We stayed Feb. 20-27 in the Gardenia room, a quick decision due to our son's housing situation. Bed was very comfortable, room was spotless and this location very quiet. Convenience is wonderful! 5 minutes to downtown Kailua, where you'll find many upscale restaurants and shops. Kailua Beach park is also just a 4 minute walk. Pool is immaculate and grounds excellent. Barb and Lionel are great hosts and wonderful conversationalists. Barb's son Matt does a great job of filling in when needed and his fine oil paintings are featured throughout the house. All in all, a great value and you'll not be disappointed.

Pillows in Paradise is a quaint, clean and private B&B in Kailua, which is a town that's pretty off the beaten track. If you're looking for a place to relax, read a few books, get some sun and enjoy your alone time, this would be a place to stay for sure. The host, Barbara, was a really easy going lady with a tidy almost ghost-like demeanor (sorry Barbara, I don't mean that the way it sounds...), one minute she's there talking to you, the next you're not sure where she went.
The B&B is a series of room extensions on their home on a nice quiet residential street. We had no problem parking our rental car on the side street just outside our window. We had a big, clean room with a lovely kitchenette (no real place to prepare or cook food, but a portable burner, small fridge, coffee maker, and all that you need to make breakfast, and a small lunch), a big shower-only bathroom, nice closet space, etc.
They left us a fruit and bread basket on the first day we arrived, which was wonderful, though I wouldn't call it breakfast. It sure helped, though, as a pineapple on the island ranges from $5-$9 depending on where you buy it. Stores in Kailua aren't exactly stocked for visitors, in fact, the town is really not meant for much of anything except living quietly out of the way of busier towns.
PiP is about a 15 minute walk to the center of "town", which consists of Starbucks and a string of chain-restaurants, a couple smoothie stores, and not much else. There are two dive shops nearby that are nicely equipped for day-snorkel rentals.
The beach is almost equally close, 15 minutes or so, but beware, there are no comforts you'd find at a bigger beach, this beach is nice smooth sand and that's it. You'd be hard pressed to find a cold water or sandwich, and forget about trying to have a drink while you get out of the almost constant flash-flood-like 2 minute downpours this part of the island is famous for.
The pool in back is cute, if a bit overgrown with surrounding palms and native plants, which shade it a bit from mid-day onward, but otherwise it sure is nice to have a quiet clean pool to just read and relax by after a day of walking to and from beach/town.
I would probably look for a hotel closer to the beach if I were to go back to Kailua, but if I was looking for a hide-away far from anyone else, PiP would be my first stop.
I did enjoy myself, the place is nice. Clean is an understatement!

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.

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.