My Airbnb Hotel Stay: Staypineapple New York [Review]

I visited New York City earlier this summer to attend the grand unveiling of Delta’s new terminal at LaGuardia and a sneak peek at its new Sky Club. I stayed in Manhattan for a few days and split up my stays across two different properties: Staypineapple New York and the Crowne Plaza HY36 Midtown Manhattan (read my review of that hotel after you finish this one!).

Staypineapple is where I spent my first night in New York.

Why Did I Chose Staypineapple New York?

I became a Capital One Venture X Rewards Credit Card member when it launched and featured a now-expired promotion: a $200 statement credit for vacation rental stays made through companies such Airbnb and Vrbo.

I’m not the biggest fan of staying at other people’s homes. But I discovered that both Airbnb and Vrbo offer various hotels!

I had IHG One Rewards points and IHG® Rewards Premier Credit Card anniversary night certificate to burn. The Crowne Plaza HY36 Midtown Manhattan offered the best redemption for my dates. So, I booked those nights and searched Airbnb for the remaining one night.

Staypineapple New York was one of the options and cost $207 for that night. Plus, it’s about 300-ish feet and across the street from the HY36. Bingo! Seven bucks out of pocket for room and tax is a pretty grand deal in my book. The place looked artsy, quirky, and comfortable. So, I gave it a shot.

Where is Staypineapple New York?

Staypineapple New York is at 337 W 36th St., 10018, in midtown Manhattan. You’ll find it on 36th between 8th and 9th Avenues.

It’s a short walk from Penn Station, which is nice if you want to take the subway. Plus, you can grab the LIRR to the AirTrain to JFK at Penn’s Moynihan Hall.

The neighborhood is not fantastic, though.

Checking In at Staypineapple New York

If you plan to arrive at Staypineapple (or anywhere else in the neighborhood), I highly recommend taking a cab or rideshare.

I didn’t show up until about 11:30 PM. I rode the train and felt safe on my walk on 8th Avenue. But then I got to 36th and started walking west.

There were all sorts of interesting street people hanging out and eyeing me: the out-of-towner rolling his suitcase, laptop bag, and camera case. (For what it’s worth, a Staypineapple employee recommended using 9th Avenue and then walking east on 36th.)

The Staypineapple door was locked. Of course it was. (Though I appreciate the security feature.) I rang a buzzer and it was remotely unlocked.

I was impressed with the lobby.

The young lady who checked me in was welcoming, helpful, and friendly. She offered me a few bottles of water — which was great, considering it was a warm, humid New York City night.

Because my stay was already paid with my Capital One Venture X Rewards Credit Card, the only thing outstanding was an amenity fee and credit card hold for incidentals. I put that on my Chase Sapphire Reserve® because it earns 3X on travel (after earning the card’s $300 Annual Travel Credit). I didn’t charge anything to my room during my 12-hour stay. The destination fee total came to $28.69.

A “haiku plus” greeted me on the wall across from the elevators.

A pineapple was engraved on the elevator’s floor.

The “Naked Experience”

Staypineapple is big on this thing called “The Naked Experience.”

Don’t worry. It’s not a nudist hotel or anything. The property’s website says, “The Naked Experience, featuring cloud-like European-style individual duvets, cozy robes, and big thirsty towels, is easily the most comfortable you will ever be in a hotel. And it’s all crazy clean. So go ahead, get naked.”

It wasn’t the most comfortable I’ve ever been in a hotel. The bedding was a big issue for me. (More on that soon.) But the room was clean and the towels certainly were big and plush (“thirsty” certainly is an interesting adjective, I’ll give them that.).

Staypineapple New York Celebrity King Room

Most of us who’ve visited New York City multiple times know its standard hotel rooms vary in size. Some are teeny-tiny. Others are rather big. It’s sort of the luck of the draw.

The Staypineapple New York Celebrity King Room is of the teeny-tiny sort.

The desk is a pull-out table from one of the nightstands. There is no dedicated chair. So, maybe head to a coffee shop or somewhere else if you need to (comfortably) get work done during your Staypineapple stay.

This is the first time I’ve visited a hotel room with its own instruction placard.

Even the bed comes with instructions. And there’s a reason for that.

Yeah, that was too complicated for this blonde guy.

I would’ve settled for “normal” bedding that doesn’t require instructions — or something more idiot-proof. I didn’t get as good of sleep as I hoped. The pillows and mattress were comfortable — but that duvet kept uncovering my feet.

There are electrical outlets and USB ports above the nightstands on both sides of the bed.

Because there’s not a large amount of room, you can put your luggage on this little under-bed trolly and slide it back!

There’s this little personal assistant device.

I didn’t really have a need for the assistant but it seems kind of cool.

Elsewhere in the room, there are a closet and a coffee maker.

The bathroom is quite nice.

The shower’s water pressure was great — but make sure to bring your own toiletries. The shower gel and shampoo are wall-mounted.

Final Approach

Staypineapple New York was a decent find for my Capital One Venture X Rewards Credit Card‘s (now expired) $200 Airbnb credit promotion. Be aware that the neighborhood is less than ideal at night. Nonetheless, Penn Station — home to the subway and LIRR — is close. That’s a big plus for subway and other train passengers.

The small Celebrity King Room isn’t ideal for people who need to get work done in a hotel room. And the bedding can be unnecessarily confusing for some people. My room was clean and the staff was great.

I wouldn’t mind staying there again — but I don’t think it’ll be my first choice next time I visit New York City.