Vacation rentals in Key West, FL with a pool

A reflection of old Key West, Eisenhower’s Retreat was designed and built with the architectural feel of an old "Conch House", but with all the amenities of a new luxury home. Situated on the edge of Old Town Key West near everything Key West has to offer, your home boasts tall ceilings, large rooms, an expansive and well appointed kitchen with custom cabinets as well as a heated pool and private boat slip. Enjoy the convenience of two off-street parking spaces or simply bike to Duval St. Bayview Park is only a block away and was built on the premise that at one time it overlooked the bay before expanding Key West to include "New Town". Enter to a "shotgun" view (reference to old Key West homes which would allow, if fired, a shotgun shot to pass from the front door to the back door with out interruption) of the downstairs through which you can view the custom kitchen, dining area, living and lastly, back yard. The kitchen has custom cabinets and stainless steel appliances as well as all teh tools you’ll need to prepare the finest of cuisine! Just in front of the kitchen is a large wood dining table seating 6 comfortably. The Living rooms is comfortably situated with a pull out sofa and large HD flat screen with full HD cable. Wish to enjoy the tropical air? Lounge on your private porch take a dip in your private heated pool. On the next floor are two master suites with en suite bathrooms in each. Each suite has it’s own balcony and walk in closets. All your luxury linens exceed the highest of standards and we aim to provide you with the comfort to make your stay not only memorable, but heavenly as well. Bring the whole family! The top floor has a loft with 4 twin beds, which can be arranged to make two King beds (with notice) and a central bathroom. The top floor also has a private room with two twin beds as well and can also be joined to make one King bed. Whether its kids or adults, this home provides numerous options to accommodate the widest of sleeping accommodations necessary, not often found in ole Key West. We hope to have you as our guest at Eisenhower’s Retreat! RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).

"Captain’s Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropically furnished yard, a prime Old Town location, and a private 43’ boat slip. Through the sliding glass doors of the living area is the private back yard complete with a large deck and a private pool. There are chaise lounges by the heat-optional pool when it’s time for a swim and some sun. A full outdoor dining set by the pool can comfortably sit 6. Cross the parking lot of this private complex to the docks where you will find your own boat slip. The perks of this little-known location are many: walking distance to the family friendly Bayview Park and Fausto’s a local grocery store. All while still being tucked away in your own quiet neighborhood. This home includes plenty of off-street parking. The master bedroom is on the second level and has a King-sized bed, a large flat-screen TV, plenty of dresser space, and a private balcony overlooking the water. The master bathroom is en-suite with dual sinks, a large soaking tub, a glass and marble shower. The second bedroom is also on the second living level, and has a Queen sized bed, a flat-screen TV, and a private balcony. The second bathroom is also en-suite and has a tub/shower. The third level can sleep a total of 6: there is a private bedroom with two twin beds that can convert to a King upon request, and an open room with another 4 twin beds, which can convert to 2 King sized beds upon request. The third level accommodations share one full bathroom with a tub/shower. The fifth bedroom is on the main floor and has a King size bed and is also en-suite with access to the bathroom through the hallway as well. Additional sleeping area is available in the living room, as the sofa pulls out into a Queen bed. There is also a full bath off the living room next to the bedroom on the main floor. Amenities: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking, Flat Screen State-of-the Art HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Heated Pool, Private Boat Slip, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. This property will accommodate 10-12 adults. 2023: New custom dining table, new couches and chairs, new carpeting as well as new LVT on stair treads and landings! RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates). DOG FRIENDLY. Please contact us to confirm specific pet policies.

Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boasts a large two car garage with stairs leading up to the main floor consisting of a sprawling kitchen appointed with all the tools even the most experienced chefs would envy. Just in front of the kitchen is a large wood dining table to seat 6 comfortably while overlooking past the living room and towards the water. There is a kitchen bar which allows for additional seating as well. The Living rooms is comfortably situated with a pull out sofa and large HD flat screen with full HD cable. Wish to enjoy the tropical air? Lounge on your private balcony and watch the charter fishing fleet depart or return amidst their daily catch. Enjoy the spectacle and camaraderie while they unload the catch of the day with just a short walk from your oasis. On the next floor are two master suites with en suite bathrooms. Each suite has it’s own balcony and walk in closets. All your luxury linens exceed the highest of standards and we aim to provide you with the comfort to make your stay not only memorable, but heavenly as well. Bring the whole family! The top floor has a loft with 4 twin beds, which can be arranged to make two King beds (with notice) and a central bathroom. The top floor also has a private room with two twin beds as well and can also be joined to make one King bed. Whether its kids or adults, this home provides numerous options to accommodate the widest of sleeping accommodations necessary, not often found in ole Key West. 2023: New custom dining table, new couches and chairs, new carpeting as well as new LVT on stair treads and landings! The heated pool is located in the rear yard which is situated a mere distance to the water and your own private boat slip. You can choose to walk from the main floor balcony down your private steps to your private liana or through a private door from the garage. Either way, seclusion is what you have to relax in when at Bayview Retreat! RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates). DOG FRIENDLY. Please contact us to confirm specific pet policies.

"Seafarer’s Refuge” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropically furnished yard, a prime Old Town location, and a private 43’ boat slip. All of the typical Key West spots are accessible by a short walk or bike ride, but should you decide to drive there is private off-street parking for two cars with this home. The living area has a large flat screen HDTV with DVD player, which you can watch from the comfort of the plush living room furniture or the kitchen/dining areas thanks to the open living plan of this main floor. The living room sofa also pulls out to a Queen-sized bed for sleeping extra guests. The kitchen is fully equipped with state-of-the-art appliances. The dining area has seating for 8, with 4 additional seats at the kitchen bar. Through the sliding glass doors of the living area is the private back yard complete with a large deck and a private pool. There are chaise lounges by the heat-optional pool when it’s time for a swim and some sun. A full outdoor dining set by the pool can comfortably sit 6. Cross the parking lot of this private complex to the docks where you will find your own boat slip. The master bedroom is on the second level and has a King-sized bed, a large flat-screen TV, plenty of dresser space, and a private balcony overlooking the water. The master bathroom is en-suite with dual sinks, a large soaking tub, a glass and marble shower. The second bedroom is also on the second living level, and has a Queen sized bed, a flat-screen TV, and a private balcony. The second bathroom is also en-suite and has a tub/shower. The third level can sleep a total of 6: there is a private bedroom with two twin beds that can convert to a King upon request, and an open room with another 4 twin beds, which can convert to 2 King sized beds upon request. The third level accommodations share one full bathroom with a tub/shower. Additional sleeping area is available in the living room, as the sofa pulls out into a Queen bed. There is also a half bath off the living room on the main floor. Amenities: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking, Flat Screen State-of-the Art HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Heated Pool, Private Boat Slip, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. This property will accommodate 10 guests. RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).

Charming Pool Cottage in the Heart of Old Town Key West Perfectly situated in historic Old Town Key West, this quaint and inviting pool cottage offers the ideal island escape for a couple, with room for occasional guests. Thoughtfully decorated and impeccably maintained, the home features a newly renovated kitchen and beautifully designed outdoor spaces to enjoy the island breeze. Property Highlights: Comfortable Accommodations: The primary bedroom includes a king bed, while the guest bedroom offers two single beds—perfect for visiting friends or family. Modern Conveniences: A full-sized, fully equipped kitchen opens directly onto the stunning pool deck—ideal for entertaining. A stackable washer and dryer are included for added convenience. Outdoor Living at Its Best: Private Pool: Cool off or unwind by the pool, which can be heated for year-round enjoyment. Front Porch: Sip your morning coffee and watch the world go by from the charming front porch. Back Deck: Host a barbecue or relax after a day exploring Key West in this serene outdoor space. Parking: Street parking is typically available within a block of the home. This delightful cottage blends classic Key West charm with modern comforts—making it your perfect home away from home. STAYS FROM DECEMBER THROUGH APRIL NEED TO BEGIN ON THE 1ST OF THE CALENDAR MONTH - THANKS FOR UNDERSTANDING.

Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be in Coastal Comfort. This home is located in the private community of Key Cove Landings, on an exclusive lane of waterfront residential homes. The perks of this little-known location are many: walking distance to the essentials such a Publix grocery store and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. This home includes plenty of off-street parking in the private garages, as well as on the driveways in front of the house. Key Feature: 3 en’suite bedrooms This home’s highlight is the wall of floor-to-ceiling windows facing the water to provide the optimal view from every part of the house. The large open plan living room has a spacious seating area with plush couches around a large HD flat screen Smart TV. One of the couches also pulls out to a Queen-sized sleeper sofa for additional guests. There is a dining table with seating for up to 6 diners, with additional seating for 4 at the kitchen bar. The master bedroom has a King-sized bed, a large flat-screen HD TV, and an en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The master bedroom also has a wall of floor-to-ceiling glass doors opening out to your waterfront balcony. The second bedroom has a King-sized bed, a flat-screen HD TV, large walk-in closet, and a glass sliding door with access to the waterfront balcony. The bathroom is en-suite. The third bedroom is also on the 2nd floor with a Queen bed, flat screen TV, balcony access and en-suite bathroom. On the main floor there is a fourth bedroom with trundle bed. There is a half bath down the hall. Out back is one of the highlights of this home: the covered lanai and pool area. The covered outdoor dining area comfortably seats six for a poolside meal. The pool is heavenly, with views of the open water and visiting heron on the tropical greenery that surrounds the back yard. There is also a pool lounge area with comfortable chaises in a piece of deck that gets equal sunshine and shade. The backyard is complete with a large propane grill for a poolside BBQ. AMENITIES: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Garage & on Driveway, Flat Screen State-of-the Art Smart HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Heated Pool, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. Pets Considered. This property will accommodate 8. Dockage is not available at this home’s development. RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates). DOG FRIENDLY. Please contact us to confirm specific pet policies.

This compound is comprised of two homes in exclusive Key Cove Landings, by combining Coastal Comfort and 3/4 Time, two 4-bedroom homes! The perks of this little-known location are many: walking distance to the essentials such a Publix grocery store and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. This home includes plenty of off-street parking in the private garages, as well as on the driveways in front of the homes. Key Feature: 6 en’suite bedrooms in addition to a bedroom in each home off the living room, each with two twin beds. The homes have the same large open floorplan with spacious seating areas. The master bedrooms have King-sized beds, large flat-screen HD TVs, and en-suite bathrooms complete with a glass showers, large Jacuzzi tubs and separate room for the facilities. Second bedrooms have King-sized bed, flat-screen HD TVs, large walk-in closets, and glass sliding doors providing access to the waterfront balcony. The bathrooms are en-suite. The third bedrooms are also on the 2nd floor with en-suite bathroom. We suggest looking at each individual listing for more specific information on each of the homes that comprise this Key Cove Landings compound. AMENITIES: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Garage & on Driveway, Flat Screen State-of-the Art Smart HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Heated Pool, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. Pets Considered. This property will accommodate 16. This compound does not include dockage. RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).

4 Bedroom, 3 Bathroom, Sleeps 8 Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be at Mother Ocean. This home is located in the private community of Key Cove Landings, on an exclusive lane of waterfront residential homes. The perks of this little-known location are many: walking distance to the essentials such a Publix grocery store and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. This home includes plenty of off-street parking in the private garages, as well as on private driveways leading to the house. This home’s highlight is the wall of floor-to-ceiling windows facing the water to provide the optimal view from every part of the house. The large open plan living room has a spacious seating area with a sectional leather couch around a large HD flat screen Smart TV. There is a dining table with seating for up to 6 diners, with additional seating for 4 at the kitchen bar. The master bedroom has a King sized bed, a large flat-screen HD TV, and an en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The master bedroom also has a wall of floor-to-ceiling glass doors opening out to your waterfront balcony. The second bedroom has two twin beds that can be converted to a king with ample notice, a flat-screen HD TV, large walk-in closet, and a glass sliding door with access to the waterfront balcony. The third bedroom is also on the 2nd floor with a full size bed, flat screen TV, and also with balcony access. On the main floor there is a fourth bedroom with twins bed. There is a full bath down the hall for convenience. Out back is one of the highlights of this home: the covered lanai and pool area. The covered outdoor dining area comfortably seats six for a poolside meal. The pool is heavenly, with views of the open water and visiting heron on the tropical greenery that surrounds the back yard. There is also a pool lounge area with comfortable chaises in a piece of deck that gets equal sunshine and shade. AMENITIES: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Garage & on Driveway, Flat Screen State-of-the Art Smart HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Heated Pool, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. Pets Considered. This property will accommodate 8 adults. Dockage is not available at this home’s development. RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates). DOG FRIENDLY. Please contact us to confirm specific pet policies.

Casa Azul is a luxe modern cottage with an open-concept living area that ends up filled with natural sunlight. Take a dip in the heated saltwater plunge pool with waterfall feature and night lighting. The best of Key West is at your fingertips - in Old Town only two blocks from Duval Street! Pet friendly, private parking & perfect for your next extended stay in Key West. Casa Azul is the perfect mix of comfort and stylish. Sleek grey quartz countertops, stainless steel appliances and loads of storage space await you! Get ready to cook with state-of-the-art appliances where you can serve up your goods at the breakfast bar offering up a spot for morning coffee or switch on over to the six-top kitchen table. Bedroom 1: Queen bed Features: Full bathroom with walk-in shower and plunge tub, private porch facing Elizabeth street, wardrobe, smart TV & closet. Bedroom 2: Full bed Features: Modern full bathroom, smart TV, blackout shades & closet. Unwind with high-speed wifi, a third full bathroom for guest use & an 80 inch TV for entertaining. Or sit in the sun loungers by the amazing pool to soak in the afternoon rays. Our self check-in makes the process seamless. Guests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay. Parking for 1 vehicle in the driveway and a corresponding space in front of the driveway on the street, both of which are reserved for this property. Any additional street parking is first come first serve and can be difficult to find. There are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi or by feet. This unit is located in downtown Key West and many attractions are within walking distance. Feel free to ask us for recommendations! - 28-night minimum rental only - Private laundry room - Entire home is Solar powered with back up energy - Pets welcomed

"Banana Breeze" is an upscale escape by the sea, and considered by some to be a hidden gem. Tucked away in your own oasis in a private waterfront retreat, with your own heated pool. Look out at the open water views while enjoying the professionally decorated interior and spacious outdoor patio. Imagine relaxing at "Banana Breeze" with friends, family or both while listening to island music and casting away into delightful bliss. Key Cove estates is an exclusive group of homes all located on the waterfront and provides hard to find privacy. Centrally located in the middle of Key West, you and your guests will have the convenience of walking to grocery stores as well as shopping just across the street. Old Town, Key West’s Historic area is just a few minutes away by transportation. Whether you bring your own vehicle or rent one of the many local options like mopeds, electric cars, or bikes, you can easily park in one of two garages or your own private driveway. The first floor of the home is located atop of a grand set of exterior stairs which lead you to the front door, through which you will find a expansive floorplan consisting of a professional kitchen fully functional for even the most advanced chefs. This area also consists of a large living room and dining area suitable for all your guests to congregate. The far wall is comprised of glass doors allowing breathtaking views at the Florida Bay and the waters edge below. This floor as a whole is your central area for entertaining guests and gathering families together. Accommodations This home has one master suite located on the top floor. The master bedroom has a King sized bed and a beautiful en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate facilities room. The bedroom opens out to your waterfront balcony, with gorgeous water view. The other rooms are down the hallway, one with a Queen size bed and the other third bedroom has two twin beds that may be converted into 1 King upon request, with ample notice. Both have a glass sliding door with access to the same waterfront balcony and share a full bathroom. On the main floor there is a fourth bedroom with two twin beds that also seamlessly convert to a King bed, upon request and a full bathroom down the hall for convenience. Outdoor Entertaining On the ground floor is one of the highlights of this home: the outdoor landing and entertainment area with a heated kidney shaped pool. The outdoor dining area comfortably seats six for an outdoor meal. The pool is heavenly, with views of the open water and visiting heron on the tropical greenery that surrounds the back yard. There is also a lounge area with comfortable chaises in a piece of deck that gets equal sunshine and shade. The backyard is complete with a large propane grill for BBQs. Additional space under the house also offers another covered indoor/outdoor area for playing, additional storage, etc. Each floor has its own outdoor area with furnishings for what ever your mood might be. Whether you’d like to entertain a larger group on the ground floor, or have a more intimate occasion on the first floor balcony overlooking the water, or if you’d simply like to take in the morning views while sipping coffee out your master suite, Banana Breeze offers numerous different options AMENITIES... Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Garage & on Driveway, Flat Screen State-of-the Art Smart HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Pool, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. Pets Considered. This property will accommodate 8 guests. Dockage is not available at this home’s development. RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).

If you’re looking for an upscale escape by the sea, Havana Daydream is your Key West hidden gem. Enjoy the island life in your own oasis tucked away from the bustle of Old Town in a private waterfront retreat, with your own private waterfront pool. Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor space. Slow down, relax and prepare for life the way it should be at Havana Daydream. Key Features: 2 en’suite bedrooms each with porch access 4 full bathrooms LOCATION: This home is located in the gated community of Key Cove, on an exclusive lane of waterfront luxury homes. The perks of this little-known location are many: walking distance to the essentials such a grocery stores and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. The excitement of downtown Old Town is just a few minutes away by car, moped, or bicycle. This home includes plenty of off-street parking in the private garages, as well as private driveways. LIVING AREA & KITCHEN: The main entrance to this home is at the top of the stairs leading from the ground level. This home’s highlight is the wall of floor-to-ceiling windows facing the water to provide the optimal view from every part of the house. The large open plan living room has a spacious seating area with plush couches around a large HD flat screen Smart TV. One of the couches also pulls out to a Queen-sized sleeper sofa for additional guests. There is a dining table with seating for up to 8 diners, with additional seating at the kitchen bar. The gourmet kitchen has state-of-the-art appliances and is fully equipped with all of the tools and utensils one could want or need. The sliding glass doors open up to a wide waterfront deck with additional space for a light meal, coffee, a glass of wine, or just taking in the view. ACCOMMODATIONS: This home has two master suites, both of which are located on the top floor. The first master bedroom has a King size bed, a large flat-screen HD TV, and a beautiful two-room en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The first master bedroom also has a wall of floor-to-ceiling glass doors opening out to your waterfront balcony, with gorgeous water views. The second master suite is down the opposite hallway, with a King size bed and an en-suite bathroom. The second master suite also has a flat-screen HD TV, large walk-in closet, and a glass sliding door with access to the waterfront balcony. The third bedroom is beside the second master suite, with two twin beds that covert to 1 King upon request, flat screen TV. An additional bathroom is situated in the hall next to the stairs and across from the third bedroom. On the main floor there is a fourth bedroom with two twin beds that also convert to a King bed upon request. This bedroom also has a flat screen TV, and a full bathroom down the hall. LANAI: Out back is the covered outdoor dining area comfortably seats six and has ample room for entertaining. With visiting heron on the tropical greenery that surround the back yard, your guest will enjoy the natural splendor Havana Daydream and Key West have to offer. Enjoy the brand new, kidney shaped, heated pool. The backyard is complete with a large propane grill. Additional space under the house also offers another covered indoor/outdoor area for playing, additional storage, etc. Dockage is not available at this home’s development. RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates). DOG FRIENDLY. Please contact us to confirm specific pet policies.

Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be at Southern Comfort. This home is located in the private community of Key Cove Landings, on an exclusive lane of waterfront residential homes. The perks of this little-known location are many: walking distance to the essentials such a Publix grocery store and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. This home includes plenty of off-street parking in the private garages, as well as on the driveways in front of the house. Key Feature: 3 en’suite bedrooms each with porch access This home’s highlight is the wall of floor-to-ceiling windows facing the water to provide the optimal view from every part of the house. The large open plan living room has a spacious seating area with plush couches around a large HD flat screen Smart TV. One of the couches also pulls out to a Queen-sized sleeper sofa for additional guests. There is a dining table with seating for up to 6 diners, with additional seating for 4 at the kitchen bar. The master bedroom has a King size bed, a large flat-screen HD TV, and an en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The master bedroom also has a wall of floor-to-ceiling glass doors opening out to your waterfront balcony. The second bedroom has a King size bed, a flat-screen HD TV, large walk-in closet, and a glass sliding door with access to the waterfront balcony. The bathroom is en-suite. The third bedroom is also on the 2nd floor with twin beds, flat screen TV, balcony access and en-suite bathroom. On the main floor there is a fourth bedroom with twin bed. There is a half bath down the hall. Out back is one of the highlights of this home: the covered lanai and pool area. The covered outdoor dining area comfortably seats six for a poolside meal. The pool is heavenly, with views of the open water and visiting heron on the tropical greenery that surrounds the back yard. There is also a pool lounge area with comfortable chaises in a piece of deck that gets equal sunshine and shade. The backyard is complete with a large propane grill for a poolside BBQ. AMENITIES: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Garage & on Driveway, Flat Screen State-of-the Art Smart HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Heated Pool, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. Pets Considered. This property will accommodate 8 guests. Dockage is not available at this home’s development. RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates). DOG FRIENDLY. Please contact us to confirm specific pet policies.

Island Dreaming – Your Luxury Key West Getaway - MONTHLY RENTAL Welcome to Paradise *** Please note for 2027 High Season rentals Jan- February - Arrival after the 5th of January for 6 week minimum is required in order to get accurate pricing*** Discover the ultimate island retreat at Island Dreaming, a spectacular Key West vacation home nestled between the charm of Old Town and the tranquility of the Meadows District. Whether you’re traveling with family or friends, this private oasis blends upscale amenities with the laid-back lifestyle of the Keys. Property Highlights Location: Quiet yet central – walk to downtown, yet enjoy serene privacy Bedrooms: 4 spacious bedrooms including two primary suites Bathrooms: 3.5 modern bathrooms Parking: Off-street parking for 1 vehicle Size: Comfortably sleeps 8+ guests Outdoor Oasis Private Saltwater Pool: 12’ x 18’, heated (by request), custom-tiled with waterfall & in-pool loungers Outdoor Kitchen: BBQ grill, sink, and ice-maker – perfect for entertaining Multiple Outdoor Living Spaces: Expansive front porch for morning coffee Back deck for cocktails under the stars Shaded & sunny lounging areas Lush Landscaping: Tropical flora, paver walkways, irrigation, and outdoor lighting Interior Features Seamless Indoor-Outdoor Living: 9-ft ceilings & 16-ft glass doors connect the living area to the poolside deck Gourmet Kitchen: Fully equipped for all your culinary needs Wine Lovers’ Dream: 600-bottle, walk-in, climate-controlled wine room Two Primary Suites: First-floor suite with private bath Second-floor suite with vaulted pine ceiling & private balcony Bright Living Room: Natural light and pool views with wall-to-wall glass doors Additional Amenities Whole-house water filtration system Custom-designed staircase Pool heat available (fee applies; must be requested in advance) High-speed WiFi & smart TVs Washer & dryer Perfect Location Located in a diverse, upbeat neighborhood, Island Dreaming puts you close to: Duval Street nightlife Local restaurants & bars Art galleries, shops, and attractions Beaches & marinas Ideal For Families Groups of friends Extended stays Guests seeking a luxury, peaceful vacation with easy access to the action Additional fees may be added after booking: Pool heating fee of $300 per month for the months of November-March(optional) Reservations of more than a month require a mid stay cleaning fee Book Your Stay Today and Start Living the Island Dream!

If you’re looking for an upscale escape by the sea, 3/4 Time is your Key West hidden gem. Enjoy the island life in your own oasis tucked away from the bustle of Old Town in a private waterfront retreat, with your own private waterfront pool. Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be at 3/4 Time. KEY FEATURE: 3 en’suite bedroom each with porch access 4 full bathrooms LOCATION: This home is located in the community of Key Cove Landings, on an exclusive lane of waterfront residential homes. The perks of this little-known location are many: walking distance to the essentials such grocery stores and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. The excitement of downtown Old Town is just a few minutes away by car, moped, or bicycle. This home includes plenty of off-street parking in the private garages, as well as private driveways. LIVING AREA & KITCHEN: The main entrance to this home is at the top of the stairs leading from the ground level. This home’s highlight is the wall of floor-to-ceiling windows facing the water to provide the optimal view from every part of the house. The large open plan living room has a spacious seating area with plush couches around a large, wall mounted, HD flat screen Smart TV. One of the couches also pulls out to a Queen-sized sleeper sofa for additional guests. There is a dining table with seating for up to 8 diners, with additional seating at the kitchen bar. The gourmet kitchen has state-of-the-art appliances and is fully equipped with all of the tools and utensils one could want or need. The sliding glass doors open up to a wide waterfront deck with additional space for a light meal, coffee, a glass of wine, or just taking in the waterfront view. ACCOMMODATIONS: This home has three en-suite rooms, three of which are located on the top floor. The first master bedroom has a King size bed, a large wall mounted flat-screen HD TV, and a beautiful two-room en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The first master bedroom also has a wall of floor-to-ceiling glass doors opening out to your waterfront balcony, with gorgeous water views. The second master suite is down the opposite hallway, with a King size bed and an en-suite bathroom. The second master suite also has a wall mounted flat-screen HD TV, large walk-in closet, and a glass sliding door with access to the waterfront balcony. The third bedroom is beside the second master suite, with two twin beds and a flat screen TV. On the main floor there is a fourth bedroom with two twin beds that can be seamlessly converted to a King bed, upon request. This bedroom also has a wall mounted flat screen TV, and a full bathroom down the hall for convenience. LANAI: Out back is the covered outdoor dining area comfortably seats six and has ample room for entertaining. With visiting heron on the tropical greenery that surround the back yard, your guest will enjoy the natural splendor 3/4 Time and Key West have to offer. Enjoy the brand new, modern pool with a dip area, which of course is heated for an added level of comfort. The backyard is complete with a large propane grill, outdoor furniture, and lounge chairs. Additional space under the house also offers another covered indoor/outdoor area for playing, additional storage, etc. Dockage is not available at this home’s development. RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).

Welcome to The Watson House, a historic gem at 522 Simonton Street, where old-world luxury seamlessly blends with modern elegance in Old Town Key West. This expansive two-story, 4-bedroom, 4.5-bath retreat is ideally situated just steps from Duval Street and the iconic Conch Harbor. The main-floor master suite boasts a king bed and luxurious ensuite bath. The spacious living room and additional seating area lead into an open-plan kitchen and living space, seamlessly extending to the outdoor terrace through 20-foot retractable glass doors. The gourmet chef’s kitchen is equipped with top-of-the-line appliances. Upstairs, you’ll find three more ensuite bedrooms: one with a queen bed, another with a full bed, and a kids’ room offering a queen bed and bunk bed. Assigned parking is a valuable bonus. Outside, indulge in the outdoor kitchen with a built-in grill, and unwind in the pool, illuminated by LED lights, or relax in the jacuzzi. This is Key West living at its finest! The Watson House offers a spacious, historic home with four bedrooms and 4.5 bathrooms. The main floor features a master suite, large living and seating areas, and an open kitchen with retractable glass doors leading to an outdoor terrace. Upstairs, three ensuite bedrooms include a mix of queen, full, and bunk beds. The property boasts a gourmet kitchen, assigned parking, an outdoor grill, a pool with LED lights, and a relaxing jacuzzi. Private Entry Key will be available when check in. Most visitors get around Old Town Key West by walking, biking, or using golf carts, as everything is close by. Taxis, rideshares, and the Duval Loop shuttle are also convenient options for exploring the island. 🚲🌴

This captivating modern home with a striking exterior and vaulted ceilings makes for the perfect vacation home. Just one block from Duval Street in a highly sought-after location, Contra House is a must-see and must-stay in downtown Key West. With an amazing pool, Contra House is comprised of two one-of-a-kind homes, each with two bedrooms and two bathrooms. The galley kitchen in the front house has all of your essentials along with a wine cooler! The back house has a state-of-the-art, open concept living area that is bright and airy as the back sliding doors open up the private pool area. The gourmet kitchen includes a wine cooler and spacious countertops for all of your backyard barbecuing and delicious dinners! Splitting the two homes is a heated in-ground pool with seating. Along with the pool you can find a grill and plenty of backyard entertaining space. The bed layout is as follows: Front House sleeps up to 6 guests: Bedroom 1: Queen (on first floor with shared bathroom access) Bedroom 2: King (on second floor with en-suite bathroom) Extra Sleeping: queen pull out couch in living room Back House sleeps up to 6 guests: Bedroom 1: King (with en-suite bathroom) Bedroom 2: King (with shared bathroom access) Extra Sleeping: Queen pullout couch in living room Our contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to check-in to enter the unit. Parking Information: Two off-street parking spots are included with your stay. If you need additional parking, there are spots along Simonton Street. The other spaces are for neighboring properties. We can provide you with recommendations for parking additional vehicles upon request! There are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance. ​​- Contra House features a private washer/dryer in both the front & back house.

Quintessential Key West Retreat Experience the best of island living at this beautifully updated **3-bedroom, 2.5-bath** vacation home in the heart of Old Town Key West. Perfectly situated just steps from Duval Street, you’ll be within walking distance of the island’s best restaurants, nightlife, shopping, galleries, and historic attractions. Designed for comfort and entertaining, the first floor features a bright, open-concept living and dining area, a fully equipped kitchen, and a convenient powder room. Upstairs, you’ll find three spacious bedrooms and two full bathrooms, providing plenty of room for family and friends. Step outside to your private backyard oasis with a refreshing **pool**, the perfect place to relax after a day of exploring Key West. A rare bonus in Old Town, the home also includes a **designated assigned parking space**, making it easy to come and go without the hassle of searching for parking. Whether you’re looking for a relaxing getaway or an adventure-filled vacation, this quintessential Key West home offers the perfect combination of comfort, style, and an unbeatable location. Downtown Key West 3BDR/2BA Home

If you’re looking for a luxury escape on the water, Paris Mango is your island gem. Named after Jimmy’s "Last Mango in Paris", your luxury leather seating throughout will transport you to the lifestyle of the rich and famous. Enjoy the island life in your own oasis tucked away from the bustle of Old Town in a private waterfront retreat, with your own private heated pool. Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be at Paris Mango. Key Features: 2 en’suite bedrooms each with porch access. 4 full baths LOCATION: This home is located in the gated community of Key Cove, on an exclusive lane of waterfront residential homes. The perks of this little-known location are many: walking distance to the essentials such a Publix grocery store and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. The excitement of downtown Old Town is just a few minutes away by car, moped, or bicycle. This home includes plenty of off-street parking in the private garages. LIVING AREA & KITCHEN: The main entrance to this home is at the top of the stairs leading from the ground level. This home’s highlight is the wall of floor-to-ceiling windows facing the water to provide the optimal view from every part of the house. The large open plan living room has a spacious seating area with leather couch around a large HD flat screen Smart TV. There is a dining table with seating for 8, with additional seating at the kitchen bar on white leather stools. The gourmet kitchen has state-of-the-art appliances and is fully equipped with all the tools and utensils one could want or need. The sliding glass doors open up to a wide waterfront deck with additional space for a light meal, coffee, a glass of wine, or just taking in the waterfront view. ACCOMMODATIONS: This home has two master suites, both of which are located on the top floor. The first master bedroom has a King size bed, a large flat-screen HD TV, and a beautiful two-room en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The first master bedroom also has floor-to-ceiling glass doors opening out to your waterfront balcony, with gorgeous water views. The second master suite is down the opposite hallway, with a King size bed and an en-suite bathroom. The second master suite also has a flat-screen HD TV, large walk-in closet, and a sliding glass door with access to the waterfront balcony. The third bedroom is beside the second master suite, with two twin beds and a flat screen TV. An additional bathroom is situated in the hall next to the stairs and across from the third bedroom. On the main floor there is a fourth bedroom with two twin beds that seamlessly convert to a King bed upon request. This bedroom also has a flat screen TV, and a full bathroom down the hall. LANAI: On the ground floor is the covered outdoor dining area comfortably seating six and has ample room for entertaining with large lounge chairs. With views of the open water and visiting heron on the tropical greenery that surround the back yard, your guest will enjoy the natural splendor Paris Mango and Key West have to offer. The backyard is complete with a large grill. Additional space under the house also offers another covered indoor/outdoor area for playing, additional storage, etc. AMENITIES: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Garage & on Driveway, Flat Screen State-of-the Art Smart HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. This property will accommodate 8 adults. Boat dock not available. RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).

This 3 bed 2 bath home with an amazing HEATED pool is located right off the quieter end of Duval St. The home consists of 2 separate units "Poolside Suite" and "Poolside Retreat" which are side-by-side and have their own living rooms and kitchens. This property is perfect for larger groups looking for a memorable time in Key West and is walking distance to popular restaurants, attractions, shops and bars! Bring the whole family together for a reunion or holiday celebration at this spacious, Key West home located just a block from the non-stop fun of Duval Street. This rental, with space for up to 10 guests, features an enclosed yard, a private pool, a furnished patio, two full kitchens, and off-street parking for two vehicles (a real rarity in Key West). And dogs up to 40 pounds are welcome for a small nightly fee. Poolside Retreat Bed Layout: Bedroom 1: Queen Living Room: Queen pullout couch Poolside Suite Bed Layout: Bedroom 1: King Bedroom 2: Queen Living Room: Queen pullout couch Ideal for an extended family or a few couples traveling together, this home offers free WiFi, four cable TVs, two full kitchens, and a gas grill for a family cookout on the furnished patio. Our contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival. Parking Information: There are 2 private off street parking spots on the Olivia St side of the property. They are labeled "Poolside Retreat" & "Poolside Suite." There are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance. Feel free to ask us for recommendations! - Private washer/dryer located outside. - This unit is pet friendly. Our requirements are as follows: •40lb maximum per pet •$25/per night •2 pet maximum Please let us know if you plan on bringing your pet. - Are you within 90 days of your check in date a & have a smaller group? Rent just Poolside Retreat or Poolside Suite!

Welcome to ’Keys Breeze’, your perfect private getaway in the heart of Key West! This fully renovated island home showcases the vibrant colors and charm of paradise. Located just a short walk from iconic spots like the Southernmost Point, Duval Street, and Key West’s historic landmarks, you’ll have endless opportunities for adventure right at your doorstep. Relax year-round by your private pool, ideal for lounging or entertaining guests. The luxury kitchen opens directly to the back patio through large sliding doors, making it easy to serve drinks and snacks poolside. At ’Keys, Please,’ comfort and Key West charm come together to create the ultimate vacation experience!" Enjoy the comforts of privacy as you enter through the picket-fence and make your way into your own resort-like oasis. Enter the front gate and find space to park your bike, sit on the front porch, or enjoy the seclusion of a front yard set away from the street. As you go up the front steps to the entryway, you will find a long hallway that provides separation from the sleeping spaces and living space. This home features three large bedrooms. The master bedroom on the second floor overlooks the pool and provides a king size bed and private en-suite bathroom. On the first floor, there are two guest bedrooms each with a queen size bed, allowing space for four more guests. There is a second full bathroom located on the first floor as well. There is fully-functional kitchen including all stainless-steel appliances and cooking essentials like pots & pans, silverware, and a Keurig coffee maker. The open floor plan makes hosting easy along with high-speed internet, wifi & a premium TV package. Plentiful storage spaces give you the option to unpack, relax and make Key West your home! Our contactless check-in procedure makes check-in easy. Guest will receive a personalized access code prior to arrival. Parking Information: There is no designated parking for this home. Parking on the street is on a first-come first serve basis including parking a compact vehicle on the rocks in front of the home. For additional parking here are some parking lot options: • 204 Simonton Street • Caroline Street Outdoor Parking Lot • Park N Ride Old Town Garage Street parking information: • There are pay-to-park spots and meters - it is free from 12am - 8am. There is a 3 day limit. • The neighborhoods of Old Town offer some free parking spaces, but be aware that many of the spots are marked “Residential Only” and visitors are NOT permitted to park in them. There are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance. Feel free to ask us for recommendations! - House features a private pool. - Private washer/dryer. - Not pet friendly

Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be at Seaside Retreat. This home is located in the private community of Key Cove Landings, on an exclusive lane of waterfront residential homes. The perks of this little-known location are many: walking distance to the essentials such a Publix grocery store and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. This home includes plenty of off-street parking in the private garages, as well as on the driveways in front of the house. This home’s highlight is the wall of floor-to-ceiling windows facing the water to provide the optimal view from every part of the house. The large open plan living room has a spacious seating area with plush couches around a large HD flat screen Smart TV. There is a dining table with seating for up to 8 diners, with additional seating at the kitchen bar. The gourmet kitchen has state-of-the-art appliances and is fully equipped with all of the tools and utensils for an upscale meal at home. The master bedroom has a King size bed, a large flat-screen HD TV, and an en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The master bedroom also has a wall of floor-to-ceiling glass doors opening out to your waterfront balcony. The second bedroom has a Queen size bed, a flat-screen HD TV, large walk-in closet, and a glass sliding door with access to the waterfront balcony. The third bedroom is also on the 2nd floor with two twin beds, flat screen TV and its own access to the back balcony. These two bedrooms share a full bathroom in the 2nd floor hallway. On the main floor there is a fourth bedroom with two twin beds that seamlessly convert to a King bed upon request. This bedroom also has a flat screen TV, and a full bathroom down the hall. Out back is one of the highlights of this home: the covered lanai and pool area. The covered outdoor dining area comfortably seats six for a poolside meal. The pool is heavenly, with views of the open water and visiting heron on the tropical greenery that surrounds the back yard. There is also a pool lounge area with comfortable chaises in a piece of deck that gets equal sunshine and shade. The backyard is complete with a large propane grill for a poolside BBQ. AMENITIES: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Garage & on Driveway, Flat Screen State-of-the Art Smart HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Heated Pool, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. Pets Considered. This property will accommodate 8 guests. Dockage is not available at this home’s development. RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates). DOG FRIENDLY. Please contact us to confirm specific pet policies.

Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be at Nautical Wheeler. This home is located in the private community of Key Cove Landings, on an exclusive lane of waterfront residential homes. The perks of this little-known location are many: walking distance to the essentials such a Publix grocery store and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. This home includes plenty of off-street parking in the private garages, as well as on private driveways leading to the house. This home’s highlight is the wall of floor-to-ceiling windows facing the water to provide the optimal view from every part of the house. The large open plan living room has a spacious seating area with a sectional leather couch around a large HD flat screen Smart TV. There is a dining table with seating for up to 6 diners, with additional seating for 4 at the kitchen bar. The master bedroom has a King sized bed, a large flat-screen HD TV, and an en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The master bedroom also has a wall of floor-to-ceiling glass doors opening out to your waterfront balcony. The second bedroom has a King sized bed, a flat-screen HD TV, large walk-in closet, and a glass sliding door with access to the waterfront balcony. The third bedroom is also on the 2nd floor with twin beds, flat screen TV, and also with balcony access. On the main floor there is a fourth bedroom with twins bed. There is a full bath down the hall for convenience. Out back is one of the highlights of this home: the covered lanai and pool area. The covered outdoor dining area comfortably seats six for a poolside meal. The pool is heavenly, with views of the open water and visiting heron on the tropical greenery that surrounds the back yard. There is also a pool lounge area with comfortable chaises in a piece of deck that gets equal sunshine and shade. AMENITIES: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Garage & on Driveway, Flat Screen State-of-the Art Smart HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Heated Pool, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. Pets Considered. This property will accommodate 8 adults. Dockage is not available at this home’s development. RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates). DOG FRIENDLY. Please contact us to confirm specific pet policies.

Runaway Bills- 2 BDR Main house with 1 BDR Cottage and pool in the Key West downtown. This charming and stylish Conch home is tucked away on a quiet lane in the heart of Old Town Key West, offering the perfect island retreat. Surrounded by historic architecture and vibrant neighborhoods, this inviting property is just a short stroll from the famous Duval Street, placing you within easy walking distance of restaurants, galleries, shops, and nightlife. The main house features two comfortably sized bedrooms, each with king beds, and one full bathroom. Beautiful hardwood floors throughout create a warm coastal character that blends perfectly with the relaxed Key West atmosphere. The fully equipped chef’s kitchen is ideal for guests who enjoy cooking, while the open living area flows seamlessly to a covered outdoor dining space overlooking the pool and deck, perfect for entertaining or relaxing. Across the pool, a separate pool house cottage provides additional privacy and includes a third bedroom with a full-size bed, a half bath with toilet and sink, and a private outdoor shower, creating a unique tropical guest suite. The fully fenced backyard surrounds a refreshing swimming pool and sun deck, offering a private oasis where guests can unwind after a day exploring the island. Pets are welcome with a non-refundable pet fee, and the property includes the rare convenience of two assigned parking spaces. Additional Features • Central air conditioning and ceiling fans throughout • Washer and dryer • Wireless high-speed internet • Linens, bath towels, and pool towels provided • Fully stocked kitchen with cookware, dishes, flatware, and glassware • Starter supply of paper and cleaning products • Outdoor shower • Optional housekeeping services available Sleeping Arrangements Roadside Bedroom – King Bed Middle Bedroom – King Bed Living Room – Futon Pool House Bedroom – Full Bed This peaceful yet centrally located home offers the best of Key West living—a private tropical setting just minutes from the island’s most iconic attractions. E- lock code will be provided Getting around Key West is easy and part of the fun of visiting the island. Most guests enjoy walking or biking, as many of the main attractions, restaurants, and shops are within a short distance. From the home, you can easily stroll to Duval Street and explore Old Town at a relaxed pace. Bicycles and golf carts are also very popular ways to get around and can be rented nearby. Taxis and rideshare services are readily available, and the Duval Loop shuttle provides a convenient free service throughout much of Old Town. With the island being just a few miles long, it’s simple to explore everything Key West has to offer. 🚲🌴

Welcome to Southern Palms, the ultimate home base for your Key West adventure! Perfect for couples, friends, or large groups, this versatile property is made up of three separate units, Coconut Palm, Traveler’s Palm, and Royal Palm. With its own private pool, hot tub, BBQ grill, five bedrooms, and four bathrooms, Southern Palms is your tropical oasis. The lush backyard is perfect for relaxing between excursions, while its prime location on Whitehead Street puts you just steps from the excitement of Duval Street. From world-class bars and restaurants to Key West’s iconic attractions, everything you want to explore is right at your doorstep. Southern Palms offers exceptional value, comfort, and convenience for those who prioritize adventure and unforgettable experiences in paradise! The whole property allows for a maximum occupancy of 16, the bed layout is as follows: Coconut Palm: Bedroom 1: Queen Bedroom 2: Queen with attached living area & queen pullout couch Bedroom 3: King with en suite bathroom Traveler’s Palm: Studio: 2 Kings & a queen pullout couch in the living room Royal Palm: Studio: King Bed Coconut Palm has three bedrooms, a fully equipped kitchen, and a spacious backyard with a BBQ grill. The bedrooms include 1 king, 2 queens, and a pullout couch attached to the king bedroom, sleeping up to 8 guests. Traveler’s Palm is a separate studio located upstairs from Coconut Palm. It has its own private entrance, a large balcony with a hammock and a kitchenette. This unit includes 2 king size beds and a pullout couch, sleeping up to 6 guests. Royal Palm is located on the other side of the backyard. It is a cozy studio with its own patio, kitchenette and hot tub. This unit features a king size bed sleeping 2 guests. Our contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to check-in to enter the unit. Parking Information: If you reserve all three units in Southern Palms (including: Coconut Palm, Travelers Palm & Royal Palm), there is space for two compact cars in the gated driveway. Please note, you may need to tuck in your side mirrors to enter the driveway. There are a variety of great ways to explore Key West including by bicycle, pedi-cab, Moke, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance. Feel free to ask us for recommendations! - There are 2 washer/dryers on site: one located just off of the back deck and one in the driveway. - Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/per stay •2 pet maximum Please let us know if you plan on bringing your pet. - If you are within 90 days of your check in date: you can reserve the compound properties individually (Coconut Palm, Travelers Palm & Royal Palm)