9 Best Vrbo Vacation Rentals in Kailua - Updated 2024

Marilia
Marilia 
Updated
| 5 min read

Kailua is a beach town only 30 minutes away from the hustle and bustle of Honolulu. In the 4 km (2.4 mile) long beach, you can enjoy the sun and the sea or try windsurfing in one of the top destinations in the world. Sometimes, all you need for a vacation is a home by the beach, where you can hear the waves on the shore while you fall asleep. Maybe you could even jump in the sea and enjoy the water without taking a car, or bike. Just walk a few meters and jump in. Find a home away from home in your search for ‘vitamin sea’ in one of the following Vrbo vacation rentals in Kailua.

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 04, 2024.

1. Charming home overlooking Kailua Bay (from USD 330)

This vacation home in Kailua offers comfortable accommodations near Kailua Bay Beach and Kalama Beach Park. Sit in the sitting area and enjoy a view of the Kailua Bay and mountains while you sip your morning coffee or you can lay a blanket and have a picnic in the backyard. The property also features a fully equipped kitchen. On lazy afternoons, stay indoors and watch a show on TV or read one of the books in the rental while you wait for a view of the sunset.

Stayed at this property?
Kailua, Hawaii, United States
17.43 km (10.9 mi) from Diamond Head State Monument
Apartment 2 Guests 1 Bedroom 1 Bathroom

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2. Spacious home with a private balcony (from USD 375)

Perfect for families or big groups, this lodging in Kailua, Ohau, offers a private balcony so you can enjoy the island’s beauty while sitting in one of the loungers. Head to the beach, within walking distance, and sunbathe on the beach or enjoy swimming in the beautiful blue waters. On good days, have a fun cookout on the grill and dine in the first-floor lanai while the fresh sea breeze stimulates your appetite. The property also features a fully equipped kitchen indoors.

Stayed at this property?
Kailua, Hawaii, United States
16.74 km (10.4 mi) from Diamond Head State Monument
PRIVATE VACATION HOME 10 Guests 5 Bedrooms 6 Bathrooms

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3. Oceanfront property with a hot tub (from 1750 USD)

If luxury is what you are looking for, then this accommodation in Kailua will most certainly not let you down. This amazing property offers 4 bedrooms and 3 bathrooms where you can enjoy gorgeous views of the famous Mokulua Islands and Lanikai Bay. The contemporary decoration will make you feel like you are in a 5-star hotel, only with more privacy and without the rest of the travelers. The best feature of this house is the beach access to the ocean. Other than that you can also find a hot tub, WiFi, cable TV, a guest computer, and an amazing fully equipped kitchen. This property can also contribute to the realization of your dream wedding.

Luxury Ocean Front Lanikai 4/3.5

Price: from 1750 USD

Number of Guests: 10

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4. Hawaiian-style home in front of a secluded beach (from USD 712)

This is the perfect vacation rental for a family vacation and chill, fun times by the beach. The house is fully equipped with a pantry and all the beach accessories you can possibly imagine. The house is built in front of a secluded private beach but it is also in walking distance from the popular for windsurfing, Kailua Beach. The four bedrooms are furnished in Hawaiian style and the hosts will ensure that you wont get bored or miss any beach toys during your stay in this amazing property.

Stayed at this property?

16.86 km (10.5 mi) from Diamond Head State Monument
49 reviews   Wifi Available
House 8 Guests 4 Bedrooms 5 Bathrooms

Accommodates: 8
Minimum Nights: 30
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Host:
daniel and virginia were wonderful hosts
the owners were welcoming and helpful
owners were very easy to deal with
and they are wonderful owners who take great pride and care of their home
the owners and this place are impressive in every way
Location:
the location is great
this is the ideal location if you are looking for a hawaiian house vacation
what a fantastic location and home
this is an an amazing property location with simple access to kailua town honolulu and anywhere on the island
thank you for an amazing stay in an amazing location
Read more reviews
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5. Cozy apartment with views of Lanikai Beach (from 195 USD)

Feel at home and relax on the hammocks at the balcony of this cozy apartment very close to the beach. This beautiful Hawaiian style decorated house offers everything you will ever need for the perfect beach vacation. You can enjoy amazing views of Lanikai Beach while you spoil yourself in the Softub Spa. Rumor has it that Patty your host is super friendly and might even cook a traditional meal for you.

You Could be Here - Sweeping Views of Kailua, 1.1 Mi To Beach

Price: from 195 USD

Number of Guests: 4

Stayed at this property?

6. Serene and gorgeous beachside retreat (from 375 USD)

This location is perfect for a relaxed and quiet vacation a little bit further away from the center of the noise and party. You can access the beach on foot in only a few minutes. This amazing studio has everything you need for the perfect beach vacation and comes in a size that is just right. However, we have to mentioned that it is extremely popular and usually gets booked fast, so plan your vacation here in advance.

Serene and Gorgeous Beachside Retreat. Peerless Location, Easy Beach Access

Price: from 375 USD

Number of Guests: 3

Stayed at this property?

7. Beautiful hideaway best for families (from 895 USD)

Have you ever dreamed of waking up and falling asleep right by the beach? This amazing vacation rental with a private pool with traditional Hawaiian decoration is the perfect place for families who want to live right by the beach and enjoy a fun and private vacation together, swimming carelessly in the pool and cooking meals on the outdoor BBQ. It is close to restaurants and just as secluded as you would want it to be, away from the noise and hard-partying crowds in a city like Honolulu.

One of a Kind - Fun Family Home on Beach Access, Private

Price: from 895 USD

Number of Guests: 8

Stayed at this property?

8. Peaceful retreat with ocean views (from USD 2350)

If privacy and quiet are what you are seeking, right at the end of Lanikai you will find this amazing cottage rental in Kailua with an exclusive secluded beach, accessed only by 5 houses. The cottage, overlooking the crystal clear sea, is right in front of the beach that you will be able to enjoy just by yourself. Your only disturbance will probably be the giant sea turtles that often visit the shore to greet the tourists.

The newly decorated bright interiors overlook the ocean and you can choose between 3 double bedrooms, where you will listen to the waves from. If you get bored of all the peace and quiet, you can visit Kailua where there are plenty of shops, bars and restaurants.

Stayed at this property?

16.35 km (10.2 mi) from Diamond Head State Monument
71 reviews   Wifi Available
House 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
beds are so comfortable linens plentiful kitchen beautifully stocked with everything you can think of (waffle iron? amazing)
Cleanliness:
the wildlife:keep the kitchen clean to deter the ants
Host:
the owner is easy to communicate with and helpful
the property owner and manager gina couldn’t have been more accommodating and helpful
gina is the most gracious and hospitable owner
gina was so helpful and a pleasure to deal with
Location:
yet it’s an easy walk to lanikai beach
the perfect house and location for our family of 6
yes the house is that close to the gentle waves
Read more reviews
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9. Charming cottage with a pool and hot tub

Nicky, the cat and the owners of the Blue Ginger Cottage will welcome you to this wonderful property that you can rent for two nights or more. You can chill in the hammocks in the serene garden, choose where to relax between the hot tub or the pool, or walk to the beach. Every Sunday, the host family organizes Bubbly Sunday with potluck, some prosecco, and sometimes the hot tub. Together with the house comes fresh flowers, breakfast items and a full fridge.

Stayed at this property?

16.29 km (10.2 mi) from Diamond Head State Monument
52 reviews   Wifi Available
cottage 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
the place might be cozy for 5 people but the outdoor space was enjoyable
the cottage was well presented with comfortable beds and a beautiful outdoor area and garden
it is a beautiful property with wonderful yard space and access to the hot tub and swimming pool
the backyard is so welcoming with a pool and jacuzzi
thank you perfect location and yard and pool were such a great fit for the children
Cleanliness:
the unit was clean and very comfortable
Host:
our hosts were fabulous
most hospitable hosts that made you feel like family
we had a great stay at kailua and cannot thank our hosts enough for sharing their home with us
susan and claude are very gracious hosts and answer any questions you may have about the area
if we ever return to visit oahu again we will certainly stay with our hosts again
Location:
great location so close to restaurants stores and beaches
we loved the gorgeous quiet location and the beautiful beaches of kailua
it really was so welcoming and convenient in it's location for a quick stop between excursions
we love this side of the island because it is so calm and beautiful
Read more reviews
Oops, this listing is currently inactive. Check out these alternative properties in the same location.
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Kailua Beach: a serene vacation spot

There are more than enough options for a relaxed and chilled vacation in Kailua for either families or couples. Kailua, which in Hawaiian means “two seas” or “two currents,” a contraction of the words “kai” (meaning “sea” or “sea water”) and “elua” (meaning “two”), has enough secluded accommodation options for everyone who wants to avoid the noises and disturbances of Honolulu.

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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Marilia Kaisar is a multidisciplinary storyteller from Greece. She identifies as a traveler, an artist, a writer, a journalist or an architect according to the circumstances. She is currently...Read more

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