Key West Vacations

Your Key West vacation

From family vacations to last-minute romantic getaways, make Orbitz your first and only stop for Key West vacations. You can customize your trip with flights, hotels and activities to match your travel plans and tastes. Sweeten the pot with extra savings when you book your flight and hotel together.

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Vacation Packages

Key West Vacation Packages

Parrot Key Hotel and Resort

3 stars
4.1 / 5 44 reviews
Newly opened waterfront hotel offers rooms, suites and cottages Newly opened in 2008, the Parrot Key Hotel and Resort sits on five acres of lushly landscaped property overlooking the Gulf of Mexico. Located bayside on U.S. 1, the Parrot Key Hotel and Resort offers guestrooms, suites, and sprawling cottages just outside Old Town Key West. Guests of the Parrot Key Hotel and Resort can find high-tech amenities like free property-wide Wi-Fi access; on-site activities, including four swimming pools and a fitness center; and the lively shopping and nightlife of Duval Street and Mallory Square sit just 3 miles away. Highlights Accommodations include spacious cottages with full kitchens and up to three bedroomsFour swimming pools nestled among lush tropical gardensWi-Fi access (free) throughout the property and guestrooms Rooms The Parrot Key Hotel and Resort offers a wide range of open-floor-plan, and brightly decorated accommodations. With 118 hotel-style deluxe guestrooms, one- and two-bedroom suites, and two- and three-bedroom cottages, The Parrot Key Hotel and Resort can accommodate any group or family size. Deluxe rooms feature king beds or pairs of queens, while suites have luxurious private bathrooms for each bedroom, and the cottages boast full-size kitchens and dining areas. All accommodations have patios or balconies with either garden or water views. In-room amenities include flat-screen TVs, and free Wi-Fi access. Features Situated on five lavishly landscaped acres with impressive sculpture gardens, the Parrot Key Hotel and Resort offers a colorful and comfortable island escape. Guests can find four swimming pools throughout the property, and the on-site restaurant and tiki bar, Café Blue, serves casual salads and sandwiches poolside. On-site amenities include a fitness center, white-sand sunbathing areas, and free Wi-Fi access. The on-site concierge can help arrange local watersports, golf, spa services, and tours of Key West. Transportation Key West International Airport (3.1 mi./5 km)Miami International Airport (159 mi./254.4 km) Attractions Mallory Square (2.8 mi./4.5 km)Harry S. Truman Little White House (2.8 mi./4.5 km)Smathers Beach (2 mi./3.2 km)Ernest Hemingway Home and Museum (2.1 mi./3.4 km) Business Free Wi-Fi access
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Nightly rates from $169

The Reach Resort - Waldorf Astoria Collection

Luxury resort, on-site water sports along Key West's only natural beachThe Reach Resort underwent a major renovation and now features sumptuous accommodations and abundant amenities on the island's only natural beach. Located at the end of Simonton Street just east of the Southernmost Point Marker, Reach Resort sits a short walk frofm the Duval Street scene and about a mile from Mallory Square.  Guests can unwind in rooms with private balconies overlooking the ocean, relax by the outdoor pool or arrange water sports on the beach. HighlightsLocated on 450 feet of Key West's only natural sand beachBeachfront water sports centerWi-Fi access (fees apply) RoomsThe resort has many flavors of rooms and suites, all of which open onto private balconies--some have ocean views, others have pool or island views. Reach Resort rooms come with single king or two double beds, and suites have king beds and sitting areas with sleeper sofas. Bathrooms are stocked with plush bathrobes and LXR Clear beauty products, while in-room amenities include espresso machines, mini refrigerators, work desks and high-tech gear like LCD TVs, iHome clock radios and Wi-Fi access for a fee. DiningStrip House restaurant serves breakfast, lunch, dinner and room service, including prime-cut steaks and an extensive wine list.    RecreationDuring 2006 and 2007, Reach Resort underwent a $37 million USD renovation. Sitting along 450 feet of the island's only natural beach, the property features an outdoor pool and a beachfront water sports operator for boat, bike, kayak and Jet Ski rentals along with scuba, snorkeling and fishing excursions. Reach Resort guests have access to the facilities at a sister property, Casa Marina Resort, including spa services. TransportationKey West International Airport (3.2 mi/5.1 km)Miami International Airport (159 mi/254.4 km) AttractionsMallory Square (1.4 mi/2.2 km)Key West Golf Club (5 mi/8 km)Ernest Hemingway Museum (.6 mi/1 km) BusinessWi-Fi access (fees apply)4,706 square feet of flexible meeting space Policies and FeesA $25 USD ($28.13 USD including tax) daily resort charge includes Wi-Fi, in-room espresso, local and 800 phone calls, weekday newspaper and access to Reach Resort and Casa Marina property amenities.
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Nightly rates from $228

Lexington Hotel Key West

Well-equipped motel offers reasonable rates on east Key WestLexington Hotel Key West boasts amenities to accommodate leisure and business travelers alike. Located on U.S. 1 right at the entrance to the island, Lexington Hotel Key West sits just a few minutes from the Key West Airport and about five miles from Mallory Square and the famous nightlife of Duval Street. The Key West Country Club and the botanical gardens are just minutes away from Lexington Hotel Key West on nearby Stock Island. Guests can also find a variety of fishing, diving, and snorkeling charters close to the hotel. HighlightsAffordable hotel near Key West AirportOn-site restaurant and barOutdoor poolFree Wi-Fi RoomsThe spacious guestrooms and suites at Lexington Hotel Key West feature single king beds or pairs of queen beds. In-room amenities include luxury bedding, air conditioning, coffee makers, irons, hairdryers and cable TVs with HBO. Some rooms also have pullout sofas, refrigerators and microwaves. Guests who want to stay connected can access Wi-Fi for free. Some rooms also come equipped with work desks and desk-level electrical outlets. FeaturesThis modest and well-equipped, motel-style property offers reasonable rates and decent amenities just a few miles from the historic district of Key West. Guests can sunbathe and swim in the heated outdoor pool and spa tub, work out at the on-site fitness center and arrange boat trips and island tours from the Lexington Hotel Key West concierge desk. InKahoots, the on-site restaurant, serves meals all day--as well as room service--plus drinks at the poolside tiki bar. Lexington Hotel Key West also boasts free parking with space for trailers and buses, and other on-site amenities include laundry facilities and business services like free Wi-Fi access, guest computer with print, fax and copy services. TransportationKey West International Airport (1.6 mi/2.6 km)Miami International Airport (155 mi/248 km) AttractionsSmathers Beach (2.5 mi/4 km)Tennessee Williams Theater (1.4 mi/2.2 km)Mallory Square (4.3 mi/6.9 km)Key West Botanical Forest and Garden (.5 mi/.8 km) Business500-square-foot meeting spaceGuest computer with print, copy and fax servicesFree Wi-Fi  
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Nightly rates from $227

Ibis Bay Resort

2 stars
3.4 / 5 38 reviews
Located just outside of Old Town Key West, the Ibis Bay Resort provides a true feel of Key West with great food, fun, and excitement, while still giving you the rest and relaxation that brought you to this famous little island. This little diamond in the rough is the perfect place for you to stay for your weekend get-a-way in Key West. Enjoy friendly staff, cool rooms, and an atmosphere that make you come back for more. The welcoming staff at the Ibis Bay Resort is happy to have you as their guest. Rather than feeling like a guest, you`ll be treated as a long lost friend who`s come for a visit and you`ll never want to leave. This waterfront resort offers guests with budget-friendly accommodations while providing an upbeat atmosphere and a unique overall feel of Key West. Build in the 1950`s, this cool Waterfront Resort takes pride in the individuality that was created when the resort was initially built. The bright Key West colors mixed with the feel of the Caribbean make the Ibis Bay Resort stand out from all the rest. The Hotel Does NOT provide Roll Away Beds
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Nightly rates from $151

Hyatt Key West Resort and Spa

5 stars
4.4 / 5 89 reviews
Downtown luxury hotel with spa, water sports and event spaceThe Hyatt Key West Resort and Spa underwent a $10-million-dollar renovation, which included updates to all 118 guestrooms. The resort reflects old-world flair combined with modern amenities, along with impeccable service and a premier location on Front Street near Mallory Square. Hyatt Key West Resort and Spa guests can step out the front door to find sunset sails, fishing charters and the world-famous attractions of the Key West waterfront and historic district.   HighlightsDowntown location steps away from Mallory Square and Duval StreetJala Spa offers massage, facial and full-body treatmentsWireless Internet access throughout the hotel (fees apply) RoomsAll 118 renovated guestrooms at the Hyatt Key West Resort and Spa undergo Hyatt's signature Respire hypoallergenic cleaning process to reduce airborne particles and ensure the utmost cleanliness of all fabrics and surfaces. Rooms have either single king beds or pairs of double beds fitted with luxurious linens and plush pillow-top mattresses. Guests can relax on private furnished balconies with pool and ocean views. In-room amenities include mini refrigerators, flat screen TVs, iHome stereos with iPod docking stations, in-room safes, work desks and Wi-Fi access (fees apply). DiningFor meals, Hyatt Key West Resort and Spa guests indulge in gourmet plates at the SHOR American Seafood Grill, or lighter fare and cocktails at the Blue Mojito Pool Bar and Grill. The hotel also provides  room service and catering. RecreationThe luxuriously renovated Hyatt Key West Resort and Spa offers immaculate amenities at the heart of Key West's historic district. Guests craving to be pampered book massages, facial or body treatments at Jala Spa, while adventure seekers can find a host of water sports, including scuba diving, Jet Skis and fishing charters. A fitness center allows guests not to miss a workout. For the ultimate leisure experience, guests flock to the outdoor pool and hot tub overlooking the Gulf of Mexico TransportationKey West International Airport (4 mi/6.4 km)Miami International Airport (159 mi/254.4 km) AttractionsMallory Square (0.2 mi/0.3 km)Sloppy Joe's Bar (0.2 mi/0.3 km)Ernest Hemingway Museum (1 mi/1.6 km)Fort Zachary Taylor (1.3 mi/2.1 km) BusinessBusiness centerFlexible indoor/outdoor meeting spaces Policies and fees Valet parking fee is $15.00 per night; self parking is already included in the resort feeThere will be Resort Fee of $20 plus tax per room, per night. The fee covers the following items: High Speed wireless Internet access in the guest room, local telephone calls, 800/888 telephone surcharges, incoming faxes, complimentary self-parking, in-room bottled water, and Stay Fit 24 hour access.
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Nightly rates from $344

Silver Palms Inn

3 stars
4.2 / 5 33 reviews
Affordable elegance for a luxury vacation or weekend getawayThe Silver Palms Inn Key West is located in Historic Old Town. This Florida hotel offers guests a contemporary appearance, with aquamarine accents set against a background of earth-tone accents. Regardless if guests are here on business, enjoying a romantic getaway or traveling with children, the Silver Palms Inn offers amenities and services to facilitate everyone's needs. Guests also enjoy a daily continental breakfast. 3 Reasons To Stay:World-class galleries, nightlife, restaurants and shopping within walking distanceTrendy, stylish and comfortable accommodation unitsPool and courtyard Silver Palms Inn Key West roomsAll rooms in the Silver Palms Inn Key West feature pillow-top mattresses complete with silky sheets and hypoallergenic pillows. The 50 rooms here surround the pool, courtyard and deck. A daily housekeeping service maintains all rooms. Silver Palms Inn Key West Hotel guests enjoy in-room amenities such as a 40-inch flat-screen LCD TVs, balconies, iPod compatible clock-radios, comfortable lounge chairs, coffee facilities, iron and ironing boards, microwaves and refrigerators.Business travelers staying at the Silver Palms Inn Key West Hotel can enjoy amenities including a desk with ergonomic chair and wired Internet, available in each room. All guest suites at the Silver Palms Inn Key West Hotel also have island views and sofa beds. Things to Do:Duval Street (0.2 mi/0.3 km)Harry S. Truman Little White House (1 mi/1.6 km)Lighthouse Museum (1 mi/1.6  km)Fort Zachary Taylor Historic State Park (1.4 mi/2.3 km)J.N. Ding Darling Natural Wildlife Refuge (4.6 mi/7.4 km) Policies and feesThe hotel charges a resort fee of $10 (plus tax) per day.
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Nightly rates from $199

Coconut Mallory Resort and Marina by Kees Vacations

3 stars
3.7 / 5 24 reviews
Quiet, apartment-style accommodations with marina on Key West east endThe Coconut Mallory Resort and Marina offers vacation-rental waterfront condominiums on the east end of Key West with amenities that include two pools, a playground and a clubhouse. Located just after the entrance to the island, the resort sits near the Key West airport and less than five miles from Mallory Square and the popular attractions along Duval Street. The small, private marina has slips for 18 boats, and Coconut Mallory Resort and Marina makes a good base for fishermen and divers looking to hit the water. Highlights Condominium-style accommodations have full kitchensMarina has 13 slips and boat launchProperty features two pools and a playground for children RoomsCoconut Mallory Resort and Marina features studio units, and one- and two-bedroom condominiums with full kitchens, including stoves, microwaves, dishwashers and refrigerators. The condominiums also feature washers and dryers and private balconies. Bedrooms come furnished with double beds, and some units have pullout couches in the living rooms. In-room amenities include flat-panel TVs, air conditioning and phones. FeaturesThe Coconut Mallory Resort and Marina sits apart from the raucous downtown area of Key West. This vacation rental property on the east side of the island offers easy access to the airport, south-side beaches and local boat charters, and the on-site amenities include two swimming pools, a Jacuzzi, a boathouse, a BBQ area and a playground. In addition, the resort features a small marina with 18 boat slips and boat launch. Guests can find parking and waterfront views within this tropical resort. Transportation Key West International Airport (1.5 mi/2.4 km)Miami International Airport (157 mi/251.2 km) Attractions Key West Lighthouse Museum (3.8 mi/6.1 km)Ernest Hemingway Home and Museum (3.9 mi/6.2 km)Harry S. Truman Little White House (4.6 mi/7.4 km)Key West Aquarium (4.6 mi/7.4 km)Mallory Square (4.6 mi/7.4 km)Fort Zachary Taylor (4.9 mi/7.8 km) Policies and feesFront desk hours 9 a.m. to 5 p.m. daily. Minimum age required at check-in is 21. Check-in is at 4 p.m. Check-out is at 10 a.m. All guests should go to the welcome center upon arrival to the resort. If you plan to be arriving after the scheduled check-in time, please call ahead so that we can arrange your after-hours check-in.
Value 20% OFF 3 NIGHTS OR MORE
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Nightly rates from $139

The Westin Key West Resort & Marina

4 stars
4.2 / 5 55 reviews
Island luxury overlooking Sunset Pier, just steps from Duval Street The Westin Key West Resort & Marina sits at the heart of Old Town Key West near the famous Sunset Pier at Mallory Square, and just a block from Duval Street. Guests of the Westin Key West Resort & Marina can step out the front door to stroll along the waterfront promenade or experience the endless boutiques, cafes, and island bars of downtown Key West. The Westin Key West Resort & Marina also offers the largest on-site marina of any hotel on the island, and conference and event groups can find 16,000 square feet of indoor and outdoor event space. Highlights Prime downtown location just steps from Mallory Square and Duval StreetOn-site, 37-slip marina accommodates boats from 25 to 200 feetFree Wi-Fi access public areas, fees apply in guestroomsHotel has a pet policy Rooms The Westin Key West Resort & Marina offers 178 immaculate guestrooms and suites. Guestrooms have either king beds or pairs of queens, and the one- or two-bedroom suites have king-size beds and pullout sofas in the living areas. Suites and deluxe guestrooms have patios or balconies with ocean or garden views. In-room amenities for all accommodations include flat-screen TVs, Wi-Fi access (fees apply), coffee makers, and stocked mini bars. The Westin Key West Resort & Marina has a pet policy and can provide dog beds on request. Bathrooms come equipped with fluffy bathrobes and slippers. Features The Westin Key West Resort & Marina has earned the AAA Four-Diamond rating every year since 1999, and this waterfront Key West resort in downtown Key West boasts a full-service, 37-slip marina that can accommodate boats up to 200 feet long. Guests of the Westin Key West Resort & Marina can arrange watersports and charters, and on-site activities include an outdoor heated pool and Jacuzzi, 24-hour fitness room, and massage studio. Guests can find both fine and casual dining at the hotel-the premiere restaurant Bistro 245 serves seafood and steaks overlooking the harbor. Business travelers and event groups can find a 24-hour business center with free Wi-Fi, and more than 16,000 square feet of flexible, indoor and outdoor event space. Transportation Key West International Airport (4.2 mi./6.7 km)Miami International Airport (159 mi./254.4 km) Attractions Mallory Square (next door)Smathers Beach (3.3 mi./5.3 km)Harry S. Truman Little White House (0.2 mi./0.3 km) Business 24-hour business center16,000 square feet of flexible indoor/outdoor event spaceFree Wi-Fi in public areas
Value Save 25% on your stay
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Nightly rates from $239

Almond Tree Inn

3 stars
4.6 / 5 80 reviews
Old Town Key West bed and breakfast with elegant rooms off Duval Street The elegant Almond Tree Inn offers a quiet, tropical oasis in the heart of Old Town Key West. Located just a half block off Duval Street, near the intersection with Truman Avenue, the Almond Tree Inn sits within easy walking distance of the southern beaches and the restaurants, shops, and attractions of the downtown historic district. Colorful guestrooms at the Almond Tree Inn feature four-poster beds and monogrammed bathrobes, and the inn's grounds boast a secluded pool and spa nestled among its tropical gardens. Highlights Located at the heart of Old Town Key WestComplimentary continental breakfastComputer data ports (free) in guestrooms Rooms The Almond Tree Inn features 22 exquisitely appointed guestrooms with either single king beds or pairs of queens. Suites feature separate living rooms with queen-size sleeper sofas. All room have open floor plans and private balconies or patios, and all have 27-inch color TVs with premium channels, iHome stereos, climate control, refrigerators, microwaves, digital safes, coffee makers, and phones with voice-mail and computer data ports. Private baths feature showers, hair dryers, irons, and Egyptian cotton bathrobes. Features Situated at the heart of Old Town Key West, just blocks from the beach and steps from Duval Street, the Almond Tree Inn boasts all the amenities of a bed and breakfast, including complimentary continental breakfast every morning and evening happy hours with free beer, wine and soft drinks. The Almond Tree Inn offers limited off-street parking (fees apply), and the lush tropical garden features a hot tub and secluded swimming pool with a waterfall. Transportation Key West International Airport (3.3 mi./5.3 km)Miami International Airport (160 mi./256 km) Attractions Mallory Square (0.9 mi./1.4 km)Key West Lighthouse Museum (0.2 mi./0.3 km)Smathers Beach (2.4 mi./3.8 km)Audubon House (0.8 mi./1.3 km)Ernest Hemingway Home and Museum (0.2 mi./0.3 km)Southernmost Point (0.4 mi./0.6 km)
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Nightly rates from $270

Azul Key West

3 stars
Not yet reviewed
Azul Key West is a classic Victorian mansion, just three blocks from Duval Street and Hemingways House. Located in the center of Key Wests Historic District, this former cigar barons mansion boasts tri level, downpour blue decks which surround the carriage house, outbuildings and a shimmering swimming pool. Listed on the National Register of Historic Places, Azul Key West was exquisitely crafted by local carpenters and shipwrights until its completion in 1903. Testament to a time gone by, when Key West was the United States wealthiest city per capita, this fanciful structure complete with spiral staircases, wooden verandas and gingerbread whimsy remains to this day a beautifully restored work of art. Kickstart your stay with a healthy breakfast which includes fresh fruits, tropical yogurt, cereals, juice, toast, eggs, preserves, coffee or tea and a selection of our freshly baked muffins. Then head out for a day sightseeing in town or snorkeling, jet skiing, sailing, ecoadventuring and more on the water. And later on if its night life you are looking for, that is when Key West really lights up. Known as a dining mecca and cultural center for theatre, galleries and shows, the town is equally renown for its festivals, frivolity and general joie de vivre. In fact you are just as likely to see a fire eater or sword swallower as you are a spectacular sunset or stylish exhibit. And later on, at the end of an evening, retire to Azul which remains far from the madding crowd and yet so close to everything.
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Nightly rates from $199
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Flights

Flights to Key West

Departure Arrival Travel dates Round-trip
Boston Key West Tue, Feb 5 - Wed, Feb 13 $396
Chicago Key West Sun, Feb 3 - Fri, Feb 8 $415
Philadelphia Key West Mon, Jan 21 - Wed, Jan 23 $393
New York Key West Sat, Mar 2 - Sat, Mar 9 $346
Newark Key West Tue, Feb 5 - Tue, Feb 12 $364
Detroit Key West Tue, Jan 15 - Thu, Jan 17 $429
Washington DC Key West Tue, Feb 5 - Thu, Feb 7 $332
Nashville Key West Tue, Jan 29 - Sat, Feb 2 $407
Hartford Key West Mon, Jan 21 - Wed, Jan 30 $365
Baltimore Key West Tue, Jan 15 - Thu, Jan 17 $349
Atlanta Key West Mon, Feb 4 - Fri, Feb 8 $419
Minneapolis Key West Mon, Jan 28 - Sun, Feb 3 $482
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More on Key West from AOL Travel

  • Physically linked to the American mainland by the Overseas Highway, Key West is the southernmost point in the continental United States. However, for those who live there or visit often, Key West is not just a physical presence but also a state of mind. A laid-back party town cast adrift from the rest of the country, Key West is perhaps the most tolerant and accepting small city in the United States. All are welcome; a fact that becomes readily apparent when one surveys the diversity of the crowd that assembles for the nightly sunset celebration in Mallory Square. For sightseers, Key West abounds with attractions, including multiple “southernmost” sites. Literati interested in learning more about what inspired some of the most memorable writing of the 20th century must pay a visit to the Ernest Hemingway House, which includes the stand-alone studio where the author worked on of several of his vaunted novels. Key West has helped inspire a number of other writers, artists and musicians, including Tennessee Williams, Shel Silverstein, Winslow Homer, John James Audubon, Mario Sanchez, Jerry Jeff Walker, and Jimmy Buffett. Because Key West is a compact city covering less than eight square miles, it’s easy to get around. Newcomers to the city might want to take the Conch Tour Train to orient themselves to the high points and attractions of Key West. Other popular attractions include the Audubon House and Gardens, the Key West Aquarium, and the Mel Fisher Maritime Heritage Museum. Fishing is very popular throughout the Florida Keys, and Key West is no exception. Visitors looking to try their luck in the waters around Key West should head over to Garrison Bight Marina to rent a boat or pick up bait and tackle. Key West’s restaurants feature seafood prominently on their menus, although dining options run the gamut from storefront Cuban restaurants to the haute cuisine of France. After the sun goes down, stroll down Duval Street to sample the live music coming through the open doors of the many clubs that line Key West’s main drag. The party goes on till the sun comes up.

    AOL Travel’s Key West Guide

    AOL Travel's Best Key West Hotels

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