Hotels with Private Pools in Key West

With a stay at The Key West Hotel, you'll be centrally located in Key West, steps from Duval Street and within a 10-minute walk of Mallory Square. This guesthouse is 0.4 mi (0.6 km) from Florida Keys Beaches and 0.5 mi (0.9 km) from Ernest Hemingway Home and Museum. Take advantage of recreation opportunities including an outdoor pool and bicycles to rent. Additional amenities at this guesthouse include complimentary wireless internet access and concierge services. Take advantage of the guesthouse's room service (during limited hours). The front desk is staffed during limited hours. Make yourself at home in one of the 12 individually decorated guestrooms. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms feature showers with rainfall showerheads and bathrobes. Conveniences include desks and complimentary bottled water, and housekeeping is provided daily.

With a stay at Suite Dreams Inn by the Beach in Key West (Old Town Key West), you'll be a 4-minute walk from Florida Keys Beaches and 11 minutes by foot from Duval Street. This bed & breakfast is 0.6 mi (1 km) from South Beach and 0.7 mi (1.1 km) from Southernmost Point. Take advantage of recreational opportunities offered, including an outdoor pool, an outdoor tennis court, and karaoke. This bed & breakfast also features complimentary wireless internet access, concierge services, and wedding services. Breakfast is available for a fee. Featured amenities include complimentary newspapers in the lobby, multilingual staff, and luggage storage. Free self parking is available onsite. Make yourself at home in one of the 5 guestrooms.

With a stay at The Gardens Hotel, you'll be centrally located in Key West, steps from Duval Street and within a 5-minute walk of St. Paul's Episcopal Church. This bed & breakfast is 0.3 mi (0.4 km) from Ernest Hemingway Home and Museum and 0.3 mi (0.5 km) from Tennessee Williams Key West Exhibit. Dip into one of the 2 outdoor pools or enjoy other recreational amenities, which include bicycles to rent. Additional features at this bed & breakfast include complimentary wireless internet access and concierge services. At The Gardens Hotel, enjoy a satisfying meal at the restaurant. Relax with a refreshing drink from the poolside bar or one of the 2 bars/lounges. A complimentary cooked-to-order breakfast is served daily from 8:30 AM to 10:30 AM. Featured amenities include complimentary newspapers in the lobby, dry cleaning/laundry services, and luggage storage. Self parking (subject to charges) is available onsite. Make yourself at home in one of the 21 air-conditioned rooms featuring plasma televisions. Your Tempur-Pedic bed comes with Egyptian cotton sheets. Rooms have private furnished balconies or patios. Complimentary wired and wireless internet access keeps you connected, and cable programming provides entertainment. Private bathrooms have deep soaking bathtubs and rainfall showerheads.

With a stay at H2O Suites - Adults Only in Key West (Old Town Key West), you'll be steps from Duval Street and 3 minutes by foot from Key West Butterfly and Nature Conservatory. This hotel is 0.2 mi (0.4 km) from South Beach and 0.3 mi (0.5 km) from Southernmost Point. Don't miss out on recreational opportunities including an outdoor pool and a fitness center. Relax with your favorite drink at the bar/lounge or the poolside bar. Featured amenities include complimentary newspapers in the lobby, dry cleaning/laundry services, and a 24-hour front desk. Self parking (subject to charges) is available onsite. Make yourself at home in one of the 22 individually decorated guestrooms, featuring refrigerators and minibars. Your pillowtop bed comes with premium bedding. Rooms have private balconies or patios. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Private bathrooms with showers feature complimentary toiletries and hair dryers.

With a stay at Tropical Inn in Key West (Old Town Key West), you'll be steps from Duval Street and Ernest Hemingway Home and Museum. This bed & breakfast is 0.2 mi (0.2 km) from Tennessee Williams Key West Exhibit and 0.2 mi (0.4 km) from City Zoo Gallery. Take advantage of recreational opportunities offered, including an outdoor pool, a hot tub, and bicycles to rent. Additional features at this bed & breakfast include complimentary wireless internet access and concierge services. A complimentary continental breakfast is served daily from 8:00 AM to 10:00 AM. The front desk is staffed during limited hours. Limited parking is available onsite. Make yourself at home in one of the 11 individually decorated guestrooms, featuring refrigerators and iPod docking stations. Your pillowtop bed comes with premium bedding. 36-inch flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Private bathrooms with showers feature complimentary toiletries and hair dryers.

The iconic William Skelton Home in downtown Key West offers an ideal retreat for your group of 16 guests. The six bedroom Victorian mansion features multiple spacious living areas, a private backyard with a swimming pool, and a newly renovated chef's kitchen. On the first floor you will find a spacious living room, three bedrooms, and two bathrooms. There is a kitchenette and living area with sofa bed in the back of the home facing the backyard. On the second floor is the kitchen, dining room, another spacious living room, two bedrooms, and one bathroom. Don't miss the unforgettable front porch and back deck with comfortable seating. The third floor is reserved for the luxurious master suite - a king bedroom with a seating area and beautiful private bathroom.The best of Key West is steps away with this home's incredible central location on Eaton and Duval Street. The William Skelton Home may be reserved for 1+ nights throughout the year, either as the entire 6 bedroom home, or the upstairs portion with 3 bedrooms.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.

With a stay at this condo in Key West (Meadows), you'll be within a 5-minute drive of Florida Keys Beaches and Duval Street. This golf condo is 1.4 mi (2.3 km) from Southernmost Point and 1.5 mi (2.4 km) from Mallory Square. Be sure to enjoy recreational amenities, including an outdoor pool, an outdoor tennis court, and a fitness center. This condo also features babysitting, tour/ticket assistance, and a picnic area. Featured amenities include ATM/banking services and an elevator. Free self parking is available onsite. Make yourself comfortable in your condo.

Welcome to Bottom’s Up Bungalow — Your Private Tropical Escape in Old Town Key WestStep into a world of comfort and island charm at Bottom’s Up Bungalow, perfectly situated in the serene Meadows subdivision, just minutes from the vibrant heart of Key West. This immaculate 2-bedroom, 2-bathroom single-family home combines classic Florida bungalow appeal with modern amenities to create an inviting retreat that has earned over 100 glowing five-star reviews from delighted guests.Home Highlights & FeaturesSpacious & Inviting Living RoomBright and airy, the living room is designed for relaxation and socializing. Sink into the plush sectional sofa that easily converts into a sleeper for additional guests, or unwind in the comfortable sitting chair while enjoying your favorite shows on the large flatscreen TV. Natural light floods the room through large windows, creating a warm and welcoming atmosphere.Elegant Formal DiningJust off the living room, the formal dining area comfortably seats four — perfect for intimate dinners or leisurely breakfasts. The classic design complements the polished hardwood floors that flow throughout the home.Chef’s Dream KitchenThe heart of the home is a spacious, open-concept kitchen featuring generous counter space, high-quality appliances, and all the essential cookware and utensils to prepare anything from casual snacks to gourmet meals. A breakfast bar with stools offers a casual dining option, while the adjacent informal dining nook provides a cozy spot for family meals. Double French doors open onto the poolside patio, inviting fresh air and natural beauty inside.Tranquil Primary SuiteThe primary bedroom is a serene sanctuary, outfitted with a luxurious king-size bed, a sturdy chest of drawers, and a large closet with a full-size washer and dryer tucked inside for your convenience. Step through elegant French doors to the pool and garden, perfect for early morning coffee or evening relaxation under the stars.Spa-Like Primary BathroomLocated just outside the primary suite, the hallway bathroom boasts a spacious custom shower with sleek tilework, a large vanity with ample storage, and a linen closet to keep all your essentials neatly organized.Flexible Guest BedroomThe second bedroom features two twin beds that can easily be converted into a king bed upon request, ideal for couples or friends traveling together. This room also includes a chest of drawers, a roomy closet, and a private en-suite bathroom complete with a shower, vanity, and toilet — providing comfort and privacy for your guests.Resort-Style Pool & Outdoor LivingStep outside to your private tropical paradise. The oversized pool, heated from December through May, is perfect for a refreshing swim any time of year. The attached whirlpool spa (note: not a hot tub) offers soothing bubbles to relax tired muscles. Surrounding the pool is an elevated deck with two sun loungers — ideal for soaking up the Florida sun. Enjoy meals or drinks at the outdoor dining table shaded by an umbrella, or retreat to the custom-built gazebo featuring a wet bar and bespoke seating, making it the ultimate space for entertaining or unwinding.Lush Tropical Gardens & PrivacyThe beautifully landscaped gardens are enhanced by tasteful lighting and privacy fencing, creating a secluded oasis that feels worlds away from the bustle of downtown Key West. The tranquil greenery invites you to savor quiet moments with family and friends in any season.Parking & ConvenienceOne assigned parking space is available in the driveway for your ease and security. Additional vehicles can be parked roadside, subject to availability, allowing you to bring along extra guests or rental cars with peace of mind.Prime Location Near the Best of Key WestTucked away on a quiet one-way street within a peaceful community, Bottom’s Up Bungalow offers the perfect balance of tranquility and accessibility. You’re less than one mile from the excitement of Duval Street, famous beaches, and the marina. Enjoy the vibrant nightlife, eclectic dining, and unique shops of Old Town, then retreat to your calm, private sanctuary at day’s end.Why Choose Bottom’s Up Bungalow?Whether you’re here for a romantic getaway, a family vacation, or a fun trip with friends, Bottom’s Up Bungalow provides the perfect home base. With its spacious layout, thoughtful amenities, lush outdoor spaces, and unbeatable location, this bungalow promises a memorable Key West experience filled with relaxation, adventure, and island charm.We invite you to be our guest and experience the magic of Bottom’s Up Bungalow on your next trip to Key West!About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 28.About events:No events allowed.