Tradewind Bungalow, in Kailua on Oahu

Kailua · Oahu · 2 bedrooms · 1 bathrooms · Sleeps 6 · 9.8/10 · 146 reviews

Rental Details

Property Overview

Attractive, ground floor, 2 bedroom 1 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.

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. Whenever I have four or more adult guests booked, I make a second full private bathroom available at no additional charge.

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 C&C also imposes an 17.96% 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 & Counter Regulations.

Registration Number: TA-086-379-5200-01, GE-086-379-5200-01

Rental FAQ

Frequently Asked Questions

Where is this vacation rental located?
  • City: Kailua (postal 96734) Hawaii

Nearby highlights

  • Location: Kailua, HI (Downtown Kailua – Windward Coast – 1.32 km to center), United States
  • Near a health or beauty spa
  • Near a zoo
How many bedrooms and bathrooms does it have?

2 bedrooms and 1 bathroom.

How many guests can it sleep?

This rental sleeps up to 6 guests.

What amenities are available?
  • Private vacation home
  • Local culture & ecosystem education
  • Recycling
  • Unit size: 600 sq ft (56 sq m)
  • Water efficient toilets only
  • 2 bedrooms
  • Bed sheets provided
  • 1 bathroom
  • Hair dryer
  • Shower
  • Soap
  • Toilet paper
  • Towels provided
  • Air conditioning
  • Free WiFi
  • Blender
  • Coffee/tea maker
  • Cookware/dishes/utensils
  • Microwave
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster
  • Laundry facilities
  • Near laundromat
  • Washing machine and dryer
  • BBQ grill grill
  • Fenced yard
  • Garden
  • Outdoor furniture
  • Lanai / balcony
  • Car recommended
  • Onsite parking
  • Wheelchair accessible parking available
  • A/C
  • BBQ grill
  • Crib
  • Dryer
  • Free Parking
  • Internet
  • Kitchen
  • Laundry
  • Living Area
  • No Smoking
  • Outdoor Hot tub / space
  • TV
  • Washer
What should I know about check-in?
  • Check in starts at 3:00 PM
  • Check out before 10:00 AM
  • Minimum check in age: 21
  • Check in time starts at 3:00 PM
  • Contactless check in available
  • Contactless check out available
  • You will receive an email from the host with check in and check out instructions
  • Government issued photo identification and a credit card, debit card, or cash deposit may be required at check in for incidental charges
  • Onsite parties or group events are strictly prohibited
  • Property Registration Number TA 086 379 5200 01, GE 086 379 5200 01
What are the house rules and policies?
  • 2 total (up to 50 lbs per pet)
  • Note from host: Please call me regarding pets.
  • Pets allowed
  • Restrictions apply; for more information contact the property at the number on the booking confirmation
  • Service animals are welcome, and are exempt from fees
  • Welcoming dogs only
  • Children are welcome.
  • Onsite parties or group events are strictly prohibited
What are popular things to do nearby and on Oahu?
  • Basketball nearby
  • Bodyboard on site
  • Fishing nearby
  • Fitness facilities nearby
  • Hiking nearby
  • Hiking/biking trails nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Sailing nearby
  • Snorkeling nearby
  • Surfing/body boarding nearby
  • Location: Kailua, HI (Downtown Kailua – Windward Coast – 1.32 km to center), United States
  • Near a health or beauty spa
  • Near a zoo
Do I need a rental car on Oahu, and what about parking?

A rental car is recommended for this area, especially if you plan to explore beaches, restaurants, activities and nearby towns. Parking notes: Car recommended, Onsite parking, Wheelchair accessible parking available.

What kind of rental is this?

This is a bungalow rental.

Is the Check Availability button the official booking link?

The button opens the partner listing page where you can review final rates, fees, availability, policies and booking details.

Guest Reviews

Reviews

Rebecca D.10.0/10
Dec 21, 2025

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!

Mairis O.10.0/10
Sep 1, 2025

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!

Lars I.10.0/10
May 4, 2025

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!

Tammy B.10.0/10
Feb 28, 2025

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

Daniel M.10.0/10
Jan 14, 2025

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!

Rebecca D.10.0/10
Dec 12, 2024

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!

AARON B.10.0/10
Jun 5, 2024

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.

Charles C.10.0/10
Apr 3, 2024

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

Joyce C.10.0/10
Mar 3, 2024

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.

Connie D.10.0/10
Jul 19, 2023

Enjoyable stay. All was fine. Just as described.

Nicholas T.10.0/10
Jun 24, 2023

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.

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Kailua, Oahu

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