Key West Hotels with Private Pools

With a stay at Tropical Inn in Key West (Old Town Key West), you'll be steps from Duval Street and 3 minutes by foot from Tennessee Williams Key West Exhibit. This bed & breakfast is 0.2 mi (0.3 km) from Ernest Hemingway Home and Museum 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.

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. Be sure to enjoy recreational amenities, including an outdoor pool, a fitness center, and bicycles to rent. 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 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 swimming 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 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 1.8 mi (2.8 km) from Mallory Square. 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 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.

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.

Poolside Paradise is a cozy, 1930s-era pool cottage lovingly renovated into a studio suite. The sage-green exterior blends Caribbean, Victorian, and contemporary influences: crisp white trim and sky-blue Bermuda shutters. This intimate, poolside cottage is set back from the street and shaded by gardens, mature palms, and gumbo limbo trees in a quiet, upscale, gated courtyard community of five historic Old Key West vacation rentals. The spacious pea-gravel courtyards boast tropical landscaping, coral and rock hardscaping, and walkways leading to the shared pool area. The central common area, with a pool, picnic tables, and gas grill, is shared by guests of this upscale, gated enclave of six historic Old Key West vacation rentals. There’s also a shared laundry area with commercial washers & dryers. Poolside Paradise was once the guest suite/pool cottage of Toon Hall. Toon Hall was owned (and aptly named) by Jeff MacNelly (1947-2000), lauded as one of the most brilliant political cartoonists. In 1977, MacNelly launched his comic strip Shoe, characterized by wit, wry humor, and cynicism. He became The Chicago Tribune’s syndicated editorial cartoonist. Newsweek Magazine described MacNelly’s style as “goofy gracefulness.” In his lifetime, MacNelly received three Pulitzers and two Reuben Awards, the highest honor of the National Cartoonists Society. Since Jeff MacNelly’s death in 2000, the Shoe comic strip has been kept alive by Chris Cassatt, Gary Brookins, and Susie MacNelly. Jeff MacNelly and his wife Susie cherished the vibrant Key West arts scene as a wintertime retreat. Today, Poolside Paradise offers a cozy island suite beside the pool and courtyard in a gated enclave of elegant vacation properties. Sip Cafe Cubano at the covered, alfresco dining table as Caribbean breezes rustle the palm fronds, or relax poolside with a Margarita. Prepare a light tropical meal in the kitchenette. Dine alfresco when nights are fragrant with jasmine and frangipani. Stroll to great seafood, fine dining, beaches, and iconic attractions like the KW Butterfly & Nature Museum, Southernmost Point, Higgs Beach, and West Martello Tower. Street parking is available out front. Poolside Paradise has one King Bed, ideal for couples or solo travelers. The home has an all-new water filtration system. Are you interested to learn more about the life and work of Jeff MacNelly? Pop into The Gallery on the Greene, the exclusive KW gallery representing MacNelly. Cartoons, pen and ink drawings, and original canvases are on display. Living: Poolside Paradise is a bright, airy, one-room living space with tile floors, large windows, raised ceilings, exposed beams, a ceiling fan, and an interior color palette of crisp white and earthy neutrals. A built-in desk/TV stand boasts a Smart TV with Roku. Stream your favorite shows or movies. French doors open to a covered alfresco dining area with rattan benches. Enjoy easy-breezy indoor/outdoor living space. Kitchen/Dining: The sunny kitchenette has tile floors, abundant cabinets, and Formica countertops. Appliances include a compact fridge, microwave, farmhouse-style sink, coffee maker, and toaster. Prepare sandwiches or a light island-style meal after a day at the beach! The kitchenette has a dinette with seating for two. French doors from the kitchen lead directly to covered alfresco dining and to the pool deck, making for seamless indoor/outdoor entertaining. Bedrooms/Baths: Poolside Paradise has one air-conditioned bedroom and one bathroom. There is one King bed. Matching rattan-style bedside tables have reading lamps. A built-in TV stand/desk boasts a Smart TV. The sparkling-clean, remodeled bathroom has a single-sink vanity, a walk-in glass door shower, a water-saving toilet, toiletries, and a hair dryer. Bedroom Overview: Primary: King Bed, Ensuite bath w/ walk-in shower Outdoor Amenities: A tall exterior fence, lush gardens, and mature trees provide privacy, security, shade, and a peaceful, tropical ambiance. Enjoy a private dining space on your fenced patio. This dining space seats two. The whitewashed fence buffers your private space from the central common area. Cool off in the sparkling blue swimming pool, or doze poolside on a cushioned lounge chair. This swimming pool will delight families, children, the very young, and the young at heart. (The common pool area is shared by guests of this upscale, gated enclave of six historic, Old Key West vacation rentals.) The poolside deck features a gas grill and two wrought-iron picnic tables with seating for eight or more. Gather for an afternoon cookout in paradise! Mature palms, mango trees, and vibrant bougainvillea shade the pool deck. Since laundry never sleeps (even when you're on vacation), the common area offers a laundry shed with two commercial washers and two commercial dryers. Discover the ultimate amenity: stroll just two blocks to Higgs Beach. Dip your toes in the emerald ocean. Collect seashells and savor serene Caribbean sunsets in pink, violet, and gold hues. Park your car in shaded street parking spots out front. Stroll or bike to attractions. The Neighborhood: The proximity of Toon Hall to the Casa Marina Hotel and the beautiful beaches adds to the appeal, making it a perfect blend of history, culture, and coastal living. Picturesque south island streets are lined with beautifully preserved Conch-style homes, each exuding character and charm. Lush, tropical landscaping adds to the serene atmosphere, making every walk or bike ride a delightful experience. A car is not necessary on the island. Make the green choice. Park out front or along shaded side streets and enjoy the island on foot, by bicycle, scooter, trolley, or bus. The island trolley stop is one block away. The Duval Loop City bus stop is four blocks away. Stroll .07 miles to The Ernest Hemingway Home and Museum, which offers a fascinating glimpse into the life of one of America's greatest writers. Enjoy the diverse culinary scene with various restaurants, cafes, and bars offering everything from fresh seafood to classic Cuban cuisine. Local favorites such as Blue Heaven, Louie’s Backyard, and Sloppy Joe’s are within easy reach, providing unforgettable dining experiences. Don't miss the chance to explore West Martello Tower during your stay! Just a 10-minute walk or a quick 3-minute bike ride from Toon Hall, this hidden gem is a tropical garden paradise on the site of a historic Civil War fort. The gardens, maintained by the Key West Garden Club, are open to the public. Higgs Beach, approximately 0.5 miles (a 10-minute walk or a 3-minute bike ride), is the closest beach to Southern Cross. Enjoy crystal-clear waters, perfect for swimming or snorkeling. The nearby White Street Pier offers panoramic sea views and excellent fishing opportunities. Approximately 1.5 miles away, Smathers Beach is Key West’s largest public beach. This two-mile stretch of sugary sand is ideal for sunbathing, beach volleyball, and water sports such as kayaking, paddleboarding, and windsurfing. Fort Zachary Taylor Historic State Park Beach, approximately 2 miles away, offers natural beauty and historical intrigue. Visitors and locals gather here and at Mallory Square to celebrate each and every exquisite island sunset. Seeking family-friendly activities or rainy-day excursions? Check out the Key West Aquarium, the Butterfly and Nature Conservatory, The Shipwreck Treasure Museum, and the Lighthouse and Keepers Quarters Museum. Nightlife and live music abound in Key West! Take in a show at the Tropic Cinema. Catch a live band at the Green Parrot. If you’ve been charmed by the magic of Toon Hall and wish to learn more about the life and work of Jeff MacNelly, tour the island art galleries and pay a visit to Gallery on the Greene, the exclusive gallery representing MacNelly. While cartooning was MacNelly’s livelihood, he was skilled in many media, including oil, acrylic, and clay (sculpture). Today, The Community Foundation of the Florida Keys honors the legacy of Jeff MacNelly with a youth scholarship, The Jeff MacNelly Memorial Scholarship Award, which helps students in Monroe County to further their art careers. Minimum age to book this property is : 25

. Orange Blossom Suite is one of three units that comprises the group property Conch Republic Cottages. The three cottages can be booked separately or as a group. There are stairs to the loft master bedroom. Orange Blossom Suite may not be suitable for people unable to climb stairs well. PLEASE NOTE THAT THIS PROPERTY DOES NOT HAVE A PRIVATE POOL ON SITE! . Orange Blossom Suite is one of three units that comprises the group property Conch Republic Cottages. The three cottages can be booked separately or as a group. There are stairs to the loft master bedroom. Orange Blossom Suite may not be suitable for people unable to climb stairs well. PLEASE NOTE THAT THIS PROPERTY DOES NOT HAVE A PRIVATE POOL ON SITE! Minimum age to book this property is : 25

Seashore at the Shipyard Boasting a great location in the Truman Annex, a shared pool, and easy beach access, you won't have to go far to dive into the beachside fun! Less than a mile to the picturesque Mallory Square and just under a mile to Fort Zachary Taylor Historic Park, there will be no shortage of attractions to explore close by. Hop on a ferry to Sunset Key for a day trip, walk to the Little White House, or enjoy the Sunset Celebration at Mallory Square. Rent a stand-up paddleboard to get out on the waves, or reserve your spot on a high-flying parasailing adventure. Wake up with a cup of coffee on your balcony as you plan your day, then do a few laps in the community pool. Cook up your catch from deep sea fishing in the fully equipped kitchen. Unwind with your favorite cable show, or stream a show on your device with the free WiFi. The shared washer/dryer will make sure you stay looking your best during your stay. This home includes one private parking spot. No matter what you choose to do on your vacation, this Florida coast home will make sure your stay stress-free and fun-filled! *Please note that last-minute bookings cannot be made online. No dog(s) are welcome in this home. No other animals are allowed without specific Vacasa approval. Parking notes: There is free parking available for 1 vehicle. Please note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximun occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices -not any personal conversation or information. Thank you for supporting our efforts to be good neighbors! Damage waiver: The total cost of your reservation for this Property includes a damage waiver fee which covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. More information can be found from the "Additional rules" on the checkout page. Due to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation. 24025 18127 25230-102936 By booking this reservation, you agree to the additional policies, terms, and conditions below. UNIT SPECIFIC TERMS - Due to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation. - No dog(s) are welcome in this home. No other animals are allowed without specific Vacasa approval. - The property shall not be used by more than the number of adults and children listed in your reservation. . - If early check-in is available for your reservation, you will be notified by 9 a.m. on the morning of your arrival by email. Late check-out is offered whenever possible for a small fee. - No smoking of any kind is permitted anywhere on the premises. - No commercial photography or filming is permitted on the property. Tents or other structures may not be erected. - Renter is liable for any damage to the property and agrees to accept charges to the card on file should damage occur during occupancy. - Permit ID: 25230-102936 - Tax ID: 102936 - Due to local laws, regulations, or Homeowner Association rules, guests may be required to agree to additional terms of service. A signed paper contract is required to be completed and returned to Vacasa. - Property Specific terms: Individual making the reservation must be 25 years of age or older and must occupy the rental property the entire term of the reservation. If individual on the reservation is under the age of 25, the individual and guests will not be allowed to check-in, and no refund will be issued. DAMAGE WAIVER The total cost of your reservation for this Property includes a damage waiver fee (USD) with the following costs, plus tax if applicable: 0 bedrooms: $60 for stays 1-3 nights, $15 per night for stays 4+ nights. 1 bedrooms: $60 for stays 1-3 nights, $15 per night for stays 4+ nights. 2 bedrooms: $80 for stays 1-3 nights, $20 per night for stays 4+ nights. 3 bedrooms: $100 for stays 1-3 nights, $25 per night for stays 4+ nights. 4 bedrooms: $100 for stays 1-3 nights, $25 per night for stays 4+ nights. 5 bedrooms: $120 for stays 1-3 nights, $30 per night for stays 4+ nights. 6 bedrooms: $120 for stays 1-3 nights, $30 per night for stays 4+ nights. 7 bedrooms: $140 for stays 1-3 nights, $35 per night for stays 4+ nights. 8 bedrooms: $140 for stays 1-3 nights, $35 per night for stays 4+ nights. The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to Vacasa prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit. How to Report Damage Please report accidental damage as soon as it occurs so we can assess and minimize the extent of the damages. Damage Waiver Additional Terms and Conditions The Damage Waiver only covers damage that occurs during the authorized rental period and that Renter or an authorized guest reports PRIOR TO CHECK OUT. The Damage Waiver does not cover intentional damage or damage caused by smoking, pets or other animals brought onto the Property, or criminal activity. The Damage Waiver does not cover damage to any structure other than the Property covered by your confirmed, non-fraudulent reservation. Renter is responsible for any accidental damage that exceeds $3,000. Damages for covered claims in excess of $3,000 or for uncovered claims will be charged to the Renters credit card. The Damage Waiver program is provided and administered by Vacasa and is not an insurance policy. The Damage Waiver does not provide liability coverage and does not cover vehicles or guest personal items.24025 18127 25230-102936