Pillows in Paradise Bed & Breakfast

Pillows in Paradise Bed & Breakfast

336 Awakea Rd, Kailua, Oahu, HI 96734-3451
view from the Magnolia room
Traveler (16)
Poolside at Pillows in Paradise
Pool & Beach (5)
locking screen door.
Room & Suite (3)

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About

4.5
#3 of 10 B&Bs in Kailua
4.4 of 5 bubbles
Location
4.7 of 5 bubbles
Cleanliness
4.4 of 5 bubbles
Service
4.4 of 5 bubbles
Value

Finding an ideal family-friendly bed and breakfast in Kailua does not have to be difficult. Welcome to Pillows in Paradise Bed & Breakfast, a nice option for travelers like you.

You’ll enjoy relaxing rooms that offer a kitchenette, air conditioning, and a refrigerator, and you can stay connected during your stay as Pillows in Paradise Bed & Breakfast offers guests free wifi.

Plus, Pillows in Paradise Bed & Breakfast offers a pool and free breakfast, providing a pleasant respite from your busy day. For guests with a vehicle, free parking is available.

During your visit, be sure to check out one of Kailua's popular crab restaurants such as Cinnamon's Restaurant, Buzz's Original Steak House, and Kalapawai Cafe & Deli, all a short distance from Pillows in Paradise Bed & Breakfast.

During your visit, be sure to check out Lanikai Pillboxes (1.0 mi), which is a popular attraction within walking distance of the bed and breakfast.

Pillows in Paradise Bed & Breakfast puts the best of Kailua at your fingertips, making your stay both relaxing and enjoyable.

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Property amenities
Free parking
Free High Speed Internet (WiFi)
Wifi
Pool
Outdoor pool
Non-smoking hotel
Room features
Air conditioning
Kitchenette
Refrigerator
Room types
Non-smoking rooms
Good to know
HOTEL STYLE
Family
Romantic

Location

336 Awakea Rd, Kailua, Oahu, HI 96734-3451
Getting there
Somewhat walkable
Places to stay are graded on a 0-100 scale. The higher the grade, the easier it is for travelers to find restaurants and things to do within walking distance.
Grade: 71 out of 100
71
Honolulu Intl Airport
21.9 km
See all flights
Molokai Airport
65Reviews5Q+A12Room tips
Traveler rating
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Detailed Reviews
Lisa F wrote a review Jan 2020
San Antonio, Texas1 contribution
5.0 of 5 bubbles
We absolutely loved our stay! The owners were welcoming and even took care of our luggage for us after an airline issue. Bed was comfy and sheets were soft even on a sunburn. We had everything we needed for breakfast in the mornings and prep our snacks for outings. We were thrilled to NOT be in the Waikiki area. Traffic was non-existent and it was easy enough to navigate anywhere we wanted to go on the island. The best swim and sun beach on the island is nearby and there are lovely restaurants and many activities nearby. Bear in mind, you’ll need a rental car, but that gives you all the freedom to explore this beautiful island. We loved having our coffee and breakfast by the pool each morning. Don’t miss the nearby Farmer’s Market! We’d recommend Pillows in Paradise to anyone and hope to return one day.
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Date of stay: January 2020Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
MominOC wrote a review Feb 2020
Orange County, California4,852 contributions729 helpful votes
4.0 of 5 bubbles
We stayed in the Magnolia room that is quite small. No seating other than the bed since the chairs were needed to keep the suitcases off the floor. It was very nice to have coffee in the morning in the room. Owners leave coffee & creamer for you to use. They also cut the fresh pineapple for you upon arrival....we enjoyed it all week. The lighting in the room is well done - especially the bathroom! Owners were kind.
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Date of stay: January 2020
5.0 of 5 bubblesLocation
5.0 of 5 bubblesCleanliness
4.0 of 5 bubblesService
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
steeler2005 wrote a review Oct 2003
north carolina17 contributions22 helpful votes
5.0 of 5 bubbles
we stayed at a b&b for the fist time in oahu,hi. we were suppose to stay at a condiminium but they had some damage and had to close it for repairs the week before we were suppose to leave so the people found us this b&b in kailua,hi. on the windward side. it was very private and comfortable. the room that overlooks the pool is the best. (she has three rooms) the hostess gives you a breakfast basket the first morning .we didn't like the beach there only because it was very windy everyday ,so we traveled the island and everyday went to a different beach. nothing was more than 30 min. away and if it was raining on one sde it was usally nice on the other. we loved waikiki but we were glad we didn't stay there due to the noise and congestion. we found free parking in waikiki by the "shell" which is across from the zoo. everywhere else is metered!!!for the money i would highly reccomend a bed and breakfast if you want to stay in the older section of oahu where it is quiet.
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
LenoreA wrote a review Nov 2004
Mill Valley, CA3 contributions28 helpful votes
1.0 of 5 bubbles
It was a traveler's worst nightmare. Booked with Barbara, the owner - I had a confirmation number & she had my credit card number. Arrived at the Honolulu airport late at night on a business trip & called Barbara to let know I was on my way. Cause of my late arrival, she had wanted me to call ahead. But she knew nothing of me! Said her party had already arrived. So there I was, single woman alone with nowhere to sleep. Her answer? I had to go to an airport hotel! After my insisting she look up my confirmation number, her memory refreshed & she mentioned how her daughter booked the other party. My reservation was 'lost.' How hard can it be? After more insisting, she called around Kailua but everything was booked (there are no hotels/motels there, only B&Bs). Finally, she found a neighbor's 2 bedroom cottage, which was more money, more than I needed & dirty. But I took it cause I had a morning meeting in Kailua. So be careful. This woman is a travel agent & should know better.
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
lhhint wrote a review May 2015
Bedford6 contributions16 helpful votes
1.0 of 5 bubbles
I have been all over the world and I have been to Oahu 11 times, so I am being fair in my assumption. Not once when booking or on the website are you told there is a dog roaming the grounds, I took my 12 month grandson so would of been nice to have been told, the owner Barbara also knew I was bringing a baby. when you arrive you are given an A4 list of instructions of shutting gates so the dog cannot get out, do not feed the dog etc. If you leave your door open he will come in. there is a pool, which you are not encouraged to use and if you do you are watched out the window by Barbara the whole time making you feel so uncomfortable you leave. We were even told the next morning our grandson had dropped TWO fruit loops yes TWO and the dog had found them. The accommodation is just a refurbished garage which leads off the owners kitchen so every night all you can hear is the dishes being washed and put away etc. The sheets on the beds are so old they have gone very course and the beds are by no means new or comfortable. I have never felt so uncomfortable staying anywhere in my life. I would never stay there again, it was convenient as our son was getting married locally, I wish we had stayed else where and traveled in daily.
Staying here totally ruined our stay and because of this it will be a while before we re, visit Oahu.
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Date of stay: May 2015
1.0 of 5 bubblesRooms
3.0 of 5 bubblesLocation
1.0 of 5 bubblesService
Trip type: Traveled with family
Room Tip: if you are looking for somewhere in Kailua look elsewhere
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
AUGradAtlanta wrote a review Jun 2006
Madison, New Jersey21 contributions18 helpful votes
3.0 of 5 bubbles
My wife and I returned from 8 days in Oahu. We stayed 3 nights at Pillows in Paradise. We wanted to avoid the craziness of Waikiki but still stay near the SouthEast end of the island. Kailua is a great location if you want to stay away from Waikiki. It was much quieter and the beaches on the Windward coast were great. But, you could be in Honolulu in 20 minutes if desired.

Pillows was a decent place. Nothing to write home about. Based on the rate I paid, I think it was a fair price for what we got. Owner was nice enough but don't expect much in the way of communication. We saw her maybe twice. Breakfast was provided the first day only and was nice fresh fruit and English Muffins with jelly and butter. Room has a fridge, dishes, toaster, hotplate, etc and was well stocked. Coffee provided too. The rest of the trip we stayed at Turtle Bay. I would have likely been disappointed if the entire trip had been at Pillows in Paradise. It was a fine place to use to store our stuff and sleep, but otherwise not a place to hang out. Pool area was nice and tranquil. But I would highly recommend not making this the only place you stay in Oahu. Treat yourself to a few nice nights at Turtle Bay or one of the other really nice resorts.
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Date of stay: May 2006
3.0 of 5 bubblesValue
3.0 of 5 bubblesRooms
3.0 of 5 bubblesCleanliness
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Yslandgyrl wrote a review Mar 2007
Beaverton, Oregon44 contributions33 helpful votes
3.0 of 5 bubbles
My grown son and I stayed here for 8 days in September of 2005. I grew up in Kailua and had not been back for 20 years. I was really looking forward to my first visit home since graduating high school. One of the reasons I booked this room was because of the queen and full beds in the Lanikai Room. The host was nice enough, but average at best. The breakfast consisted of a basket with coffee, english muffins, a mini pineapple, and a couple of bananas. I'm not sure enough breakfast for two days really qualifies as a B&B. It was extremely hot during our stay (mid 90's most days) and the host requested we not run the a/c when we weren't in our room. Problem is that it took 2 hours for the room to cool back down.

Bottom line. I don't think I would stay here again. It wasn't bad but it wasn't great and for the money I think there are much better accomodations available.
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Date of stay: September 2005
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
ronald w wrote a review Jul 2015
Modesto, California7 contributions14 helpful votes
5.0 of 5 bubbles
I was raised in Kailua most of my life and always referred to it as God's country. I know Kailua like the back of my hand although there are many changes, some good and some bad. I discovered Pillows In Paradise through a friend who two years ago stayed at this awesome B&B. This past 4th of July weekend six of us returned and booked all three rooms for two weeks. I can't imagine another B&B in Kailua that can provide the same wonderful accommodations. First of all the location is convenient as it's located so close to Kailua town, Kailua and Lanikai beach, the number 1 and number 2 beaches in the nation. The parking is more than ample in a quiet cul-de-sac and it's free. The rooms all have private entrances and are cool, clean, spacious and very comfortable. The tall Areca palms provide a lot of privacy as well as security surrounding the grounds as well as the swimming pool and gives you that relaxing and peaceful atmosphere.

For those of you that are not satisfied with the fruit basket provided for breakfast, you might google "Restaurants in Kailua" and discover hundreds of places to dine at to fit your palate. Some of my favorites are places like Zippy's, Cinnamon's, Moke's, Assaggio's, Baci Bistro, Big City Diner, Mexico Lindo's, New Mui Kwai Chop Suey, L&L Drive Inn, Bob's Pizzeria and of course Buzz's Original Steakhouse. And if that's not enough then there's always places to dine at in Kaneohe.

I can't say enough about Barbara and Lionel, two of the most gracious and congenial hosts that you will ever meet. They actually treat you like family. As for Rune he is a very clever, kind and gentle dog. He's not frisky like most dogs but well behaved and is not a problem what so ever. And let's face it folks he happens to be part of the fixture. And for those of you that are still not satisfied with the accommodations, then there is still Waikiki where you can enjoy the noisy, rowdy crowd with the no rules barred tourist trap. You can also expect to be charged almost double for the cost of a room and don't forget to add the daily charges for parking and the unforeseen "resort fees". I would highly recommend Pillows In Paradise to all my friends and family as well as to anyone seeking a place to stay in beautiful Kailua and I would give it a rating of at least six stars.

Much Aloha,
Champion
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Date of stay: July 2015
5.0 of 5 bubblesCleanliness
5.0 of 5 bubblesService
5.0 of 5 bubblesSleep Quality
Trip type: Traveled with friends
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
llnjams wrote a review Oct 2011
llnjams29 contributions30 helpful votes
2.0 of 5 bubbles
This place is OK, but quite a disappointment considering the price. The yard and pool are heavily overgrown, and the pool is cold with no sun getting to it. The room was dingy by day and noisy by night with other people's AC units clanking and banging, cutting in and out. We had the largest room, with the King and Queen bed, which really cram up all available space. The bed was comfortable at least, but what really put us off was the kitchen being inside the bathroom; you'd better time your cooking and bodily function requirements carefully. Others have mentioned the one time only "breakfast" which consisted of a .79 cent pineapple and 4 stale bagels with a small pot of jam - they're bang on about that, and also about your hostess vanishing after your first meeting. We took this because we went at the last minute and this was all we could find at the time. If you have time to shop around try to find another place.
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Date of stay: February 2011
1.0 of 5 bubblesValue
2.0 of 5 bubblesRooms
2.0 of 5 bubblesLocation
3.0 of 5 bubblesCleanliness
2.0 of 5 bubblesService
2.0 of 5 bubblesSleep Quality
Trip type: Traveled as a couple
Room Tip: Don't get the big room with the King and Queen unless you're OK with having a toilet in...
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
hugrant171 wrote a review Apr 2009
Denver2 contributions9 helpful votes
2.0 of 5 bubbles
We travel a lot and frequently stay at B&Bs because they are usually charming and offer wonderful insights into the community. We were very disappointed with Pillows in Paradise. It was more like rent a room/daily rates than a Bed and Breakfast. We were booked for three nights and left after two.

While our Lanikai room was clean and spacious, the air conditioner hissed and clanked all night. Access to the room was from street parking through two small gates that made moving suitcases difficult. No information such as local restaurant menus or written directions to places of interest was provided.

Barbara greeted us graciously, and we never saw her again. We had the option of calling her cell phone. The website says a complimentary welcome breakfast basket will be provided for the first morning. It was fruit and a coffee cake from the grocery bakery. Breakfast was up to us for the remainder of our stay- not my idea of a Bed and Breakfast. A note on the table said there would be an additional $35 charge if we did not wash our own dishes.

There was a decided lack of hospitality at Pillows in Paradise, which did not match our expectations.
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Date of stay: March 2009
5.0 of 5 bubblesValue
3.0 of 5 bubblesRooms
3.0 of 5 bubblesLocation
5.0 of 5 bubblesCleanliness
1.0 of 5 bubblesService
Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
allirivera24 wrote a tip Feb 2018
New Fairfield, Connecticut3 contributions4 helpful votes
5.0 of 5 bubbles
"Look at the pictures on line - very accurate."
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winnieconner wrote a tip Jul 2017
Pittsburgh, Pennsylvania1 contribution1 helpful vote
5.0 of 5 bubbles
"Lanikai room"
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Kem wrote a tip Jan 2017
13 contributions7 helpful votes
5.0 of 5 bubbles
"Go to website to choose a room that fits your budget. Price is fair."
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ronald w wrote a tip May 2016
Modesto, California7 contributions14 helpful votes
5.0 of 5 bubbles
"Make your reservations early in order to get the days required."
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Cheri M wrote a tip Mar 2016
Reno, Nevada7 contributions5 helpful votes
5.0 of 5 bubbles
"If you are more than two people choose the white room but the yellow room is perfect for a couple."
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LOCATION
United StatesHawaiiOahuKailua
NUMBER OF ROOMS
6
Prices are the average nightly price provided by our partners and may not include all taxes and fees. Taxes and fees that are shown are estimates only. Please see our partners for more details.
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PILLOWS IN PARADISE BED & BREAKFAST - B&B Reviews (Kailua, HI) - Tripadvisor

Frequently Asked Questions about Pillows in Paradise Bed & Breakfast
Which popular attractions are close to Pillows in Paradise Bed & Breakfast?
Nearby attractions include Manoa Chocolate Hawaii (1.0 km), Kailua Farmers Market (0.7 km), and Kalapawai Historic Market (0.9 km).
What are some of the property amenities at Pillows in Paradise Bed & Breakfast?
Some of the more popular amenities offered include free wifi, a pool, and free parking.
Which room amenities are available at Pillows in Paradise Bed & Breakfast?
Top room amenities include a kitchenette, air conditioning, and a refrigerator.
Is parking available at Pillows in Paradise Bed & Breakfast?
Yes, free parking is available to guests.
What are some restaurants close to Pillows in Paradise Bed & Breakfast?
Conveniently located restaurants include Over Easy, Le Crepe Cafe Kailua, and Moke's Bread and Breakfast.
Are there opportunities to exercise at Pillows in Paradise Bed & Breakfast?
Yes, guests have access to a pool during their stay.
Are there any historical sites close to Pillows in Paradise Bed & Breakfast?
Many travellers enjoy visiting Ulupo Heiau State Monument (1.9 km).