Vacation Condo Rentals By Owner In Key West, FL

$25,00 Renovation completed end of 2016/beginning of 2017!! Different than ANY other Efficiency at the Galleon!! You will not be disappointed!brbrLocation..Location...Location...this one has it all! Resort is located on the Ocean and is within steps of famous Duval Street. The Galleon Resort offers many amenities to enhance your vacation needs.brThe Efficiency Unit features a King Size Bed, Mini Kitchenette, Walk-in Closet and French Doors that lead to a small private balcony with a resort view.brStay in one of the most demanded locations on the Island!brYour stay includes one free off street parking spot.

Galleon Resort Efficiency Historic District

Key West, Florida, United States

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Bath

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$776.54

Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. The Villa Grande is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway. The number one reason why people choose the Rose Lane Villas is our fabulous location and proximity to all things worth doing in Key West. br1/2 block to Hard Rock Cafebr2 blocks to Margaritavillebr2 blocks to Sloppy Joe’sbr3 blocks to the Historic Seaportbr4 blocks to Mallory Squarebr4.5 blocks to Schooner Wharfbr6 blocks to Hemingway’s HousebrbrEmail us for availability, even if we look full. Please be aware of scams asking for wire transfers or offers from Craigslist. If you have any questions, please call our reservations desk.

Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West

Key West, Florida, United States

3

Bed

Bath

6

Sleeps

$143.75

Sunset views over the water has this large 1/1 with 1 assigned parking space. Only a few minutes from the Island of Key West, and many seafood restaurants on the water. Catch fish steps away from your home, ride your bike in the overseas trail, very quiet area at night, minutes from the Boca Chica air base.

Sunsets over the water

Key West, Florida, United States

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Select Dates for Price

If island living in a verdant park setting sounds appealing, this 2 bedroom, 2 bath condo fits the bill perfectly. Nestled in Truman Annex, Key West’s most exclusive gated waterfront community, this second-floor residence named Poolside Palms is centrally located for easy walking or biking to all there is to do and see. Plus it offers loads of amenities: reserved parking; a spacious balcony that lets you enjoy what locals call “the sweet weather”; and close access to a residences-only pool with lots of comfy lounge chairs. Yet impact doors and windows guarantee you absolute peace and quiet inside the residence. brbrLocated down a garden path past wooden structures reminiscent of 17th century New England architecture are double-story condos called The Shipyard. Poolside Palms is located on the second story which creates more privacy and better views. Behind a coded security lock and up a short flight of stairs, the first thing you notice is the striking abundance of natural light from windows and doors. The living, dining, and kitchen flow together in an open floor plan with high ceilings. The eye is immediately drawn to the French doors at the living room end that open onto a balcony with chairs, table for two, and an inviting lounge recliner. The balcony is so spacious it can be accessed from the Master bedroom as well. The tree-top view is of vibrant green palm trees swaying in a warm ocean breeze which begins to explain the condo’s apt name. From here you can even smell the refreshing crispness of salt water close by.brbrThe living room area provides what you need for comfortable seating whether you want to have a conversation, read your vacation book or magazine, or watch sports and movies on the large flatscreen TV conveniently located for viewing. Choose the large, comfy couch or one of the equally comfy chairs. A rattan and glass coffee table make it easy to imagine having beverages and snacks here. Under the TV is a rattan, white-washed wood cabinet with three drawers and two doors that is not only decorative but also great for storing stuff out of sight. Of course there’s central AC, cable, high-speed internet, DVD player, three flat-screen TVs, hardwood floors, and ceiling fans throughout. The whole residence is immaculate. brbrWhether you choose to dine alfresco on the balcony or inside, a dining table and four rattan chairs are located very conveniently between the living and kitchen areas. It’s the ideal spot to enjoy a morning pastry or lunch plate of leftovers warmed in the microwave from a meal out the night before. The galley kitchen is extremely ergonomic with key functions clustered near each other. Cabinets above and below store all the accoutrements you’d need to prepare a four-course meal or make a simple sandwich. The essential appliances are at your fingertips: refrigerator, stove, microwave, dishwasher, disposal, coffee maker, and more. And with cabinets above and below, there’s plenty of storage. Two artisan stools at the far end of the kitchen counter provide a perfect informal place for sitting, snacking, or sipping any kind of beverage you can think of. At the other end is a large window overlooking tropical landscaping and the inviting pool below that is for the exclusive use of Shipyard guests.brbrIn a closet just off the kitchen is Whirlpool’s latest style stacked washer/dryer in case you need to do a load or fluff some beach towels. To the right is the King bedroom where the bed can easily be separated into two twins if that configuration suits your needs. This bedroom has a generous window looking out at tropical foliage and down at the sparkling pool. But remember that the impact glass means full sight but no sound echoes. There’s a ceiling fan, a flatscreen TV perfectly located for viewing from the bed, bedside tables with lamps and drawers, and a closet with plenty of space for hanging items and folded items. The full bath is adjacent and perfectly laid out in terms of floor plan. The other bedroom, the queen bedroom that opens onto the balcony, offers similar amenities: very comfy bed, ceiling fan, flat screen TV, side tables, closet storage for hanging and for folded items, and a full ensuite bathroom. brbrWhen you’re ready to explore Key West, leave your car in its reserved space because world-famous Duval Street is only two blocks away. Stroll through the manicured landscaping, verdant palms, and interconnecting pathways that give this Truman Annex neighborhood its park-like atmosphere. Then head out through the wrought iron privacy gate to find yourself immersed in the sights and sounds of Duval’s attractions. brbrCheck out the tours, museums, shopping, and over four hundred restaurants/bars, many with open-air seating, some on the first floor, some on the second, and some right on the water. If you’re interested in watersports, there’s all kinds: diving, fishing, parasailing, snorkeling, and jet skiing to name a few. Don’t miss the Butterfly & Nature Conservatory at the Atlantic Ocean end of Duval and the nightly sunset celebration at Mallory Square on the Gulf of Mexico. Gather with other visitors and locals alike to applaud as the sun slips below the horizon. After sunset, stick around for the street party that follows. 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.

Poolside Palms - Truman Annex 2/2 Shipyard Condo

Key West, Florida, United States

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Bath

Sleeps

$242.67

Explore Key West during the day and evenings are quiet. brNature's boutique offer you an exceptional view of key west's native birds right from your private balcony. It is furnished with all of the comforts of home. Large flat screen tv, in-suite bath, full laundry center, fully stocked kitchen, assigned parking bay and inviting open living room and dinning room. The bedrooms are furnished king beds in each bedroom. The sofa also has a sleeper for extra guests or family. The resort offers a gated community with a heated pool that is so inviting, an outdoor jacuzzi to relax you, a tennis court and bbq grills for your use. Come experience your dream vacation and enjoy, relax and take in a beautiful key west sunrise!

Steps To The Beach And The Sunrise

Key West, Florida, United States

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Bath

Sleeps

$223.22

Breathe the fresh ocean air and gaze upon tropical sunsets on your next trip to Key West with this one-bedroom, one-bathroom condo. You'll enjoy entertainment, private parking, and a great central location that lets you make the most of your vacation.brbrPart of a complex with three other condos in the middle of downtown, you'll be an easy walk from the bars and restaurants on Duval Street, not to mention historical attractions and the golden sands of the beach.brbrOrchid Suite is the perfect place to recuperate after a long day. Kick back on the couch to watch some cable TV, freshen up in the shower, or prepare a small bite to eat before heading out for a night of dancing. Free WiFi makes it easy to plan your days in advance, and air-conditioning gives you a break from the heat.brbrThis Key West vacation will be a hard one to top - secure your accommodations today!brThis property is managed by Seven Keys Vacations by Casago.

Elegant Condo with Entertainment & Private Parking - Great Central Location

Key West, Florida, United States

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Bath

4

Sleeps

$293.63

Relax under azure skies and the gently rustling fronds of palm trees when you stay at this elegant and dog-friendly Key West condo! A community pool and hot tub, tennis courts, a parking space, and pool views from your private balcony add to an atmosphere of luxury and total relaxation.brbrThis rental is part of the upscale Sunrise Suites Resort, located on the eastern shore of the island just a short distance from Smathers Beach and Southernmost Point. Spend your days wandering through Key West's historic downtown - including the homes of Ernest Hemingway and Harry S. Truman - then retire back to your condo for a quiet night away from the crowds. Park your car in the provided parking spot. brbrThis rental provides a terrific space to while away the hours in the Florida sun. Cool off with a dip in the pool, get your heart rate up with an exhilarating game of tennis, or rent a bike to explore the island. Free WiFi is provided, and, you can bring your dog along as well to join in the fun. brbrThe perfect vacation is waiting, so don't delay! Book your stay in this wonderful Key West condo today, and let the relaxation begin.brbrTHINGS TO KNOW

Dog-Friendly Retreat with Pool, Hot Tub, Tennis - Balcony with Pool Views

Key West, Florida, United States

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Bath

6

Sleeps

$260.13

Soak up incredible west-facing views from the comfort of this elegant, dog-friendly Key West condo. First-rate amenities like a shared pool, exquisite tropical landscaping, and a private deck create a serene atmosphere that'll have you relaxed in no time.brbrThis condo is part of the upscale Sunrise Suites development, located on the eastern edge of Key West, conveniently near the Key West International Airport. Restaurants, scuba shops, and the vibrant streets of downtown are all just a few miles away, making it easy to enjoy the best of Key West. An on-site parking space is provided.brbrBack at the rental, cool off with a dip in the community pool or get your blood pumping with a visit to the exercise room. Upstairs, cable and free WiFi are provided, and the kitchen is fully equipped with modern appliances and cookware. For a special treat, enjoy your meal out on the private balcony while the sun sinks into the sea. And, your dog is welcome to come along too to share the fun with you.brbrBook your reservation in this wonderful Key West condo today, and let the relaxing begin!brbrTHINGS TO KNOW

Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family

Key West, Florida, United States

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Bath

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$1139.63

Looking for a place in sunny Key West where your whole group can bask in the pleasures of island life without sacrificing privacy This complex of three condos is your ticket - featuring entertainment, private parking, and beach access nearby, you'll have everything you could hope for on a tropical vacation!brbrSitting only one block from the central activities on Duval Street, you'll have plenty of restaurants at your fingertips, as well as famous historical attractions like the Ernest Hemingway Home and Museum, the Southernmost Point, and Fort Zachary Taylor Historic State Park to keep you busy.brbrEscape the tropical heat in these air-conditioned homes and relax with a book, browse the free WiFi, or watch something on the flatscreen TV. You can also use the kitchens to whip up a small meal for the whole group. brbrTraveling with a group doesn't have to be complicated - save yourself a headache and book today!

Three Condos w/ Entertainment, Private Parking & Beach Nearby - Great for Groups

Key West, Florida, United States

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Bath

Sleeps

$496.8

Ease into the pleasures of a tropical vacation with this one-bedroom, one-bathroom condo in Key West. With a charming atmosphere, entertainment, and two private parking spaces to save you any headaches, you'll speak nothing but praise during your stay in paradise!brbrLocated in the downstairs of a historic building just one block from the excitement of Duvall Street, you'll be close to all the action while having a quiet place to retire to at the end of a long day. Visit the Hemingway Home or Mallory Square. Sail into the sunset, and dine at as many delicious eateries as you can to sample the local flavors!brbrRest up between excursions in your comfortable, air-conditioned condo, whip up a light snack in the kitchen, and plan upcoming adventures with free WiFi. If you're looking to enjoy a night in, you can put a movie on the TV.brbrYour vacation in paradise just became a reality with this charming condo - book today!

Charming Condo w/ Entertainment & Private Parking - Great In-Town Location

Key West, Florida, United States

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Bath

6

Sleeps

$377.92

Exquisite 2-bedroom condo that has been extensively updated and completely remodeled, featuring beautiful new vinyl plank flooring, stainless steel appliances, granite countertops, and fully renovated bathrooms, along with many additional upgrades. brbrBring your family and friends along for the ride to this home in Florida's sunny Key West! Between the great location and modern amenities, everyone in your group will find something to love.brbrIf you'd like to spend your days lounging in your condo instead of going out, you have plenty of options for staying entertained. The kitchen lets you whip up homemade meals as you enjoy cable on the flatscreen TV. When you need fresh air, simply head out to the balcony, enjoy the shared hot tub, or dive into the shared pool! One dog up to 25 lbs. is welcome. brbrGet your next sunny vacation started and save your dates today!brbrTHINGS TO KNOW

Resort condo with pool & hot tub, private parking

Key West, Florida, United States

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Bath

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$397.4

Escape to Key West's beaches during a stay at Atlantic Ocean View, where you'll enjoy prime island location and access to a shared pool. This condo accommodates up to six, so it's a great choice for the whole family!brbrThe Florida Keys Overseas Heritage Trail sits right outside the building, offering you easy access to Smathers Beach (half a mile east) and Indigenous Park (half a mile west). Once at the park, you can spend the day enjoying Higgs Beach, Higgs Beach Pier, and West Martello Tower. You'll also be two miles east of the Ernest Hemingway Home and Museum and less than three miles south of Mallory Square, where you can shop, dine, or explore museums at your leisure.brbrThe whole family is welcome at Atlantic Ocean View. Step out onto your private balcony with your morning coffee - there's plenty of seating for everybody. If it's too hot, relax inside with the condo's central air conditioning.brbrPrepare the catch of the day in this condo's full kitchen. Cleanups are easy here with a private washer and dryer. Three cable TVs and free WiFi provide your group's entertainment during your stay. brbrBook Atlantic Ocean View for your family's next Key West adventure!brbr*Atlantic Ocean View has a $65 Condo Association Fee.*brbr*Please note that last-minute bookings cannot be made online.

Comfortable Condo with Pool, Private Balcony, & Beach Access

Key West, Florida, United States

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Bath

Sleeps

$387.53

This Key West condo boasts deluxe amenities like a shared outdoor pool, a hot tub, tennis courts, and a fitness room. It has everything you need for a memorable Florida Keys getaway!brbrLocated right near the water, you'll be in a prime spot to sample all of the island's many charms. Easily walk or bike to popular Smathers Beach, a great place to rent a stand-up paddleboard and get out on the ocean. Key West also offers excellent scuba diving, snorkeling, kiteboarding, fishing, and more.brbrTHINGS TO KNOWbrIf you want to dock a boat, you can rent a boat slip at one of the many marinas.

Resort condo with pool & hot tub - walk or bike to beach

Key West, Florida, United States

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Bath

Sleeps

$387.53

Exquisite 2-bedroom condo that has been extensively updated and completely remodeled, featuring beautiful new vinyl plank flooring, stainless steel appliances, granite countertops, and fully renovated bathrooms, along with many additional upgrades. New photos coming soon!brbrMake those dreams of a beach getaway a reality and book your next Florida vacation at this luxurious Key West condo. With upscale resort amenities like a shared pool and hot tub, tennis courts, a fitness center, and a covered parking space, your vacation will be packed with tropical excitement from start to finish. One dog is allowed.brbrThis rental is part of the exclusive Sunrise Suites Resort, conveniently located only a short drive from the Key West International Airport on the east side of the island. With a covered parking spot, bicycle rentals, it's easy to reach Key West's most popular attractions in just a few minutes! Stroll along the historic boardwalk, try to spot Cuba from the Southernmost Point, or go snorkeling through the island's colorful coral reefs.brbrIf you'd rather stay closer to home, you'll find plenty at the resort to keep you entertained. Take a nap in the shade of a palm tree beside the lagoon-shaped pool, sink into the bubbling waters of the community hot tub, or get your heart rate going in the fitness room. Upstairs, you'll find cable, free WiFi, and a fully equipped kitchen for your use, along with a private balcony for relaxing on. With tropical landscaping at every turn, you'll never be far from Key West's beautiful scenery.brbrYour next favorite vacation is waiting! Book your reservation today.brbrTHINGS TO KNOW

Resort suite with pool, hot tub, tennis & full kitchen

Key West, Florida, United States

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Bath

Sleeps

$391.53

Welcome to Sunset Suite -- Catalina Suite 311, your slice of paradise in vibrant Key West! This inviting two-bedroom condo is part of the upscale Sunrise Suites Resort, where tropical comfort meets resort-style amenities.brbrStep onto your private deck to soak in the island breeze, then spend your day swimming in the heated pool, unwinding in the hot tub, or hitting the on-site tennis courts and fitness center. With marinas, beaches, Old Town shops, and Key West's lively dining scene just minutes away, every day can be as relaxing—or adventurous—as you choose.brbrInside, Sunset Suite -- Catalina Suite 311 offers all the comforts of home, including central AC, free WiFi, cable TV, and a fully equipped kitchen. Two spacious bedrooms ensure restful nights, while on-site parking and elevator access make getting around a breeze. Even better, your pup can join the fun—this condo is dog-friendly for a small nightly fee.brbr✨ Highlights of Sunset Suite -- Catalina Suite 311br • ️ 2 bedrooms for comfort and privacybr • Private deck with tropical viewsbr • Resort pool & hot tubbr • Tennis courts + fitness centerbr • Dog-friendly (small fee)br • Free WiFi + cable TVbr • Fully equipped kitchen with modern appliancesbr • On-site parking + elevator accessbr • ✈️ Minutes to Old Town, marinas, and the airportbrbr Points of Interest Nearbybr • Smathers Beach – 1.5 milesbr • Higgs Beach – 2.5 milesbr • Southernmost Point – 3.5 milesbr • Duval Street / Old Town Key West – 3.5 milesbr • Mallory Square Sunset Celebration – 4 milesbr • Key West Butterfly & Nature Conservatory – 3 milesbr • Ernest Hemingway Home & Museum – 3.5 milesbr • Fort Zachary Taylor Historic State Park & Beach – 4 milesbr • Key West Golf Club – 3 milesbrbr ️ Shopping & Diningbr • Publix Super Market – 1.5 milesbr • Winn-Dixie Grocery – 2 milesbr • Local Boutiques & Galleries – Along Duval Street (3.5 miles)br • Key West Farmers Market (Thursdays) – 1.5 milesbr • Popular Restaurants Nearby:br • Hogfish Bar & Grill – 2 milesbr • El Siboney (authentic Cuban) – 3 milesbr • Conch Republic Seafood Co. – 4 milesbrbr Your Key West Escape AwaitsbrbrWhether you're here for laid-back beach days, world-class fishing, or the nightlife of Old Town, Sunrise Suites – Catalina Suite 311 is the perfect home base for your Key West adventure.brbr Book your stay today and experience the island lifestyle in comfort and style!brbrTHINGS TO KNOWbrUnit offers a shared, paid laundry room on site

Cozy Dog-Friendly Condo w/ Shared Pool, Hot Tub, Private Deck & Parking

Key West, Florida, United States

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Bath

Sleeps

$454.28

Spend your next Key West vacation at this lovely condo in the Florida Keys. This rental comes equipped with a shared pool, hot tub, and tennis courts, along with central air-conditioning, a private balcony, and a fitness room. brbrThis condo lies on the eastern side of the island, close to the Key West International Airport. You'll be about four miles from downtown Key West and its many attractions, including the Hemingway House, the Southernmost Point of the United States, and myriad bars and restaurants. brbrTHINGS TO KNOW

Sunny Condo with WiFi, Hot Tub, Pool & Tennis

Key West, Florida, United States

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Bath

Sleeps

$230.47

Find your own little piece of paradise at Tarpon Watch, a waterfront escape offering gorgeous views of the Gulf of Mexico, plenty of room for you and your loved ones to relax, and an ideal location close to Key West's most beloved attractions. At the end of each beautiful day, mix up a favorite beverage at the wet bar, step out onto the large balcony overlooking the Gulf, and take in one of the breathtaking sunsets Key West is known for.brbrTarpon Watch is part of Sunset Marina Residences, a gated Gulf-front community on Stock Island, also known as 'the new Key West.' On the grounds, you'll have access to a waterfront pool and hot tub, a long meandering dock for wildlife-watching, and a dedicated parking space in a covered garage (along with ample visitor parking). For boating or fishing, feel free to inquire for details about boat rentals/slips. Or, simply drive or hop in an Uber to Old Town or Smathers Beach.brbrNewly and beautifully renovated throughout, this first-floor condo is full of bold colors, comfortable furnishings, and elegant finishes. There are thoughtful touches at every turn, including a well-equipped kitchen with stainless steel appliances, a wet bar with a wine fridge for evening cocktails, and TVs in the living room and both bedrooms. Each bedroom is paired with its own bathroom, including a primary suite with a walk-in closet, both a shower and a jetted tub, and direct access to the balcony.brbrBonus features of the condo include a sleeper sofa in the living room, a private washer/dryer to help you pack light, and central air conditioning and heating to keep you comfortable all year round.brbrThings to Know:brStreaming services are available with guests' own account credentials.brCheck-in time: 4:00 PM.brCheck-out time: 10:00 AM.brAll guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM.brNo smoking is permitted anywhere on the premises.brThis property is managed by Seven Keys Vacations by Casago.

Dog-friendly, Gulf-front condo with pool, hot tub & gorgeous sunset views

Key West, Florida, United States

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Bath

Sleeps

$271.7

An exceptional stay awaits at this three-bedroom, two-bath condo. Inside, the suite is open and inviting, with a large flatscreen TV and comfy furnishings in the living room, plus a well-equipped kitchen with stainless steel appliances that include a French-door refrigerator. You'll have plenty of counter space to help you prepare your favorite meals and you'll love dining al-fresco on the balcony. This complex enjoys a location just walking distance from beautiful Smathers Beach. After spending the day on the shoreline, come home to bask in the suite's central A/C while the private washer/dryer gets your laundry nice and clean. Spread out some board games or catch up on a good Netflix movie or show on the TV. The free WiFi will make it easy to research a fun outdoor adventure and post your best selfies to your social media. Don't forget to take a walk to explore all the fantastic on-site amenities that include a shared pool and a tennis court then take advantage of the elevator to access this first-floor condo.brbrThings to Know:brFree WiFibrSnowbird-FriendlybrThere are six beach chairs and one adult bike available for guest use.brbrThis property is managed by Seven Keys Vacations by Casago.

Wonderful Condo in Key West w/Free WiFi, Lanai, A/C, Shared Hot Tub & Pool

Key West, Florida, United States

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Bath

Sleeps

$257.0

Slip into island time at this one-bedroom, one-bath condo for four in Key West, where you'll have entertainment and nearby beach access in an awesome central location. brbrSitting right downtown on Simonton Street, you're one street over from all the restaurants and bars on Duval, and within easy walking or biking distance from all the main attractions. You'll even have a coveted private parking spot off the street - lucky you!brbrRelax in this air-conditioned home and watch cable TV, browse the free WiFi, and whip up a light snack in the kitchen. Head to the covered porch while you listen to bird songs floating over from the secret garden nearby.brbrSay goodbye to your worries and hello to seafood and sunshine - book your escape today!brThis property is managed by Seven Keys Vacations by Casago.

Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby

Key West, Florida, United States

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