Luxury Hotel · USA
Sunset Key Cottages
Tailor-made, always
Every trip built from scratch around your dates, pace and preferences.
Your own specialist
One named person and a 24-hour number while you travel.
Hundreds of five-star reviews
Rated Excellent on Trustpilot across ten years of LGBTQ+ luxury travel.
At a glance
Sunset Key Cottages is a private-island resort a few minutes by launch off Old Town Key West.
Sunset Key is a 27-acre private island about 500 yards off Mallory Square. The crossing takes minutes, but the island feels a world away. The 40 standalone cottages, from one to four bedrooms, have tin roofs, wraparound porches, and full kitchens; the largest have private plunge pools.
Latitudes, the island’s waterfront restaurant, is one of Key West’s most sought-after dinner reservations, especially at sunset, with a pool bar for the daytime. The Opal Spa handles massages and facials, and there is a lagoon-style heated pool, a private white-sand beach with cabanas, and tennis courts.
The multi-bedroom cottages work for couples, families, and groups, and it is pet-friendly. It suits couples, gay or straight, on a honeymoon as much as a family week. Old Town, with Duval Street and the Hemingway Home, is a short launch ride away.
Highlights
- Private island of 40 cottages off Old Town Key West
- One-to-four-bedroom cottages, some with private plunge pools
- Latitudes, one of Key West’s top sunset restaurants
Accommodation
One Bedroom Garden View Cottage
This luxury cottage comes with a wrap around veranda and an outdoor dining area. Ideal for “Rise And Dine” breakfast which is delivered to your door each morning. You’ll have a living and dining room with a large dining table. The cottages have either a full or en-suite bathroom.
Luxury Three Bedroom Ocean Front Cottage
This luxury cottage has 1,700 square feet of space with uninterrupted ocean views wherever you look. You won’t find a more luxurious setting in Kew West. The cottage comes with a spacious living area and kitchen. Breakfast is delivered to your door each morning.
Four Bedroom Ocean Front Cottage
With 2,500 square feet of space this luxury cottage will be like your very own kingdom. It comes with a private plunge pool and beach area. There’s one bedroom on the first floor, two upstairs with shared bathrooms and also a master suite with a private balcony and jacuzzi in the bath.
Enquire for information about other cottages.
Further information
Dining
Latitudes is the island’s restaurant, and one of the best-known tables in Key West, set right on the water for breakfast, lunch, and dinner. Sunset is the prized slot, and reservations are worth booking weeks ahead. Flippers, the pool bar, handles casual daytime food and drinks, and a “Rise and Dine” breakfast basket can be delivered to your cottage. With full kitchens in every cottage and a resort grocery service, you can also self-cater.
Wellness
The Opal Spa at Sunset Key offers massages, facials, and body treatments in a quiet setting on the island. The real draw, though, is the water: a lagoon-style heated pool, a private crescent of white-sand beach with cabanas, and beach yoga in the mornings. There are tennis courts and a fitness center too, and fishing straight from the dock. With no cars and few day-trippers, the island stays calm in a way Key West itself rarely is.
Location
Sunset Key is a private island about 500 yards off Old Town Key West, reached by the resort’s launch, which crosses to and from the marina at Opal Key roughly every half hour. That puts the whole of Old Town within easy reach: Duval Street’s bars and restaurants, Mallory Square’s sunset celebration, the Hemingway Home, and the Southernmost Point are all a short ride and a walk away. Key West International Airport is about 15 minutes from the dock.
USA
Getting Around The US is best navigated by a combination of air and ground transport. Domestic flights are frequent and reasonably priced, making them the practical choice for covering long distances, particularly between the coasts.
Our Experts
The thing about the USA is that it's just so diverse. It doesn't matter what you're looking for, you can find it in the USA. I personally love San Francisco because it's hotels are arty and luxurious at the same time.
There's nowhere quite like New York for an ultra-lux city break. I always recommend visiting in December for the dream Christmas experience, complete with high-end shopping, Broadway shows and walks in Central Park.
Stellar service. Stellar products. Stellar people and it gets so much better when you pick up the phone and call.
Anthony S.
Super client centred service. From first contact I have had warm, efficient, friendly and flexible service.
John
I’m confident in giving Out Of Office a 5-star review! They are one of the leaders in this space without a doubt.
Tiberiu
Suggested tours
Luxury New Mexico: Santa Fe, Los Alamos & Breaking Bad Locations
Tailor-made VacationNew Mexico doesn't look like anywhere else in America, and it doesn't feel like it either. The light is different, the landscape is different, and the culture, shaped by centuries of Native American, Spanish colonial, and Anglo-American layering, sits apart from anything on the coasts. This itinerary runs three threads simultaneously.
8 days View trip
Luxury Hawaii Adventure
Tailor-made VacationEmbark on an unforgettable Hawaii island-hopping adventure combining the dramatic landscapes of the Big Island with the lush natural beauty of Kauai. Over the course of this journey, you’ll experience two of Hawaii’s most spectacular islands, where volcanic landscapes, tropical rainforests and golden beaches create one of the most diverse destinations in the Pacific. Begin on the Big Island of Hawaii, home to powerful volcanoes, black sand beaches and world-class marine life.
9 days tailor-made from $7,975 per person View trip
Aspen in Winter: A Luxury Gay Ski Escape
Tailor-made VacationAspen is one of those places that rewards arriving with no particular agenda. It's one of the top luxury travel destinations in the USA. The skiing across four mountains is as good as anywhere in North America, but the town itself pulls equally hard: the restaurants are exceptional, the hotels are world-class, and the cultural life punches well above what you would expect from a mountain resort of this size.
8 days tailor-made from $10,500 per person View tripSee your complete itinerary before you decide.
Frequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specializing in tailor-made vacations and extraordinary journeys around the world. We create bespoke luxury vacations, LGBTQ+ honeymoons, safaris, cruises, beach escapes, private tours and group trips, with every itinerary designed around you. Our travel specialists combine global expertise, first-hand destination knowledge and trusted local partners to create seamless, highly personalized experiences.
Is Out Of Office a gay travel agency?
Out Of Office is an LGBTQ+ owned and run luxury travel specialist, with particular expertise in gay and LGBTQ+ travel. We understand the additional considerations that can come with traveling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveler, including friends, families and allies. Many of our clients are not members of the LGBTQ+ community, but choose Out Of Office for our luxury travel expertise, personalized service and discretion.
Do you create tailor-made LGBTQ+ vacations?
Yes. Every tailor-made trip with Out Of Office is designed from scratch around your interests, travel style, budget and the way you want to experience a destination. We can arrange luxury hotels, private transfers, flights, guides, excursions, cruises and special experiences as part of one personalized itinerary. The journeys shown on our website are there to inspire you rather than restrict you; only clearly identified group departures operate as fixed itineraries.
How do you choose LGBTQ+ friendly hotels and destinations?
We combine first-hand destination knowledge with trusted local expertise to recommend luxury hotels, resorts and experiences where LGBTQ+ travelers can feel informed and welcome. We also consider the laws, customs and attitudes of each destination, because LGBTQ+ rights and experiences differ around the world. Our team regularly visit many of the properties we work with and where a destination requires greater awareness, we give you clear and considered advice so that you can make an informed decision about where and how you travel.
We plant trees for every booking
For every booking made with Out Of Office we commit to planting trees in your name to help reduce the impact of travel on future generations. You'll even get a link to see where your trees are planted in the world via our partner Ecologi.
We donate to Rainbow Railroad with every booking
Rainbow Railroad helps LGBTQ+ people escape state-sponsored violence and persecution. A donation goes with every trip we sell, funded by us and never added to your price.
Start Planning Your Trip
Tell us where you would love to go, when you are thinking of traveling and what kind of trip you have in mind. One of our LGBTQ+ travel specialists will create a tailor-made itinerary designed around your destination, style and preferences.
One named specialist, first inquiry to homecoming. No call center, and nothing is charged until you decide to book.