Kailua Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Kailua

Pool
Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!
10.0 out of 10, Exceptional, (3)
"My husband and I enjoyed six wonderful weeks in this house. From the moment we drove down that palm tree-lined road and stepped into the walled off courtyard, we knew we had picked the right place for our get-away. The house was tastefully and comfortably appointed. The kitchen, laundry room and bathrooms were all fully outfitted. We slept so well in the luxurious bedrooms, lulled by trade winds at night and waking to birds chirping in the morning. The outdoor lanai and backyard furniture made...
Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!
On the beach, beach towels
BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LUSH PROPERTY
9.2 out of 10, Wonderful, (114)
"Great location."
BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LUSH PROPERTY
Suite, 2 Bedrooms, Ocean View
Aston Waikiki Sunset
4.0 star property
7.8 out of 10, Good, (2720)
"Overall everything was great. I gave it a 4 because we paid for the week of parking and 3/5 days they oversold the parking so we had to park and pay at the zoo. Also bigger vehicles not a good idea as we couldn’t park one of our vehicles here at all due to height. We know for next time to get a smaller car too. But we paid for 5 days of parking and 3/5 days ended up paying somewhere else for parking. Property also didn’t fill our soaps and towels fully each time so we had to ask for...
The price is CA $245
CA $346 total
includes taxes & fees
Jun 19 - Jun 20
Aston Waikiki Sunset
Save an average of 15% on thousands of hotels when you're signed in
Lobby sitting area
Kuhio Banyan Club
2.0 star property
6.8 out of 10, (1668)
"Overall good - staff (friendly and helpful), location outstanding to Waikiki Beach, shopping, food, and local markets/events. Room clean and sufficient for overnight stay (we were heading out on a cruise next day). Murphy bed was comfortable enough but difficult to get to go back in properly. Overall stay was good but was surprised at the high additional resort charge for a 1 night stay! "
The price is CA $145
CA $228 total
includes taxes & fees
May 27 - May 28
Kuhio Banyan Club
Condo, 1 Bedroom, City View (Unit 55 ,1Bath) | Terrace/patio
Regency on Beachwalk Waikiki by OUTRIGGER
3.5 star property
8.0 out of 10, Very good, (337)
"Jacques was amazing and so helpful!! Everyone who worked there was so friendly and helpful!! The outside of the hotel wasn’t impressive, but the room was really nice and updated. The full kitchen was awesome with so many appliances with the rice cooker and the blender. It was very comfortable and functional. Worked perfectly for me and my kids. "
The price is CA $247
CA $852 total
includes taxes & fees
Jun 15 - Jun 16
Regency on Beachwalk Waikiki by OUTRIGGER
Interior entrance
Aston at the Waikiki Banyan
3.0 star property
7.2 out of 10, Good, (2393)
"It was great only thing was food was left behid in refrigerator and cabinets found some molded bread in cabinet… couplle roaches in tub…."
The price is CA $218
CA $309 total
includes taxes & fees
May 27 - May 28
Aston at the Waikiki Banyan
View from property
Aston Waikiki Beach Tower
4.0 star property
9.2 out of 10, Wonderful, (1638)
"Very boutique service and the staff was extremely responsive. "
The price is CA $997
CA $1,248 total
includes taxes & fees
Jun 4 - Jun 5
Aston Waikiki Beach Tower
Beach nearby
Royal Kuhio
3.5 star property
8.6 out of 10, Excellent, (333)
"It was very clean and quiet!"
The price is CA $314
CA $371 total
includes taxes & fees
May 28 - May 29
Royal Kuhio
Studio, Ocean View (Unit #1305)
Waikiki Shore by OUTRIGGER
3.0 star property
8.0 out of 10, Very good, (374)
"Waikiki Shore is great, great location, great view from balcony, easy, clean. We will be back. "
Waikiki Shore by OUTRIGGER
On the beach, sun loungers, beach umbrellas
Castle Waikīkī Shores
3.0 star property
8.2 out of 10, Very good, (1107)
"The weather was bad most of the time, but it was a great stay!"
Castle Waikīkī Shores
Exterior
Hilton Grand Vacations Club at Hilton Hawaiian Village
4.0 star property
8.6 out of 10, Excellent, (698)
"Property was very safe and walkable. The 2 bedroom with 2 bathrooms was spacious. It even had 2 large balconies. "
The price is CA $436
CA $579 total
includes taxes & fees
Jun 2 - Jun 3
Hilton Grand Vacations Club at Hilton Hawaiian Village
Outdoor pool
Espacio The Jewel Of Waikiki
5.0 star property
9.8 out of 10, Exceptional, (14)
"Beautiful property and condo like accommodations with the floor all to ourselves. Highest level concierge services I have experienced with transportation services to and from airport included in stay. Will definitely be back! "
The price is CA $2,349
CA $2,772 total
includes taxes & fees
Jun 26 - Jun 27
Espacio The Jewel Of Waikiki
Exterior
Aqua Skyline at Island Colony
3.0 star property
7.2 out of 10, Good, (1913)
"Rooms need to be updated. Drapes were extremely past due to be replaced. Can’t beat the view of the ocean, canal & Diamond Head. Pool area and laundry were great. "
The price is CA $204
CA $280 total
includes taxes & fees
May 28 - May 29
Aqua Skyline at Island Colony
Beach nearby, white sand, sun loungers, beach umbrellas
Tropical Studios at Marine Surf Waikiki
3.0 star property
8.2 out of 10, Very good, (291)
"Good location "
The price is CA $167
CA $358 total
includes taxes & fees
May 27 - May 28
Tropical Studios at Marine Surf Waikiki
Property grounds
COZY STUDIO WITH WAIKIKI, OCEAN AND DIAMOND HEAD VIEW. FREE WI-FI.
9.6 out of 10, Exceptional, (109)
"We really enjoyed our visit to Hawaii and Michael’s property was perfect for us there was a strange smell from fridge which did linger on items we chilled so refrained from using but overall good and worked for us and our budget! Would stay again"
COZY STUDIO WITH WAIKIKI, OCEAN AND DIAMOND HEAD VIEW. FREE WI-FI.
Pool
Clean studio in the heart of Waikiki!!
8.6 out of 10, Excellent, (22)
"Great spot for the price, perfect walking distance to pretty much everything. A ton of food trucks right across the street and just around the corner from some really cheap (for hawaii) bars. Will definitely be staying here again."
Clean studio in the heart of Waikiki!!
Studio | Pool
Spacious & Sophisticated Palms Studio Condo by RedAwning
3.0 star property
Spacious & Sophisticated Palms Studio Condo by RedAwning
Beach
Oceanside Estate - Spacious home with Pool & AC
10.0 out of 10, Exceptional, (1)
"We all enjoyed the property. It was a ways away from most activities but was quiet and we fit perfectly. The family all travel extensively and use B and B's and other means.. We did enjoy our stay and would recommend it."
Oceanside Estate - Spacious home with Pool & AC
Reception
Ala Moana Condo by Orgoto
3.5 star property
5.8 out of 10, (22)
"Air conditioning wasn’t working for first two days, room was moldy, hit and miss communication "
The price is CA $210
CA $560 total
includes taxes & fees
Jun 11 - Jun 12
Ala Moana Condo by Orgoto
View from property
Aloha Suite Near the Sea I, 3 min Walk to Beach! Great Location!
9.8 out of 10, Exceptional, (139)
"This stay was in a great location, even closer to the beach than I pictured! Perfect for people renting a car (the parking garage underneath has windows with lots of spots). If you are concerned about parking - early morning and late night (after 8 pm) are best times to get zoo parking. During the day we had luck with the garage right underneath this unit. Peter was very helpful, check in and checkout were a breeze. A great deal compared to some of the pricier hotels surrounding!"
The price is CA $101
CA $388 total
includes taxes & fees
Jun 3 - Jun 4
Aloha Suite Near the Sea I, 3 min Walk to Beach! Great Location!
Don't see what you're looking for?
See all available properties in Kailua
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Kailua you may be interested in

Pool
Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!
10.0 out of 10, Exceptional, (3)
"My husband and I enjoyed six wonderful weeks in this house. From the moment we drove down that palm tree-lined road and stepped into the walled off courtyard, we knew we had picked the right place for our get-away. The house was tastefully and comfortably appointed. The kitchen, laundry room and bathrooms were all fully outfitted. We slept so well in the luxurious bedrooms, lulled by trade winds at night and waking to birds chirping in the morning. The outdoor lanai and backyard furniture made...
Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!
View from room
Hilton Hawaiian Village Waikiki Beach Resort
4.0 star property
8.2 out of 10, Very good, (6546)
"Hilton went over and beyond to make sure me and my family enjoyed our first trip to Hawaii. We had zero bad experiences here. Would definitely take my family here again. Kids were 12 and 9 and they loved it here. Dont hesitant to book here if you're family traveling "
The price is CA $458
CA $621 total
includes taxes & fees
Jun 1 - Jun 2
Hilton Hawaiian Village Waikiki Beach Resort
On the beach, beach towels
Hyatt Regency Waikiki Beach Resort & Spa
4.0 star property
8.6 out of 10, Excellent, (3288)
"Beautiful beaches "
The price is CA $343
CA $484 total
includes taxes & fees
Jun 16 - Jun 17
Hyatt Regency Waikiki Beach Resort & Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Kailua. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Kailua?

Yes, we offer vacation rentals near the most popular sights in Kailua, or you can select a more secluded option if you want a relaxing place to stay. Nature enthusiasts will enjoy the popular beaches in Kailua.

What are some of the best vacation home rentals in Kailua?

Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!: This Kailua vacation home rental is located near the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the spa tub in this rental home to help you unwind. Another good choice for your trip to Kailua is BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LUSH PROPERTY.

How many vacation rentals are there in Kailua?

With 181 Expedia vacation rentals, you're sure to find just the right place for your Kailua stay.

What’s there to see and do in Kailua?

Kalama Beach Park and Kailua Bay Beach are a couple of lovely local spots to get outside and enjoy nature. You’ll find favorite places to visit like Ala Moana Center and Waikiki Beach Walk in the larger area.

What’s a vacation rental in Kailua like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Kailua. Vacation rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a small group gathering.

Recent reviews of Kailua properties
Expedia verified reviews