These Key West Vacation Rentals Combine the Best of Hotels and Airbnbs

I flew into Key West this time, which felt like flying into the Caribbean. The small international airport makes travel easy, from dealing with your bags and renting a car to sipping cold drinks in transit. Adding to my smooth arrival, the Lunara Bay team had texted me by the time I landed, with a driver letting me know he’d arrived and where to find him — a modern alternative to a chauffeur holding a sign with my name on it.

This, followed by proactive communication about the house and room codes, set the tone for my stay in a Lunara Bay vacation rental.

Photo: Neha Shah

Lunara Bay is just under five miles from the airport, promising equally easy access for those relying on rideshares or rental cars rather than a pickup service. When I arrived in the residential neighborhood housing the luxury rentals, I smiled at the contrasts — peacocks cooed and cawed while I oohed and aahed as the homes came into view.

My enclave, a set of four homes, was quiet. I was thrilled to see the multi-story home with the backdrop of a blue sky and a hint of waterways. I was slightly dismayed at the entry — stairs to the main floor and first floor of the home — but I was made aware of this in advance, and I travel light: a rolling carry-on and a weekender bag that doubles as a beach bag, ideal for carrying essentials while exploring during the day.

These luxury homes, all with views of the water, have a lot of appeal for travelers: your own pool and hot tub, plenty of patio space for outdoor meals, and kitchens outfitted inside and outside for a chef (or your group) to enjoy simple or multi-course meals. Foosball, table tennis, hammocks, and a fire pit complete the scene to beckon those intent on reveling in relaxation at a home away from home.

Photo: Neha Shah

Before my stay, I wondered what would be different about Lunara Bay compared to an upscale beach vacation rental or timeshare. For one thing, sustainability-minded guests will appreciate that all of Lunara Bay’s homes are new (almost entirely constructed by local Keys companies) and therefore outfitted with modern, energy-efficient mechanical systems, as well as astroturf that cuts back on water usage, maintenance, and agricultural chemicals. But the balance between service and privacy is probably the biggest difference.

Where Airbnb has superhosts and bookable experiences, Lunara Bay has Guest Experience Managers (GEMs). Airbnbs provide guests with assurances of reliability and responsiveness, plus peace of mind through the consistency of previous guests’ experiences, from reservations to questions throughout the stay. This is helpful to know before you book to establish a higher level of trust with your host. Lunara Bay’s GEMs add a layer of nuance to the experience, with a dedicated individual and team managing your stay in a concierge-like capacity.

GEMs can assist with planning, both before and during your stay, yet generally remain invisible like an Airbnb host. It’s the best of both worlds: You can enjoy your visit without interfacing with traditional hotel staff while still being supported by an expert team if you have any questions or a wish list.

Photo: Neha Shah

This is particularly significant given the many markets to which Lunara Bay appeals. Brides, for example, or anyone celebrating a special occasion, will appreciate having a GEM to handle additional services — finding a local bakery, booking an excursion, recommending a private chef, having gift baskets ready for guests on arrival, etc. You can incorporate add-ons before and throughout your experience, a key benefit for those traveling with a group for an event or function.

The benefits of a Lunara Bay stay extend to pretty much anyone, however. That not only includes groups — such as families, friends, corporate retreats, or bachelor and bachelorette parties — but also couples or remote workers who’ll appreciate staying in an environment that’s conducive to productivity, with the option to take breaks as needed and to stay as few as three days or longer.

I had the opportunity to visit many of the Lunara Bay homes, not just the Starboard, where I stayed. Each was slightly different in layout, but they all had the benefit of having a few homes within close distance so you can visit with those in your group. I could envision sharing a house with my immediate family or best friends while vacationing with a wider group staying in the homes nearby — say, visiting their pool or having dinner in one home while having a suite for me-time as needed.

Photo: Neha Shah

Starboard, like the other Lunara Bay homes, is designed tastefully, with earth tones that aren’t muted but offer subtle nods to sand, surf, and sky. Warm latte colors and a variety of blues tones — robin egg, cornflower, and cyan — are inviting but don’t dominate the atmosphere of the homes. Varied furniture provides different lounging options in the living area, including roomy circular seats that allow you to hug a pillow while swiveling to see the water, talking to someone in the kitchen, or viewing the bookshelf to scan for a beach read. Modern appliances and spacious dining areas, inside and outdoors, are a chef’s dream — and therefore a guest’s dream.

My room allowed for as much light or privacy as I needed. The king bed, comfortable pillows (not just the decorative kind that you can’t sink into), and appealing fragrance of the refillable lotion and body wash all added to the luxuriating and Zen-like hints reminding me to relax and allow myself to fully immerse into the Lunara Bay philosophy: life on idle time.

The group of creative professionals I was traveling with appreciated the little details, from the questionnaire we got in advance asking if we’d like the home stocked with any favorite snacks (not included in the rental rate) and beverages to the s’mores basket of goodies ready for a first-day arrival by the firepit. We took advantage of the organized transportation, which made it easy to go on excursions and explore without having to worry about parking or driving.

The home serves as an attraction itself. Since I had a few days, I found a balance in spending time in the pool and exploring Key West with a local friend who generously shared her favorite places to grab drinks, sit and watch the sea, eat, listen to music, etc. On one occasion, I happily traded the pool’s warm waters for a sunset sail with my housemates, complete with a sandbar excursion.

Photos: Neha Shah

Key West shines, even in the rain, so although there were a few showers during our time on the boat and at dinner, we were lucky enough to watch it until they passed, under safe cover. Lunara Bay partners with Brightwild, a travel platform centered around “personalized experiences and standout stays,” to facilitate excursions. This served as an extension of the sanctuary feel that the home provided — being in the water, without any activity beyond the 360-degree view, watching the blues and greens merge into each other while seeing the warm sand below.

I was happy to return to the cocoon to find the private chef preparing our meal. The dress code was as casual or as dressy as we wanted (layering athleisure apparel with the Lunara Bay robe wins for best-dressed for a cozy dinner prepared at home by a private chef).

Photo: Neha Shah

I split my time in Key West between Lunara Bay and the city itself. Starboard provided the necessary sanctuary for a genuine beach vacation. Key West provided the necessary social activities for a beach escape.

I spent time with a friend who lives locally. We compared notes on her favorite spots in Key West and the places I visited during my stay. Our group had lunch at Thirsty Mermaid, which is known for fresh catch and locally sourced ingredients. It’s a good location to walk around and see local art galleries, a wine shop, and the serene Key West Butterfly and Nature Conservatory. We capped our local walk with the best way to spend an afternoon: Louie’s Backyard. And what a backyard — the end of the road, the southernmost point, and the ocean.

We ate at Dorada — part of Casa Marina Key West, Curio Collection by Hilton — for dinner outside, with soft lighting and a few good options for vegetarians like myself. My local pal highly recommends Roostica for the pasta and starters. As locals, her family frequents this place as their go-to for Italian food. Another night’s meal was at Tavern N Town, with an excellent table in view of the chefs at work. It was another night of good drinks (Coco-jito) and food, including the shishito peppers, pizza, and the Tavern salad (white balsamic vinaigrette gives this salad a winning taste).

My local connection reminded me that the perception of Key West — all bars and no culture or good food and drink — is not entirely true. Key West offers theater, museums, water sports, and a range of local dining and drinking options. Between cozying up in Starboard and experiencing the broader destination, my time at Lunara Bay gave me exactly what I was seeking: life on idle time, my way, with all the indulgences for an idyllic stay.

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