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Key West Vacation Rentals

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272 rentals are available

  • Alexandria's Secret is a private retreat in the historic district of Key West. With impeccable location and amenities, this three bedroom home is a Key West favorite for its secluded ambiance.This serene hideaway is just moments away from Duval Street and the most exciting spots the southernmost city has to offer- complete with a secret direct access to Duval Street, placing the best dining, shopping and nightlife right at your backdoor.

    Upon entering the enclosed retreat of Alexandria's Secret you won't be able to miss the beautiful smells, wonderful breeze and inviting space of the outdoor living area. Spend your sunny days relaxing on one of the 6 lounge chairs next to the private heated salt water cocktail pool, cooking on the gas BBQ grill and eating in the fresh air under the outdoor gazebo on the vast wrap around deck.

    Experience the true "secret" nature of your stay through the private door that will lead you right from your lounge chair to Duval Street.

    After you're done experiencing the unique flair Key West has to offer, come back to your hideaway to spend the evenings sleeping in one of the 3 thoughtfully decorated bedrooms: each offers king sized beds, two of which can be converted to Twins for larger groups: Alexandria's Secret sleeps up to 8 people so utilize the large plush sofa in the shared space as it transforms into a king size American leather comfort sleeper.

    Lay back and watch your favorite shows on your own TV or on the 55" TV in the shared space. The two upper bedrooms include attached balconies and each bedroom includes en-suite bathrooms, and ceiling fans with remotes. The master bedroom also has a safe to store important belongings. In true Island Style, Alexandria's Secret is equipped with central air conditioning. As you walk through the light and inviting home you won't miss the custom Marilyn Monroe painting and original Keys photographs decorating the home. One off street parking spot is also included.

    We had a fun time in Key West and this house was nice too. It was located right off of Duval street, but It was secluded from the main foot traffic, it offered 10’ to 12’ foot privacy fencing, and the property/house were in great condition.

    Key West
  • Almost Southernmost Retreat on the 400 block of Truman Avenue is the perfect location between Duval Street and Whitehead Streets.

    This style is common throughout the islands. Located in a row of identical cigar-maker cottages, the front porches are perfect for people watching in old town. There is also a second story deck at 417 for sunbathing. A gate at the rear of the two houses allows folks to enjoy each other's company, heated pool and large hot tub in total privacy!

    Between both homes you will have 2 King bedrooms (one upstairs at 415 and one down at 417 with an en-suite bath), a Queen bedroom (downstairs at 415), a Queen bedroom upstairs with a half bath separating the adjacent bedroom with 2 Queen beds (at 417) and 2 Queen sleeper sofas in each of the two living rooms.

    417 Truman had a complete downstairs renovation in October, 2011, which includes new bamboo flooring, a new King bedroom downstairs with a gorgeous deep blue en-suite bath with large walk-in shower, a new state-of-the art kitchen with granite counter tops and bar. A French door off the living room opens up to the newly installed heated pool with waterfall.

    Each home offers French doors off the kitchen/living room to wonderful decks where you have outdoor seating, two BBQ grills, two outdoor showers and lots of outdoor entertaining and fun areas. Add romantic, soft outdoor lighting and you won't even want to do the Duval Crawl, yet you are walking distance to all the great venues Key West has to offer!

    The property is located in the heart of Old Town in Key West and allows you to park your car and walk everywhere. It is a perfect house for entertaining family and friends - lots of areas to gather outside with decks, the hot tub and the pool. It was very clean and the kitchen was full of everything you need to cook and be comfortable. Parking is a challenge - only two spots for two houses that sleep 16 and it is very hard to find something close. We had a luau party and a brunch with friends over surrounding a wedding and it was a perfect house for that. Definitely would recommend to large groups.

    Key West
  • Tropical Retreat, at 519 Catherine Street, is on a quiet lane half a block off the upscale Upper end of Duval St. where there are many sophisticated restaurants, high-end art galleries and shops. Downtown Duval St. is within easy walking distance from Tropical Retreat to enjoy the exciting nightlife, music, bars and fun Key West has to offer. The Southernmost Point and the sandy beaches of the Atlantic are a short 4-block, 7 minute walk away.

    Built in the 1920's, this incredibly spacious bungalow-style home has 12 foot high ceilings and large, sunny rooms. The main house includes a living room with queen sleeper sofa, dining room with a very large table to seat your group, a fully-equipped kitchen with high end features and fixtures and powder room.

    The 2 bedrooms feature a queen bed in one, the other with two twins which can be converted to a king bed. Each bedroom has an ensuite tiled bath. The third bedroom with king bed includes a private bath and efficiency kitchen and is in the stand-alone cottage adjacent to the pool at the rear of the property. The sunny 13' x 25' heated pool and deck sit in a totally secluded, private area surrounded by tropical and lush bougainvillea, hibiscus and palms.

    Tropical Retreat also has the added bonus of off street private parking which makes it a rare gem in Old Town!

    It was a perfect getaway from a terrible winter! The heated pool was really welcoming after enjoying sight seeing all day. It fit three couples well.

    Key West
  • This Truman Avenue home is the perfect location, located between Duval Street and Whitehead St.

    The style is common throughout the islands. Our shotgun was renovated in March, 2008. Located in among a row of identical cigar-maker cottages, this gem features a King pillow top bed upstairs, another Queen pillow top bed in a downstairs bedroom and a Queen sleeper sofa in the living room which features beautiful pine floors.

    The state of the art kitchen is equipped with granite counter-tops, glass-top stove, microwave, dishwasher, under cabinet lights and everything necessary to prepare gourmet meals or just grill your fresh catch on the grill under the private covered lanai.

    The large bath features a walk-in shower with glass doors, hair-dryer and beach towels.

    Open your double french doors opening from the kitchen to the lanai and you have outdoor table and seating, washer/dryer and the extra spacious spa! Add romantic, soft outdoor lighting and you won't even want to do the Duval Crawl, yet you are walking distance to all the great venues Key West has to offer!

    This is the second time staying in Almost Southernmost and it is the perfect place in Key West for two couples or a small group. A short walk to Blue Heaven or the Green Parrot- just off Duval and around the corner from the Hemingway House. You can't beat the price or location!

    Key West
  • With 3 bedrooms (K, 2 Q, plus 2 Q sleeper), 2 full baths and 2 full kitchens. This historic home is perfect for up to 10 persons. The front portion features a King bedroom, a Queen bedroom and a Queen sleeper sofa in the living room. The bath with large walk-in shower is off the kitchen so the bedroom guests won't be disturbed during the night.

    The full kitchen has a beautiful granite counter top and is equipped with everything you will need to cook a gourmet meal. With French doors off the living room and kitchen opening to your private pool with waterfall, it has a light, airy feel.

    The rear half of Poolside Paradise has a separate entrance with a comfy Queen bedroom with an en-suite bath with a large walk-in shower. It also has a full kitchen with granite counter tops. The living room also has Queen sleeper sofa and French door opening to your private pool. A private gas BBQ grill is on-site.

    Two private parking spaces are included, a rarity in Old Town Key West! Poolside Paradise is unsurpassed in amenities, location and price! Call today to book this exclusive house for your next Key West vacation!

    I have rented many times with this property agency and they do an excellent job-one of the reasons I always rent from them. This property is a little dated-needs some work outside around the pool area. Overall had good experience here.

    Key West
  • This spacious 2 bedroom apartment takes up the first floor of this historic home. From the off street parking and shared courtyard entrance off Simonton opening into the kitchen to the private front entrance with sweeping front porch over Caroline Street- this rental has a lot to offer!

    Coming in from the front gate off Caroline Street you are welcomed with a large private porch, perfect for people watching before setting out for the night or morning coffee or margaritas! Entering from the front door you come into the spacious living room that opens into the dining room. The home has vaulted ceilings and gorgeous wood floors. The master bedroom opens off the living room and has an en suite master bath with a shower. The large bedroom has corner windows and a king size bed. The 2nd bedroom opens off the dining room and also has an en suite bathroom that opens to the kitchen as well. The 2nd bedroom features handsome woodwork and a king size bed. Each bedroom also has a flatscreen TV.

    The living room will offer a nice reprieve to enjoy some quiet time with comfy overstuffed furniture and a large flat screen over the mantle. The home can comfortably accommodate up to 6 guests with the living room sofa pulling out to a queen size sofa bed. There is also a ½ bath off the living room. The shared courtyard with BBQ grill and community plunge pool can be accessed off the dining room or though the large L-shaped kitchen. The kitchen has ample prep space and is fully appointed, including a built in wine cooler! Combined with the shared off street parking on Simonton, this property is certainly a sweet spot!

    Une location au rdc d'une maison coloniale ancienne, mais arrangée de façon moderne. Les 2 lits King size sont moelleux : on s'enfonce jusqu'au oreilles :). Néanmoins il faut prévoir les bouchons d'oreilles : les coqs sont omniprésents sur l'île et se rappellent à notre bon souvenir dès l'aube ....

    Key West
  • Welcome to Artist House: a 2 bedroom 2.5 bath rooftop townhome located within the gated community of Duval Square. Beautifully decorated with bright colors and unique art work, this property will give you a great Key West experience and is perfectly located so that you can park your car in the private lot and walk to everything Key West has to offer Key West restaurants specialty stores, attractions and night life of Old Town Key West.

    When you enter The Artist House you will find a fully equipped kitchen, dining area, spacious living room with up to date entertainment systems and half bath. Off the living room french doors open to the private back deck with dining table and chairs perfect for outdoor entertainment along with a private hot tub to relax and unwind after days of sun, swimming, exploring Key West and enjoying the sites. On the second floor, you will find 2 bedrooms suites each with their own private bathroom and an additional private balcony off the master suite.

    The honeymoon was good just was jot aware that key west didn't hav many beaches but other than that everything was great! The room was very clean everyone was super nice there and you cant beat the artist house so many nice paintings all by the same artist comfy bed only bad thing was me and my wife got stuck in the elevator there and seems like it was not going to get fixed because it happened about a year Ago from another review that I saw so just a warning to not chance the elevator just take the stairs... Pool was nice good view above duval street

    Key West
  • Almost Southernmost Too in the 400 block of Truman Avenue is the perfect location, located between Duval Street and Whitehead St. Just around the corner from Hemingway's House and the Historic Lighthouse Museum, Almost Southernmost Too is a perfect example of shotgun architecture with a front porch and back deck. The style is common throughout the islands. The rear second story deck is perfect for working on that Key West tan or star gazing!

    Upon entering this newly remodeled historic home, you will notice beautiful bamboo flooring throughout the first floor. At the rear, there is an expansive Living Room with a Queen sleeper sofa, comfy chairs, a large 46" flat screen TV, breakfast bar with stools and a bright new kitchen with state of the art appliances, granite counter tops and tiled backsplash. The double door refrigerator has enough space for enough food and beverages for your group. Lots of cabinet space makes this the perfect place to cook at home or go out to many of Key West's eclectic mix of restaurants close by.

    This gem features a King bed downstairs with a fabulous new en-suite bath with brilliant blue walls and large shower. There is also a hallway bathroom with a tub/shower. Upstairs are two Bedrooms, one with a Queen bed and the other with 2 Queen beds and a half bath between them.

    Open the French door from the Living Room to the wonderful deck where you have outdoor seating, BBQ grill, outdoor shower and a newly installed heated pool with a waterfall. Add romantic, soft outdoor lighting and you won't even want to do the Duval Crawl, yet you are walking distance to all the great venues Key West has to offer.

    The upper bedrooms are a bit tough on taller people due to the slanted roof, but overall it's a great property and a perfect location. Just a half block from Duval, half block to CVS,Hemmingway's house right around the corner and Blue Heaven just a short walk.

    Key West
  • Located inside the Villas known as Old Town Garden Villas Little Havana suite is a bi-level suite with a very spacious bedroom upstairs with king bed, down pillows, TV/DVD player, cordless telephone, writing desk and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, air conditioning and colorful Caribbean bedspread and carpet. The upstairs large tiled walk-in shower with hair-dryer makes this private bath luxurious.

    Downstairs is a large and comfortable queen sleeper sofa in the living room with air conditioning and ceiling fans. Color cable TV, VCR, stereo with CD player makes the entertainment center so comfortable you might not want to do the 'Duval crawl', which is just ½ block away. Outdoor table and chairs overlooking the gardens is perfect for a romantic evening conversation.

    This spacious suite has a dining room and state-of-the-art kitchen which included a glass-top stove, refrigerator with ice-maker, microwave, coffee maker, blender, dishwasher and everything you desire to prepare a gourmet feast or just warm-up leftovers from the fabulous restaurants (over 22) surrounding this ideal location on a quiet old-town lane.

    Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door!

    The grounds were beautiful and well-maintained, better than any I've seen. The unit itself needs a facelift. It's old--like, window A/C old. Some little things would go a long way to improve. However, overall, we had a wonderful visit to Key West.

    Key West
  • Tropical Village Cottage - is a two bedroom, two bath vacation cottage that overlooks a large shared seasonally heated pool, sun-deck and pool-side grilling station. With all the amenities of contemporary living set in island style and decor. Tropical Village Cottage is your ticket to a stress free vacation. Perfect for families, this Key West cottage has ample living space.

    The living room features 1 Full Sleep Sofa, CATV, DVD, and stereo with CD player. and wireless internet to keep you connected to the outside world.  The adjoining, fully equipped kitchen has all the necessities, including, but not limited to, full size refrigerator, microwave, toaster, blender, coffee maker and dishwasher. The second full bath lies adjacent to the kitchen. The French doors open to your private lattice enclosed porch and gas BBQ grill. All necessities are provided for you.

    Just a short stroll takes you to the Atlantic Ocean and to the infamous Duval Street. Tropical Village Cottage is one of the best locations and values on the Island!  Other little things: Large seasonally heated pool and washers/dryers (shared by only six units), A/C, ceiling fans, CATV, wireless internet, clock radio, CD player, full bath, all bed and bath linens including pool towels, full kitchen, iron and ironing board & hairdryer.

    The cottage was in a great location. It was cozy and as described in the ad. The only issues we had were that the floors were very dirty. My children took there shoes off when we got there and within 3 minutes the bottom of their feet were as black as coal. There is no way they have be washed in a long time and the pullout couch was horrible. Altogether it was a good vacation. We would stay again as long as we didn't need the pull out.

    Key West
  • On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool or combines for a wonderful four bedroom retreat. Downstairs enjoys a large, open floor plan with living and dining room, french doors opening up to the porch and lushly landscaped garden/pool area.

    The two bedrooms have a queen four poster bed or queen wrought iron bed along with oversized showers in each bath. The two one bedroom suites are located on the second floor, each accessed from a covered porch overlooking the garden and pool below, providing a cool spot on a hot afternoon. Each suite is decorated with it's own tropical color palette and queen beds. Great for extended families or a couples getaway! Pricing is given for 8 persons max. Additional person charges apply up to 14 persons and will be added when contract is written. Bedding: 4 queens, 3 sleeping sofas.

    Amenities include Central Air, Air Conditioning, Ceiling Fans, High Speed Internet, Blowdryer, Private Washer & Dryer, Nice Furniture, Deck, BBQ Grill, Gas Grill, Private Pool, Off Street Parking, Heat Optional Pool, Close to Town.

    Bed Configurations: Bedroom 1: Queen | Bedroom 2: Queen | Bedroom 3: Queen | Bedroom 4: Queen | Living Room: 3 Sleeper Sofas.

    Square Footage: 2236 Square Feet.

    Location Distance: Sarabeth's: 0.06 mi | Antonia's: 0.15 mi | Michael's: 0.19 mi | 2 Cents: 0.20 mi | The Green Parrot Bar: 0.23 mi | Azur Mediterranean Cafe: 0.31 mi | Blue Heaven: 0.36 mi | Santiago's Bodega: 0.43 mi | Flaming Buoy Filet Co.: 0.47 mi | Camille's Restaurant: 0.49 mi | Danger Charters: 0.53 mi | Ambrosia Sushi: 0.67 mi.

    Great location close to everything.The house is perfect for 8 to 10 people the pool is awesome it was hot all week we were there I would highly recommend this house.There is a good cheesesteak and pizza place called MR.Z the owner is from philly place right up the street we were there all week.If I go back to key west I would stay here again.

    Key West
  • This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle.

    The living room features French doors across the living room opening to your own private outdoor patio with table and chairs. Two sleeper sofas (queen-size and full-size) accommodate three guests for those occasional overnight guests who want to get a glimpse of Duval Street living at its finest.

    Off the master bedroom is another private balcony. This unit is the perfect place for access to watching Key West’s various street parades, including during fantasy fest, overlooking Duval Street and the judging stands.

    The condo was really nice and we were happy with the overall stay. There was quite a bit of construction noise while we were there. Our unit was right by the pool and near Duval street. We never has any issues with noise from the pool, just every other day, a garbage truck would come and empty the garbage at the business right outside the back porch. Also due to the construction I believe there were some issues with the parking.

    Key West
  • Seaport Suite is available for daily or weekly vacation rentals and located on the second floor of 219 Simonton in Old Town Key West. The location is as close to perfect as you can get, being one block off Duval Street and within walking distance to every single thing you could possibly want to do. With four bedrooms and two baths the space accommodates large groups with ease.

    The stainless steel commercial kitchen is fit for a chef and the wide hallway does double duty with a large table ready to accommodate a banquet. The living room includes two spacious sofa's, one that converts to a queen-size sleeper, and even a couple of overstuffed bean bag chairs for the kids. Just off the living room is access to a spacious front porch where you can rock the afternoon away.  Last but not least is the ground floor patio and charming garden that is complete with gas grill and private hot tub. Le Bon Temps Roule!

    Perfect location near the marina and all of the best attractions, cannot wait to return to this apartment.

    Key West
  • Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete restoration with exceptional attention to details.

    Enjoy the cherry floors and cabinets, granite kitchen counter tops, intricately tiled baths, private hot tub on your private rear deck. Draw the colorful awning drapes around your private hot tub for unrivaled privacy!

    The kitchen is equipped for the gourmet chef. Enjoy breakfast on your front porch with the 100 year-old Woman's Tongue tree and beautiful historic homes across the street.

    French doors lead from the bedroom to the deck with table and chairs and spa. The hallway leads to the very romantic bath with room for 2 in the completely tiled walk-in shower.

    Tropical art throughout this exclusive unit will make you feel right at home, our new White Street compound is for the discriminating guest who enjoys the finest life has to offer.

    Enjoy the lushly landscaped gardens with table and chairs.

    This is a nice complex with good access using a bicycle. There are fitness and yoga classes one block away on White Street to keep you in shape. It is in a real life Key West area, but with other friendly tourists on your block. Grocery store is in walking distance and headquarters just down the street. Bicycle rentals have a delivery and return service. We got a tandem and it was great. Cab fare to the rental is $8 per passenger, but you need to stop and get the keys from the rental agency. We called them from the airport and the keys were ready. Plenty of room for a couple. More than that and you would be stepping on and over each other. We will stay here next year. Enjoy.

    Key West
  • A Key Escape 3 bedroom, 2.5 bath with private heated pool. Professionally decorated in a Coastal Living style, this elegant yet very comfortable custom built 3 bedroom, 2.5 bath, 3 story home has a living room (Q sleeper sofa) with rose hardwood floors, a gourmet kitchen with granite countertops and stainless steel appliances outfitted for the professional chef. A bank of French doors open onto the heated private pool and sunny deck. Large windows, high ceilings and tropical colors make this a cheerful and welcoming home that you will want to call your Key West Escape!

    The master bedroom suite occupies the entire 2nd floor and has a king bed with fine linens. There is also a large bathroom and 2 balconies overlooking the pool and gardens.

    The other 2 bedrooms are on the 3rd floor, one with queen bed, the other with 2 twins that can be converted to a king upon request and share a spacious bath.

    Just one block off famous Duval Street, A Key Escape has location, location, location!

    We loved staying at the beautiful Key Escape and will be back next year.

    Key West

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