To Airbnb, or Not to Airbnb? It Isn't Even a Question: The Best Airbnb's I've Ever Stayed At

This Airbnb cabin rental in Bailey, Colorado, comes with morning mountain views that are hard to beat (Photo: Melissa Oliver)

*Note: Some of the Airbnb rentals mentioned in this post are no longer available on the site.

The evolution of an idea into a full-blown success is truly remarkable, when you stop to think about it. In the beginning, there are all these questions: what are we getting ourselves into? Will people really buy into this? Will it really work? On top of that, there are the haters constantly getting in your ear, telling you the whole thing will be a massive failure.

But you go for it anyway. Sometimes you see a moderate return on your investment; sometimes you have to go back to the drawing board. But, sometimes, your idea is such a colossal success that you look back and wonder why you weren’t asking different questions from the outset (e.g. why wouldn’t we do this?).

I’d imagine that’s the case with the people behind Airbnb, the vacation rental site that serves as a go-to for travelers from all around the world, whether they’re looking for a secluded cabin in the mountains, a cottage on a lake, or an apartment in the city to call their own for a few nights. A decade ago, mentioning the term “Airbnb” might have gotten you some funny looks; these days, people would think you were a weirdo for not knowing what it is.

Over the past few years, I’ve stayed at a number of Airbnbs in a number of different places, from the smog-filled skies of Los Angeles to the solitary mountains of Vermont, and beyond. Not every experience has been a good one, but that’s why it’s important to do your homework. If you read the host’s bio, look through all the photos, peruse previous guests’ reviews, and find out if the property’s general location is near where you’re trying to be, etc. etc., you should end up staying at a killer spot.

The formula has worked for me in the past, and I don’t see that changing as I continue to #KeepCalmAndAirbnbOn. Based on a number of factors, including cleanliness, size, amenities, location, and the overall “wow” factor, here are the best Airbnb rentals I’ve ever stayed at:

The guest house in Reykjavik doesn’t look like much from the outside, but modern touches abound on the inside (Photo: Airbnb)

One of four bedrooms inside Rosa’s Reykjavik rental, which sits smack dab in the middle of the Icelandic capital (Photo: Airbnb)

5. Great Room Heart of Down Town (Reykjavik, Iceland)

Only the second international Airbnb I’ve ever rented, this guest house smack dab in the downtown area of the Icelandic capital features single-, double-, triple-, and four-person private rooms and a common kitchen and living room, as well as two common bathrooms (full baths, that is). What it lacks in size and overall flashiness, if you will, it makes up for with its location on a main street that passes right through the middle of Reykjavik.

Three friends and I stayed here back in October 2018, during what I alliteratively dubbed “The Intrepid Icelandic Expedition”, and it was just what we needed for the five days and four nights we were there. In the mornings, we had the option of grabbing any snacks we might need at the grocery store across the street before heading out on our adventures, and at night, we were only a couple blocks away from a handful of bars and nightclubs, such as Lebowski Bar and Kíkí.

The view from the balcony of the 32nd floor suite in downtown Toronto

A shot of the shared living room area in the Toronto suite (Photo: Airbnb)

4. Modern Private Suites in Downtown Toronto (Toronto, ON)

Not so much a private room as a shared space with the host, this high-rise apartment/suite in downtown Toronto was just enough space for my traveling companion and I to settle into life in the big(gest) city (in Canada) for a couple of nights in August 2017. Initially, we thought we would be spending a lot of our time there trying to stay out of our host’s way — but then he took off sometime after we checked in and just, kind of, never came back. We were left with the place to ourselves, and neither of us were complaining.

When you stay here, you have access to a number of amenities, including a large indoor pool, a rooftop track, and a gym. However, the primary reason this one makes the list is because of its location (very near the University of Toronto’s St. George Campus in the heart of downtown), as well as the views of the city from the apartment’s perch on the 32nd floor.

This secluded cabin in the mountains in Bailey, Colorado, is the perfect off-the-grid getaway

The interior is cozy, but don’t forget about those marvelous mountain views just outside the windows (Photo: Airbnb)

3. Mt. Rosalie Cabin (Bailey, CO)

For my first trip out to Colorado, back in December 2018, I was transfixed on finding a cabin in the mountains, preferably with a hot tub, that would truly feel like an escape. While the Mt. Rosalie Cabin in Bailey didn’t come with everything I wanted (namely, the hot tub), it checked every other item off my list. Comfy little cabin perfect for a romantic getaway? Check. Just far enough off the beaten track to feel like we’d left civilization behind? Check. Gorgeous mountain views right outside the window? Check.

The cabin was the perfect base of operations for our little skiing adventure, and felt really nice to “come home to” after our day out on the slopes was done. A bit of advice though: I would recommend renting a vehicle with four-wheel drive if staying here, as the cabin is located on a dirt road and has a rather steep driveway (also unpaved).

The best part about this centrally-located studio apartment in Los Angeles is that it’s a centrally-located studio apartment in Los Angeles (Photo: Airbnb)

The pool looked inviting, but we didn’t spend much time at the Airbnb during the day; alas, it went unused (Photo: Airbnb)

2. Centrally Located Private Studio Apt with Pool (Los Angeles, CA)

Sometimes when it comes to Airbnb, it’s all in the name. That’s clearly the case with this rental, which can be found in the Baldwin Hills neighborhood in South Los Angeles. As with many of the spots listed here, this one is again all about location, location, location. Plopped down very near the halfway point of Santa Monica and downtown L.A., my significant other and I minimized the time we spent in L.A. traffic by staying at this studio apartment, which came with sweeping views of the surrounding area.

We never managed to take a dip in the pool, but the time we did spend at the Airbnb was comfortable and quiet, giving us the chance to unwind each night after gallivanting all around the Hollywood hills and boulevards (including a lovely morning spent in Silver Lake).

Mike & Gail’s spot in Silverthorne makes for a perfect space to cozy up after a long day on the slopes

Modern touches abound at the Buffalo Mountain Retreat, but we all know the hot tub is the most important piece (Photo: Airbnb)

1. Mike & Gail’s Buffalo Mountain Retreat (Silverthorne, CO)

Numero uno on this list brings us back to the Centennial State, which apparently has very nice Airbnb listings. It’s not difficult to imagine why, especially when you consider what we’re dealing with here. Mike & Gail’s Buffalo Mountain Retreat in Silverthorne is the stuff of ski porn magazines. With three bedrooms, two bathrooms, that all-important hot tub, and modern touches everywhere, it’s just the place to bring a group of friends for a weekend ski trip.

The house is located very near several popular ski resorts/areas, including Keystone, Breckenridge, Copper Mountain, Loveland, and Arapahoe Basin, which equates with numerous opportunities to take advantage of all that fresh pow and totally shred the gnar, bruh (sorry, I’ll see myself out). Just make sure you know what you’re getting into if you do decide to hit the slopes.

-LTH