Vacation Condo Rentals By Owner In Key West, FL

This 2,000-square ft-condo is unique in that it has two large master bedroom suites with changing areas and private baths plus a third bedroom w/bath. A pull out sofa bed allows for total accommodations for 8 people. With the master suites on opposite ends of the condo, it is a great set-up for 2 or 3 couples as well as for friends or families who want additional space with luxury surroundings. There is a well equipped kitchen if you wish to dine in, free high speed internet, washer/dryer, iron & board, hairdryers, 3 TVs, DVD player and more. The sliding glass doors on each bedroom and living room all open to the large wrap around patio with a partial ocean view. The gated complex has a large beautiful tropical courtyard with grills and picnic tables, and the large pool and hot tub overlooking the ocean. brbrThe Olympic-size pool overlooking the Atlantic ocean with private beach is absolutely breath taking. The huge, tropical courtyard inside the complex truly makes you feel like you are in a tropical haven. In addition, for your enjoyment is an over-sized hot tub and men's & women's saunas to relax in. Feel free to use the barbecue grills and picnic tables to have your picnic in paradise, or you can get some exercise using the 3 tennis courts (1 clay), hard ball court, or walking the beach. The 400 ft. beach front is adjacent to Smather's Beach to the east, or walk a 1/2 mile to the west and arrive at Higgs Beach. All this helps set the tone for a fabulous vacation. brbrKey West is a Caribbean Island with all the luxuries and conveniences of America. It is surrounded by the turquoise water of the Caribbean and Atlantic oceans, loaded with history, art galleries, performing arts, symphony, tropical foliage, fabulous restaurants, sports activities, 7 public beaches, shopping, entertainment, music and watering holes. Weddings on the beach are a common site. brbrbrCONSTRUCTION NOTICE- Balcony Restoration Project – 1800 AtlanticbrStart Date: May 2025-Estimated Completion: Spring 2026brPlease be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026.brImportant Notes:br-Units available for booking will not be under construction.br-All amenities, including the pool, spa, and sunning beach, will remain open and fully operational throughout the project.

Spacious Ocean Front Resort - 3 Bedroom Condo

Key West, Florida, United States

3

Bed

3

Bath

8

Sleeps

$293.66

Welcome to On the Rocks – Your Oceanfront EscapebrbrExperience coastal living at its finest in On the Rocks, a spacious and beautifully designed 3-bedroom, 2-bathroom condo with breathtaking views of the Atlantic Ocean. Located just steps from the shore, this open-concept vacation home offers the perfect retreat for relaxation, entertaining, and soaking in the natural beauty of Key West.brbrKey Features:brStunning Ocean Views: As soon as you step inside, you’ll be greeted by floor-to-ceiling sliding glass doors that offer an uninterrupted, panoramic view of the Atlantic Ocean. The wrap-around balcony is perfect for dining al fresco, morning coffee, or simply taking in the fresh ocean air and stunning Key West sunsets.brbrOpen-Concept Living & Dining: The expansive living area is filled with natural light and is perfect for both relaxation and entertainment. With ample seating, you and your guests can enjoy the sea breeze while lounging or hosting a gathering. The sliding glass doors can be opened in the winter to let in the refreshing ocean breeze.brbrGourmet Kitchen: The large, fully equipped kitchen is ideal for whipping up anything from a quick breakfast to a full dinner party. With counter seating for four and a dining table that also seats four, there’s plenty of space for everyone to enjoy meals together.brbrGuest Bedrooms: Down the hall, you’ll find two beautifully appointed guest bedrooms. One features a queen bed, while the other has a king-size bed. Both rooms are equipped with their own TVs and share a spacious bathroom with dual sinks and a large shower.brbrMaster Suite: The master bedroom is your personal sanctuary, complete with a luxurious en suite bathroom featuring a jetted tub, separate shower, and a walk-in closet for all your belongings. Like the guest rooms, the master bedroom also has its own private entrance to the balcony, where you can enjoy your morning coffee or relax with a good book.brbrOutdoor Living: The wrap-around balcony is the highlight of the condo, offering breathtaking views of the ocean and providing the perfect setting for outdoor dining or lounging. Each bedroom has direct access to the balcony, allowing you to step outside and take in the beauty of Key West at any time.brbrImportant Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. brbrGuests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check. brbrAdditional Amenities:brbrTVs in every bedroom for your entertainmentbrHigh-speed Wi-FibrAmple closet and storage spacebrProximity to local dining, shopping, and attractionsbrOn the Rocks is the perfect choice for those looking for a luxurious oceanfront getaway with all the comforts of home. Whether you're traveling with family or friends, this condo has everything you need to make your Key West vacation unforgettable.brbrBook your stay today and enjoy the beauty and tranquility of On the Rocks!

On the Rocks, 3 Bedroom, 2 Bath Condo right on the beach

Key West, Florida, United States

Bed

Bath

Sleeps

$164.72

Stunning Renovated 2-Bedroom Condo with Island ViewsbrbrWelcome to your perfect island retreat! This beautifully renovated two-bedroom condo offers breathtaking island views and a prime location with easy access to everything Key West has to offer.brbrInside, you’ll find a spacious master bedroom with a king-size bed, a guest room with a queen-size bed, and a queen sleeper sofa in the living area—comfortably accommodating up to six guests. The modern kitchen is fully equipped with sleek stainless steel appliances, making it easy to prepare meals during your stay.brbrEnjoy peace of mind with one assigned parking space (vehicles under 6'2).brbrAs a guest at 1800 Atlantic, you'll also have access to exceptional amenities, including:brbr Olympic-sized heated poolbr 20-person jacuzzibr Three tennis courts (including a clay court)br Lush tropical gardensbr BBQ picnic areasbr Private sunning beachbrbrWhether you're here to relax or explore, this island-view condo is the ideal home base for your next Key West getaway.

1800 Atlantic Condo in Key West – Stylish 2BR with Pool, Tennis & Beach

Key West, Florida, United States

Bed

Bath

Sleeps

$1624.48

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrWalking along Duval Street dreaming of the ideal Key West vacation destination, scanning the rooftops for possibilities, at first you’ll miss this hidden gem completely…but once you discover MAYA’S SECRET TREASURE, you will know you have found the ultimate home base to enjoy Key West. Perched above Duval Street, this beautifully modern condo offers the best of all things downtown Key West mixed with the best of a high end vacation home: a private rooftop deck overlooking Duval, a location just steps from all of the action, all with the privacy of a hidden entrance off a tiny lane, a private pool all your own, and three large bedrooms with en-suite bathrooms to steal away and enjoy your space. Pair this once-in-a-lifetime vacation home with Last Key Realty’s Five Star Guest Services and your vacation in paradise will be the lasting memory you treasure (until your next visit of course…)brbrYOUR PRIVATE POOL AREA & LANAI...brbrThe entrance to this property takes you through the private pool area, a fully fenced oasis of sunshine you won’t believe is just a stone’s throw from the famous Duval Street. Plenty of lounge furniture and chaise lounges offer a variety of sunbathing options by the pool. The pool can be heated upon request to your desired temperature (additional fees apply.) The BBQ grill is perfect for a poolside cookout, and we include the propane. Climb the stairs to the covered lanai area with a designer lounge swing, an outdoor dining table, and even an outdoor TV for watching the game in the island breezes.brbrYOUR EXCLUSIVE ROOFTOP DECK…brbrThe true crowning gem of this exceptional condo is the private rooftop deck perched right over Duval Street. A front row seat to the magic of the most desirable location in Old Town, this deck has been designed to host the evening of your dreams. There is a custom bar with bar stools to sit and look down on the action below or gather around the tables with inset fire pits to enjoy evening cocktails. You won’t find a better, more exclusive location in all of Key West, and this one is all yours!brbrTHE LIVING AREA...brbrMAYA’S SECRET TREASURE is the ultimate discovery for a group ready to experience all that Old Town Key West has to offer just outside your door, while offering the privacy of luxurious separate bedrooms with en-suite bathrooms. The living area is ideal for relaxing after a day full of adventure on island or out on the water, or for game planning the day's festivities over breakfast as a group. Around a large flat screen TV you'll find comfortable seating for the group. There is a dining set off the living area for a quick bite in. The artistic kitchen sits off the living area with luxury appliances and tools, equipped with everything you'll need to prepare a meal at home in between enjoying the fantastic array of Old Town restaurant options, all just a few blocks walk away. There's also a queen size sleeper sofa in the living room and a private reading nook with a sofa and armchair situated above the living area .brbrTHE ACCOMMODATIONS....brbrFirst Floorbr** Master Suite #1 - One King bed, a flat screen TV, walk-in closet, seating area, luxurious Master bathroom with soaker tub & glass shower.brbr** Master Suite #2 - One King bed, a flat screen TV, built-in cabinetry, en-suite bathroom with a glass shower.brbrSecond Floorbr** Bedroom #3 - Two Twin beds OR One King bed, a flat screen TV, a desk overlooking the pool area, en-suite bathroom with a glass shower, access to the rooftop balcony overlooking Duval.brbrFor the room with Twin beds that convert to a King, just give us a heads up of how you'd like these beds prepared for your particular group and we'll have them ready for your arrival.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & 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 & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced & Lushly Landscaped Private Yard br** Private Pool with available Pool Heatbr** Propane BBQ Grillbr** Rooftop Deck overlooking Duval StreetbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** Max of 2 Pets Allowed with Additional Fee of $200 per petbr** THIS HOME DOES NOT INCLUDE OFF STREET 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.

**MAYA’S SECRET TREASURE @ DUVAL** Pool & Balcony over Duval + LAST KEY SERVICES

Key West, Florida, United States

Bed

Bath

Sleeps

$537.85

Thirteen-hundred-fifty square feet of fabulous living space located on the second floor with garden and partial ocean views from a 38-foot private balcony accessible from the living and both bedrooms will make your vacation a memorable one and keep you coming back year after year.brbrClick on the calendar icon to check dated that are available. If the dates you need are not available check my other Key West vacation rental (Henry's Penthouse) located in the same (1800 Atlantic) complex.brbrBoth these Key West vacation rental properties were decorated and are managed (and maintained) by me personally, assuring you of a memorable vacation in a property that is way above the average investor owned rentals offered by management companies.brbrCall me now or any time within reason (9am to 11pm 7 days a week) to make the reservation or if you have any other questions. - I'm easy to reach and easy to talk to. Henry. brbrNotes:br1. My on line calendar is active and updated dailybr2. After reviewing you’ll know you found the right property with the right location at the right price.brbr

Henry's Piece of Paradise on the Ocean in Key West - Weekly / Nightly

Key West, Florida, United States

Bed

Bath

Sleeps

$369.7

This beautiful 2-bedroom condo in the quiet and private gated Shipyard Community. It has rave reviews & 2 blocks from famed Old Town & Duval St. with its legends like the original Margaritaville, Sloppy Joe's, the Hemingway House and Treasure Museum. Outdoor deck for relaxing or secluded dining. Enjoy our pool and nearby Fort Zachery Taylor's sand beach. First-Floor Convenience: Easier access and no stairs to climb.brbrUnique Features:br* Gated Community: Enhanced security and peace of mind.br* Private Terrace: Outdoor living space for relaxation and entertaining.br* Swimming Pool: Enjoy refreshing dips on hot days.br* Proximity to Duval Street: Easy access to the heart of Key West's entertainmentbrbrOld Town Key West is packed with iconic landmarks and attractions! Here are a few of the most famous:br* The Southernmost Point Buoy: This iconic landmark marks the southernmost point of the continental United States.br* Duval Street: The heart of Key West, Duval Street is a vibrant mix of bars, restaurants, shops, and street performers.br* Mallory Square: This waterfront park is famous for its nightly sunset celebrations, with street performers, musicians, and artists.br* Ernest Hemingway Home and Museum: Explore the former home of the renowned author and see his famous six-toed cats.br* Key West Lighthouse & Keeper's Quarters Museum: Climb the lighthouse for stunning views of the island and learn about its history.br* Fort Zachary Taylor State Park & Beach: Relax on the beach, explore the historic fort, and enjoy water activities.br* Key West Butterfly & Nature Conservatory: Discover a tropical paradise filled with colorful butterflies.brThis is just a small taste of what Old Town Key West has to offer. You'll find something to fascinate everyone, from history buffs and art lovers to beachgoers and nightlife enthusiasts.

Dee's Dream Sunset Condo with WiFi and AC in Key West - 2 bdrm - Shipyard #151

Key West, Florida, United States

Bed

1

Bath

5

Sleeps

$314.6

The Salt Cay | Updated! Stunning Sunset View, Pool!brbrEscape to The Salt Cay, a serene, beautifully updated, and well-appointed 2-bedroom condo nestled in the tranquil Sunrise Suites community on east side of Key West. Just a mile from the beach, this charming getaway offers the ideal combination of relaxation and adventure. Whether you're lounging by the pool, exploring nearby attractions, or enjoying the comfort of your condo, The Salt Cay is the perfect place to unwind and make lasting memories.brbrThe Ambiance:brStep into The Salt Cay and experience a tasteful blend of modern coastal charm, where sleek quartz countertops, modern white cabinetry, and an open-concept layout create the perfect space for gathering with family or friends. This gorgeous two-bedroom suite accommodates up to six guests, featuring a king-sized bed in the master bedroom, a queen-sized bed in the second bedroom, and a queen pullout sofa in the living area for additional guests. The fully equipped kitchen, complete with a Keurig and electric stove, makes meal preparation a breeze, while the private balcony offers spectacular sunset views. For added comfort, enjoy cable TV, WiFi, and central air conditioning throughout your stay.brbrGuest Access:brEnjoy a smooth arrival with our contactless check-in process, where you'll receive a personalized access code to enter your unit. During your stay, take advantage of the shared amenities, including:brbr- Shared heated pool and hot tubbr- Tennis courtbr- Walking paths and biking trailsbrbrLocation Highlights:brThe Salt Cay is ideally located within the peaceful Sunrise Suites Resort, just a short distance from Key West's best attractions. A quick 10-minute drive will take you to the lively Duval Street, where you'll find a vibrant mix of restaurants, bars, and entertainment. For added convenience, the Key West airport is just a short drive away, making travel easy and stress-free.brbrGetting Around:brWith parking available, you'll have easy access to explore the island by car. If you prefer to travel by bike, scooter, or golf cart, rentals are nearby for your convenience. Key West's walkability means many attractions are just a short stroll away, and for longer distances, taxis and rideshare services are readily available.brbrOther Things to Note:br- Pet-Friendly! 1 dog (40lbs maximum) with a $20 per pet per night feebr- Private washer/dryer in unitbr- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, walkways, pool, parking areas, and common outdoor areas. No cameras are placed in private or interior spaces.brbrAt Colocada Vacation Rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

The Salt Cay | Updated! Stunning Sunset View, Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$154.03

City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to Island Escape! brbr brbrThis beautifully adorned condo is your ticket to the best of Key West living. Nestled just steps from the iconic Duval Street and a short six-block stroll from the Southernmost Point in the Continental US, this is the perfect base for your island adventures. Step out of your front door, and you'll find yourself immersed in the vibrant culture of Key West. Sample the delectable cuisine at the many restaurants and bars the island is famous for. Explore unique shops and discover captivating attractions around every corner. For beach lovers, several sandy shores are within walking distance, while the sprawling Smathers Beach, with its powdery soft sands and crystal-clear turquoise waters, is just 8 minutes away. Whether you're seeking relaxation, adventure, or a taste of local life, Island Escape has it all. brbr brbrSLEEPS MAXIMUM OF 4 GUESTS: brbr brbrBedroom: Full Bed, En-Suite Bathroom, Smart TV brbr brbrLiving Room: Sofa With Pull-Out Queen Bed, Smart TV brbr brbrKitchen: Nicely equipped (everything needed to prepare and serve meals) brbr brbrAMENITIES: brbr brbr- Shared Pool brbr brbr- Private Patio brbr brbr- One Parking Space Included brbr brbr- Linens and towels provided brbr brbr- half block to Duval Street brbr brbr- 0.4 miles to Southernmost Point brbr brbr- 0.9 miles to Key West Historic Seaport brbr brbr- 1.0 miles to Fort Zachary Taylor State Park Beach brbr brbr- 1.1 miles to Mallory Square Sunset Pier brbr brbr- 2.3 miles to Smathers Beach brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAmenity Fee: HOA requires booking tenant to pay a $100 amenity fee. (Subject to change and collected at time of booking) brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPeak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking. brbr brbrNo Pets: Pets are strictly prohibited. To help maintain a pet-free environment for all, we require every guest to confirm they are not bringing a pet/animal. It's free, and does not require creating an account. After booking, you'll receive a link to complete the process. brbr brbrSmoking Policy: Smoking is strictly prohibited to maintain a smoke-free environment. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time.

Island Escape: Charming Condo Just Steps From Duval Street, Near Southernmost Point, Shared Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$320.63

This 2 bedroom (one King and one Queen, plus Queen size pull out couch in the living room), 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located one mile from Smathers Beach, two miles from Higgs Beach and just minutes away from the Key West Lighthouse Museum. Many species of birds inhabit the salt ponds preserve that borders this property.br

Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

Key West, Florida, United States

Bed

Bath

Sleeps

$243.61

Treat your family to an unforgettable stay in Key West with this dog-friendly condo. Modern conveniences combine with a great location and first-class resort amenities - you'll love this adventure so much, you'll never want to head back home!brbrWhen you're done swimming in the shared pool or soaking in the shared hot tub, you can towel off and head indoors to relax. The private balcony provides amazing views of lush plants and wide-open blue skies, with the flatscreen TV of the living room right nearby. Whip up a delicious meal in the kitchen before retiring with your loved ones when it's time for bed. A dog is welcome. brbrGet started on your next great adventure - save your dates today!brbrTHINGS TO KNOW

Breezy Condo with Pool & Hot Tub, Private Parking & Great Location - Dog OK

Key West, Florida, United States

Bed

Bath

Sleeps

$653.21

Part of the Papa's Hideaway complex, this charming historic Key West cottage is an ideal home away from home for your next vacation. Thoughtful upgrades include a high-end kitchen, loads of modern amenities, a shared swimming pool, a sundeck, and a tropical courtyard. Street parking is available during your stay.brbrLocated two blocks from the southernmost beach and one block from Duval Street where you can dine in the best restaurants, shop in unique local stores, and sample live music and entertainment in popular nightspots. Those looking to dig into the history of Key West will want to visit the Ernest Hemingway Home and Museum as well as the historic Key West Lighthouse, the Truman Little White House, and the Key West Art & Historical Society, all located within a mile of this rental.brbrSpoil yourselves back home with high-speed Wi-Fi, three cable TVs, and a covered porch where you can dine alfresco or cool down with a refreshing beverage while the ocean breezes play in the palm trees above. Swim in the shared saline heated pool or relax poolside on one of the provided lounge chairs.brbrThings to KnowbrLast-minute bookings cannot be made online.

Classic Key West cottage with pool & courtyard - walk to beach & Duval St dining

Key West, Florida, United States

Bed

Bath

Sleeps

$419.76

The ideal location of this super-comfortable corner property makes it the perfect blend of convenience, tranquility, and tropical Key West scenery. Sit back and relax as you sip cocktails on the balcony, prepare a light meal in the newly renovated kitchen, and unwind in front of the living room smart TV after a day at neighboring Fort Zachary Beach. Or head down to the community's newly renovated, heated swimming pool to work on your tan.brbrWhat's nearby:brThe Shipyard Condos enjoy an enviable location in the Truman Annex area of Key West, just a short walk from the white sands of Fort Zachary Beach. You'll be amazed by how quiet this location is, despite being half a mile south of Mallory Square and two blocks from Duval Street's renowned shops, restaurants, and nightlife. You can easily stroll to the famous Ernest Hemingway House (a quarter-mile east) and the USCGC Ingham Maritime Museum (half a mile west) as well.brbrThings to know:brFree WiFibrFull kitchen

Alluring corner unit w/ full kitchen & pool - close to beach/ nightlife

Key West, Florida, United States

Bed

Bath

Sleeps

$179.6

In the heart of Old Town and just two steps up to enter, this charming single-story cottage is the perfect setting for your next getaway with family or friends. This snowbird-friendly condo boasts an unbeatable location within walking distance of lively Duval Street, fantastic local restaurants, Higgs Beach (with volleyball and tennis courts), a drug store, gym, and neighborhood grocery store.brbrStep inside this centrally air-conditioned retreat and you'll be welcomed by a bright, airy floor plan featuring half-vaulted ceilings, exposed wood beams, and cheerful beach-inspired décor. Enjoy relaxing evenings with free WiFi, cable TV, or streaming on the smart TVs using your own accounts. A variety of puzzles and board games —Dominos, cards, Uno, Backgammon, Scrabble, Monopoly and more—offer plenty of entertainment options.brbrWhen it's time to dine, the spacious, well-appointed kitchen makes cooking a pleasure. It features all-new stainless steel appliances, including an induction cooktop with air fryer oven and a convenient beverage fridge. Additional highlights include a newly renovated bathroom, an in-unit washer and dryer, and complimentary off-street parking for one vehicle.brbrOutdoors, the property truly shines. The expansive shared common area is surrounded by magnificent palm trees and includes a heated outdoor pool, poolside loungers, and an outdoor dining space—perfect for soaking up the Key West sunshine. You'll also enjoy a private enclosed patio complete with a gas grill and a beautiful teak outdoor shower.brbrWith a 28-night minimum stay, this home invites you to truly settle in and experience the vibrant charm and laid-back beauty of picturesque Key West.brbrThings to KnowbrPermit number: 25230-138528brbrYou must be 25 years or older to rent this property.

Dog-friendly condo near beach with pool, grill, outdoor shower, W/D, AC

Key West, Florida, United States

Bed

Bath

Sleeps

$203.0

Find the best of Key West at your doorstep with this beautiful two-bedroom condo, a lovely South Florida escape with a private deck and patio, a shared swimming pool, and a wonderful location close to restaurants, beaches, and more!brbrPerfectly located between Truman Annex and Bahama Village, this comfortable condo sits only two blocks from the fantastic restaurants, nightlife, and shopping on Duval Street. Park your car in the off-street space, walk a quarter-mile to the Ernest Hemingway Home and Museum, and take afternoon bike rides to the soft sand at Fort Zachary Taylor Historic State Park three-quarters of a mile west.brbrThe living space has been meticulously decorated by one of Key West's preeminent designers, offering travertine floors, central A/C, free WiFi, and French doors that open to the deck. When you're not dining at Blue Heaven nearby, you can sip cocktails outside among the palms and orchids, flip through the cable offerings on the HDTV, and splash around in the shared swimming pool. A full kitchen with granite countertops, a private off-street parking spot, and a private washer/dryer are also on hand.brbrLet your Key West escape begin today - don't wait another minute to book this elegant condo!brbr*Please note that last-minute bookings cannot be made online. Contact us for details.*

Beautiful Condo with Deck, Patio, & Pool - Walk to Duval Street & Beaches

Key West, Florida, United States

Bed

Bath

Sleeps

$176.65

Book this wonderful, ground-level, Old Town getaway with all the comforts of home including central air conditioning and complimentary internet access! This vacation rental features a spacious floor plan with doors that open out to the back patio to create an indoor/outdoor living space. Kick back in the living area and watch your favorite TV show or gather with your group and plan your next adventures. Bring the snacks made in the well-equipped, full kitchen outside and enjoy the breeze as you kick back in the outdoor dining area. Then take a dip in the shared swimming pool.brbrWHAT'S NEARBYbrSteps from Duval St. and a variety of entertainment, dining, and shopping options, you won't get bored here! Easily walk or bike to attractions such as Hemingway House, Key West Lighthouse, Harry Truman Little White House, Southernmost Buoy, Key West Butterfly and Nature Conservatory, and much more.brbrTHINGS TO KNOWbrShared laundry facilities on-site.brBeach/pool towels provided for guest use.brSnowbird-friendly. Please contact us for details.brPlease note that the pool, pool deck, and gas grill are occasionally shared with the owners when they visit.brThis home has a 28-night minimum stay per city regulations.brThis property is managed by Seven Keys Vacations by Casago.

Ground-level getaway with free WiFi, private deck, & shared outdoor pool

Key West, Florida, United States

1

Bed

1

Bath

Sleeps

$172.02

Welcome to Periwinkle Place—a bright, dog-friendly escape in the vibrant heart of Old Town Key West! Just one block from famous Duval Street, this charming two-level home offers the perfect blend of island relaxation and city excitement. From your front door, walk to top attractions like the Ernest Hemingway Home & Museum, Key West Lighthouse, Southernmost Point, and the crystal-clear waters of South Beach.brbrDesigned for both comfort and style, Periwinkle Place is ideal for couples, solo travelers, or small families—with room for one well-behaved pup up to 50 lbs. The upstairs bedroom features a luxurious king-size bed beneath vaulted ceilings, while the downstairs living area includes a comfortable double sleeper sofa to accommodate extra guests. A fully equipped kitchen and dining nook provide everything you need to enjoy meals at home.brbrFor those working remotely, you'll love the spacious desk area just off the bedroom—a perfect, quiet spot with plenty of elbow room and natural light to keep you focused and productive between island adventures.brbrEnjoy your morning coffee or evening cocktail from your semi-private balcony as you take in the lively energy of Old Town. Whether you're here for relaxation, discovery, or a little of both, Periwinkle Place offers a stylish and convenient home base for your unforgettable Key West escape.brbrTHINGS TO REMEMBER

Charming island retreat with balcony, king bed, desk space & dog-friendly vibe

Key West, Florida, United States

Bed

Bath

Sleeps

$423.23

Caribbean comforts await at this lovely Key West condo just five miles from the island's historic downtown. With amenities like a private pool and hot tub, tennis courts, a private balcony, and a covered parking spot, this comfortable condo is perfect for anyone who plans to explore the island by day and relax peacefully at night.brbrLocated on the eastern side of Key West, this condo is part of the exclusive Sunrise Suites Resort. When you're ready to explore, your rental is just a short drive to many of the island's most popular attractions. Scuba dive through crystal-clear waters, book a deep-sea fishing trip, or explore Key West's bustling shops and boardwalk. When you're ready for a break, you're never far from home, where you can rest up and refresh for another day of adventure!brbrCool off with a dip in the shared pool, enjoy a leisurely walk around the lush tropical grounds, or get your pulse up with a game of tennis. Cable and free WiFi are both provided, along with comfortable furnishings and a private balcony for taking the air. The family dog is also welcome to join you for an additional nightly fee.brbrTreat yourself to an incredible Key West getaway with this wonderful condo. Book your reservation today!brbrTHINGS TO KNOW

Sunrise Suites Condo w/ Balcony, Pool & Hot Tub, Tennis & Covered Parking

Key West, Florida, United States

Bed

Bath

6

Sleeps

$360.8

Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom and luxury king bed in the guest bedroom. Two living room sofas adds extra sitting. Nicely decorated with a Key West Flair. Full kitchen with all appliances, washer/dryer, electric range and microwave. Central air conditioning with ceiling fans. Flat screen TV and Wireless Internet provided. Large pool with hot tub and sauna. Lighted tennis court. Gated community with BBQ area. Dedicated, covered parking spot. brbrNote: The property is set up for no contact check-in. Two inflatable twin size blow up mattress are provided for additional guest over four. Max allowed is six guests.

Direct Ocean View from Your Condo-No Contact Check-In

Key West, Florida, United States

Bed

Bath

Sleeps

$334.64

Escape to the sunshine and soft sands of the Florida Keys with this amazing home in Sunrise Suites Resort in Key West with a shared pool. Sporting updates such as brand-new appliances, new sound-proof flooring, and a stackable washer/dryer, your stay is guaranteed to be a comfortable one.brbrBack at home, you can stroll down a wooden walkway past a pristine pond, enjoy the shared hot tub or take a dip in the shared swimming pool. When you've toweled off, head inside to whip up a delicious meal in the kitchen, or simply kick back and relax with some cable on the TV. Stroll out to your private balcony and indulge in watching the birds at the Salt Ponds Preserve.brbrGet your next vacation started now - place your reservation today!brbrSHARED AMENITIESbr-Poolbr-Hot tubbr-Fitness roombr-Tennis courtbrbrTHINGS TO KNOW

Dog-friendly condo with pool, hot tub, balcony, central AC, W/D, & fitness room

Key West, Florida, United States

Bed