Vacation Rentals By Owner In Key West, FL

Tucked away in a quiet Old Town Key West neighborhood you'll find Nauti's Nest, a cozy and comfortable two bedroom cottage with all of the comforts of home. brbrThis carefully curated space features two charming queen bedrooms, an open-layout kitchen and living area, peaceful front porch, tranquil swimming pool, and essential amenities like AC, washer/dryer, and fast WiFi. The home offers convenient off-street parking - a true luxury in Key West! brbrThis cottage's ideal location is within a short stroll to Key West's beaches and lively Duval Street where music, nightlife, and world-class dining await.brbrSoak up afternoon rays by the pool, cool off in the cold central AC, or open the windows and let those famous tropical breezes drift through. Sip cocktails with friends on the front porch or poolside. Prepare breakfast in the well-equipped kitchen before heading out to explore the island. Nauti's Nest is your ideal home-base in Key West.brbrDogs are welcome guests if registered and approved in advance. The maximum size is 30 lbs. They must be crated when left alone in the home and not barking or disturbing neighbors. The guest must clean up all pet messes inside and outside of the home. Damages or extra dirtiness will result in additional fees. Please place a tray under your pet’s water and food bowls to prevent moisture damage to the wood floors. Please ensure the dog is groomed with nails trimmed and filed prior to arrival to prevent scratches.

Charming 2 Bedroom Cottage in Old Town Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$282.45

Upon waking in the morning we hear the murmuring of tropical birds , feel the gentle sea breezes and the fragrance of jasmine. When we go out from the apartment we can see the sea across the street and catch the sun rise if we wake early. Relax with a drink on the south facing balcony that looks out onto a spacious enclosed garden with palm trees, bougainvillea and 2 pools. Walk across the street to Smather's Beach for swimming and and snorkeling. Later take a stroll in Old Town or visit Fort Taylor Park and its beautiful beaches. In the evening pick up some fresh shrimp to prepare a gourmet meal in our full kitchen with the freshest seafood on the east coast. Or if you prefer head for downtown where there are literally dozens of sophisticated and alluring restaurants. The apartment is spacious and bright and filled with the art of my wife Marina's father. Key West is the ultimate winter beach destination.brATTENTION: Utilities included. Tenant will pay amounts exceeding $100 per month for ELECTRICiTY usage brbrKeywords: flat, apartment

Seaside Condo, DECEMBER SPECIAL

Key West, Florida, United States

Bed

Bath

Sleeps

$585.49

Key West's Crown Jewel is a penthouse condominium at 1800 Atlantic Condominium development with two-bedroom, two-bath with approximately 1350 square feet of living space. Guests will enjoy absolutely breathtaking ocean views and the colors of the sunset from the 35-foot balcony, as well as from both bedrooms and the living room.brbrThe Living spaces:brThe wood beamed, soaring ceilings of the living room provide an extremely open feeling. Upgraded appointments include high speed (up to 100 mbps) wireless internet access via cable modem (via your wireless device), a 65” Samsung Ultra HD LED TV with high-definition Cable TV, Blu-Ray Player and a Bose Soundtouch music system in the living room. Queen-size sleeper sofa with memory foam topper in living room. A large, fully-equipped renovated kitchen with granite countertops and stainless steel appliances. Keurig Coffeemaker.brbrThe Bedrooms:brThe main bedroom has king-size bed with Tempur pedic Brand memory foam mattress with ensuite bathroom. The bath has 'spa style' shower with body sprays.brbrThe second bedroom has king-size bed with memory foam mattress and luxurious linens on the beds.brbrSamsung flat-screen TV's with Hi-Definition Cable TV and Blu-Ray Players in both bedrooms, access to YOUR Netflix, Hulu, HBO GO, Amazon Video accounts via Smart TV Hub in living room and both bedrooms, USB charging station at all bedsides, Bluetooth speaker at bedsides. Enjoy Key West IN STYLE!brbrThe property features a 70 ft pool fronting the Atlantic Ocean. A 12-person jacuzzi awaits. A courtyard changing room sauna is yours to enjoy. There is a Fitness Room, large picnic and barbecue area surrounded by the tropical gardens.brbrOne clay and two hard court lighted tennis courts are yours to enjoy at no additional cost. The largest beach in Key West, Smather's Beach, is adjacent to this condominium complex, offering white sand, palm trees, lounge chair and umbrella rentals, volleyball nets, sailboat rentals, and parasailing. An extensive leisure trail for walking, jogging, and bike riding fronts this beach.brbrOld Town, Key West's hub of shopping, dining, live entertainment, art galleries, and sightseeing, is just one-and-one-half miles away. Here you will enjoy all that ''downtown Key West'' has to offer, but will greatly appreciate coming back to your peaceful surroundings at the end of the day (or night!) to recharge. Parking for one vehicle in reserved space in the gated garage is also included. There is also elevator access. br*Disclaimer**br*The peak sargassum season in Key West is typically from July thru September and possibly June. You may see significant amounts which can impact your stay. While the naturally occurring seaweed itself is not dangerous, it can accumulate on beaches, producing a foul odor and potentially harboring organisms that cause skin irritation. We do not provide discounts for the situation.

Key West's Crown Jewel

Key West, Florida, United States

Bed

Bath

Sleeps

$1002.32

2 BDRM 2.5 BATH. SLEEPS 6. OPEN OCEAN VIEW.brPOOL, PRIVATE BEACH, RESTAURANT, BAR, GYM, TIKI, LAUNDRY ON BOARD.br15 MIN FROM DOWNTOWN.brbrTwo queen bedrooms on first level. Open ocean view second level salon & galley, floor to ceiling windows, sliding glass doors leading to spacious fore and aft decks and spiral stairs to expansive, furnished, 3rd level sun deck. Full Kitchen.brbrbrRead More:brbrFIRST LEVEL: brEnter the boat from the cushioned floor front deck through full size sliding glass doors and step into the air-conditioned, high ceiling (7'4), crisp white and gloss black trimmed wheelhouse/entry foyer. Ceilings are 7'4 throughout the entire boat and all exterior decks have cushion decking underfoot.brbr Two solid maple pocket doors ahead lead to the Master and Guest Staterooms (bedrooms) on your left and right. An indoor spiral staircase leads upstairs to the second floor living area and exterior 2nd level decks.brbrMASTER STATEROOM:br To the left, the Master Stateroom is down a short hall flanked with three floor to ceiling windows and a gently curving maple paneled wall. A 42 tv sits above granite counters topping a 9 drawer solid maple built-in dresser with matching granite top 3 drawer maple bedside table beside your plush adjustable queen size bed. brbr There are two closets en suite with space for luggage and gear in one and hangers for clothes in both. The attached private bath has cool tile floors, a large tiled shower with frame-less glass enclosure and a two flush mount sinks set in a matching granite topped vanity with generous mirrored upper cabinets.br A full sliding glass door at the rear of the master stateroom provides access to and from the 1st level stern deck with a two-story outdoor spiral staircase to the second level aft deck and the 500 square foot furnished sun deck on the 3rd level above.brbrGUEST STATEROOM:brFrom the entry foyer to the right,br The Guest Stateroom, while smaller than the Master, features the same luxurious adjustable queen bed and its own private tile floor bathroom with large, glass enclosed shower with gently curving tile wall. The flush mount sink in granite counter are topped with a spacious maple vanity and large mirrored cabinet doors.brbrIn the bedroom you'll find a bedside 3 drawer built-in maple cabinet and another 3 drawer cabinet, more granite tops and a 32 wide full height hanging closet. A 32 tv is also set on an articulating wall mount for easily adjustable viewing in bed. Light filtering and black-out blinds cover the 5 foot wide operable bedside window.brbrbrSECOND LEVEL:brUpstairs, On the 2nd level there are large fore and aft decks. The forward deck has a wide view of the harbor, bay and ocean beyond. On the stern deck, a cushioned seating area sits 4-6 comfortably with surrounding views of green mangroves topped with blue ocean and sky. brbrBetween the second level decks, in the spacious 30 foot long 14 foot wide Main Salon and Galley area (living room and kitchen) there's air conditioned space to relax and entertain. A stylish sectional sofa and very comfortable recliner face 3 floor to ceiling windows with plenty of room to relax, watch a movie or just take in the view. The unique design of the sectional sofa allows it to convert into a queen size bed for your additional (5th and 6th) guests.brbrMore than three quarters of the 2nd level is wrapped in glass. The floor to ceiling windows, sliding glass doors on either end and 5 more windows bring tropical blue-green Caribbean waters that float just above lush green mangroves into the living space as sailboats and yachts bob in the harbor. brbrIn the galley, next to to the living room, more granite tops the kitchen counter with full size stainless steel double sink, full size fridge, dishwasher, oven, microwave, and Keurig combo coffee maker.brbrThe adjacent 5 ft x 3 ft granite breakfast island/bar with 4 comfortable low-backed, adjustable height bar stools is a popular spot for hanging out, sharing company and catching a game or movie on the 56 4K HD tv. brbrIn the evenings you control the hidden lighting system that glows softly to surround the room to with colors to accompany your evening mood. There's dozens of colors to chose from and you can customize the scene with hundreds of combinations from cool blues, pale yellows and greens to warm oranges, purples and fiery red.brbrTHIRD LEVEL:brAnd Finally, up on the 3rd floor sun deck there's comfortably cushioned lounge seating for 10 and a round day bed with sunshade for catching some tropical rays. The truly panoramic view overlooking the open Caribbean ocean is difficult to fully describe. Incomparable, blazing sunsets, stargazing away from the lights of downtown and stunning sunrises. Epic photo ops.brbrHope to see you soon!brbrBrad

House Boat

Key West Luxury Houseboat

Key West, Florida, United States

Bed

Bath

Sleeps

$441.0

Featuring direct marina access and located just 2 miles from picturesque Smathers Beach, this well appointed two bedroom, two bath condo is ideally situated in Key West. Explore all Key West has to offer, located just 3 miles from vibrant Duval Street, and 4 miles from historic and majestic Mallory Square.brbrThis two bedroom condo features a spacious primary bedroom with a king size bed and hardwood flooring, a connecting ensuite full bathroom with shower and bathtub. The guest bedroom features a queen size bed with wood flooring as well. The condo also features a full kitchen, with full sized refrigerator, microwave, stove, oven, dishwasher, coffee maker (drip style), toaster, blender, dishes and utensils. The living room features a queen-size sleeper sofa, HDTV, dining area and access to a private patio. Most condos are two stories and the bedrooms are upstairs.brbrThe property features two pools (seasonally heated), a jacuzzi, park-style grills, picnic tables, and much more.brbr*Please note, unit may have stairs, use of stairs may be required to occupy the unit.brbrGuest must be at least 25 yrs of age to rent and check-in to the unit.brbrGumbos is not currently operating as a bar or restaurant.brbrLaundry facilities located on top floor of buildings for a fee. The property does not offer towel exchange.brbrPictures are representative of units on property. All feature similar layouts, decor and amenities. Property features most 2 story units. There exists a chance you may be assigned a single story unit. Specific unit is assigned at check-in by the front desk.brbrOccupancy is limited to six guests total, per two-bedroom unit. With two people, per bedroom plus an additional two people on the sleeper sofa. Property will not allow overcrowding of the unit beyond the existing bedding, with no exceptions.brbrNo RV's, campers or mobile homes may be parked on the premises. Parking is limited to two vehicles per unit.brbrEarly check-ins are not available. Check out time is 10 a.m. Please observe this rule, as the housekeeping staff needs time to prepare for the next arrival. Upon leaving, please secure all windows and doors, load the dishwasher and start, remove all trash, and strip beds.brbrLimited - service availability of marina onsite. Boat slip is $200. Parking on gravel is $75 (very limited availability). Parking boat in a parking spot is $150. (No boat ramp - no fuel supplied on premises). Please inquire for availability prior to booking. (subject to change at any time).brbrAlthough Coconut Mallory is a non-pet friendly resort the property does allow Service Animals in accordance with the Americans with Disabilities Act. Guests may also be accompanied by a certified Emotional Assistance Animal as long as written documentation of the Emotional Support Animal's legitimacy is provided at check-in. A Non-refundable $320.00 Cleaning Fee for your Assistance Animal will be due at the time of check-in.brbrThe property will provide bed linens, starter packages of detergents, bath soap and paper products. Please be sure to pack any specialty items that you may require during your stay.brbrCoconut Mallory requires a credit card and photo id at the time of check-in. This credit card is held for potential unit damage, missing items, or incidental charges during the stay.brbrPictures are representative of the unit, decor may vary. Units are assigned after booking, in seven night increments. Multiple week stays may be booked, room moves may be required.brbrWe do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service.

Waterfront Property - Marina Access - Spacious - Excellent Key West Condo

Key West, Florida, United States

Bed

Bath

Sleeps

$282.38

Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect setting for a laid back and quiet afternoon. Enjoy alfresco dining in the tropical gardens while you enjoy the wonderful weather that Key West offers!! brbrThe Hollinsed House's 1st Floor - ShangriLa Suite is a large deluxe studio with a queen bed, living area, bath and kitchen that is tucked away for privacy with its own private courtyard. Sleeps 2brbrHave a group coming to Key West Or maybe need just one or two more units Go to Click Here to see All My Rental Listings just above the Map Feature to see the rest of my listings at the Hollinsed House!brbrRATES for SPECIAL EVENTS:brPlease note that rates for Fantasy Fest, Meeting of the Minds (formerly Jimmy Buffet Parrothead Days), Race Week, Thanksgiving, Christmas, New Years, Songwriter's Festival, Memorial Day Weekend, Hemingway Days, and Poker Run all have minimum stays and different rates than are listed on the Rates page of this VRBO listing. brbrbrDEPOSITS:brA deposit equal to the cost of one half of your stay or one night, whichever is greater, is required to guarantee a reservation. The balance is due 30 days prior to arrival. Sorry, no refunds for early departures.brbrCANCELLATION AND REFUNDS:brCancellations from time of booking to thirty (30) days of arrival date will be charged a $50.00 processing fee per unit rented. All bookings of one week or longer will be charged a $100.00 processing fee per unit rented if cancelled more than thirty (30) days prior to arrival. Cancellations within thirty (30) days of arrival date will be charged for one night per unit rented or may extend their reservation for six months. Cancellations within seventy-two (72) hours to twenty-four (24) hours have a 50% cancellation fee or can be extended for six months. Cancellations within twenty-four (24) hours are non-refundable but will be offered a six-month extension. Sorry, no refunds for shortened stays. We reserve the right, to change your unit number if you are reserving for 3 nights or less.brbrCancellations for Special Events: Fantasy Fest and Christmas/New Years. Reservations of 5 days or longer that are cancelled within 2 weeks of arrival will be charged a $250 cancellation fee. Reservations cancelled within 1 week of arrival will be charged a $500 cancellation fee. Reservations cancelled within 72 hours of arrival are non-refundable. All cancelled reservations will be offered a six-month extension. brbrHURRICANE SEASON CANCELLATION POLICY, EFFECTIVE JUNE 1 -DECEMBER 15TH:brWe do not refund for inclement weather or other circumstances beyond our control. We strongly encourage the purchase of Travel Insurance to protect your vacation investment! In the unlikely event that a hurricane evacuation is ordered while you are a guest, and you have not purchased travel insurance, you will be issued a voucher for the unused portion of your stay. Guests holding a confirmed reservation who are unable to travel to The Hollinsed House because of the closing of the Key West Airport or connecting roadways due to a mandatory evacuation and have not purchased travel insurance will receive a voucher in the amount of the room deposit held. Vouchers are redeemable between June 1 and December 15, up to one year from the issue date, excluding special events and holidays. (Exception: Vouchers issued for cancellations of Fantasy Fest reservations can be applied to future Fantasy Fests in the ensuing two years.) No voucher will be issued if the hurricane is not a threat to Key West and you are unable to travel because of canceled flights or adverse travel conditions outside the Keys. We strongly encourage the purchase of Travel Insurance to protect your vacation investment!brbrKeywords: Guest House, Condo, B&B

ShangriLa Suite / Queen Studio / Sleeps 2

Key West, Florida, United States

Bed

Bath

2

Sleeps

$253.13

Book it before it's gone - 7 day rental - available from Saturday 11/14/26 to Saturday 11/21/26 only.brbrCozy and comfortable 1 BR efficiency condo at the spectacular Coconut Beach Resort! Enjoy the lap of luxury at this private Timeshare property in beautiful Key West, located along the southern coast of the island. With its private beach, large pool, and sun deck, this exclusive property is a paradise, complete with lush tropical landscaping everywhere you look. This unit itself was completely renovated recently, has a private entrance, faces the street, and is well appointed and comfortable. It features a king-size bed, a full bath and central air conditioning. Enjoy sitting out on the private balcony outside of your room, where you can relax and listen to the breeze through the palm trees. The hidden closet provides with some unexpected surprises too - including a microwave, a toaster, small refrigerator, even a coffee maker. You’ll spend your days where everyone does, around the magnificent common area facing the ocean, where the trees and tropical foliage abounds. The pool area is amazing, with plenty of places to relax – either right in the sun, or in your own shady spot. The heated pool itself is magnificent, and you’ll love the swimming. You’ll want for nothing – enjoy the hot tub, gas grills, rest rooms, even a water cooler to keep you hydrated. You can even enjoy your own private sunsets, right on the premises if you like. CBR is a stunning, beautiful place and it’s a short walk (or bike) to all the fun on Duval Street. brbrThis is a Timeshare Resort, and I’m the owner of this specific week. This is a Saturday-to Saturday-rental. Check-in time is Saturday at 4pm (you can usually get in earlier), and you’ll need to check out on the following Saturday by 10am. There is a mid-week housekeeping crew that will tidy things up as well – no extra charge.brbrI’ve posted some of my own personal photos, and have been an owner at Coconut Beach Resort for over 20 years. Check out more photos on CBR’s site - coconutbeachresort . combrbrRent elsewhere for MUCH MORE per night, and you won’t get the amenities that CBR has. The dates and price are not flexible, and this unit is a 7 Day rental only, and available from Saturday 11/14/26 to Saturday 11/21/26 only.

Key West-Coconut Beach Resort - Avail 11/14/26 to 11/21/26

Key West, Florida, United States

Bed

Bath

Sleeps

$167.75

Welcome to the best of Key West! Poolside Paradise is located in the Key West Golf Club. Our townhome is located directly off of the elegant, resort style pool and you are just steps away from relaxation! We offer a two-story townhome with kitchen, dining area, powder bathroom and living area downstairs that opens to a large, screened in patio. Upstairs offers two bedrooms with a main, full bathroom. The primary bedroom has a king bed with an adjoining screened in patio that looks directly to the lush, tropical setting of the pool. The second bedroom offers a king bed with available desk space to work from paradise. The home does offer a full size washer and dryer for use during your stay. You are just a short jaunt to the clubhouse where you can play a nice round of golf at the Southernmost Golf course. All the necessities are available to you, all you need is your swimsuit and a pair of flip flops! Pack you bags and head to Poolside Paradise!

Poolside Paradise in Key West Golf Club

Key West, Florida, United States

2

Bed

Bath

4

Sleeps

$413.44

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrAfter landing in Key West and arriving at your door, FLIGHT OF THE FLAMINGO will have you feeling like it was love at first flight! The light colors, natural wood finishes, and Caribbean-inspired art radiate an energy and warmth reflecting Key West’s tropical vibes. From the rocking chairs on the veranda to the inviting interior and the lushly landscaped oasis in the backyard, FLIGHT OF THE FLAMINGO will have you relaxing in no time. Paired with Last Key Realty’s renowned Five-Star Guest Services and Concierge Team, FLIGHT OF THE FLAMINGO is the perfect place to perch yourself for a month (or longer!) in Key West.brbrTHE LIVING AREA…brbrThe spacious living area is situated at the rear of the home, featuring a large flat-screen TV surrounded by comfortable seating options for everyone in your group. The wall-to-wall glass sliding doors allow a ton of natural light to flow in. Preparing gourmet meals from home is easy thanks to the fully equipped kitchen with top-of-the-line appliances. The indoor custom-made dining table sits right next to the kitchen and offers seating for five with four more seats at the kitchen island. In the hall, you will find the powder room, which was beautifully hand-painted by local artist Katlin Spain!brbrTHE POOL AREA...brbrA truly distinctive feature of this home is the large sliding doors on the back of the house that create an unrivaled indoor/outdoor living space. Step out to the fully fenced backyard, surrounded by tropical landscaping that provides maximum privacy. brbrTake a dip in the pool, which can be heated in the cool months or cooled in the warm months, to relax after a long day of exploring the streets of Old Town. The backyard gets plenty of sun, allowing you to take full advantage of the chaise lounges on the pool deck for soaking up some rays. The unique mural enhances the colors and vibrance of this backyard oasis.brbrTHE ACCOMMODATIONS...brbr** Primary Bedroom: Features a king bed, a flat screen TV, a closet, and en-suite bathroom with a walk-in shower.brbr** Second Bedroom: Features a queen-size bed, a flat screen TV, a closet and shares a Jack & Jill bathroom with Third Bedroom.brbr** Third Bedroom: Features a full bed, a flat screen TV, and shares a Jack & Jill bathroom with Second Bedroom.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen Smart TV in Living Roombr** Fully-Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access and full cable is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced & Landscaped Private Yardbr** Private Heated Poolbr** Outdoor Showerbr** Propane BBQ Grillbr** Pool ChillerbrbrOther notes:brbr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 5 adultsbr** Pets Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

** FLIGHT OF THE FLAMINGO @ OLD TOWN ** Home & Private Pool + LAST KEY SERVICES.

Key West, Florida, United States

Bed

Bath

Sleeps

$188.91

PLEASE BE ADVISED IF BOOKING THIS UNIT FOR AUGUST 2026: The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. The HOA expects the project to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. There is no other pool available at the Shipyard, so we have adjusted our rates to offset the inconvenience.brbrCHARMING 2ND FLOOR CONDO IN STUNNING SHIPYARD COMMUNITY OF TRUMAN ANNEX…brDelight in this cozy gem of southernmost island living, a 2 bedroom, 1 bath second floor dwelling with a balcony that overlooks verdant landscaping and a sparkling shared pool! Slide on your comfiest sandals and immerse yourself in the excitement of Duval Street, just 2 blocks away. You are walking distance to the island's hot spots: Fort Zachary State Park Beach, The Green Parrot, Sloppy Joe's, Hemingway's Home and Mallory Square - home of the famous nightly Sunset Celebration.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brEnter this light and airy open living area that is colorfully and tastefully decorated to ease you into a sense of well-being and tropical tranquility. You and your loved ones will enjoy a cool respite after a day in the sultry sun, sharing relaxed conversation on the cozy furnishings or decompressing with your favorite movies on the wall-mounted TV. The fully equipped and well-stocked kitchen will inspire you to practice your culinary skills, complete with granite countertops, stainless steel appliances and all the tools a chef will need. Dine or play your favorite board game at the table for 4. brbrSLEEPING ARRANGEMENTS…brSlip into a peaceful sleep in one of the two bedrooms with plush queen beds. Both rooms offer flat screenTVs, cooling ceiling fans, clothing dressers and nightstands with power ports. The shared bathroom has been updated with a walk-in shower and there is a full washer/dryer closet for your convenience.brbrOUTDOOR LIVING…brOpen the French doors of the coastal living room to your balcony with umbrella table and chairs, a superb spot for morning coffee or dining outdoors. a second balcony resides just off the kitchen, with a lounge chair for napping or reading your favorite novel. The Shipyard in Truman Annex is a charming, tree-shrouded hideaway with serene walking paths and lanes. The beautiful community pool is lined with lounge chairs and is perfect for soaking up the Key West sun.brbrPARKING...brThis home does offer parking for one vehicle, just steps from the front door - (vehicle cannot exceed 18 ft), but oversized trucks and extra large SUVs are not permitted and will have to park outside of this community.brbrPETS...brThis is a pet friendly home with a required pet fee. Please include the size and breed when inquiring. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrYOUR SLICE OF PARADISE IS CALLING...

THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex!

Key West, Florida, United States

Bed

Bath

Sleeps

$192.25

Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s Old Town area. brThese condos are located 2 blocks from Duval Street and all the Old Town Key West attractions. The properties are also ¼ mile from Fort Zachary Taylor State Park. The property is outfitted with washer/dryer, pots/pans, towels, linens, have central air conditioning, off street parking, and pool access. This second floor Shipyard Condo has big, beautiful French doors in the living room. They open onto both front and back balconies with views of the treetops and Old Town Key West. Away from it all has full amenities, including flat screen TV’s in the living room, both bedrooms and wireless internet access. The master bedroom has a queen size bed and the guest bedroom has the option of 2 twins or a king size upon request. After a full day of taking in the island’s many wonderful experiences, come back to the comforts of home. The manicured landscaping, verdant palms, and white picket fences give the Shipyard and Truman Annex a lovely park atmosphere. All this tranquility makes it hard to imagine that Duval Street, Key West’s central artery of entertainment is only two blocks away. Both bedrooms do have flat screen TV's. brPlease note: This property is rented by the month, 27 nights or more

Apartment

BEACHY KEEN with Compass Realty Truman Annex - Close to the pool - 2 decks!

Key West, Florida, United States

2

Bed

Bath

4

Sleeps

$130.98

The front door to this second floor 1 bedroom / 1 bath vacation spot opens to a perfect lesson in space mastery and historic spirit. Hardwood floors, a myriad of bright windows, and vaulted ceilings bring warmth and light in. Step out onto the front balcony or the back balcony to experience the stunning weather of the island firsthand. There’s a lovely, heated pool & spa for the exclusive use of guests in this compound of four units. Another coveted amenity is the assigned off-street parking. And if that’s not enough, the location, less than four blocks off the amazing Duval Street, puts you in very easy reach of all that Key West has to offer. brbrWalking through the front door finds you in an open room design so prevalent in old Florida floor plans. Straight ahead is the living space. A ceiling fan and contemporary spotlights dot the ceiling. The area is appointed with a couch that can convert to a full bed. Two handsome and comfortable recliner chairs round out the seating. All are perfectly positioned for watching sports or movies or whatever suits your taste on the large flat screen TV. Of course there’s A.C., high speed internet, and cable TV to make you feel right at home. A flax-colored sisal area rug over the darker hardwood floors delineates the space nicely.brbrIn the flow of things, a rectangular dining table is located to the right and can serve many purposes. Four can sit here comfortably to eat a meal or to play a round of Key West Monopoly. Or maybe sometimes it becomes a workspace for writing or checking email.brbrThe kitchen is next. The dark wood floor and extended blue tile back splash anchor the space visually. Cabinets above and below provide space for all the kitchen accoutrements and appliances you would need to make a cup of coffee, to warm leftovers from dinner out the night before, or to prepare a three-course meal. Here also is a cabinet for the all-in -one washer/dryer topped with blond hard wood matching and extending the kitchen counter workspace. Refrigerator, cook-top stove, microwave, dishwasher are all arranged ergonomically in a U shape. Behind a louvered door is a closet for cleaning supplies. brbrStraight through from here you can see out French doors to the back balcony. But before you get that far, there’s a glass-top table and two chairs just perfect for a morning coffee and a delicious croissant from Frenchie’s Café just a few blocks down the street. The doors open onto a private balcony overlooking a spacious and gleaming pool and spa. The whole back area oasis is ringed by green palms that provide beauty and privacy for the exclusive use of the four units in the building. An ample brick deck surrounds the pool and provides chaise loungers and chairs for your comfort when you decide you are finished swimming or floating leisurely. Or maybe it’s time to return to your second-floor balcony where there’s a table, two chairs and a market umbrella that provides shade and distinction. It’s the perfect place for morning coffee or evening cocktails or for reading that novel you brought along.brbrBack inside is the bedroom and full bath. You’ll be happy to find the bed is a very comfy queen as you sink into it at night. Two small bedside tables with drawers hold lamps and leave a space for your cell phone. The room has plenty of windows for light or you can close the venetian blinds for darkness. A chest of drawers and a closet create plenty of put-away room for your hanging things or your foldable things. Adjacent is the full bath with shower and tub. Here again is a window that gracefully brightens the whole space.brbrBesides being a perfect vacation residence, the location is only blocks off the famous/infamous Duval Street. Closest to Upper Duval or what is known as “Uptown,” this end of Duval runs toward the Atlantic and has a reputation for being quieter and more relaxed than Lower Duval. Upper Duval boasts of multiple beaches such as Dog Beach, Higgs Beach, Reach Beach, and Smathers Beach. But of course, it has its bars and restaurants too. Most prominently Louie’s Back Yard, Dorada at Casa Marina, and Salute! On The Beach.brbrThe whole fourteen blocks of Duval, upper and lower, provide access to food, drink, tours, museums, galleries, and shopping. Cultural activities such as live music, art exhibitions, and plays are also plentiful. Perhaps let a butterfly land on your shoulder at Key West Butterfly and Nature Conservatory or catch a movie on one of the three screens at the locally run Tropic Cinema. Then stop in at Books & Books to catch a glimpse of the author Judy Blume stocking the shelves. And don’t forget to set your watch for sunset so you don’t miss the world-famous sunset party at Mallory Square at the Gulf end or lower end of Duval.brbrCredit Card Surcharge Notice: The owner of this unit asks guests to cover the processing fees for credit card payments. If you’d like to avoid the 3% surcharge, please reach out to our office to make your reservation and arrange payment by check. brbrThe Property may only be used for residential accommodations. No special events, parties, or functions of any kind are permitted on the Property. If this is your first trip to the Conch Republic, a guidebook from Books & Books on Eaton Street or a stop at the Chamber of Commerce Information Center on Greene Street will help make sure you don’t miss anything. Other info on the current music scene, movies, plays, gallery openings, and charitable events can be found at milezerokeywest.com (calendar section). Historic Hideaways' informative Area Guide/Events page located on our website also has a Calendar of Events. We do not guarantee that the information VRBO (and affiliated sites) obtains from our site to display on theirs is 100% accurate, particularly the amenities. If you come to us through them, be sure to look at all the information on our site related to your rental once you book to be sure you have accurate and up to date information.brbr**For Pet Friendly (dog) homes there are restrictions that include, but may not be limited to, the following: pet friendly means dogs, no other animal is permitted. Dogs are restricted to one (1) large dog or two (2) small dogs per stay. Due to Homeowner Insurance restrictions we are unable to accommodate the following breeds: Pit Bull Terriers, Staffordshire Terriers, Rottweilers, German Shepherds, Presa Canarios, Chows Chows, Doberman Pinschers, Akitas, Wolf-hybrids, Mastiffs, Cane Corsos, Great Danes, Alaskan Malamutes, Siberian Huskies nor any mixed breed that contain one of the preceding as part of that mix. Guest is responsible for an additional pet fee of $200.

Back to the Island - Old Town Key West 2nd Floor Condo

Key West, Florida, United States

Bed

Bath

Sleeps

$1262.64

THE PROPERTY: Awarded the Florida Keys Preservation Star, this stunning home and outdoor space will entice you to live like a local. From its covered front porch to its rear entertaining area, you won’t want to leave. As you enter via the sunny yellow doors you will be captivated by the gingerbread balustrade, staircase book nook and beautiful Dade County pine walls. brbrMoving into the open concept kitchen and living room, high ceilings, designer finishes and natural light will greet you. The sleek white kitchen is equipped with stainless steel appliances and everything you need to prepare meals or snacks. The oversized island has seating for six and allows you to mingle with guests in the comfortably furnished living room. You will be drawn to the outdoors via the double set of sliders that spill onto the lanai. Unlike other lanais this one is generously furnished and includes a large screen TV and an air conditioned half bath. From here you can take a dip in the pool, sip cocktails or simply relax with a good book. The pool includes a water feature, and the entire area enjoys privacy via fencing and lush landscaping. Nap on a lounger while surrounded by palm trees and sunshine. A wonderful island option is alfresco dining. The chef in your group will enjoy the gas grill and large dining table. brbrAll three bedrooms in this home have ceiling fans and en suite baths with walk in showers. Two king bedrooms are located on the first floor, and one has direct access to the pool. You will appreciate the beautiful linens, natural light, and closet space. The third bedroom is located on the second floor. It has a queen bed and provides a bit of privacy for those who may need it. This room also has a vaulted ceiling, closet, TV, and plenty of natural light. brbrThis lovingly restored home has unique island charm and is in a fabulous location. If modern amenities, outdoor living, and walk-ability are on your Key West bucket list, Lilly's Pad is the vacation home for you!br brBED CONFIGURATION: There is a king en suite bedroom on the first floor. The second king en suite bedroom is also on the first floor. The third queen en suite bedroom is located on the second floor. brbrOUTDOOR AMENITIES: The covered lanai provides an outdoor living space with TV and plenty of seating. The dip pool with water feature is delightful after a day exploring the island. Dine alfresco on your large outdoor dining table. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. A grill is available for cooking up the catch of the day. A convenient and air conditioned half bath is located off the lanai. Sunshine, palm trees and lounge chairs on the sun deck await you. brbrPARKING: There is a convenient off-street parking space with this home, which is a rarity in Key West.brbrLOCATION: Old Town just a half block from Duval Street. Near the Key West Butterfly Museum and Southernmost Point. You will enjoy this quieter yet walkable side of town near finer shops, galleries, and restaurants. brbrPETS: This home is NOT pet friendly. (If you have pets, please browse through our many homes that are pet-friendly).brbrSMOKING: This is a non-smoking home and property.brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Managed by Historic Key West Vacation Rentals.***

~LILLY'S PAD~ Upscale elegance with a private pool and parking!

Key West, Florida, United States

Bed

Bath

Sleeps

$286.89

Unwind in the Beautiful, Tropical Paradise of Key West, in the Renowned 'Southern Comforts' 4 Bedroom Ocean Front Villa, in the Peaceful and Serene Environment of Bay Point on Lower Saddle bunch Key. Only 15 Miles Away is the Exciting, Eccentric and Much Beloved City of Key West, with its Many Attractions.br br But Before You Explore This 'Southernmost Tip' of the Us, You Are Seduced by the Comfort and Beauty of Your Vacation Home.br br the Beautiful, Designer Inspired But Comfortable and Charming Southern Comforts Villa, with a Magnificent Open Floor Plan Opens to the Ocean Front Space and the Large in Ground Heated Pool, Via Three Sets of French Doors. the Property Has Four Lovely Bedrooms; the Master Bedroom Opening to the Ocean Front Via it's Own Set of French Doors. The Master Bedroom has a large Master Bathroom. There is an Additional Full Bath Comfortably Located Between Two of the Guest Bedrooms.br br the Kitchen Has Been Recently Remodeled, as is the Rest of the Property, to Include Designer Cabinetry and All New Stainless Steel Appliances, with a New Dishwasher and Built in Microwave. the Designer Inspired Tiling Throughout the Home, Reflects the Care and Thought and Effort the Owners Have Invested in the Extensive Remodeling Project of the Property.brbr and Now, Humming Along with the Jimmy Buffett Tunes on the Stereo; You Sit by the Beautiful, Large, in-Ground Heated Pool on the Ocean Front, Sipping Your Own Personal Recipe for the Definitive Pina Colada, as You Watch the Magical Sunset of the Florida Keys! the Pool Has a Patio Adjacent to it; Making it an Ideal Location for Pool Side Dining and Entertaining.brbr However, If the Lure of the Open Water is Too Powerful to Resist, You Stroll Down to the Ocean Front Tile Patio and Dock Via a Few Gently Sloping Gracefully Curving Sets of Stairs. There You Will Find, Not Only Another Level of Possible Space for Dining and Entertaining, But Also Our Much Featured 'Sunset Swing' Under a Gently Swaying Palm Tree.brbr Heading North, Toward the Lovely Keys of Summerland and Big Pine Key with it's World Renowned Diving and Snorkeling Sites and the Key Deer Reserve or South, Toward the City of Key West, You Will Find Numerous Charming Ocean Front Dining Possibilities and Some Wonderfully Eccentric Restaurants with Great Sea Food and a Delightful Cast of Characters Serving You!brbr Margaretville, Jimmy Buffett, Ernest Hemingway, Tropical Sunsets, Swaying Palms and the 'American Caribbean' What Could Be Better Than This!brbr brbrKeywords: House

Available Florida Keys pool home near Key West. 2025 Sum/Fall 30% off discount

Key West, Florida, United States

Bed

Bath

Sleeps

$219.76

Private home located in New Town available for 4 week minimum rental. Beautifully landscaped yard with secure private back yard and pool. The home features a modern kitchen with all appliances and granite counter top. The master suite opens onto the pool deck and is furnished with a king size bed and walk-in closet, a private bath with a large shower. Another bedroom also opens to the pool deck area and is furnished with a queen size bed. The third bedroom has two twin beds. A second bathroom serves the guest bedrooms. Two walls of the living room have sliding doors that open completely onto the pool area.brbrKeywords: single family home in residential neighborhood available for 4 week minimum rental period

Single Family Home, 3 Bedroom, 2 Baths, Pool. Great Value!

Key West, Florida, United States

Bed

Bath

Sleeps

$370.96

Pool & Jacuzzi Resurfacing NoticebrbrPlease be advised that the pool and jacuzzi area will be closed for resurfacing beginning:brJuly 6th – August 30th (weather permitting)brbrThe entire pool and jacuzzi area will be fully closed off during this time to allow the contractor to safely complete the work.brThis project is part of our ongoing efforts to maintain and improve our community amenities for everyone’s enjoyment.brbrbrOceanfront Oasis – 2BR/2BA Condo with Balcony Views at La Brisa brbrWelcome to your perfect tropical getaway! This beautifully appointed 2-bedroom, 2-bathroom condominium on the 3rd floor of the East Building at La Brisa offers sweeping ocean views and all the comforts of home—plus resort-style amenities.br Comfortable & Flexible Sleeping Arrangements:brbr Primary Bedroom: King bed, en suite bathroom, and direct balcony access.brbr Guest Bedroom: Two twin beds (convertible to a king).br Living Room: Queen-sized sleeper sofa—perfect for extra guests.br brFully Equipped Kitchen:brbrWhip up your favorite meals with ease. The kitchen features:brbr Keurig & drip coffee makersbr Crock-potbr Full cookware and utensilsbrbrRelax & Recharge:brbr Spacious balcony for sunrise views and ocean breezesbr Tile flooring throughoutbr Washer & dryer in-unit for conveniencebr Cable TV & high-speed Wi-FibrbrResort-Style Amenities at La Brisa:brbr Heated swimming pool & hot tubbr Sauna for ultimate relaxationbr Hard tennis courtbr Direct access to walking & biking trails along Smather’s BeachbrbrWhether you're here to unwind or explore, this condo is the ideal blend of comfort, location, and style. Your Oceanfront Oasis awaits!

Oceanfront Oasis Smathers Beach Condo Sunrise views Island Charm Book today

Key West, Florida, United States

Bed

Bath

Sleeps

$1722.99

Welcome to Key West OasisbrbrLuxury | Privacy | Iconic Location in Truman AnnexbrbrTucked away on one of the most exclusive lanes in the Truman Annex, Key West Oasis is a sophisticated, meticulously maintained estate that offers an unparalleled island escape. With 5 bedrooms, 5.5 bathrooms, and over 2,796 sq. ft. of beautifully designed living space, this estate is the ideal sanctuary for discerning travelers seeking comfort, style, and an unbeatable location.brbrPROPERTY HIGHLIGHTS:brbrTotal of 5 bedrooms / 5.5 bathroomsbrbr4-bedroom main house + 1-bedroom guest cottagebrbrLagoon-style heated saltwater pool & spabrbrRooftop observation deck with panoramic 360° Key West viewsbrbrLocated steps from Truman Waterfront Park, Duval Street & the beachbrbr4 cruiser bikes includedbrbrGated carport & lush tropical landscapingbrbrMaximum 8 guests | No pets | No eventsbrbrMAIN HOUSE (4 Bed / 4.5 Bath)brbrMain Floor:brStep into elegance with gleaming mahogany wood floors, a formal dining room with seating for 8, and an adjacent study complete with a built-in workstation. The open-concept kitchen connects seamlessly to the living area and features black granite countertops, stainless steel appliances, breakfast bar for 4, and fully stocked cooking essentials.brThe living room is centered around a 75” smart TV with sound system and opens directly to the stunning outdoor patio and pool area.brbrSecond Floor:brTwo guest bedrooms share a balcony overlooking charming Noah Lane—one with a queen bed, the other a full—plus a shared full bath. The spacious primary suite features a king-size bed, 55” smart TV, large walk-in closet, and a spa-like en-suite bath with soaking tub, dual vanities, and walk-in shower. French doors open to an expansive Ipe balcony—perfect for sunset cocktails.brbrThird Floor + Rooftop:brThe third floor features a cozy 4th bedroom with a full bed and an adjacent full bathroom. A second flexible room serves as an office, yoga studio, or meditation space, and includes a wet bar. French doors lead to a ship ladder ascending to the rooftop observation deck, offering 360-degree views of Key West and the surrounding turquoise waters.brbrGUEST COTTAGE (1 Bed / 1 Bath)brbrDetached for maximum privacy, the 239 sq. ft. guest cottage includes a queen bed, 55” smart TV, full bathroom, mini kitchen, and closet—ideal for visiting friends or family.brbrOUTDOOR LIVINGbrbrLagoon-Style Saltwater Pool & Spa – Heated with tranquil water featurebrbrOutdoor Dining & Lounge Areas – With ceiling fans for warm afternoonsbrbrGas Grill – Perfect for al fresco BBQsbrbrOutdoor Shower – Ideal after beach or pool timebrbrTropical Landscaping & Lighting – Enhancing the charm and ambiance of this classic Conch-style estatebrbrCARPORT & TRANSPORTATIONbrbrGated carport with space for vehicle or golf cartbrbr4 cruiser bikes provided—ride to the beach or Duval Street in minutesbrbrLOCATION, LOCATION, LOCATIONbrbrSteps from Truman Waterfront Park and AmphitheaterbrbrWalk to Fort Zachary Taylor BeachbrbrMinutes from Duval Street, Mallory Square, and top-rated restaurants, bars, and galleriesbrbrGOOD TO KNOWbrbrStrict maximum of 8 registered guestsbrbrNo parties, events, or amplified noise allowedbrbrNo pets permittedbrbrSecurity cameras on exterior only (front, rear entry, and driveway)brbrProfessionally maintained and cleaned to the highest standardsbrbrExperience Key West at its finest. Whether you’re sipping cocktails on the rooftop deck, enjoying a morning swim, or biking to local favorites, Key West Oasis is the perfect blend of luxury, privacy, and island charm.

Key West Oasis - Truman Annex Estate

Key West, Florida, United States

Bed

Bath

Sleeps

$285.32

READ ADDITIONAL REVIEWS -Old Town -Whitehead St- BEST LOCATION -On Whitehead St. -Steps to Duval -Any discounts offered will be taken off price shown-will send special offer that you can accept or decline…Sleeps 7 Walk to new Truman Annex water park & Ft Zach Beach or FREE community pool 7-8 blocks..OUTSIDE SHOWER.. As seen in the March 2015 issue of Island Jane Magazine, this Hemingway inspired Villa sits on the Old Samaritan Hall site where they held lots of weddings! Such a good vibe! ( James Brown played here!!) This unique home w/ 10 ft ceilings offers lush private gardens on double lot, & plenty of off street parking. Hemingway's house, Lighthouse, mm0, Southernmost Pt, & Mallory Sq are all located right here! Duval is one block, Ft Zach beach is 2 blks- Water park and playground 2 blocks away near Coastguard Ship. Large free community pool blocks away. It is never crowded and overlooks the ocean. It is a monthly rental since we do not have a transient license to rent it out for less than 28 nights. ( 4 weeks) You can go in on the house with friends and family for the entire month and share the house. Please inquire if you have any questions. Thanks for considering staying at the Little Hemingway House! We look forward to accommodating you! brbrSee below for additional reviews. ( copied & pasted because guest reviews after 3 years are hidden) We especially love our repeat guests! (however they don’t leave additional reviews each year -but here’s what some had to say) brbr 5/5brGreat house & location can't be beat!brWe had a great time staying at the Little Hemingway House! The location is fantastic, so close to everything and yet still in a quiet section. We adopted a family of chickens out front - Mamma and her babies stayed with us almost the entire time. Brenda was super easy to work with, and answered every question we had lightning fast. We wouldn't hesitate to rent again - thanks so much for everything! Megan Pbrbrbr 5/5brExceeded Expectations...A lotbrLocation and Privacy. What a gem, located in the heart of everything Key West. One block from Blue Heaven restaurant, half a block off Duval and a short walk to Mallory Square. And amazingly the house is completely private with three off street parking spots two of which are behind a private gate solely for the house. Great gardens enable guests to have coffee and people watch while remaining secluded. Decorated with fantastic touch. We liked the house better and better each day and didn't want to leave. Finally 'little' is misrepresentative, the house has plenty of room with the two master suites and downstairs bedroom. You'll pinch yourself if you’re lucky enough to rent the Little Hemingway House. Can you tell we loved it ! Zach M

Villa

Villa 3 Bdrms/3 baths/close to everything/off st prking/Old Town/15% off Aug

Key West, Florida, United States

Bed

Bath

Sleeps

$703.13