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Confession: There’s no such thing as a truly all inclusive resort anywhere in the Florida Keys. But there are some really incredible Key West resorts that include tons of awesome amenities. We’ve rounded up the ones that are closest to all inclusive and put them into this handy dandy list for you.
Best Private Island Resort – Sunset Key Cottages
Imagine being whisked away from the hustle and bustle of Key West on a quick 7-minute cruise to a gorgeous 27-acre private island. You’re led to your own dreamy tropical cottage with wrap-around veranda, situated amidst swaying palms and lush flowering plants. You head to the blissful white sand beach or the zero-entry temperature-controlled pool to relax and watch the sailboats drift by on the crystal clear sea. A friendly server brings you a complimentary popsicle and fruity beverage.
Have you died and gone to heaven? No! You’ve just taken a vacation to Sunset Key Cottages. This place is a friggin’ sanctuary located just a quarter mile off the coast of Key West. The grounds are absolutely gorgeous, the food is to die for and they have the absolute best beach in the Key West area.
Photos courtesy Sunset Key Cottages
- 24-hour transportation to and from Key West
- Award-winning restaurant
- Incredibly tranquil floating dock
- Full service spa
- Tennis courts, fitness center and yoga on the beach
- Grocery shopping services to pre-stock your cottage
- “Rise and Dine” basket of fruit and fresh-baked pastries delivered to your porch every morning
Best Heart of Key West Resort – Margaritaville Key West Resort & Marina
Have you heard the Jimmy Buffet classic, “Margaritaville”? It’s about a guy who spends a season at a tropical beach resort, playing guitar, eating cake and drinking Margaritas. It’s classic Key West and so is this resort.
The resort is located on the waterfront in Old Town Key West, a block away from busy Duval Street, so you can walk to all the restaurants, attractions and entertainment options Key West has to offer. Even though it’s in the heart of all the Key West festivities, the resort maintains a tranquil atmosphere. You can lounge by the pool and watch the cruise ships come in while serenely sipping on their complimentary smoothies under the tropical sun.
Photos courtesy Margaritaville Key West Resort & Marina
- Full-service spa suites with attached tropical patios
- First-class marina for all your yacht’s needs
- Waterfront and poolside dining
- Stunning private pool
- Top of the line fitness center
- Valet parking
Best Tranquil Oasis Resort – Santa Maria Suites
Although this resort is just a block away from lively Duval Street, it’s like a peaceful island surrounded by lush gardens. The two heated pools, 24-hour concierge and the relaxing beach make it a truly luxurious resort.
And if you like food, this place has you covered. They’ve got fresh fruit, delicious smoothies, wine and other snacks – all included with your stay. Even better, you get Dove ice cream bars and chocolates during the nightly turndown service. If that’s not enough, check out the on-site Japanese restaurant, Ambrosia, for high-end sushi dishes that look like works of art.
Photos courtesy Santa Maria Suites
- Beach attendant for all your lounge chair and umbrella needs
- Fully equipped kitchens and in-room laundry facilities
- Bath & Body Works toiletries
- Fitness center with Cybex equipment
- Chilled pool towels
- Poolside bar
Best Secluded Paradise Resort – Parrot Key Resort
If you like the excitement of downtown Key West, but you prefer retiring to somewhere more peaceful each day, Parrot Key is the resort for you. They offer free shuttle service to Old Town so you can still enjoy all of Key West’s dining and shopping options without worrying about finding a place to park (or finding your car after one too many Pina Coladas).
This resort was completely renovated after Hurricane Irma, so everything is brand spanking new. Contemporary styling plus lushly landscaped grounds and four sparkling swimming pools make it a refreshing haven located right on the water. The cherry on top is the resort’s sculpture garden featuring local and international artistic treasures.
Photos courtesy Parrot Key Resort
- Watersports including snorkeling, kayaking and paddleboarding
- Private sunning terrace with powder soft sand
- Patio, porch or balcony on every room
- Concierge and valet service
- Well-equipped fitness center
- Poolside bar and cafe with live music
Best Beachfront Resort – Pier House Resort & Spa
Pier House has all the ingredients to make the perfect Key West resort. Located at the north end of Duval Street, the resort is in easy walking distance of Mallory Square and many restaurants and shops. And they provide free shuttle service around Key West if you prefer being a lazy beach bum. All of their rooms feature balconies or patios for those classic Florida Keys sunset views, which you can also enjoy from their peaceful pier.
But the true star of this Key West resort is the private, white sand beach. Although it’s small, the beach is raked every morning to keep it looking pristine, and the view from the shore is to die for. The resort provides lounge chairs, beach umbrellas and cocktail service to the water’s edge.
Photos courtesy Pier House Resort & Spa
- 3 on-site restaurants and bars
- Temperature-controlled pool
- Full-service spa
- Fitness center / health club
- Steam room
- Concierge service
Best End of the World Resort – Southernmost Beach Resort
Wanna pretend you’re Kate Winslet in Titanic, arms outstretched over the sea as Leonardo diCaprio wraps his arms around your waist and whispers sweet nothings in your ear? “I’m flying!” Well, you can totally do that at the Southernmost Beach Resort’s private tanning pier. (Leonardo diCaprio not included.) This glorious catwalk extends out over the turquoise waters of the Atlantic, making you feel like you’re truly at the edge of the world.
The resort is located just a block off Duval Street in Old Town, with 261 rooms spead over six acres. More numbers for you: They’ve got two beaches, three pools and four bars and restaurants. Southernmost is known for their lively events including Beer School, Astronomy Series, Cannonball Contests, wine tastings, ice cream socials and more.
Photos courtesy Southernmost Beach Resort
- Poolside and beachfront cabana rental
- Aqua yoga and yoga on the beach
- Full-service spa
- Family games like corn hole and ping pong
- Concierge service
- Live music
How to Choose the Best Key West Resort
Live like the rich and famous and try them all! Or, if you’re a mere pleeb like the rest of us, sign up for notifications from a site like Hotwire for the best deals. Bon voyage!
P.S. – If you’re looking for things to do while you’re in Key West, check out our list of 42 delightful things to see and do in Key West.