Key West Hotels with Private Pools

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 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.

Pagitt House – Historic Charm Meets Modern Luxury in the Heart of Key WestWelcome to Pagitt House, a beautifully restored historic home originally built in 1933 and completely renovated in 2025. Located on charming Elizabeth Street, you're just steps away from the Key West Historic Seaport, restaurants, shopping, nightlife, and many of Key West's most popular attractions.As you enter through the classic white picket fence and make your way up to the home, you'll be greeted by a spacious, covered front porch—the perfect place to relax with a morning coffee, unwind in the afternoon shade, or enjoy some of the best people-watching in Key West.Inside, this spacious 2,100-square-foot home blends historic character with modern luxury. With four bedrooms, multiple living spaces, and an expansive private pool area, Pagitt House is ideal for families and groups looking to enjoy their own private island retreat.HOME FEATURES: - 2,100-square-foot historic home- Fully renovated interior (2025)- Private heated pool (seasonal heating available)- Large outdoor entertainment area- Covered cabana with lounge seating- Modern kitchen with island and dining area- Smart TVs throughout the home- Washer and dryer- Prime Old Town Key West locationFirst Floor- Comfortable living room with flat-screen TV- Fully equipped kitchen with island- Dining area- Laundry Room PRIMARY SUITE #1 - King bed- Flat-screen TV- Ensuite bathroom with soaking tub and separate showerPRIMARY SUITE #2- Ensuite bathroom with walk-in shower- Half bathroom (powder room)SECOND FLOOR - Shared full hallway bathroom with showerBEDROOM 3- Queen bed- Flat-screen TVBEDROOM 4- Two twin beds- Flat-screen TVOUTDOOR LIVINGStep outside into your own private oasis featuring:- Large sun deck- 10' x 20' private pool- Pool loungers- Covered outdoor cabana with seating- Spacious entertainment area- Pool heating is available seasonally (November 15 through April 15) for an additional fee. Please contact management before your stay if you would like the pool heated.PARKING: Please note that the home includes one assigned parking space, located in the alley behind the property. This space accommodates only a compact car or a single golf cart.SUVs, trucks, and larger vehicles will not fit.Additional parking is unassigned street parking, which can be limited.Metered parking in the area can be expensive.Because parking is limited in this part of Old Town, we generally do not recommend bringing a vehicle. Most guests find it easy to explore Key West on foot, by bicycle, golf cart, or rideshare.We look forward to welcoming you to Pagitt House and helping make your next Key West vacation unforgettable!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.

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.

The Tropical Inn provides a great place for travelers to relax after a busy day. Visitors to Key West will find that the Tropical Inn is a fantastic accommodation choice. The hotel is conveniently located a short 6km drive from Key West International Airport. There's plenty to do nearby, with Key West, Fort Zachary Taylor State Park and Yankee Freedom Dry Tortugas Ferry all within a short distance. When guests have some time on their hands they can make use of the onsite facilities. For those driving themselves, parking is provided on site. Guests tell us the location of this hotel is fantastic. This hotel is particularly popular with those traveling with friends.

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 0.7 mi (1.1 km) from Southernmost Point and 0.6 mi (1 km) from South Beach. 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.

28 Night Minimum. Welcome to "The Saltbox"!Featured in design magazines.710 Ashe Street is a charming house circa 1889. This historic Eyebrow home offers classic elegance and history with modern comforts. A spacious living area, sleek kitchen, three tropically decorated bedrooms (1 King and 2 Queen Beds). 6 person max.Conveniently located in Old Town, walking distance to shops and attractions and Duval St. A perfect Key West vacation rental capturing Key's West unique island allure. Private heatedLocal Key West Artist Designed, one of a kind.pool. About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 23.About events:No events allowed.

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.

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 events:No events allowed.

Welcome to OFF THE HOOK — Your Perfect Key West Getaway!Escape to this stunning, meticulously updated 3-bedroom, 3-bathroom home located in desirable mid-town Key West. Just under a mile from the vibrant heart of Duval Street, local beaches, and Garrison Bight Marina, OFF THE HOOK offers the ideal blend of comfort, style, and convenience for your next vacation.Property Highlights:Bedrooms: 3 (King Primary Suite, Queen Family Suite, Guest Suite with 2 Twins/convertible King)Bathrooms: 3 full baths, including ensuite in primary bedroomLocation: Mid-town Key West, less than 1 mile from downtown and beachesParking: Private gated parking plus ample street parking for boats/trailersInside the Home:Step inside to a bright and airy living space filled with natural light and featuring wood-like tile flooring and recessed lighting throughout. Relax in the spacious living room with a 65” Smart TV and easy access via French doors to the private pool area.The kitchen is fully equipped and opens to a cozy bistro-style dining area—perfect for meals at home or entertaining guests.Guest Suite: Located on the main floor, this room offers two twin beds that can be converted to a king bed upon request, perfect for flexible sleeping arrangements.Primary Suite: Upstairs, enjoy a peaceful retreat with a king bed, Smart TV, ample closet space, and a luxurious ensuite bathroom.Family Suite: Also upstairs, the large family suite includes a queen bed, full-size futon, large closet, Smart TV, and access to a shared full bathroom with tub/shower combo.Outdoor Oasis:Your backyard paradise awaits with a private swimming pool surrounded by loungers and a comfortable artificial turf area. Enjoy outdoor dining and entertaining in the dedicated patio space. For cooler months (Nov 15–May 1), pool heating is available for an additional daily fee.Additional Amenities & Details:Impact-resistant windows and doors for added safety and comfortSecure property access with a 6-foot privacy/security fence around the compoundBeach chairs and towels provided for your convenienceClose proximity to local attractions: Duval Street nightlife, beaches, Garrison Bight Marina (1 block away)Boat owners: Ample street parking available for trailersImportant Notes:Pool Heat: Optional Nov 15–May 1, $20/day, must be arranged before check-in.Pet Policy: Pre-approval required for dogs. Max 1 dog, up to 50 lbs. Pet fee $20/day, reduces total guest occupancy by 1. Fees due prior to arrival.Get OFF THE HOOK from everyday life and experience the best of Key West in style and comfort. We look forward to hosting you!About pets:Pets allowed: dogs less than 20 lbs per pet (limit one pet total).PETS MUST BE APPROVED PRIOR TO BOOKING.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:Pool Heat Option: Arrange with manager prior to arrival. $20.00 per day..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.