Vacation Condo Rentals By Owner In Key West, FL

The Orchid Suite is a bi-level suite decorated in a rich contemporary Danish style. The bedroom is located upstairs with a bookcase divider separating two different sleeping areas, each with a queen bed. The upstairs bathroom features a tiled shower with a glass door, hairdryer, and all necessary linens. Large beach towels are also provided.brbrDownstairs is a living room There is a lovely dining room with plenty of seating, a tiled breakfast bar, and stools. We have recently added a new half bath.brbrAll the amenities of a luxury property are included: a fully equipped kitchen, dishwasher, refrigerator with ice-maker, microwave, drip coffee maker, blender, and everything needed to prepare, and serve a gourmet meal. There are two shared gas BBQ grills, coin-operated washer/dryers, and on-street parking.brbrOrchid Suite is a half-block from the famous Duval Street, just a short walk to the infamous night life. Several blocks away is the sunny South Beach with ocean swimming and a restaurant. If you prefer a pool, it is onsite and just a few steps away from the cottage.brbrOrchid Suite is bi-level, with the bedroom upstairs. It may not be suitable for persons unable to climb stairs well.brbrParking in Key West is very limited. This property has no assigned parking and is street parking only. You are responsible for finding parking for your vehicle. The maximum number of people allowed in this property is 4. If there are more than 4 people are in your party upon arrival, your party will be asked to leave without compensation. Violation of ANY house rules will result in your party being asked to leave without compensation.

Orchid Suite on Center St - 1/2 block from Duval Sleeps 4

Key West, Florida, United States

Bed

Bath

Sleeps

$346.08

Located in the heart of historic Old Town Key West, just steps away from world-renowned Duval Street, La Casa de Luna is a ground-level one-bedroom, one-bathroom condo that is part of a large house with a relaxing veranda. This modern property is within easy walking distance to all your favorite restaurants and bistros.brbrOpen the door to the full kitchen offering a refrigerator, stove/oven, microwave, and coffee maker. Your group's chef can keep up the chatter with friends or family sitting in the living room with La Casa de Luna's open floor plan. There is a queen sleeper sofa in the living room, so it will accommodate up to four people. The full bath comes supplied with all the amenities you need, including plush towels and wash cloths. brbrThe primary bedroom features a comfortable king bed and two nightstands for the late night reader. Walk out onto the porch from the bedroom with a cup of coffee or margarita to enjoy people watching! brbrPLEASE NOTE THAT THIS PROPERTY DOES NOT HAVE A POOL.brbrYou may use the pool at Dante’s if you utilize their food and beverage services or you may purchase a day pass using the link below at any of the hotels located near your rental. br brhttps://www.resortpass.com/s/us/fl/key-west/pool search_term=Key+West%2C+Florida&city_alias_id=26brbrParking in Key West is very limited. This property has no assigned parking and is street parking only. You are responsible for finding parking for your vehicle. The individual making the reservation must be 25 years or older with proper identification and be an occupant of the property. The maximum people allowed in this property is 4. If there are more than 4 people are in your party upon arrival, your party will be asked to leave without compensation. Violation of ANY house rules will result in your party being asked to leave without compensation.

La Casa de Luna - 1 Bd/1B condo just off upper Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$384.19

The perfect space in the perfect place.brbrA quiet oasis on the 2nd floor nestled amongst palm trees in the shipyard section of the Truman Annex, it is perfectly located steps from Duval street, Mallory Square, Zachary Taylor State Beach, Truman Waterfront Park, Bahama Village and all the best that Key West has to offer.

The Palms...A beautiful space in the perfect place.

Key West, Florida, United States

Bed

Bath

Sleeps

$697.46

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrThis modern Old Town condo is designed for the real downtown experience in the Conch Republic, ideal for anyone looking to indulge in Key West’s famous late night scene. VILLA ANGELITA is located right in Old Town, half a block away from Duval Street and smack dab in the center of the entertainment district. Although this property does not include parking, you couldn't be any closer to the late-night scene and attractions of downtown. Fair warning... It can get a little noisy out there! This tropical three-bedroom retreat is hidden within a renovated Old Town home, with all of the charm of the famous conch houses of Key West.brbrTHE LIVING AREA...brbrVILLA ANGELITA is the second floor of this converted Old Town home. As you enter the apartment by climbing the stairs from the front door of the home, you are greeted with modern tropical decor in the light-filled living room. Tall ceilings and high end finishes complete this renovated condo. A large flat screen TV on the wall overlooks the spacious living area with plenty of seating. The sofa pulls out to a full sized bed to sleep an extra guest in a pinch.brbrTHE KITCHEN...brbrOff of the living area, the upscale kitchen is fully equipped with all the high-end tools and appliances you'll need to whip up a meal at home. If you can resist the temptation of all of the famous Key West restaurants within walking distance, that is! The dining area off the kitchen seats six by the windows for a relaxing evening in or can be used as your stay at home office in Paradise (high speed, password-protected WiFi included.) The front and back of the condo have doors to the wrap-around decks for you to enjoy your morning coffee and some prime Old Town Key West people watching.brbrTHE ACCOMMODATIONS...brbrThe accommodations of VILLA ANGELITA are designed to accommodate a family or several couples comfortably. brbr• Master Bedroom: Queen bed, overhead fan, flat screen TV, and an en-suite bathroom with a glass shower. brbr• Second Bedroom: Queen bed, overhead fan, flat screen TV, and direct access to the wrap around deck. brbr• Third Bedroom: King bed, overhead fan, flat screen TV, and direct access to the wrap around deck. brbrThere is a shared full bathroom in the hallway for the Second and Third bedrooms, with a glass shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr• Washer and Dryerbr• Central Heat and A/Cbr• Ceiling Fansbr• Flat Screen Cable TVs in Living Room and All Bedroomsbr• 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 ServicebrbrOther notes:brbr• Interim housekeeping provided upon requestbr• This property will accommodate up to 7 adultsbr• Pets Considered - Max of 2 allowed and if approved an additional fee of $200 per pet will applybr• This home does not include designated parkingbr• 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.

**VILLA ANGELITA @ OLD TOWN** Renovated Condo Off Duval + LAST KEY SERVICES...

Key West, Florida, United States

Bed

Bath

Sleeps

$192.25

Welcome to our comfortable and delightful 2nd floor condo in the Shipyard section of Truman Annex. Unit #258 is a tastefully decorated 2 bedroom, 1 bath condo with views of the pool. The master bedroom has a queen sized bed; the 2nd bedroom has 2 twin beds. The remodeled bathroom has a walk in shower enclosure. The fully equipped kitchen opens to the front porch which overlooks the pool area. This covered porch offers protection from the hot Key West sun as well as the occasional tropical shower. The back porch is great for sunbathing & star gazing! All is provided to make your stay enjoyable including high speed internet, blender, beach towels, and washer/dryer. So grab a cool drink and a towel and head down to your lounge chair by the pool! brPlease note: This property is monthly rental - the minimum rental period is 28 nights

Green Spot at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$171.99

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrThis property is a 30 night minimum. Boat slips available for rent! Inquire with us. brbrFEATURES:brBedrooms: 2 (1 king and 2 twins-can be converted to a king)brBathrooms: 2brLocation: Sunset Marina Gated CommunitybrSquare Feet: 1171brParking: 1 assigned covered parking space (NO ELECTRIC VEHICLES/SCOOTERS/BIKES ALLOWED)brAmenities: Wifi, TVs, in-unit laundry, balcony, shared pool, near the golf course, boat slip availablebrbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

Boater's Dream 2Bed 2Bath Condo, 30 night stay w/ water views, balcony, pool

Key West, Florida, United States

Bed

Bath

Sleeps

$182.29

Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into 5 condo units. Tony's Conch Retreat, unit 5, is on the 2nd floor, at the top of the stairs, and encompasses the rear of the home from end to end. It has a lovely view of the back yard and the pool! brbrThe large foyer and living area with high ceilings convey a spacious and open coastal feel! The dining table and chairs are custom designed with specialty hardwoods and the owner spared no expense with local original art and other high quality art pieces. The kitchen and is stocked with everything you need! brbrThe quaint den off the living room can be closed off with the accordion doors and curtains. It has an antique desk and comfortable chair. Free WIFI is provided! The couch is a queen sleeper sofa and there is also a small closet for personal items. brbrAlso provided are beach/pool towels, beach chairs and two bikes! brbrThere is not designated parking at this property.

Old Town! Spacious Condo in Historic Home w/Pool!

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. The 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 AND each bedroom. They open onto both front and back balconies with views of the treetops and Old Town Key West. Elegantly furnished, Blue Heavens spa-like atmosphere features vaulted ceilings, ceramic floors and full amenities, including flat screen TV’s and wireless internet access. The living room has a sleeper sofa for guests. 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. New flat screen TV's in living area and primary bedrooms. brPlease note: This property is monthly rental - the minimum rental period is 28 nights

Blue Heaven at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$158.76

Live steps from everything that makes Key West unforgettable. This first‑floor Shipyard condo blends comfort with island charm, offering a bright interior, tile floors, and seamless indoor‑outdoor living through double doors that open to a lush private patio. The gated Truman Annex community provides resort‑style amenities, including a sparkling pool and dedicated parking. From morning walks to the beach to evenings on Duval Street, this location puts the best of Old Town right outside your door.brPlease note: This property requires a 28 night minimum stay

Oyster's Pearl at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$159.33

Impressive. Distinctive. Comfortable. The perfect spot for your tropical get away. This second floor, two bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can enjoy breathtaking views just steps from the Gulf of Mexico. Watch passing tall ships, cruise ships, pleasure boats, party boats, and sport boats as you sun yourself or take a swim. The inviting pool is surrounded by lush tropical foliage and has plenty of comfy patio furniture for your lounging comfort. The water is temperature-controlled, and the facility is for the exclusive use of Harbour Place guests. brbrTwo stories up (by elevator or stairs), the balcony of this professionally decorated condo has limited water views from the balcony off the living/dining area. While in another part of the residence, the Master bedroom balcony offers wonderful views of Truman's Little White House Museum where United States Presidents and many other world heads of state have resided over the years. Weddings and other stately ceremonies frequently take place on the lawn under the huge presidential shade trees. brbrBanana Key is beautifully appointed in all new and striking furniture and accessories featuring the lush colors of Key West-ocean blue, sand beige, vegetation yellow and green, with accents of orange and magenta. As you enter from the carpeted and soundproof hallway, you find yourself in the elegant foyer. To the immediate right is one of the two bedrooms. This one has twin beds with fluffy bedding and three large windows to let in plenty of sunlight and moonlight. The white oak floor is dotted with colorful area rugs while a Casablanca-type ceiling fan whirs above circulating air and adding ambience. A three-level dresser, a full closet, a cushioned chair, bedside table with sea shell reading lamp complete the scene. A flat screen TV is perfectly positioned for comfortable viewing from the beds. Immediately to the right of this this room is a full bath with mirrored shower doors, a linen closet stuffed with nubby towels, and tile floor.brbrA right turn from the foyer puts you in a hallway that leads past the washer/dryer closet into the kitchen but not without a door on the right that opens into the Master bedroom with full en suite bath. The four poster king bed has been crafted in a handsome dark wood and dressed in a flower and seashell motif comforter. Nearby a leather loveseat and ottoman offer a place for upright relaxation. A dark wood dresser and ceiling fan continue the striking wood tone throughout the room. In popping contrast to the dark are the cloud white walls and a wall of windows with slatted blinds. Best of all, a glass door opens to a small balcony with seating for two. The one-of-a-kind view is of palm trees framing the Truman White House and grounds. Although you didn't come on vacation to sleep, this room is a true temptation.brbrThe next room is the galley kitchen with double sinks and all the appliances and cabinet space you could wish for. Contemporary spot lighting dots the ceiling in case you want to prepare a meal after dark. A wide and decorative pass-through from the kitchen to the dining area is convenient and adds openness and architectural interest. The square dining table and four high-backed chairs are as ideal for a game of cards or Trivial Pursuit as for a meal. brbrRight beyond is the living room space delineated by a stunning blue & sand hued area rug and blue curved sectional couch that can seat up to six. A glass-top coffee table, green banana plants, and a tropical ceiling fans make this the heart of the living space where you'll sit to watch TV or movies on the flat screen. Also available is cable, high-speed internet, DVD player, and shelf sound system. Ambient light fills the room from the many windows and from the glass door out onto the long balcony outfitted with deck chairs and glass-top table.brbrWhile your condo comes with reserved and covered parking, you'll probably find you don't really need a car. From your central location, everything is easily accessible by foot or bike. Steps from your door enjoy the manicured landscaping, verdant palms, and interconnecting pathways that give your Truman Annex neighborhood its park-like atmosphere. Stroll out the private gates to find yourself immersed in the sights and sounds of the fabulous Duval Street, the island's main artery for tours, museums, and shops of all descriptions. Of course there are bars galore and over two hundred restaurants, many with open-air seating, some right on the water. Don't miss the Butterfly & Nature Conservatory, the Key West Aquarium, and especially the nightly sunset celebration where visitors and locals alike gather in Mallory Square to applaud as the sun slip below the horizon. brbrIf 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) scrapes 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.

Banana Key

Key West, Florida, United States

Bed

Bath

Sleeps

$127.44

PLEASE NOTE the pool will be closed during the month of AUGUST for repair/resurfacing. Please contact our office if you wish to reserve during this time as we will be offering discounts.brbrThis cozy two-bedroom, one-bath condo lies hidden behind wrought iron gates and down a winding pathway. The Shipyard, part of the Truman Annex neighborhood named for President Harry Truman, is Old Town's premiere gated waterfront community. The manicured landscaping, verdant palms, and white picket fences give the Annex a lovely park-like atmosphere. Don't be surprised if you see exotic birds like the snowy egret taking a stroll right in the Shipyard gardens. All this tranquility makes it hard to imagine that Duval Street, Key West's central artery of entertainment is a mere two blocks away.brbrThe two-story white wooden structure at Shipyard has a condo below and above. Yours is above and features front and back balconies. Either is ideal for enjoying what locals call sweet weather, a cup of coffee, or that newspaper or novel you brought along. If you're thinking of a swim, a heated pool with spacious patio is just steps away. For your convenience and comfort, the Shipyard Residents Only pool area provides chaise lounges, high-speed internet, bathrooms, and shower. If you prefer the real beach, the sun and sea breezes at Fort Zachary Taylor are right in the neighborhood. At the beach, have a sandwich and beer at the snack bar or rent an umbrella and chairs to watch the world of swimmers, divers, sailors, kayakers, and jet skiers pass by.brbrBut wait, you aren't even unpacked yet. Enter your vacation home from the front porch, unlock the door to your left, and head up the carpeted stair case. At the top you'll find a welcoming, fluid open floor plan that combines the kitchen, dining area, and living room. A door at the back of the kitchen opens to the front balcony and the living room door leads to the back balcony. The galley kitchen has everything you need to cook a meal at the stove. There's plenty of cupboard space above and every appliance conveniently tucked in below. brbrNext to the kitchen, the dining area provides a round, glass-topped table, colorful table linens, and four chairs. Sitting here you can enjoy the view out the French doors to the back balcony with blue sky and palm trees beyond. Or take your meal outside using the balcony's dining table and chairs. The living area features a bamboo couch, coffee table, and arm chair, all the same warm honey color as the Travertine tile floors. Colorful fish add tropical decoration to the walls. A Casablanca fan whirs above, circulating air throughout. In fact white ceiling fans cool every room whether you're using the central air conditioning or not. A corner-situated TV provides convenient viewing from the couch or chair. Need more seating Just bring in the dining area chairs. brbrJust off the living/dining area are the master bedroom, which features a queen bed, chest of drawers, wall-mounted TV, and plenty of natural light from a large window; a full bath; and a second bedroom with twin beds. Each bedroom offers plenty of closet and drawer space for your flip-flops, shorts, swimwear, sunglasses, camera, hat, you name it. brbrOnce you've settled in, the free-spirited fun of America's only Caribbean island awaits you at the Historic Seaport, on Duval, at the Southernmost Point, or at the beaches along the Atlantic. Check out the tours, museums, water sports, shopping, bars, and over two hundred restaurants, many with open-air seating, some right on the water. While your condo comes with reserved parking, you don't really need a car. From your central location, everything is easily accessible by foot, bike, pedicab, or taxi. Strolling Duval, you might find yourself posing for a photo-op with a pirate, a six-foot-tall drag queen, a Hemingway look-alike, or maybe even Jimmy Buffet in person. brbrWhen you've had enough for one day and head back to your condo to relax and plan for the next day, make one last stop at the Green Parrot for a little live music, a libation, and free popcorn among writers, artists, locals, and visitors. At the corner of Southard and Whitehead (the first and last bar on Highway 1), it's right on your way back to the Shipyard.brbrIf 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) scrapes 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.

Shipyard - 2/1 Condo in Shipyard @ Truman Annex

Key West, Florida, United States

Bed

Bath

Sleeps

$190.05

2 Bedrooms 2.5 Bathrooms. Comfortably Sleeps 4, Max occupancy 6. 1240 total sq. ft.brBedroom nr. 1: 1 King bed, with a balcony.brBedroom nr. 2:, 1 Queen bed. brExtra Sleeping: Queen size fold out sofa couch in the living room, opens to a large patio. brbrWelcome to Duval Street Place - the best location in Key West! Just steps from the exceptional shops and restaurants of the world-famous Duval Street. Within a few minutes walking distance there are many great attractions like the Hemingway House and Museum, Historical Lighthouse, Southernmost Point, and Butterfly and Nature Conservatory. Many other enjoyable sites are also within easy reach on foot: Key West Aquarium, Key West Shipwreck Treasure Museum, Mel Fisher’s Maritime Museum, Harry S. Truman Little White House, and many more! Head to Mallory Square and join the crowds for a nightly sunset celebration. Rent a bicycle, scooter, or an electric cart from a nearby shop and explore the entire island at your pace, or relax at Fort Zachary Taylor Park with the prettiest beach in Key West. brbr28 Day Minimum Rental Only - get a month for the price of a week! A shared pool with plenty of chaise lounges is 45 feet away, adjacent to a large, covered picnic pavilion. A dedicated parking space is located under the building. This two-story town home is on the second floor, nestled above popular restaurants and delightful shops, and is accessible via a secured stairway or elevator either from the garage or entrances outside of the building. If you have additional vehicles you will have to find street parking, as parking in the exterior lot is strictly for Duval Square Mall patrons per the HOA. If you choose to rent mopeds or electric carts, please be sure they all fit in your parking space in the garage. There are bicycle parking racks both inside the garage and outside of the building. New impact windows and doors.brbrUnfortunately, pets are not allowed at this home. brCentral A/C, free WiFi, and cable TV.brUltra-quiet window AC in master bedroom for supplemental temperature control. brWasher and dryer inside the unit. brNo smoking, please.brYou must be 25 years or older to rent this property.brThe rental is non-transferable.

Duval Sq., Old Town, very walkable, full kitchen, pool, parking, 2 BR/2.5 BA.

Key West, Florida, United States

Bed

Bath

Sleeps

$335.3

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrBOAT SLIP INFORMATION:brOne boat slip is included with this Retreat. Each Retreat can only accommodate one boat; no exceptions. Trailer parking is not available on property. Trailer parking and additional boat slips are available across the harbor at the City of Key West Marina. Please contact the dock master’s office to make arrangements for trailer storage and/or additional boat slips atbrbrFEATURES:brBedrooms: 2 ( 1 king, 2 queens in 2nd bedroom) brBathrooms: 2 en suitesbrLocation: Garrison Bight Marina off Eisenhower DrbrSquare Feet: 1215brParking: 2 parking spaces includedbrAmenities: Wifi, TVs, in-unit laundry, 1 complimentary boat slip, water viewsbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

Bermuda Retreat-waterfront 2BR 2BA condo w/ pool & boat slip

Key West, Florida, United States

Bed

Bath

Sleeps

$368.71

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrBOAT SLIP INFORMATION:brOne boat slip is included with this Retreat. Each Retreat can only accommodate one boat; no exceptions. Trailer parking is not available on property. Trailer parking and additional boat slips are available across the harbor at the City of Key West Marina. Please contact the dock master’s office to make arrangements for trailer storage and/or additional boat slips atbrbrFEATURES:brBedrooms: 2 ( 1 king, 2 queens in 2nd bedroom)- THE SLEEPER SOFA IS NOT RECOMMENDED FOR ADULTSbrBathrooms: 2 en suitesbrLocation: Garrison Bight Marina off Eisenhower DrbrSquare Feet: 1215brParking: 2 parking spaces includedbrAmenities: Wifi, TVs, in-unit laundry, 1 complimentary boat slip, water viewsbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

Flamingo Retreat-waterfront 2BR 2BA condo w/ pool & boat slip

Key West, Florida, United States

Bed

Bath

Sleeps

$503.74

Duval Square is a charming community with shops and restaurants downstairs and secure, quiet, private residences, pool and pavilion upstairs. Although the condo includes one assigned parking space in the gated garage, you can stroll anywhere from this conveniently located condo. All of the shops, galleries, restaurants, and attractions on and around Duval Street and nearby beaches are just a leisurely stroll away. brbrWhen you enter the home you will find a fully equipped kitchen, dining area, spacious living room and a convenient half bath. French doors let in the natural sunshine and open to the private back deck with dining table and chairs perfect for outdoor entertaining. brbrOn the second floor, you will find 2 bedroom suites, each with their own private bathroom and an additional private balcony off the main suite.brbrBedding: 1 king, 1 queen, queen sleeper sofa.brbrElevator access from ground level to the first floor of the condos. Stairs to the unit's second floor bedrooms.brbr**Construction Disclaimer** From mid May through the month of June, 2026, the pool area will be under construction. This will create noise and dust that could impact your stay and may lead to pool closure as well.

ARTIST'S CONDO @ Duval Square by Rent Key West Vacations - Located on Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$235.4

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrFEATURES:brBedrooms: 2 (1 king and 2 twins-can be converted to a king, Sleeper Sofa)brBathrooms: 2brLocation: Truman Annex - Shipyard CondosbrSquare Feet: 646brParking: 1 assigned parking space in gated lotbrAmenities: Wifi, TVs, in-unit laundry, patio area, shared pool, walkable to downtown shops & restaurants brbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

Shipyard 297-Condo in Truman Annex-2 bedroom 2 bath, close to Duval w/ pool

Key West, Florida, United States

Bed

Bath

6

Sleeps

$615.94

Tom's Oceanfront PenthousebrbrExperience coastal luxury at Tom's Oceanfront Penthouse, a stunning 3-bedroom, 2-bathroom unit ideally located in a prime spot within the complex. Just steps from the elevator, this expansive 2,000 sq. ft. penthouse offers the ultimate in comfort and convenience, including secure, covered garage parking for vehicles under 6 feet 4 inches in height.brbrEach of the three bedrooms and the spacious living room features sliding glass doors that lead out to a private 60-foot wraparound balcony—perfect for enjoying sweeping ocean views and fresh sea breezes.brbr Master Bedroom: King-size bedbr Guest Bedroom: Queen-size bedbr Third Bedroom: Two twin bedsbrbrCondominium Amenities:brbr Olympic-size swimming poolbr 20-person spabr Saunabr Fitness areabr Librarybr Tennis courtsbrbrWhether you're lounging on the balcony, relaxing in the spa, or enjoying a game of tennis, this penthouse provides everything you need for an unforgettable oceanfront retreat.brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing

Key West, Florida, United States

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Bath

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$686.47

Summary:brbrRelax and unwind in this spacious waterfront condo in downtown Key West. Ideal for families and groups, enjoy a full kitchen, open living space, and a private balcony overlooking the marina and pool. Dockage available with a fish cleaning station and ice maker, perfect for boating and fishing. Located about 1 mile from Duval Street, restaurants, and nightlife, and just 10 minutes from EYW airport. Amenities include a heated pool, tiki area, BBQ grills, free parking, elevator, and secure entry.brbrbrbrThe Space:brbrWELCOME TO DOMINICA YOUR WATERFRONT RETREAT IN KEY WESTbrbrbrbrLocated in the desirable Pelican Landing waterfront community, Dominica is a beautifully appointed 2 bedroom, 2 bath condo offering a spacious layout and comfortable coastal feel, ideal for families, couples, or small groups. Comfortably sleeps up to 6 guests, with a maximum occupancy of 8.brbrbrbrDesigned for comfort and easy living, this waterfront home features a bright, open layout, a fully equipped kitchen, and a large private balcony overlooking the marina and pool. Whether you are here for boating, exploring downtown Key West, or simply unwinding by the water, it’s an ideal place to relax and enjoy your stay.brbrbrbr✨ THE SPACEbrbr Primary Suite: King bed, marina views, private balcony access, ensuite bathroom, walk-in closet, and flat-screen TVbrbr ️ Second Bedroom: Two Queen beds, ensuite bathroom, and flat-screen TVbrbr ️ Living and Dining Area: Spacious open layout with comfortable seating, perfect for relaxing, dining, or gathering after a day on the waterbrbr ️ Kitchen: Fully stocked with cookware and essentials, ready for meals at homebrbr Laundry: Full-size washer and dryer for added conveniencebrbr Balcony: Large private balcony overlooking Garrison Bight Marina and the pool, ideal for morning coffee, boat watching, or sunset drinks. Includes direct stair access to the pool and docksbrbrbrbr DOCKAGE INCLUDEDbrbrA private boat slip is available for your stay, complete with water and a covered fish cleaning station. A commercial ice maker is available on-site, perfect for boating, fishing, and easy days on the water.brbrbrbr ️ EXTRAS AND AMENITIESbrbrPet-friendlybrbrFree on-site parkingbrbrHigh-speed WiFibrbrPrivate building elevatorbrbrbrbr COMMUNITY AMENITIES PELICAN LANDINGbrbr Heated poolbrbr Waterfront setting on Garrison Bight, located near Charter Row where many captains offer pickup directly from the dockbrbr Fish cleaning stationbrbr Private dock access for guests and ownersbrbr Tiki area and BBQ grillsbrbrbrbr LOCATION HIGHLIGHTSbrbr Bayview Park is adjacent with tennis courts and open green spacebrbr Fausto’s Food Palace 0.4 miles and Publix grocery store 1.4 milesbrbr ️ Higgs Beach 1.2 miles, Smathers Beach 1.5 miles, Fort Zachary Taylor Beach 2 milesbrbr✈️ Key West Airport about 10 minutesbrbrbrbr INSIDER TIPSbrbr Mac’s Place is right next door, a local favorite for casual food and drinksbrbr☕ Sandy’s Cafe 0.3 miles, known for Cuban coffee and breakfastbrbr Charter fishing, sandbars, and sunset cruises depart nearby from Garrison Bightbrbr Easy access to downtown, Duval Street, and the Historic Seaport, about 1 mile awaybrbrbrbrGuest Access:brbrGuests have full, private access to the entire 1,200 sq ft condo, including both bedrooms, two bathrooms, a fully equipped kitchen, and open living and dining areas. Enjoy the private balcony overlooking the marina and heated pool, along with direct access to the pool and dock area. You will also have access to the heated pool, tiki area, BBQ grills, and a private boat slip reserved for your stay. Free on-site parking is included, and a private building elevator provides easy access to the unit. Guests may also enjoy the adjacent park with tennis courts.brbrbrbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.brbrbrbrThe Neighborhood:brbrLocated in the downtown area of Key West, this waterfront condo offers easy access to everything the island is known for, while still providing a more relaxed setting just outside the busiest streets. Duval Street, the Historic Seaport, restaurants, bars, and nightlife are all about 1 mile away.brbrbrbrKey West is famous for its vibrant atmosphere, with live music, over 200 restaurants and bars, and nightly sunset celebrations. From beaches and boating to historic landmarks like the Hemingway House and Southernmost Point, everything is within easy reach. Bayview Park is right next door with tennis courts and open green space.brbrbrbrThe property overlooks Garrison Bight Marina, a hub for boating, fishing, and charter excursions. Located near Charter Row, many captains offer convenient pickup directly from the dock, making it an ideal location for guests planning time on the water.brbrbrbrGetting Around:brbrOur location is ideal for exploring Key West by foot or bicycle—everything is close by! Many guests also enjoy renting electric carts, which are widely available on the island, and we can accommodate plug-in access if needed. You really won’t need a car unless you're driving down Route 1 from mainland Florida. Lyft and Uber are also readily available throughout the area for added convenience. brbrbrbrOther Things to Note:brbr⏰ CHECK-IN AND CHECK-OUTbrbrCheck-in is 4 PM and check-out is 10 AM. The base rate includes up to 6 guests, with a maximum occupancy of 8. Guests 7 and 8 are $100 per person per night and must be included on the reservation prior to arrival.brbrbrbr PETSbrbrOne dog up to 25 lbs is welcome with a $200 non-refundable pet fee.brbrbrbr PARKINGbrbrFree on-site parking is available for one vehicle or golf cart.brbrbrbr DOCKAGE DETAILSbrbrMaximum boat length 40 ft, maximum beam 13 ft, with an 18 ft fixed bridge clearance into the marina. Overnight stays on boats are not permitted.brbrbrbr AGE REQUIREMENTbrbrAll guests must be at least 25 years of age unless accompanied by a parent. Please reach out with any questions.brbrbrbr TROPICAL ENVIRONMENTbrbrOur home is treated regularly by professional pest control. Due to the tropical climate, occasional insects may be present. If needed, we will promptly arrange service during your stay.brbrbrbrInteraction with Guests:brbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrCheck-in is simple with keyless entry. You will receive access codes for the building at least 24 hours prior to arrival and your condo access code on the day of arrival.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.

Waterfront Dock Pool Downtown Near Duval Pet

Key West, Florida, United States

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Bath

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$334.17

Rum Cay offers a quiet alternative to the downtown area of Key West. This modern condo is located a short 10-minute ride away from the nightlife, shopping, restaurants, and attractions near world-famous Duval Street. Rum Cay is a condo offering spacious bedrooms, a common area with a large screen TV, a murphy bed, plus a dining area and updated kitchen with stainless steel appliances.brbrThe condo is nestled on the edge of a nature preserve offering a quiet surrounding. There is a community pool, ample parking, and an elevator. Rum Cay offers a beautiful view of the estuary and views of the island and the water. brbrThe primary bedroom has a king bed, a large walk-in closet, and an updated bathroom offering a glass shower with rain showerhead. The primary bedroom has a flat screen TV and large dresser. The second bedroom offers a queen bed and flat screen TV. It has access to the second bathroom which is also accessible from the kitchen area.brbrThe living room and kitchen area are spacious with vibrant colors. A comfortable leather couch and two chairs offers space to unwind after a busy day around the island. Extra guests can utilize the murphy bed that folds out with a very comfortable memory foam mattress. The living room offers a large flat screen TV and there are sliding glass doors out to your own private balcony with a table and seating for four people. The kitchen is a great use of space with a larger table and four chairs. Everything you need to cook a meal at home is available. brbrRum Cay is the perfect place for a family or for friends who want to enjoy the quieter side of Key West.

Retreat to RUM CAY @ Sunrise Suites

Key West, Florida, United States

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