Package Deals from Baltimore to Key West from $2816

Beachside Resort & Residences Hotel features a private sun beach and a pool with Gulf of Mexico views. Guests can enjoy a meal at the on-site restaurant or grab a handmade cocktail at the poolside bar. A free shuttle to Key West city center is provided. All accommodations at the Key West Beachside include a flat-screen TVs with bluetooth TV speaker. A refrigerator is offered in all rooms. Select rooms feature upgraded amenities such as a full kitchen, balcony, and spa bath. A living area and dining area are also offered in select rooms. Guests may work out at the water view fitness center or soak in the outdoor hot tub. Nearby activities include the Key West Golf Club, biking and jogging trails, and several water sports. Private indoor parking with Private garage parking service is available on site. Tavern N Town ever-changing dishes include steak house favorites and seafood delicacies. The Chicken Walk Poolside Bar offers casual meals, light snacks and tropical cocktails. Key West Airport is less than 1.2 mi away.

Offering 2 outdoor pools, this Old Town Key West motel features high-speed WiFi access and a cable TV in each room. Duval Street is 2 minutes' walk away. All rooms include a microwave, refrigerator, hair dryers, and plush eurotop mattresses. Extras include daily continental breakfast, convenient bicycle on-site, beach access, and our Tipsy Rooster Bar and Liquor Store. A concierge desk and luggage storage are available at Southwinds Motel. Parking is available on-site. Laundry facilities is also at the property. The Ernest Hemingway Home and Museum is 12 minutes' walk away. Guests at the property can rent bicycles to explore the area. Fort Zachary Taylor Historic State Park is less than 2 mi away.

Located off US-1, Fairfield by Marriott Inn & Suites Key West at The Keys Collection features an outdoor pool, Tiki bar, and fitness center. Free WiFi access and a daily free breakfast buffet are also offered. A shuttle service is provided to Old Town. The 24-hour front desk can arrange a scooter or bike hire for a fee at Fairfield by Marriott Inn & Suites Key West at The Keys Collection. Free WiFi, a cable TV, and microwave as well as a refrigerator are standard in every room. Each air-conditioned room also includes a desk. Featuring a bath or shower, private bathrooms also come with free toiletries. The hotel is 1.1 mi from Key West International Airport, 3.2 mi from Duval Street and 3.8 mi from the Hemingway House. Hemingway House, Fort Zachary, and Mallory Square are less than 18 minutes' drive away.

Located centrally on lively Duval Street, Duval House offers a continental breakfast that includes Belgian waffles. The 7 Caribbean-style buildings offer free WiFi. A flat-screen cable TV is featured in each room. Some Duval House rooms include a private balcony and small refrigerator. Specialty accommodations include a full kitchen or a seating area. Guests can lounge in the outdoor pool or stroll through the garden. The Duval House also offers a beverage vending machine. This property is 3 minutes' walk from the Ernest Hemingway Home and Museum. Guests will also be 10 minutes' walk from the Southernmost Point of the continental United States of America.

Located above a nightclub on historic Duval Street in Key West, Florida, this gay male guest house features an outdoor swimming pool, a clothing-optional sundeck, and an on-site restaurant. A daily continental breakfast is available, as is daily complimentary happy hour. A microwave, refrigerator and coffee-making facilities come standard in each room at New Orleans House. A flat-screen cable TV is included. Free Wi-Fi and a fitness center are accessible at the Key West New Orleans House. Other facilities include luggage storage and laundry facilities. The property is located above Bourbon Street Pub. The Southernmost Point is just 10 minutes’ walk from this guest house. Guests will be 4 minutes’ walk from The Ernest Hemingway Home and Museum.

This historical Key West bed and breakfast is 1 mile from the Southernmost Point and 3 minute’s walk from iconic Duval Street. The Artist House guests will enjoy a daily continental breakfast and spa hot tub. All accommodations at The Artist House feature a flat-screen cable TV, small refrigerator, and microwave. In-suite tea and coffee-making facilities are also provided. This bed and breakfast offers a complimentary happy hour and free Wi-Fi. Guests can rent a bicycle and take a relaxing turn around scenic Key West streets. Key West Museum of Art and History is 7 minutes’ walk from the property. Both the Ernest Hemingway Home and Museum and Key West Butterfly and Nature Conservatory are less than 1 mile away.

Less than 2 minutes’ walk from the Ernest Hemingway Home and Museum, this historic Key West property features guest rooms with private balconies and free Wi-Fi. A flat-screen TV with cable channels is provided in each spacious room at The Casablanca Hotel. A private bathroom is also provided in every air-conditioned guest room. Guests can enjoy a swim in the outdoor pool or relax on the sun deck at The Hotel Casablanca. Within walking distance of the beaches, shopping, dining and nightlife of Key West, this property is less than 10 minutes’ drive from Key West International Airport. South Beach and the Southernmost Point are within 1 mile of the hotel.

Located just 1 mile from historic Duval Street, this Key West hotel features a heated swimming pool and a daily continental breakfast. Free WiFi is available throughout the property. A flat-screen TV with cable channels are available in each room at The Palms Hotel. A ceiling fan and telephone are included. Select rooms offer a seating area and kichenette. A picnic area and barbecue are accessible as well. Bicycle rentals are offered. The daily continental breakfast is served poolside and includes pastries, juices, and fresh fruit. The Southernmost Point is just 1.1 miles from this hotel. Guests will be 9 minutes’ drive from Key West International Airport.

Located in Key West, Florida, this motel is just 7 minutes’ walk from the Southernmost Point of the United States. It features rooms with free WiFi access. Air conditioning is available in each room at Seashell Motel for hot Florida days. Rooms are simply decorated, and guests can take advantage of a 24-hour shared kitchen. Bicycle rentals are available at the Seashell Motel Key West. Daily maid service and vending machines are provided for added guest convenience. The property offers free parking. Duval Street is a 15 minutes' walk from the Seashell Motel. Higgs Beach is a 10 minutes' walk away. Guests will be just a 3 minutes’ drive from the Ernest Hemingway Home and Museum. Please note, as part of our commitment to enhance our property and services, we are currently in the process of room and property renovations. The construction work will take place from 8:00 AM to 5:00 PM, every day from Monday to Friday, with no construction activity happening on weekends (Saturday and Sunday).

Located in Key West, this Florida hotel is 1 mi from the shopping, entertainment, and nightlife of Duval Street. Features include a shared outdoor pool with a waterfall and free property-wide WiFi. A kitchenette and a flat-screen cable TV are provided in all of the rooms at Colors on White. Rooms are individually decorated with bright colors and tropical decor. Colors on White guests can relax on the sun terrace surrounded by tropical vegetation or make meals outside at the barbecue facilities. Bicycles are available for hire and free public parking is available nearby. The Key West Historic Seaport and Harbor Walk, a popular dining area, is less than 10 minutes’ walk from the hotel. Fort Zachary Taylor Beach and Smathers Beach are within 2 mi of the hotel.

Paradise Inn - Adult Exclusive is located in Key West and features landscaped grounds with brick paths and a lotus pond with koi and tropical turtles. A complimentary continental breakfast is served in the lobby. The suites at Paradise Inn - Adult Exclusive include a sitting area with cable TV. A microwave, refrigerator, and coffee facilities are furnished in each accommodations. Free WiFi is provided. Enjoy complimentary wine and cheese hour on site at Paradise Inn - Adult Exclusive. Additional amenities include an outdoor pool with a fountain feature and an outdoor hot tub. The hotel is happy to arrange sightseeing tours. Higgs Beach and the Key West Aquarium are 5 minutes' drive from Paradise Inn - Adult Exclusive. The Key West Museum-Art & History is a 15-minute walk away.

Located just 2 minutes’ walk from the Ernest Hemingway Home and Museum, this adult-only inn features free parking and a shared outdoor swimming pool. Free Wi-Fi is also available. A microwave, refrigerator and coffee-making facilities come standard in each room at Douglas House. Guests rooms also include a cable TV. A tropical garden and access to sun terraces can help guests enjoy the Florida scenery. Luggage storage, vending machines and nonsmoking rooms are also available. As with most historical properties in Key West we do not have elevators, second floor rooms are accessed using stairs. The southernmost point of the United States is just 5 minutes’ walk from Douglas House inn. Guests will also be just 0.3 mi from Key West Lighthouse and Keeper’s Quarters Museum.

This adult-only Key West H2O Suites is 656 feet from Duval Street and features a year-round outdoor rooftop pool with a sun terrace. Guests can enjoy the on-site bar. A flat-screen TV, as well as an iPod docking station are featured. All rooms have a sitting are and view of the tropical courtyard. Certain rooms include a private pool. The rooms come with a private bathroom. Extras include bathrobes, slippers and free toiletries. The property provides a free welcome drink upon arrival and a complimentary happy hour for everyone. You will find a 24-hour front desk at the property. The resort also offers bike hire. Southernmost Point is 1312 feet from H2O Suites, while Ernest Hemingway Home and Museum is 1640 feet from the property. The nearest airport is Key West International Airport, 2.5 mi from the property.

This historic Key West Orchid Key Inn - Adults Only is on Duval Street 3 minutes’ walk from the Ernest Hemingway House and Museum. Features include a daily continental breakfast, heated pool with a hot tub, and a bar. A 42-inch flat-screen cable TV, microwave, and small refrigerator as well as an iPod dock are standard in each room. Extras include a Keurig® coffee machine, and some suites have a spa bath and a sofa bed. A Complementary single welcome drink voucher upon check in. The Orchid Bar serves specialty cocktails made with fresh herbs and infused spirits from early afternoon to late evening. Guests will receive 1 complimentary beverage per day. The inn is 3 minutes’ walk from the Historic Lighthouse and 7 minutes’ walk from the Southernmost Point. Key West city center is 1 mi away.

Facing the beachfront, Ibis Bay Resort offers 3-star accommodations in Key West and features an outdoor swimming pool, garden and private beach area. Among the facilities of this property are a restaurant, a 24-hour front desk and a concierge service, along with free WiFi. Private parking is available on site. At the resort, every room is equipped with a closet. Complete with a private bathroom equipped with a shower and free toiletries, guest rooms at Ibis Bay Resort have a flat-screen TV and air conditioning, and selected rooms include a terrace. All rooms will provide guests with a fridge. The area is popular for cycling, and bike rental is available at the accommodation. Ernest Hemingway Home and Museum is 2.5 miles from Ibis Bay Resort, while Duval Street is 2.5 miles away. Key West International Airport is 1.2 miles from the property.

This adults-only bed and breakfast is within a 10-minute walk of Duval Street and the Atlantic Ocean. The environmentally-friendly inn provides in-room refrigerators, bike rentals and a continental breakfast. Every room at The Grand features local Caribbean artwork and private entrances. In-room media includes an iPod docking station, free Wi-Fi and flat screen cable TVs. The Ernest Hemingway Museum is a 15-minute walk from the Guesthouse. The Butterfly and Nature Conservatory is a 10-minute walk from the hotel. Parking is free and available, both on site and on the street.

This all-suite hotel in Key West is only 1 block from the Atlantic Ocean and Duval Street. Each suite is equipped with a full kitchen and 48-inch flat-screen cable TVs. Two outdoor heated pools are surrounded by gardens at Santa Maria Suites Resort. A full-service concierge. Smoothies and fresh fruit are served poolside and guests can also enjoy a complimentary daily happy hour featuring wine and hummus. Free WiFi is available in each suite at the Santa Maria Resort. Washers and dryers are included. The Clinton Market Square shopping area is a 5-minute drive from the resort. The Ernest Hemingway House is an 11-minute walk away and Fort Zachery Taylor Historic State Park is 1.3 miles away. All rooms receive fresh baked muffins, Dove ice cream mini bars and chocolate sweet treats delivered daily to your suite.

This adults only Key West resort is 1 minutes' walk from Duval Street and 5 minutes' walk from the Atlantic Ocean. It features 2 heated outdoor pools, a hot tub and continental breakfast. In addition to free WiFi, all rooms include air conditioning and a flat-screen cable TV. Each room at Southernmost Inn has a unique tropical theme. Southernmost Inn provides a fitness center. Guests can also lounge on the large outdoor patio and a sun deck. A wine and cheese happy hour is provided. The Key West Butterfly and Nature Conservatory is 5 minutes' walk away. The Ernest Hemingway Museum is a 10 minutes' walk away. Southernmost Point is only 1148 feet away.

This Key West hotel is located on the Gulf of Mexico and features an outdoor heated pool with a hot tub. Free WiFi, a cable TV, and coffee facilities are available in every room at this Key West Waterfront Courtyard by Marriott. These spacious rooms also provide an in-room safe. A 24-hour reception area is offered. A 24-hour fitness center, concierge desk, and laundry facilities are on site at Waterfront Courtyard by Marriott Key West as well. Fort Zachary Taylor is 3.3 miles from the hotel. Key West Waterfront is 2.9 miles away.

Located in Key West's Old Town, this beachfront The Reach Key West, Curio Collection by Hilton features a 137-yard private beach and rooms with a private balcony. Duvall Street is 15 minutes' walk away. A refrigerator and flat-screen TV are standard in each room. The Reach Key West, Curio Collection by Hilton also includes an en suite and bathrobes. Some suites and studios have a sofa bed. An outdoor pool is on site and the full-service Spa al Mare at an adjacent sister property, Casa Marina, is available to guests. The Key West Golf Club is 5 mi away. On-site activities, including scuba diving, snorkeling, deep-sea fishing and kayaking. Earnest Hemingway Museum is just 10 minutes' walk from the The Reach Key West, Curio Collection by Hilton.

Offering a heated outdoor pool, this boutique Ella's Cottages is located in Old Town Key West 2 minutes' walk from Duval Street. Free WiFi and a poolside continental breakfast are provided. A flat-screen cable TV, an en suite, and hardwood floors and furnishings are standard in all rooms and suites. All rooms have a mini fridge. Both rooms and suites include access to a tropical garden. The guest house is 1476 feet from Ernest Hemingway Home and Museum and 15 minutes' walk from the Sunset Pier. Higgs Beach is 1.2 mi away.

Please note the deposit is charged by the property immediately at booking. Please note that the property has no elevator. Please note that there is a resort fee that includes personalized concierge services, in-room Wi-Fi, yoga mats, and coffee and tea service, along with a daily boozy lemonade at 3pm and local partner perks with some of our favorite neighborhood spots, including Old Town Bakery and Southpoint Divers.

This boutique hotel is just 10 minutes’ walk from Duval Street and Key West's nightlife and dining options. It offers a daily continental breakfast. Guests can enjoy the on-site outdoor pool. Museums, water-sports and shopping are located within walking distance of the property. The Southernmost Point of the USA is 1 mile away. Mallory Square and the Key West Aquarium are also less than 7 minutes' walk away.

Lighthouse Hotel is located in the heart of iconic Key West, opposite the Ernest Hemingway Home and Museum and the Keeper's Quarters Museum. Guests can enjoy an outdoor heated pool, complimentary continental breakfast, and on-site bar. Isabel's Poolside Bar serves island favorites and specialty drinks. Guests can explore the area by renting one of the bicycles from a specialized company. Free WiFi and a flat-screen cable TV are included in all accommodations at Lighthouse Hotel. A private bathroom is also provided in each guestroom. Duval Street is 5 minutes' walk from the hotel, and the Southernmost Point is 7 minutes’ walk away. Guests will also be 8 minutes' walk from Key West Butterfly and Nature Conservatory.

Located along Duval Street in Old Town Key West, Florida, this historic hotel offers modern amenities such as free wireless high-speed internet access and an on-site restaurant. La Concha Key West, Autograph Collection features an outdoor pool, Pool Bar, and contemporary fitness center. Mater sports (within 2 miles) and same day Dry Cleaning available. The guestrooms at the La Concha Key West, Autograph Collection boast unique services for a memorable stay. Guests can enjoy a 55-inch flat-screen TV. After a busy day, the pillow-top mattress offers a restful night's sleep. The restaurant at La Concha, Perla, offers unique, island-inspired small plates and fresh local seafood. The historic Duval Street is also home to a variety of fine dining, nightclubs, and more.

Located on a private beach along the shore, Casa Marina Key West, Curio Collection by Hilton is a historic 1920s resort offering oceanside massages and 2 oceanfront pools. Duval Street is 7 minutes’ drive from the resort. Classically-designed rooms offer a flat-screen TV, private bathroom, and coffee-making facilities. A small refrigerator is also provided. Spa al Mare features a selection of massages, facials, and aromatherapies. Deep-sea fishing, wind surfing, and water sports activities are easily accessible from Casa Marina Key West, Curio Collection by Hilton. Pick up morning coffee, pastries, and breakfast sandwiches at Flager’s Restaurant. Key West Golf Club is 13 minutes’ drive and offers 18 holes. Bicycling, fishing, kayaking, and more can be enjoyed at Fort Zachary Taylor Historic State Park, 11 minutes’ drive.

This waterfront resort features an on-site spa and fitness center and is located on Key West Island. Guests can enjoy the nightlife and restaurants of Duval Street, which is only 3 minutes’ walk from the resort. A private balcony and free WiFi are included in every cozy room at the Hyatt Key West Resort and Spa. Additional amenities include a flat-screen cable TV and a small refrigerator. On-site Jala Spa offers a number of services, including body wraps, facials, and deep tissue massages. Nail care and renewal rituals are also available, as is an on-site fitness center. An outdoor pool and hot tub offer the perfect space to rejuvenate while scuba diving, jet boats, and snorkeling are available on site or nearby. A Jet Ski island tour is available for guests looking to explore the surrounding area. Two on-site restaurants are located at Hyatt Key West Resort and Spa. Shor American Seafood Grill offers coastal fares while Blue Mojito Pool Bar and Grill serves cocktails and light bites.

Lobby Renovations through February, 2026. Valued guests - We are excited to be redesigning our main entrance and adding a stunning new lobby with a bar and lounge that will overlook our marina. Work will be completed Monday to Saturday 8:30AM to 6:00PM. Our Restaurant, Spa, Pool and Sunset Pier will be operating as normal. Overlooking the Gulf of Mexico, this luxury Key West resort and spa features an outdoor pool with gulf views. Free WiFi is provided at Ocean Key Resort and Spa. On-site SpaTerre offers massage therapies, nail treatments, facials, and other spa services. The resort houses an on-site fitness center and fishing boats, jet skis, and glass-bottom boat tours are available. From spa baths and private balconies offering partial and full ocean views, rooms and suites at Ocean Key Resort come well equipped. A coffee machine and a private bathroom are also featured. Enjoy dinner and dancing over the water at Sunset Pier or experience seafood paired with crafted cocktails at waterfront Hot Tin Roof. LIQUID Pool – Bar - Lounge serves cocktails and snacks. Mallory Square plaza is 1 minutes’ walk as are the restaurants, bars, and entertainment of Duval Street.

Located in Key West, Florida, these villas feature a heated outdoor swimming pool. They are adjacent to dining and shopping on Duval Street. and 1.1 mi from the Southernmost Point. A fully equipped kitchen is available in each villa at Rose Lane Villas. A flat-screen TV and DVD player are included. The private bathrooms offer a hairdryer and free toiletries. Select villas have a balcony or porch as well. Free Wi-Fi is available, and the property offers parking Key West Aquarium is 5 minutes’ walk from these villas. Guests will be 0.9 mi from the Ernest Hemingway Home and Museum.

This bed and breakfast welcomes guests to Old Town, Key West and features a free continental breakfast, 3 outdoor pools and a hot tub. The Ernest Hemingway Home and Museum is 15 minutes’ walk away. Free WiFi access and a flat-screen cable TV are provided in each room at this Key West NYAH - Adult Exclusive bed and breakfast. Guests can stroll through the garden or ask the tour desk for area recommendations. The 24-hour reception offers luggage storage. The nightlife, shops, and art galleries of Duval Street are 9 minutes’ walk from the property. Key West Aquarium and Key West Cruise Port are each 0.7 mi away.