Find Key West Hotels with Private Pools

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 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.

Old Town Garden Villas - Abaco Suite Whisk your special someone off to this enchanting Key West townhouse. Enjoy the shared pool and courtyard. The family dog is also welcome to join you for an additional nightly fee. Notice: This is in a residential area. Quiet Hours are 10 pm to 8 am. Park your car on the street and walk everywhere! This home is half a mile from the Southernmost Point and just one block to the Ernest Hemingway Home and Museum and Duval Street. You'll be able to explore the local attractions and dive into the beachside fun without hassle. Chill out and surf the cable channels while the shared washer/dryer takes care of any laundry that may have piled up. The first floor is newly renovated so you can enjoy a more luxurious stay. Grab a book and dip your toes into the shared pool while gentle music streams over the free WiFi. Make a few snacks in the convenient kitchen and then head down to the beach to spend the day on a paddleboard, jet ski, or just hanging out by the crashing waves. No matter how you spend your days and nights, this Florida Keys townhouse will make your vacation stress-free. *This is a dog-friendly unit with a two dog limit and a 35 pound weight limit for each dog. 2 dog(s), weighing 35lbs or less, are welcome in this home. No other animals are allowed without specific Vacasa approval. Parking notes: No parking available. 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. 2563 24682 25230-103746 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. - 2 dog(s), weighing 35lbs or less, 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: 25230-103746 - Tax ID: 103746 - 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. Your ID will be verified at our office when checking in. 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.2563 24682 25230-103746

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.

Hemingway Hideaway – Charming Townhouse in Truman Annex at Historic Foundry BuildingDiscover your perfect Key West retreat in this beautifully positioned 3-story townhouse within the coveted Truman Annex community. Just steps away from the vibrant heart of Key West, Hemingway Hideaway offers the ideal blend of comfort, convenience, and classic island charm.Property Highlights:Gated Entry & Private Courtyard: Enjoy privacy and tranquility as you enter your own peaceful oasis.Open Floor Plan: The spacious first floor seamlessly connects the living room, dining area, and fully equipped kitchen — perfect for relaxing or entertaining.Half Bath/Powder Room: Conveniently located off the kitchen.Master Suite on Second Floor: King-size bed, ensuite bathroom, two linen closets, in-unit washer/dryer, and a private balcony for morning coffee or evening relaxation.Third Floor Bedroom: Queen-size bed occupies the entire level with its own ensuite bathroom.Designated Parking: One assigned parking space located at the rear of the unit.Private Pool: Enjoy access to the Foundry building’s exclusive pool — a refreshing escape after a day exploring.Complimentary Bicycles: Two bikes included to effortlessly explore Key West like a local.Prime Location:Just steps from the Truman Amphitheater & Splash Park, Fort Zachary Taylor, the Historic Seaport & Mallory Square, Truman’s Little White House, and popular spots like the Green Parrot. Within a 4-block radius of the lively 200 block of Duval Street — where all the action happens!Booking Notes:Hemingway Hideaway – Charming Townhouse in Truman Annex at Historic Foundry BuildingDiscover your perfect Key West retreat in this beautifully positioned 3-story townhouse within the coveted Truman Annex community. Just steps away from the vibrant heart of Key West, Hemingway Hideaway offers the ideal blend of comfort, convenience, and classic island charm.Property Highlights:Gated Entry & Private Courtyard: Enjoy privacy and tranquility as you enter your own peaceful oasis.Open Floor Plan: The spacious first floor seamlessly connects the living room, dining area, and fully equipped kitchen — perfect for relaxing or entertaining.Half Bath/Powder Room: Conveniently located off the kitchen.Master Suite on Second Floor: King-size bed, ensuite bathroom, two linen closets, in-unit washer/dryer, and a private balcony for morning coffee or evening relaxation.Third Floor Bedroom: Queen-size bed occupies the entire level with its own ensuite bathroom.Designated Parking: One assigned parking space located at the rear of the unit.Private Pool: Enjoy access to the Foundry building’s exclusive pool — a refreshing escape after a day exploring.Complimentary Bicycles: Two bikes included to effortlessly explore Key West like a local.Prime Location:Just steps from the Truman Amphitheater & Splash Park, Fort Zachary Taylor, the Historic Seaport & Mallory Square, Truman’s Little White House, and popular spots like the Green Parrot. Within a 4-block radius of the lively 200 block of Duval Street — where all the action happens!Booking Notes:Minimum 7-night stay required between January 1 – April 30, 2020, with Saturday-to-Saturday check-in/check-out.Outside this period, flexible arrival and departure days.Discounts available for stays of 28 nights or longer.If this property is booked, we can recommend other great homes in the area.Pack your suitcase and get ready for an unforgettable Key West getaway in your home away from home!Outside this period, flexible arrival and departure days.Discounts available for multiple months staysIf this property is booked, we can recommend other great homes in the area.Pack your suitcase and get ready for an unforgettable Key West getaway in your home away from home!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 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 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 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.

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