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Tradewind Bungalow, in Kailua on Oahu

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A cozy kitchen with wooden cabinets, a microwave, and a dining area with a table and chairs. - Tradewind Bungalow, in Kailua on Oahu (Kailua)
A bathroom with two sinks, a large mirror, and a shower. - Tradewind Bungalow, in Kailua on Oahu (Kailua)
A patio with a table and chairs, a covered area, and a wall with dense foliage. - Tradewind Bungalow, in Kailua on Oahu (Kailua)
A cozy living room with a sofa, a dining table with chairs, a television, and a ceiling fan. - Tradewind Bungalow, in Kailua on Oahu (Kailua)
A residential property with a wooden deck, a grassy lawn, and a variety of trees. - Tradewind Bungalow, in Kailua on Oahu (Kailua)
A short walk from Kailua Beach, Tradewind Bungalow, in Kailua on Oahu provides a garden, a playground and laundry facilities. Stay connected with free in-room WiFi.

Reviews

9.8 out of 10
Exceptional

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning

Add dates for prices

About this property

Tradewind Bungalow, in Kailua on Oahu

  • Attractive, spacious ground floor, 2 bedroom, 1 split bathroom unit with a separate living room and private entry. Located on the island of O’ahu, you'll find comfort and relaxation here while on vacation. A 6-8 minute walk to the world famous Kailua Beach. The exciting night life of Waikiki is a short 25 minute drive away. The Tradewind Bungalow is the ideal location while vacationing in Hawaii. All the rooms have been repainted and feature newer wood laminate flooring throughout. The large kitchenette is brand new as of August 2024.

    ONLY ONE BATHROOM IS AVAILABLE.. NO SMOKING OR VAPING ALLOWED IN THE UNIT.

    The first bedroom is 11 by 12 sq. ft. and has a queen size bed, a dresser, a window AC and a large closet This bedroom also accesses the outside lanai. This bedroom is also the most private and quiet of the two bedrooms. A sliding glass door allows access to a private patio with a umbrella table, chairs and a gas barbecue.

    The second front bedroom is 12 by 15 sq. ft. and has a queen size bed, two side by side closets and a large dresser.

    The front room is 13 by 15 sq. ft. This room is furnished with a three person queen size Italian leather sofa bed couch, a 55 inch OLED SMART TV complete with a Spectrum cable box., a four person dining table expandable to six persons and a built in kitchen.

    High speed Internet access available. Boogie boards, 4 beach chairs, beach towels and a cooler are available for a fun day on the beach. There is a full kitchenette with a quartz countertop with a drop in sink, a full size wall mounted microwave unit, a toaster oven, a toaster, a coffee maker, a two burner hot plate, and assorted cooking utensils plus a large breakfast griddle. There is also a full size refrigerator.

    Washroom/bathroom/shower combination. The split bathroom has a privacy door separating the shower and toilet from the double sink cabinet. There are also two hallway privacy doors separating the bathroom from each bedroom. Washer and dryer available. Air conditioning in only the back bedroom.

    Convenient street parking.

    The queen size Italian leather sofa bed is of top quality and is very comfortable. It pulls out easily and can be retracted with minimal effort.

    The unit is best suited for no more than 5 adults or 4 adults and 2 children. How ever the three queen size beds can sleep 6 adults.

    Please e-mail me for any special requests as I try to be as accommodating as possible. Baby playpen available.

    Located in the beach town of Kailua which has a great assortment of restaurants and shops. The vacation unit is on Kakahiaka Street which, in my opinion, is one of the nicest residential streets in all of Kailua. Close to both the beach and Kailua Town with minimal traffic.

    Guests have free use of a large quality LG washer and dryer located conveniently outside the front door.

    The City & County of Honolulu now requires stays of 29 days or longer as per local laws and regulations. The state of Hawaii and the C&C also impose an 18.5% hotel and excise tax on all vacation rentals and hotel rooms on the island. No exceptions.

    DOGS ARE WELCOME!! Small to medium size. 1-2 dogs

    Keywords: Single family home. One level, no stairs or steps inside or outside.
    Minimum 29 Day Stay Due to City & County Regulations.

Similar properties

About the area

Located in Enchanted Lake, a neighbourhood in Kailua, this holiday home is near theme parks and near the beach. International Market Place and Waikiki Beach Walk are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Kailua Beach and Lanikai Beach. Travelling with kids? Consider Honolulu Zoo, or check out an event or a game at Blaisdell Arena. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and cycling nearby. Visit our Kailua travel guide
View more Holiday homes in Kailua
Map
Kailua, HI

What's nearby

  • A coastal town with houses, palm trees, and two prominent islands in the ocean.
    Kailua Beach
    15 min walk - 0.8 miles
  • A beach with clear turquoise water, a sandy shore, and two small islands in the distance during sunset.
    Kalama Beach
    1 min drive - 0.5 miles
  • A beach with clear turquoise water, a sandy shore, and several boats lined up on the right.
    Lanikai Beach
    5 min drive - 1.9 miles
  • A beach with palm trees, a statue, and people relaxing under umbrellas.
    Waikiki Beach Walk
    34 min drive - 18.9 miles
  • A beach with people swimming and sunbathing, palm trees, and tall buildings in the background.
    Waikiki Beach
    35 min drive - 19.1 miles

Getting around

  • Honolulu, HI (HNL-Daniel K. Inouye Intl.)
    28 min drive

Restaurants

  • Goen
    17 min walk
  • Paia Fish Market Kailua
    18 min walk
  • Maui Brewing Company Kailua
    17 min walk
  • Teddy's Bigger Burgers
    16 min walk
  • Morning Brew
    16 min walk

Frequently asked questions

Is Tradewind Bungalow, in Kailua on Oahu pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 23 kg per pet.

How much is parking at Tradewind Bungalow, in Kailua on Oahu?

On-site parking is available at the property.

What time is check-in at Tradewind Bungalow, in Kailua on Oahu?

Check-in begins at 3:00 PM.

What time is check-out at Tradewind Bungalow, in Kailua on Oahu?

Checkout is at 10:00 AM.

Where is Tradewind Bungalow, in Kailua on Oahu located?

This family-friendly Kailua holiday home is located near the beach, within 2 mi (3 km) of Kailua Beach and Lanikai Beach. Kalama Beach Park and Lanikai Pillboxes Trailhead are also within 2 miles (3 km).

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Reviews

Tradewind Bungalow, in Kailua on Oahu Reviews

9.8

Exceptional

9.6

Cleanliness

9.8

Location
Rating 10 - Excellent. 127 out of 148 reviews
Rating 8 - Good. 19 out of 148 reviews
Rating 6 - Okay. 1 out of 148 reviews
Rating 4 - Poor. 0 out of 148 reviews
Rating 2 - Terrible. 1 out of 148 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We can definitely recommend this place to other travelers! It is very conveniently located in Kailua, walking distance to both the beach and the town center (about 15 min each). Leonard is a responsive and considerate host, and the place is excellently equipped. Street parking was always available right in front of the house, as was laundry, a BBQ, and beach gear. The vegetation around the place is very well maintained and gives it a nice windward atmosphere. A place to come back to!
Stayed 30 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was our second month-long stay at Tradewind Bungalow. We return for the 10-min walk to the beach or to town, the easy parking and a nice layout for a work-vacation with two bedrooms and a back patio. Would stay again!
Stayed 30 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location and responsive host!

This location was ideal! A quick walk to the public beach access, coffee shop and restaurants. Leonard was a gracious host--there for anything we needed and even appreciated our daughter's early morning violin practice. We had a great stay here!
Stayed 30 nights in Dec 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Experience!

Our stay in Kailua was awesome! The location is perfect - close to the downtown area and walkable to Kailua beach park. Leonard is a fantastic host! We will definitely be back to stay here again.
Stayed 30 nights in Apr 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very comfortable relaxed privacy

Nice location, easy access to shops and restaurants, convenient access to transportation and road systems. Close to beaches. Host and all persons on site were helpful and
Stayed 30 nights in Mar 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous!

we had a wonderful time. Stay at this property; it had everything we needed. It was so close to the beach and nearby restaurants, it was truly a relaxing, peaceful place to be. Our host Leonard was courteous and knowledgeable and really fun to talk with. I would 100% recommend this property if you’re looking for a great place to stay!
Stayed 40 nights in Mar 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great fit for us!

We were two adults plus a 20-lb dog, stayed for a month and combined vacationing with a bit of remote work. The place is located on a wonderfully quiet neighborhood street a 10-15 min walk to the beach, also a small store and couple of restaurants. Owner is nearly always onsite if you have any issues (we did not). Enjoyed our stay!
Stayed 32 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Paradise in Kailua

Wonderful we will be back! Host Leonard is thoughtful and kind. He can give you tips on things to see or tell some of the history on Hawaii. He likes to see that his guests are happy! So close to the beach. Walked every day to the beach. Walked to lovely town each evening. Super places to eat just within walking distance. Their is a new grill at the house you can BarBQ . And eat outside after. Their is a large refrigerator so you load up on drinks and food. Many places to get fresh Hawaiian fruit. Everything you you need to make a meal at home, Loved the blender for smoothies Every Thursday in town is a lovey outside market. Live music, food booths and produce for sale. We felt very at home here. Wish we could have stayed longer than a month. Aloha till next time Tammy and Doug
Stayed 29 nights in Jan 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely small 2 bedroom

This is a lovely little two bedroom apartment with one bathroom. The first thing I have to say is it the host is an incredibly wonderful man, and very helpful with everything concerning the apartment and even my flat tires! The air conditioning unit is only in the small bedroom, but most of the time you don’t need an air conditioner the overhead fans usually suffice. The owner has two wonderful dogs and it is pet friendly. His border collie got used to coming to me for treats as I would come home from my families visit and my little teacup poodle of 5 pounds Would try to avoid her! The border collie, and his Rottweiler are very gentle, lovely dogs and they don’t bother you they don’t bother anybody. It’s a short distance from everything including the beach and I can’t say enough wonderful things about the owner.
Stayed 30 nights in Jan 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful quiet neighborhood, Leonard was a great host if we needed anything he had it to us right away. Walking distance to beach and shopping. If you have a child there’s a park the next street over, that was a fan favorite in our household! Having just a kitchenette was no problem since there is a beautiful grill in the back yard.
Stayed 31 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a fantastic stay! The location was perfect—close to everything we needed and easy to get around. We especially enjoyed the 10-15 min walk to the local, charming Kailua beach. The neighbourhood was quiet, safe, and full of charm with great local spots nearby. Our host was incredibly responsive and helpful throughout the entire stay, making everything smooth and stress-free. Highly recommend this place for anyone looking for a comfortable and well-located stay!
Stayed 32 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great long term stay!!

Great location!! There was plenty of room and had the amenities necessary for my long term stay. It was walking distance from the beach and many shops and restaurants. I look forward to staying here again.
Stayed 68 nights in Apr 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a fantastic 35 day stay! The location was perfect—it’s an easy 20 min. walk into the charming town of Kailua with stores to buy everything we needed and plenty of restaurants to enjoy. We especially appreciated the short 15 min walk to gorgeous Kailua beach - heaven! We even walked to Lanikai Beach. The neighborhood was quiet, safe, and we were impressed with the friendliness of everyone we met. The rooms were tidy, clean and very well appointed and the beds were comfortable. We had everything we needed. Our host was incredibly responsive and helpful throughout the entire stay, making everything smooth and stress-free. It was a wonderful place to stay for us and we fully intend to come back.
Stayed 37 nights in Jan 2026
Verified review

10/10 Excellent

Great location and roomy.

Great location and amenities. Obliging host. Thanks!
Stayed 7 nights in Feb 2018
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Vacation for the Family

Easy walk to the beach and a few restaurants, rental and marketplace. Everyone enjoyed being able to do what they wanted without being tied to a car for rides.
Stayed 6 nights in Jun 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful time

Excellent location. Friendly owner, not one problem
Stayed 7 nights in Mar 2020
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great!

Enjoyable stay. All was fine. Just as described.
Stayed 30 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Incredible Hawaii vacation

Our host is incredibly kind and warming with an abundance of local knowledge. The property is extremely well appointed with grill, stove burners, small oven, full fridge, great quality plates and flatware. The beds are very comfortable The beach is very close So many wonderful restaurants to enjoy your favorite “worldly” meals I am thoroughly impressed with how the owner is constantly grooming the beautiful yard and landscaping and maintaining clean and safe walkways A+ rating!
Stayed 31 nights in Feb 2023
Archival

10/10 Excellent

Great Place at a great price!

This place is only 1 mile from Kailua Beach - I rented a bike and went to the beach,the park, shopping and dining - all within 2 miles. Clean, quiet. and roomy. Owner has dogs that are friendly and well-trained & I didn't even see them untilI was leaving. This is my second stay here and I will definitely be back!
Verified review

10/10 Excellent

Great place close to the beach!

We stayed at this unit for 5 nights. It is exactly as described. We arrived late at night but Leonard had provided us with specific directions and instructions for the unit so we walked right in. The 2 beds are nice and comfortable. There are lots of windows to open to get a cross breeze through the unit so there was no need for the AC unit at all. Plenty of beach accessories were available for our use. It would be nice if the beach towels were in the unit. We had to ask for them. Washer and dryer were a greatly appreciated and nice machines. Detergent was even provided. We only heard the dogs bark a few times in the morning but it was never an issue. The yard is beautifully manicured with lots of trees and plants. Easy access to Kailua beach for your morning walk in the sand or your day at the beach. A vehicle is recommended as it is a few blocks to the stores and shops. It is very quiet and peaceful in Kailua. Away from the busy streets of Waikiki! Easy to get around in and lots to see and do within a short drive. We had to make some changes to our dates and Leonard was more than helpful and happy to do it. We would definitely stay at Leonard's place again!
Stayed 5 nights in Apr 2018
Archival

2/10 Terrible

Worst VRBO Experience

I find Tradewind bungalow is not being kept safe, clean and updated to provide positive experience for its guests. - The floor mat at the extrance is so old and dingy that I avoid touching my feet on it when I enter the front door. - The big screen tv are simply left standing on tall shelving which could be tipped over by any capable toddler. - glass sliding door is cracked and broken and masking tape and paint was used to "repair" it. It is a hazard to my toddler. - the owner has 5 Rottweilers kept in two seperate cages. they growl and bark viciously at each other and at us when we return from the beach. I can't believe previous reviewer said the dogs are cuddly, that was back in 2012, with 4 dogs. - finally my biggest complaints is that the property owner uses the same washer and dryer to washes guest sheet, bedding and towels as the dog's bedding. It's only after did my load of laundry and I saw bunches and bunches of black dog hair stuck to the washer door that made me realize we have been using sheets and towels that's been washed with dog beddings. It is simply unacceptable and unhigenic and disgusting to anyone.
Verified review

8/10 Good

Liked: Check-in, communication, location, listing accuracy

Relaxing vacation

We felt we were at home! Spacious bungalow. Nice shower(no bath tub). Was cool indoors with just the fans running even with 30C temps outside. Owner very accommodating. Willing to replace any item in disrepair. Was able to create great meals with the bar fridge, two burner elements, and griddle. Beds were very comfy. 1km walk to beach. Lots of beach chairs, etc. 250m walk to bus stop; #67 takes you to Mall in Waikiki which is a short walk from the Hawaiian Hilton Village.
Stayed 44 nights in Jun 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Absolutely wonderful

The property and homeowner (Leonard) were absolutely wonderful. Everything was clean, cozy, and comfortable. Leonard was a delight to talk to. We were a 7 minute walk to the beautiful Kailua beach and 5 minutes from shopping, grocery stores, and tasty treats. About 30 minutes from all the "big to-do's" on the island. Would definitely recommend.
Stayed 8 nights in May 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Hawaii Vacation

Perfect for our family ! Had everything we needed. Boogie boards , sand pails , mats! The rooms were comfortable. We will stay again sometime!!! Host very nice. Thank You
Stayed 6 nights in Apr 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Prefect

This place couldn’t have been more prefect! It’s located on a small cul-te-sac, with no traffic, 1/4 mile south of town, and the beaches are less than 3 minutes away. The rental has everything you need for the beach. I was initially worried about the little kitchen, especially the size of the refrigerator, as I love to cook, even on vacation. But it worked out perfectly. I had plenty of room for my culinary supplies. And Leonard was a gracious host. Accommodating in every way!
Stayed 11 nights in Mar 2022