7 Vacation Rentals In Kailua, Hawaii - Updated 2024

Felix
Felix 
Updated
| 6 min read

The coastal town of Kailua Hawaii is located in Hawaii, United States. It is known for its dry and sunny climate and many white sand beaches. This has made Kailua a tourist spot. Apart from the white sandy beaches tourist prefer Kailua as their holiday spot because of the activities offered within such as manta ray night dive, Kona coffee, snorkelling, and swimming. In Kailua, you will also get to enjoy watching the sunset outside a restaurant of your choice. While planning your vacation, you do not need to worry about where to stay in Kailua. Just check out this list of the best vacation rentals in Kailua, Hawaii.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 07, 2024.

1. Hawaiian-style studio retreat (from USD 210)

This delightful studio, perfect for couples seeking a romantic getaway, is within walking distance from the stunning Kailua Beach. Experience the essence of island living as you relax and unwind in this charming retreat.

Satisfy your taste buds with a variety of island treats. Treat yourself to the naturally flavoured ice cream or shaved ice at Island Snow. If you prefer a cosy night in, head to Kalapawai Market just a minute’s walk away, where you can stock up on groceries to whip up your favourite dishes, including mouthwatering burgers and sandwiches.

Conveniently located just a 28-minute drive from the Daniel K. Inouye International Airport (HNL) in Honolulu, this Hawaiian paradise is perfect for tourists.

Stayed at this property?
Kailua, Hawaii, United States
16.54 km (10.3 mi) from Diamond Head State Monument
Apartment 2 Guests 1 Bathroom

Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

2. Romantic bed and breakfast at Kailua Beach (from USD 295)

Escape to the ultimate romantic vacation at this enchanting bed and breakfast located at Kailua Beach. Winner of the prestigious “Most Romantic Hideaway” award, this property lets you immerse yourself in the serene surroundings of the garden or relax on the deck. For breathtaking sunsets and leisurely beach walks, Lanikai Beach is just a delightful nine-minute stroll away, providing a picturesque setting for romantic moments.

Kailua town is a mere five minutes away, offering a wide array of dining options. Indulge in culinary delights at restaurants and cafes such as Basalt, Kono’s, and Over Easy, where you can savour delicious meals and experience the vibrant local scene.

Stayed at this property?
Kailua, Hawaii, United States
16.39 km (10.2 mi) from Diamond Head State Monument
bed & breakfast 3 Guests 2 Bedrooms 2 Bathrooms

Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

3. Secluded beach bungalow with private garden (from USD 229)

You can secure this luxurious one-bedroom rental in Kailua, located 10 minutes from the beach, at an affordable price. You will instantly fall in love with this accommodation because of its strategic location close to several important amenities including bars, restaurants cafes and hotels.

If you choose to book this accommodation, you can expect your house to be fully furnished with modern amenities such as air conditioning, a cable TV and a comfy sofa. As for your meals, guests can make their own meals in the kitchen which is equipped with appliances such as a kettle, toaster, microwave, oven and utensils. An ample parking space is also available.

Stayed at this property?
Kailua, Hawaii, United States
16.74 km (10.4 mi) from Diamond Head State Monument
210 reviews   Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the bungalow is cozy and charming with a nice view of the garden and bird bath
we had our morning coffee in the garden room and just stared at the pretty plants + flowers
the small living room with picture window overlooking the garden and fountain is great for relaxing and birdwatching
really comfortable and relaxing stay after coming back from the sunshine all day
the bed is comfortable
Cleanliness:
the space was clean and cozy and the outside decor was beautiful
beautiful garden sparkling clean and best place to stay on oahu
the bungalow is the perfect size for 2 super clean and adorably furnished
the space was more than enough being cozy organized clean and well decorated
location was the best space was amazingly clean
Host:
they were very gracious hosts
hosts friendly and helpful
i can't speak highly enough of our lovely hosts
cheri is a wonderful host
cheri and scott we gracious hosts and made us feel at home
Location:
best location in kailua
the location of the bungalow is perfect
absolute perfection from the drive in to kailua to the walk to the beach
the location is perfect nestled right by the beach and not too far away from kailua town
beautiful as pictured absolutely wonderful location
Read more reviews

4. Immaculate accommodation with privacy (from USD 160)

For a peaceful night during your vacation in Hawaii, you should try out this spacious rental in Kailua located only 10 minutes from the town centre. If you choose this accommodation, you should expect to be strategically located close to various shops, bars, restaurants cafes as well as have easy access to must-do free experiences near Oahu.

For maximum comfort during your stay, the host has introduced several important amenities such as cable TV, air-conditioning, unlimited access to the internet and a comfy sofa. As for your sleeping arrangement, the bedroom is furnished with a double bed, a mirror, a dressing table and a wardrobe. An ample parking space is also available on the premises.

Stayed at this property?

18.01 km (11.2 mi) from Diamond Head State Monument
35 reviews   Wifi Available
House 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3
Minimum Nights: 30
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
The kitchen was modern and easy to make meals in
Updated kitchen and bathroom was fabulous
The beach cottage is contemporary fully stocked and
and it was never crowded
Having an outdoor area that was fenced was excellent for our 3 yr old and 10 month infant who enjoyed playing and eating outdoors
Cleanliness:
The apartment was tastefully decorated and spotlessly clean
extremely clean and very comfortable
Everything was exactly as described
This apartment was exactly as described and pictured
The property is just as clean and spacious as you see in the pictures
Host:
the dog is super sweet too Great beach access and gear
your welcome goody basket and your vacation rental is wonderful
Boo and Kaila made us feel welcome from the moment we arrived Nancy
They went out of their way to make me feel welcome
Our hosts Nancy and Gerry were very attentive and accommodating to our questions and needs yet totally respective of our privacy
Location:
The house is located on a very well kept and calm street Walk 2 minutes
There is a supermarket a few minutes away which is very convenient
This property is very close to one of not the nicest beach on Oahu "Kailua Beach"
It is in a lovely neighborhood of very nice homes
One of our best Hawaii getaway experiences
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

5. Experience Lanikai lifestyle

Come and create unforgettable memories in Kailua, Hawaii as you spend your nights in this charming studio apartment located only three minutes’ walk from the famous Lanikai beach. If you book this apartment, you will be strategically located close to many social amenities including hotels, bars and shops. The apartment is bright, spacious and furnished with all the amenities that you may need during your stay including a comfy double bed, a cable TV, a comfy couch, air conditioning and uninterrupted access to the internet. Guests also have access to their own private bathroom where they will find a walk-in shower and a water closet. A safe and secure parking space is also available.

Stayed at this property?
Kailua, Hawaii, United States
16.88 km (10.5 mi) from Diamond Head State Monument
199 reviews  
Entire apartment 1 Bed 0 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
the apartment is easily accessible and has all the amenities--including beach gear--that you need
wifi worked as well will return to stay
we didn't cook but the kitchen seemed nice and i took advantage of the keurig coffee provided
the bed was super comfortable and the kitchen was well stocked for making coffee and for cooking
the room is perfect everything you need and exactly like the photos show
Cleanliness:
very clean and very affordable
place was clean and well kept
it was also very clean and quiet
kathleen’s place is beautiful very clean and neat
the unit is very clean an confy for two persons
Host:
my host was very helpful
and host family are so kind persons
the host is very kind and generous
kathleen was a great host with quick responses and excellent tips
she was very helpful and responsive
Location:
great location for price
very cute apartment and in a great location
the location was awesome
perfect location just a few minutes walk to a beautiful white sand beach
fantastic location within walking distance of world class beaches and vistas
Read more reviews

6. Tranquil home for a couple

Now that you have decided on your destination, its time for you to select an accommodation that will sort all your needs. For that purpose, you may want to consider this luxurious one-bedroom apartment located in private and quiet in a tropical setting only five minutes’ walk from the beach and Kailua town. The first thing you will love about this accommodation is its spacious nature. Your new home consists of a living room, bedroom, kitchen and a private bathroom. For maximum comfort during your stay, you will have access to various amenities including a cable TV, air conditioning and uninterrupted access to the internet. Other basic amenities such as linen, towels, toiletries are also provided upon request.

Stayed at this property?
Kailua, Hawaii, United States
16.21 km (10.1 mi) from Diamond Head State Monument
296 reviews  
Entire guest suite 2 Beds 1 Bedroom 1 Bathroom

7. An airy yet air-conditioned cottage

Jennie invites you to spend a night or more in her luxurious apartment located less than a mile (0.8 km) from the beach and seven miles from Kailua town. You will find this accommodation very convenient because of its proximity to various social amenities including hotels, bars, restaurants cafes and boutiques. Once you book this apartment you will have access to the whole house which consists of a living room, a single bedroom, a kitchen and a private bathroom. Each room in Jennie’s home is fully furnished with important amenities such as air conditioning, comfy sofas, a cable TV and a music system. As for your sleeping arrangement, the bedroom is equipped with a comfy double bed, a dressing table and a wardrobe. Towels, linen and toiletries are also provided by the host.

Stayed at this property?
Kailua, Hawaii, United States
16.69 km (10.4 mi) from Diamond Head State Monument
103 reviews  
Entire guesthouse 1 Bed 1 Bedroom 1 Bathroom

Explore Kailua, Hawaii, and have fun

Whether you are here for fun or business, you are guaranteed to find an accommodation in Kailua that will suit all your needs, be it luxurious villas, affordable studios or beach house rentals . Book one and enjoy!

Frequently asked questions about vacation rentals in Kailua, Hawaii


Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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