxation and cultural experiences, making it an excellent spot for those seeking adventure and natural beauty in a tranquil setting.

  • Lanikai Beach: Known for its stunning turquoise waters and soft, white sand, Lanikai Beach offers the quintessential Hawaiian beach experience. It's perfect for sunbathing, swimming, and kayaking, with a serene atmosphere that invites relaxation.
  • Kaneohe Bay: Just 5km from Kailua, this picturesque bay features breathtaking scenery and outdoor activities like snorkelling and paddleboarding, making it ideal for nature lovers and adventure seekers.
  • Ho'omaluhia Botanical Garden: Located 6km away, this expansive garden showcases lush tropical landscapes, tranquil walking paths, and romantic spots, perfect for families and couples alike.

Things to do recommended for couples

Looking for a romantic getaway in Kailua? Enjoy a sunset picnic on the stunning Lanikai Beach, or take a leisurely kayak ride to the beautiful Mokulua Islands. Don't miss a stroll through the charming town for local shops and dining experiences perfect for couples.

Things to do recommended for families

Families visiting Kailua can enjoy a day at the stunning Kailua Beach, where children can play in the gentle waves, and explore the lush landscapes of Lanikai Pillbox Hike for breathtaking views. Don't miss the vibrant local markets for unique souvenirs and delicious Hawaiian treats.

Things to do recommended for groups

Groups visiting Kailua can enjoy a thrilling day of kayaking to the picturesque Mokulua Islands, followed by a relaxing afternoon on the stunning Lanikai Beach, known for its soft sands and clear waters. Don’t miss out on local food trucks for a taste of Hawaiian cuisine.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Kailua

Regardless of whether you are travelling with a group, as a family, bringing your pets along, or seeking longer stays, it’s important to apply the appropriate filters based on your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Kailua with a group: Think about how many bedrooms you require, as well as any amenities like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Kailua with young kids: Journeying with young children can present its challenges. It's essential to prioritise their comfort and safety, along with suitable amenities for their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Kailua: For many, a family holiday isn't truly fulfilling without their furry companion by their side. If that resonates with you, consider exploring Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels completely at home.
  • Planning for a long term stay visiting Kailua: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include preferences such as a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in and around Kailua

Kailua, nestled in Honolulu County, Hawaii, is a picturesque haven perfect for outdoor and family-friendly vacations. With its stunning beaches and vibrant local town, visitors can enjoy a relaxed tropical atmosphere. From exciting excursions to tranquil moments by the shore, Kailua offers a delightful blend of experiences. The pleasant weather year-round enhances the charm, while the local amenities ensure a comfortable stay, making it an ideal destination for those seeking both adventure and relaxation.

  • Kaneohe: Located approximately 6km from Kailua, Kaneohe is a vibrant city that offers an array of outdoor adventures and leisurely beach experiences. Renowned for its family-friendly atmosphere, visitors can enjoy thrilling activities such as ziplining at local adventure parks or having fun at the arcade adventure zone. Golf enthusiasts will find several picturesque courses to enjoy. Among the highlights are the beautiful beaches and urban parks, perfect for a day of relaxation or family picnics. With its stunning views of the Ko'olau mountains, Kaneohe is an inviting destination for those seeking both excitement and natural beauty.
  • Lanikai: Nestled in the vicinity of Kailua, Lanikai is a picturesque neighbourhood famed for its pristine beaches and outdoor recreational opportunities. This area is ideal for families looking to immerse themselves in nature, with access to scenic hiking trails that lead to breathtaking views of the ocean and the Mokulua Islands. The sandy shores of Lanikai Beach are perfect for sunbathing and swimming, while the nearby campgrounds offer a chance to connect with nature. With its tranquil atmosphere and stunning landscapes, Lanikai is a dreamy spot for relaxation and adventure alike.
  • Kalama Tract: Located in close proximity to Kailua, Kalama Tract is a charming neighbourhood that blends outdoor enjoyment with a bustling city vibe. Families will appreciate the variety of amenities, including shopping centres and malls, where one can find everything from local goods to international brands. The area is also home to inviting campgrounds, perfect for a family outing or a weekend getaway. With easy access to beautiful beaches and urban parks, Kalama Tract offers a delightful mix of leisure and fun for visitors looking to explore the best of what Kailua has to offer.

Best time to go to Kailua

If you're planning a trip to Kailua, it's a good idea to check both the weather and property rates. The warmest month is September. Peak season runs in March to April and July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January73.4°F (23.0°C)No Rain (Dry)Mostly SunnyAverageAverage
February72.7°F (22.6°C)No Rain (Dry)Mostly SunnyAverageAverage
March72.9°F (22.7°C)Light RainMostly SunnySlightly HighAverage
April74.1°F (23.4°C)No Rain (Dry)Mostly SunnySlightly HighAverage
May75.6°F (24.2°C)No Rain (Dry)Mostly SunnyAverageAverage
June77.0°F (25.0°C)No Rain (Dry)Mostly SunnyAverageSlightly High
July77.9°F (25.5°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
August78.4°F (25.8°C)No Rain (Dry)Mostly SunnyAverageAverage
September78.8°F (26.0°C)No Rain (Dry)Mostly SunnyAverageSlightly Low
October78.3°F (25.7°C)No Rain (Dry)Mostly SunnySlightly LowSlightly Low
November76.5°F (24.7°C)No Rain (Dry)Mostly SunnySlightly LowSlightly Low
December74.5°F (23.6°C)Light RainMostly SunnySlightly LowSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can achieve considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, make use of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a handy platform for you to plan new journeys, continue from where you last stopped, or manage your existing arrangements. You can easily access the properties you've saved or reserved, organised into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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)
  • 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)
  • Kailua Beach (0.9 mi / 1.4 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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