Key West Vacation Homes

Key West Vacation Homes has provided visitors to the island with exquisite accommodations and peerless customer service since 2015.

We are a local Key West business from top to bottom with a management team whose members are all natives of the area. They have learned their Hotel & Hospitality skills from many of Florida’s best universities from Miami to Tallahassee and their professional background in the field prior to joining our team are with some of the biggest hotel brands in the country.

Our experienced management staff is not only attentive to every need but they are eager to guide you to places, attractions and areas to enjoy in the Florida Keys that may not even appear in your standard vacation guide book that will make your stay in the Conch Republic truly magical!

Kids Free Florida Keys!

The Florida Keys extends an invitation to all families to enjoy the Conch Republic this September. During the month-long celebration your kids will be treated to free admission to attractions and tours, meals on the house and tons of other great perks throughout our island chain. With multiple offers and warm fall weather without the summer crowds or prices, big fun is in store for kids, with savings you’ll love.

2021 Offers Coming Soon!

Museums & AttractionsTours & WatersportsHotelsRestaurants

Great Locations Florida Keys & Key West Area Guidebook

Great Locations Florida Keys & Key West Area Guidebook is loaded with information about attractions, lodging, dining, shopping, entertainment, water sports, services and transportation. It’s pocket-sized to be used around town, not left in your room. Inside you’ll find our money saving coupon book and the largest area maps of any local guidebook. Florida Keys & Key West Coupon Booklet – Great Locations is the only local tourist publication with a removable coupon booklet. Comprehensive Maps – Great Locations has the largest, most detailed, removable maps covering the Florida Keys, Key Largo, Islamorada, Marathon, Big Pine & the Lower Keys and Key West. Great Locations has the largest circulation of any Florida Keys area guidebook with over 700 distribution points with locations throughout Monroe County and select locations in Broward and Miami-Dade counties. For information on how to advertise with Great Locations in the Florida Keys & Key West contact Cheryl Roll at CRoll@greatlocations.com or call 305-731-0135.

The Perry Hotel Key West

Just one bridge from Key West, the Perry’s award-winning 100-room boutique hotel is located waterfront at the state-of-the-art Stock Island Marina. Discover the allure of the original Key West at The Perry’s luxury accommodations, two sea-to-table restaurants, scheduled shuttle service to Old Town, waterfront pool, direct marina access to South Florida’s best water activities, and more. The Perry Hotel is only 2 miles from Key West International Airport and 5 miles from Duval Street.

Weddings

Recipient of the 2019 Travel + Leisure and Conde’ Nast Traveler Reader’s Choice Award for One of the Best Hotels in Florida, the 100-room boutique hotel offers an upscale twist on Stock Island’s iconic maritime heritage. Host your friends and family amongst idyllic turquoise waters at one of the 11 waterfront venues, then celebrate your vows with award-winning American coastal comfort food from our fantastic onsite restaurants. Make The Perry Hotel Key West your one-of-a-kind destination wedding getaway today.

Booking & More Information

Opal Key West Resort and Marina

The Opal Key West Resort and Marina is ideally located on the waterfront in Old Town, within walking distance of attractions, restaurants, shopping and much more! The resort offers multiple dining venues and marina vendors with a variety of watersport activities. The nightly Sunset Celebration on the pier makes The Opal Key West Resort and Marina as desirable a location as Key West itself.

Located within the Opal Key West Resort and Marina lies all of your dining needs. Ocean view and glorious sunsets await within Bistro 245 and our Sunset Deck restaurants. Our Bistro 245 offers casual dining inside or out with breathtaking reviews of the Key West Harbor. Open Daily from 7am-10pm.

www.opalkeywest.com/resort-dining

Havana Cabana at Key West

The new Havana Cabana Resort, formerly The Inn At Key West, sits waterfront in Key West, a destination steeped with charm and character. Taking nostalgic influences from the art and culture of our neighbors in Cuba, the Cabana is a lush escape from reality.

​Mid-century cars greet resort guests as they arrive, birds of paradise punctuate the outdoor landscape, and the sweet sound of Flamenco guitar can be heard poolside. Relax and unwind with a midday mojito or explore the town on a bicycle or vintage Vespa, as you indulge in the marriage of old Havana’s soul and the playful nature of our island setting.

The Gardens Hotel

The Gardens Hotel, named “The Prettiest Hotel in Key West” by The New York Time’s List, is quite simply the finest lodging establishment among Key West hotels. Rich in history and architecture, The Gardens Hotel estate houses 20 pristine guest suites within the estate of The Peggy Mills Botanical Gardens. Once the largest private estate in Key West, the expansive grounds of The Gardens Hotel comprise over an acre of lush, tropical landscaping just steps away from Key West’s infamous Duval Street. The Gardens Hotel calls to mind the best of elegant “boutique” hotels, but with a decidedly “Key West” atmosphere.  Make sure to stop by our d’vine Wine Gallery during your stay to grab a refreshing glass of wine.  By far, The Gardens is in a class all by itself.

Rated by Conde Nast Traveler as Top 50 Small Hotels and consistently rated 5 stars of Excellence by Tripadvisor.

Hampton Inn Key West

Lots of sun and fun can be found at this Key West, Florida hotel and resort – an oceanfront paradise for every guest’s enjoyment.

The brand new Hampton Inn Key West is set on a seven-acre tropical wonderland; ideal for hotel guests who want to relax and enjoy the hotel amenities including a heated oceanfront pool with a view of the Atlantic Ocean and a tropical sun deck. Poolside food and beverage services are available to ensure complete relaxation. The hotel also offers guests a complimentary full, hot Hampton breakfast.

With easy access to all that Key West offers including fishing, snorkeling, diving and parasailing. The beautiful Hemingway House, a Key West museum offering the finest relics of one of America’s true treasures is nearby. Hotel guests will also be close to popular local shops and eateries.

Our staff is attentive, courteous and will make sure any hotel guests’ stay in Key West is relaxing and memorable.

Key West Timeshare Rentals

Key West timeshares are known for their superior amenities, both in-suite and on-site and are located within some of the island’s greatest resorts. Experience accommodations featuring unparalleled spaciousness, fully equipped kitchens, charming décor, plush king and queen sized beds with luxurious linens, and living rooms often including private patios. SellMyTimeshareNow.com currently offers a variety of studio and 2 bedroom units available at the Hyatt Sunset Harbor Resort, The Coconut Mallory, and other fantastic properties. Enjoy a week of swimming, scuba diving, fishing, and other fun activities that can be found at most of these resorts. If you’re more of an explorer and would rather spend most of your vacation encountering all that Key West has to offer, you’ll delight in your timeshare’s location since all Key West timeshares are located close to Duval Street, area marinas, delectable dining, and fabulous shopping. By booking a Key West timeshare rental through a private owner on SellMyTimeshareNow.com, you’ll be saving a huge chunk of change while also helping out an owner who can’t use their unit that week. If you’re interested in spending a week in upscale luxury for less than a week in a cramped hotel room, browse our affordable inventory of timeshare rentals in Key West today!

Simonton Court Historic Inn and Cottages

The Simonton Court Historic Inn and Cottages are located in 2 acres of lush tropical gardens, this elegant collection of cottages, manor house and town house is positively idyllic for rest and relaxation at the very most southern point of the USA. Formerly a cigar factory, this collection of elegant buildings has gradually become the benchmark for attentive service in the most picturesque of settings. Vast tropical palms shade the 4 swimming pools and hot-tub and gentle sea breezes caress the verandas, whilst a series of pretty brick paths connect the various buildings by twinkling night-lights. Guests may choose to stay in one of the 6 enchanting and beautifully restored factory workers’ cottages that boast the very latest in luxurious amenities yet still retain the period charm of their 1880 origins. These make the most wonderful hideaway for privacy-seekers although the suites and guest bedrooms in the main house are breathtakingly appointed and many have private sun-decks or porches, king-size beds and Jacuzzis. The sunset over Key West is a well-fabled sight and Simonton Court is just 3 blocks walk away from the top spot from which to view. Similarly Duval Street is just a stone’s throw away, the home of many wonderful boutiques and fashionable pubs.

Amsterdam’s Curry Mansion Inn

Homesteaded in 1855, the original house was built in 1869, modernized in 1899, refurbished mid-century, abandoned in 1971 and restored to its original grandeur in 1975. It can also boast home to Florida’s first millionaire, William Curry and the birthplace of the World Famous Key Lime Pie. The Widow’s Walk atop the house provides a…

Island House

Private, clothing-optional resort for men in Old Town Key West. Poolside café and bar. Luxury rooms with our feather topped beds. Heated pool, fully-equipped gym, sauna, steamroom, two Jacuzzis, and a tanning deck with misting fans. We were recently named “The best gay mens resort in the world” by OUT Traveler magazine. All facilities of the Island House are open and available 24 hours every day. Men welcome at the restaurant and bar anytime. Daily resort passes are available for locals and men staying elsewhere. Inquire at the front desk.