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Key West Outpost: eco-vacation

The Outpost is a unique experience. This is a place where you can be completely off the grid, but still have all of the amenities. Private conch cottage on the backcountry waters surrounding Key West. Enjoy watching the amazing wildlife from your private deck. You can paddle board, kayak or do some light tackle fishing right off the boat. You can even add eco-tours to enhance the adventure. We will take you out for arrival and bring you back on your departure day, via one of our other boats.

Casa Calypso 3bed3bath sleeps 8 beautiful decorate

Bring the whole family to this great place with lots of room for fun. Very clean, organized stand alone house with everything you will need to have a great stay! Fully stocked kitchen with a kuerig and drip coffee pot. Can have twin beds downstairs or convert into a king. Two king bedrooms upstairs. Each bedroom has its own bath! A queen sleeper couch in living room with a screen divider for privacy if needed. Steps away from the large heated community pool. Several nice restaurants around.

Waterfront Condo Dock Pool Near Duval St

Relax above it all in this spacious top-floor waterfront condo in downtown Key West, offering added privacy and sweeping marina views. Perfect for families and groups, enjoy a full kitchen, open living space, and private balcony. Dockage available with a fish cleaning station and ice maker, ideal for boating and fishing. Located about 1 mile from Duval Street, restaurants, and nightlife, and 10 minutes from EYW airport, with a heated pool, tiki area, BBQ grills, parking, and secure entry.

43' Classic Yacht Views, Pools, Duval Shuttle

Create unforgettable Key West memories while staying on our long time charming liveaboard 43' Trawler. This 2 bedroom 1.5 Bath mini yacht will be the perfect home base for your adventures around town or to just sit and enjoy the incredible views and nature. Being at the award winning Perry Marina gives you all the amenities of a 5 star resort. 2 Pools, 3 Restaurants on site, free shuttle to town, hotel gym, laundry and all the charter and adventure options you could ever ask for.

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Starlight Serenity - Hideaway with Stunning Views

Escape to paradise at this serene 1-bedroom, 1-bath home in beautiful Sugarloaf Key sleeping up to four guests. Enjoy breathtaking views from the expansive wrap-around balcony, perfect for sunrise coffee or sunset cocktails. The spacious outdoor area is ideal for dining, lounging, and soaking in the tropical ambiance. Whether you're relaxing indoors or savoring the outdoors, this home offers the perfect blend of comfort and tranquility. Book your next getaway for 3 nights or more!

Spanish Queen @Venture Out

Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

Near Duval: Hot Tub, Sleeps 6, Top Location

Just 30 seconds from vibrant Duval Street, this iconic conch home is your perfect Key West escape! With two bedrooms, one bathroom, a full kitchen, and private outdoor perks—like a hot tub, second-story sundeck, and outdoor shower—you’ll have everything you need to relax in paradise. Ideal for up to 6 guests, it’s a tropical haven steps from world-class dining, shopping, and beaches. Book now and soak up the island life! Don’t forget to click the ♥ to save it for later.

The Dancing Rooster - 1 Block to Duval!

Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house. The Southernmost Retreat is part of the Simonton Historic Cottage enclave and is surrounded by fine restaurants, art galleries, shopping and proximate to all attractions in the Old Town District. No car is needed as you can walk to the beaches and all of the famous attractions.

Hemingway - Beach Houses Key West

If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. Off the beaten path you will find a unique location and a beach front bungalow with endless unobstructed views of the ocean from every bedroom. Featuring an open family area, full kitchen, deck and its own tiki, excellent for grilling, having a cold drink or just gazing at the ocean.  

Family House, 2 K BR's, Private Spa/Deck, 2 pools.

The Historic Family House is decorated in a light, Caribbean motif. It is a Cigar Maker's Cottage from 1880's. 2 K memory foam beds upstairs w/32” Smart TV's, Q sleeper sofa (memory foam mattress) in LR with 75” Smart TV. Bose blue tooth speakers and Alexa's. 1/2 bath up, full bath down plus an outdoor private shower. Full kitchen! Perfect for Families! Private rear deck with new 6 person Jacuzzi. 2 heated pools!

Castaway Cove: Pet-friendly 2/2 condo near beach!

Welcome to the tranquil, tucked away community of Sunrise Suites in beautiful Key West, Florida. When you choose to spend your vacation with us at the pet-friendly Castaway Cove Condo, you will be just 1 mile from Smather's Beach and a quick 10 minute drive to the fun and excitement of downtown Duval Street with tons of restaurants, bars, art galleries, museums, live music and people watching.