Vacation Rentals By Owner In Key West, FL

Stunning Ocean View 2BR/2BA Condo in Exclusive 1800 Atlantic CommunitybrbrWelcome to your beautifully renovated, second-floor oasis in the prestigious 1800 Atlantic community in Key West. This stunning 2-bedroom, 2-bathroom condo features custom tile work throughout, an expansive private balcony, and breathtaking views of the Atlantic Ocean and lush gardens.brbrThe primary suite includes a luxurious king-sized bed, while the guest bedroom offers two twin beds that can be converted into a king upon request—ideal for families or couples traveling together. A queen sleeper sofa in the living room adds extra sleeping space, and all rooms are furnished with brand-new beds for maximum comfort.brbrThe fully equipped kitchen, in-unit washer and dryer, high-speed internet, and cable TV ensure all the conveniences of home. A dedicated desk area allows you to send a postcard or take care of work while away.brbrStep out onto your private balcony and enjoy al fresco dining with ample seating and tranquil views of nature and the ocean. Relax in the Olympic-size heated pool, unwind in the large hot tub or sauna, or take advantage of the lighted tennis courts and nearby beach access.brbrLocated close to Key West’s vibrant nightlife, city center, and airports, this condo blends the perfect balance of serenity and accessibility. Ideal for families, couples, or business travelers, this property is available for monthly rentals.brbrResort-Style Amenities Include:br Heated Olympic-size pool & jacuzzibr Sauna & tennis courtsbr Lush tropical landscapingbr Secure, exclusive community settingbrbrYour tropical escape awaits—book your stay today!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.

Stunning Ocean View 2BR/2BA Condo in Exclusive 1800 Atlantic Community

Key West, Florida, United States

Bed

Bath

Sleeps

$698.28

Enjoy your tropical vacation, whether work-free or not, in this Old Town home only a couple of minutes from Duval and Whitehead Streets and loads of restaurants, bars, and entertainment. The quiet lane is so small and discrete that even most locals would need a map to find it. But if you do know the area, you know this home is close to all of the action in Old Town. In addition, nearby City and County bus stops are very close to aid your transportation needs on the island. brbrThe home has a heated pool, modern kitchen, and entertaining areas, both inside and out near the pool. The main level has a very large living/dining/kitchen area with French doors opening out onto a spacious deck and a very private pool and rear garden area with beautiful tropical landscaping. The first level also has several closets and a half bath. On the second level, there are two identical bedrooms with a shared bath and porches overlooking the front yard and quiet street. In addition, the upstairs master bedroom is more than ample with a walk-in closet, private bath, and its own covered porch overlooking the pool and rear garden area. There is plenty of room for two cars in the gated off-street parking area in front of the house. The house also has cable TV and high speed internet.brThe property has been newly repainted and decorated! Please check out our YouTube video by copying/paste this link: https://youtu.be/nUBKtLvcmfk to see the completion!brbrPlease note, if you have a large party of guests and need additional space, the house immediately next door has common ownership and might also be available for rent at the same time. See our other VRBO properties listing numbers 2784733 and 2232811!

The Jasmine House Just a 2 minute walk to Duval and restaurants and bars

Key West, Florida, United States

Bed

Bath

Sleeps

$408.71

NO PASSPORT REQUIRED…brA lovingly restored island retreat with luxurious coastal flair, this home’s aesthetic beauty draws you in to a world of tranquility. This home is also known as Hunter House in the name of Blake Hunter for his generous donation to a local organization. Spacious by design with 4 bedrooms and 3.5 bathrooms, a lifetime of memories await as your loved ones come together in this gem set a world apart from reality. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brAn adorable glance to your picture-perfect getaway catches your eye as you pull up to 2 off street parking with views of your long awaited dream home. A quaint sunroom begins your journey with seating for your 5 o’clock happy hour. Step foot into an attractive, open Great Room area with cozy furnishings, a flat screen TV and rich hard wood flooring throughout. A crisp, gourmet kitchen follows with ample lighted cabinetry, a gas stove, granite counters, stainless steel appliances and bar seating for 4. Dining for 6 lies just beyond overlooking your outdoor tropical oasis. brbrSLEEPING ARRANGEMENTS…brTwo comfortable bedrooms occupy the first level of the home sharing a full bathroom with a walk in shower. The first bedroom comes with a queen bed and the other with a king bed. The private king master suite lies up the stairs equipped with a large walk in closet, writing desk and en suite full bathroom with double vanity sinks, a walk in shower and clawfoot tub. Soak up the pristine backyard views from the master suite’s very own balcony with seating for two. Visiting guests can experience a poolside cottage featuring a queen bed, mini fridge and en suite full bathroom with a shower. Additional sleeping arrangements can be found on the sofa sleeper downstairs with a powder room just off the dining area. Apple TV's are provided in guest rooms so you can log in to catch up on all your Netflix favorites! brbrOUTDOOR LIVING…brSunny days are best spent out on the spacious outdoor deck surrounding a sparkling, heated pool and natural beauty of swaying palms all around. Cool off under the retractable awning and enjoy your fresh catch al fresco with seating for 6. Just a short distance to the sandy beaches of Key West and all the adored attractions, this home is the ideal destination for island perfection. brbrPARKING...brTwo off street parking spaces are available for this home.brbrPETS...brOne pet per reservation, 30 pound non-shedding dogs are considered. No kitties please! Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests. A pet fee is required.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). brbrA TROPICAL DREAM…

CLOUD 9 ~ 4 Bedroom, 3.5 Bathroom with Off Street Parking and Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$451.57

Historic 1880`s Cigar Maker`s cottage completely renovated. brbr1 K and 1 Q BR’s, half bath upstairs between BR’s, 32” Smart TV`s, Full kitchen with granite counter tops, new stainless steel appliances. brbrA newly remodeled bath with tumbled marbled tile shower, hairdryer. Also a totally private outdoor shower located in your private patio. All bath amenities provided, plus pool towels and daily housekeeping!brbrK and Q memory foam bedrooms upstairs (32 Smart TV) separated by half-bath, computer desk with USB ports and mirrors for make-up, full kitchen (granite counter tops) with dishwasher, convection microwave, refrigerator w/ice-maker, glass top stove, all cooking utensils provided. Breakfast bar with 4 swivel stools for eating inside or eat outside in your private courtyard. Private bathroom with large tumbled marble shower plus a private outside shower in your courtyard. LR with 46”Smart TV and Alexa upstairs and down. Private courtyard and 4 person spa. Daily housekeeping is also provided as well as pool towels!brbrTwo heated pools, the Family Pool and The Adults Only pool across the street. Use of 2 W/D’s after housekeeping is finished at 5 pm. Topless optional sundeck right next to your unit.brbrYou can access all common areas of the compound, outdoor shower, bathroom by pool, W/D’s after 5 pm, Weber BBQ grill, heated Family Pool and the Adult`s Only heated Pool across the street. Bicycle lockup at entrance to property.brbrHousekeepers and groundsman/maintenance are on the property daily from 9-5.brbrQuiet vacation rental neighborhood with moped/bicycle rental at corner. 24 hour CVS, Subway are just across Truman.brbrYou have access to 2 heated swimming pools, your private spa, upstairs topless optional sun deck, gazebo with games. Complimentary Alexa, coffee, sugar and creamer is provided for your convenience. Free use of 2 W/D`s after 5pm.

Sunset Suite-2 BR, sleeps 4, King and Queen, Private Spa!

Key West, Florida, United States

Bed

1

Bath

4

Sleeps

$1151.96

This listing is for a room within a hotel.brbr✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 24 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool available all year.brbr✦ Paid parking lot – 1 space(s), available for $40.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $62.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00. Only one dog under 20 pounds is allowed per roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ The property requires a damage deposit of 1-night rate + tax on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.

Hotel

Lux Gulf View Suite! Pool, Marina Access, Walk to Dining Spots & Museums!

Key West, Florida, United States

Bed

Bath

Sleeps

$1034.09

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrThroughout Key West you'll find subtle touches of coconuts; from the towering coconut palms nestled throughout the streets of Old Town to folks sipping from fresh coconuts while soaking up the sun, and now, you can add THE TOASTED COCONUT to that list. THE TOASTED COCONUT is a rare gem in the heart of Old Town Key West that captures the essence of classic Key West in a fully renovated modern design and includes all of the coveted amenities of a vacation home: a spacious living area, an ideal bedroom and bathroom layout, a private pool, and plenty of space to stretch out or come together as a group. In addition to the fabulous layout and desirable amenities, this home has an unmatched location. THE TOASTED COCONUT combined with Last Key Realty's Five-Star In-Home Guest Services is sure to make your group's stay in Key West an extraordinary one.brbrNeed more space Rent both THE ZESTY LIME and THE TOASTED COCONUT together as THE LIME AND THE COCONUT - two side-by-side private homes that can sleep a total of 16 guests with two private pools.brbrTHE LOCATION...brbrImagine being just steps from all of the shops, restaurants, and sites of Key West. Walk just one block to reach the world-famous Duval St, or take a short stroll down Simonton St to watch sunsets from the Historic Seaport. Not only will you be within walking distance of restaurants and entertainment, but you'll also be within a mile of Fort Zachary Taylor State Park, home to Key West's best beach.brbrTHE LIVING AREA AND KITCHEN...brbrThis home's classic Key West architecture is apparent from the street, with the gingerbread trim and a whimsical porch swing that define Old Town conch homes. Upon entering, you'll be pleasantly welcomed into a newly restored version of a Key West conch home. The living area boasts a large flat screen SMART TV, which can be viewed from the comfort of the plush living room furniture. The brand-new kitchen features stainless-steel appliances as well as all the tools needed to prepare a meal at home. The indoor dining table seats 4 and there's additional seating for 2 at the kitchen bar. There's also a convenient powder room just off the kitchen.brbrYOUR PRIVATE POOL...brbrPrepare your favorite beverage of choice (perhaps a Pina Colada or a Toasted Coconut Daiquiri) and head out the back door to the lovely pool area, which is fully fenced for privacy. The private 6' x 9' dipping pool can be heated to your liking and has a soothing waterfall. Comfortable patio furniture on the pool's deck provides outdoor lounging options for everyone in your group. The pool area is complete with an outdoor dining set that will comfortably seat 6.brbrTHE ACCOMMODATIONS...brbrEach of the three bedrooms in THE TOASTED COCONUT is a suite with a private en-suite bathroom. brbr** First Master Suite: Located on the First Floor with a King bed and an en-suite bathroom with a shower and tub combo. brbr** Second Master Suite: Located on the Second Floor with a King bed and an en-suite bathroom with a shower and tub combo. brbr** Third Master Suite: Located on the Second Floor with Two Twins OR One King bed and an en-suite bathroom with a spacious walk-in 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 ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced and Landscaped Backyardbr** Private Pool with Available Pool HeatbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 8 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.

**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + LAST KEY SERVICES…

Key West, Florida, United States

Bed

Bath

Sleeps

$192.25

Stunning, Modern 2 bedroom, 1 bathroom second floor condo in the Truman Annex Shipyard Complex has been recently renovated. Fully appointed, new kitchen with all new appliances, washer/dryer in unit, convenient front & back balconies with comfortable furniture for lounging and entertaining. Strategically located in the Shipyard Complex of the Truman Annex, right on Southard Street just steps from the active lifestyle of Duval Street, shopping, dining, and night life. Also steps from Mallory Square for gorgeous sunset views and the new Truman Waterfront Park. Assigned off street parking for 1 vehicle. brPlease note: This property has a 28 night minimum stay

A Bird's Eye View at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$435.76

WELCOME TO TROPICAL JEWEL brbrbrNear all the action of the historic seaport and Duval Street, you can get out into the city anytime you want, or quickly retreat back when the party is winding down.brbrDiscover the eclectic charm of this Key West home, just two blocks from the Historic Seaport. This unique property is a perfect blend of colorful, quirky elements that embody the spirit of island living. Relax on the front porch in Adirondack chairs while enjoying a cold beverage.brbrInviting and Eclectic Living Spaces:brOur living room is a cheerful space, ideal for relaxing with a good book or sharing stories of the day's adventures. Casual and relaxing colors touch the home's eclectic decor. The open-concept living and kitchen area provides a comfortable and inviting environment for you and your guests, especially when you consider that the living room extends outside to a covered dining area, alfresco dining, wet bar, and a mini fridge creates the perfect place to make your cocktails. The unit's washing machine and dryer are also hidden in a closet in this area.brbrOutdoor Living at its Quaintest:brStep out onto the covered lanai, an ideal spot for enjoying meals or a cool drink. It's a true highlight of the property, providing just the right amount of space for a gathering. The pool, a good size for Key West standards, offers a delightful retreat from the warm sun in a serene backyard setting. The pool is private and heated for when the temperatures are slightly more brisk.brbrFunctional Kitchen and Dining:brThe kitchen features granite countertops alongside distressed cabinets, creating a practical yet charming space for meal preparations. The fridge, range and dishwasher ensures your stay is convenient and enjoyable.brbrAccommodations:brThis home accommodates up to 6 guests but 4 comfortably with 2 Queen beds and 1 Full-size bed. The loft space above the primary bedroom adds a unique touch but is more suited for shorter stays or as an additional, temporary guest space as the ladder up there may be difficult for some people.brbrEmbrace the vibrant, quirky charm of our home, where each day is an opportunity to create unforgettable memories in Key West.brbrBook now before the property is no longer available.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. brbrbrNOTES:brPets considered.brThis home does not come with a dedicated parking place.brbrbrMonthly Rental Only (This property must be rented for 28 or more days by city ordinance)

Cottage

Tropical Jewel - Stay Where The Vacation Never Ends- 2BD/2Bath - Private Pool

Key West, Florida, United States

3

Bed

Bath

6

Sleeps

$305.73

Summary:brbrSpacious Retreat with Pool & Guest CottagebrbrbrbrThe Space:brbrWelcome to your tropical escape in one of Key West’s most sought-after neighborhoods — Casa Marina, where laid-back island living meets comfort and style. Just a short bike ride from the beaches, restaurants, and all the excitement of downtown, this beautiful home offers the perfect balance of serene privacy and convenient access to everything Key West has to offer.brbrbrbrThis spacious four-bedroom, four-bathroom main house features an open-concept living space with a bright and airy living room and a fully equipped kitchen, ideal for easy entertaining and gathering with family and friends. On the main floor, you’ll find two inviting guest bedrooms, each with its own private bathroom. Upstairs, the primary suite with a king-size bed serves as a luxurious retreat, complete with a private bathroom. A second upstairs guest bedroom and a cozy lounge area provide even more space to unwind.brbrbrbrStep outside into your own tropical paradise — a lush garden with a huge pool and comfortable seating area, perfect for lazy afternoons, poolside cocktails, and evening barbecues. Please note POOL IS NOT HEATEDbrbrbrbrAn added bonus is the private guest cottage, featuring a bedroom, bathroom, and kitchenette — ideal for visiting friends, extended family, or anyone who enjoys a little extra privacy.brbrbrbrSet in a peaceful residential area just far enough from the bustle of downtown, this home offers a tranquil retreat while still keeping you close to Key West’s best beaches, dining, and entertainment. Whether you’re planning a family getaway or a group escape, this Casa Marina oasis has everything you need for an unforgettable stay in paradise.

Casa del Sol

Key West, Florida, United States

6

Bed

4

Bath

12

Sleeps

$187.92

Welcome to your perfect Key West getaway! Located in the desirable Salt Ponds community, this beautifully maintained condo offers the ideal blend of comfort, convenience, and laid-back island charm—perfect for extended stays of 28 days or more. Work & Relax in Key West | Poolside Condo • BalconybrStep inside to an inviting open-concept living space filled with natural light. The updated kitchen features warm wood countertops, modern appliances, and bar seating, making it easy to cook, entertain, or simply enjoy your morning coffee. The living area flows seamlessly onto a private balcony overlooking lush tropical landscaping, where you can unwind and soak in the island breeze.brThe condo offers comfortable, well-appointed bedrooms, designed for restful nights after a day of exploring Key West. Additional conveniences include in-unit washer and dryer, making longer stays effortless and comfortable.brCommunity Amenities Include:brResort-style heated pool & spabrBeautifully maintained tropical groundsbrAssigned parkingbrQuiet, residential atmospherebrLocation Highlights:brMinutes to Smathers BeachbrEasy access to bike paths and walking trailsbrShort drive to Old Town, Duval Street, dining, and shoppingbrClose to grocery stores and everyday conveniencesbrWhether you're working remotely, escaping the cold, or simply looking to experience Key West like a local, this condo offers everything you need for a comfortable extended stay.brRental Details:br ️ 28-Day Minimum Stay (per city/association requirements)brFully furnished and move-in readybrIdeal for snowbirds, traveling professionals, or extended vacationsbrCome experience the slower pace and beauty of Key West—this is island living at its best.

Salt Ponds | Work & Relax in Key West | Poolside Condo • Balcony • Near Beach

Key West, Florida, United States

Bed

Bath

Sleeps

$244.0

First floor newly renovated 2 bedroom/ 1 bath corner end unit at the Shipyard Condominiums located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located 1/4 mile from one of the best beaches on the island. The Shipyard Condominiums are single level condominiums which have private courtyards on the first level or charming balconies on the second level. All properties are outfitted with washer/dryer, pots, pans, towels, linens, have central air conditioning, off street parking, free WIFI and pool access. brPlease note: This property has a 28 night minimum stay

Seascape at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$1096.88

Summary:brbrCommodore's Cove offers the best of Key West: a prime location and all the amenities of a home. Up to 12 can stay at this welcoming first floor condo, so bring the whole family along! Located on Simonton Street, just one block from the heart of downtown Duval St.brbrbrbrThe Space:brbrCommodore's Cove offers 4 bedrooms, each with an en suite bathroom and a large flat-screen TV. Accommodating up to 12 guests, the home includes 2 king beds, 1 queen bed, 2 twin beds, and 2 queen sofa beds. The fully equipped kitchen with stainless steel appliances makes it easy to prepare home-cooked meals. Enjoy complimentary WiFi and use the private stackable washer/dryer for added convenience.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guest will receive a personalized access code prior to arrival.brbrbrbrThe Neighborhood:brbrConveniently located between Downtown and the Historic Seaport, Commodore's offers easy access to Key West's top attractions. Watch the sunset at Mallory Square, enjoy a day out at the sandbar with Brightwild Adventures, or explore Key West history at the Shipwreck and Mel Fisher Maritime Museums.brbrbrbrJust one short block from Duval Street, you’re steps away from the best bars, restaurants, coffee shops, and attractions. Local favorites like First Flight, Bagatelle, and Two Friends Patio are less than a five-minute walk. Satisfy your sweet tooth with Kermit's Key Lime Pie in the Historic Seaport or enjoy homemade fudge from River Street Sweets.brbrbrbrNeed something in a hurry Shorty’s Market is nearby for your last-minute necessities, and Fausto’s Food Market, just two blocks away, offers locally sourced groceries.brbrbrbrGetting Around:brbrParking Information: There is one private parking space on the side of the home in the driveway located on Dey Street. Please note this is for compact vehicles and Dey Street is a one way.brbrbrbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance. Feel free to ask us for recommendations!brbrbrbrOther Things to Note:brbr- This unit is located on the bottom floor of a 3-story vacation rental. For larger groups - this property can be rented along with upstairs as Commodore's Compound! Reach out to us for more information. brbrbrbr- This unit is pet friendly. Our requirements are as follows: brbr•40lb maximum per petbrbr•$25/per nightbrbr•2 pet maximumbrbrPlease let us know if you plan on bringing your pet.brbrbrbr- Washer/Dryer located on the exterior of the unit.brbr- One private parking spot.

Commodore's Cove - One block from Duval St

Key West, Florida, United States

Bed

Bath

Sleeps

$192.25

Welcome to your slice of paradise in the Shipyard at Truman Annex. This charming first‑floor 2BR/1BA condo captures the essence of Key West living—easy, breezy, and surrounded by tropical beauty.brbrInside, natural light fills the open living space, creating a relaxed atmosphere that flows out to your private patio. It’s the perfect spot to unwind after a beach day or host friends for sunset cocktails. Both bedrooms offer comfort and flexibility, and the well‑designed layout makes the home feel surprisingly spacious.brbrLiving in the Shipyard means enjoying a gated community with a sparkling pool, lush landscaping, and unbeatable walkability. Beaches, restaurants, galleries, and the best of Old Town are all right outside your door. Whether you’re looking for a getaway, a full‑time home, or a high‑demand rental, this condo delivers the Key West lifestyle people dream about.brPlease note: This property has a 28 night minimum stay

Another Three Hour Tour at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$325.13

The Poolside Studio Villa is a stand-alone Key West vacation rental that features full kitchen appliances and a sitting and sleeping area for two people. The privacy of our Villas, our thoughtful amenities, and our convenient location near Duval Street makes Key West Villas a refreshing alternative to run-of-the-mill hotels. Make your getaway to Key West, Florida!brbr* 1 Queen Bedbr* Sleeps up to 2 Peoplebr* Full Kitchen Appliancesbr* Shared Pool Deckbr* Flat Screen TV with Cablebr* Shared Heated Poolbr* Continental Breakfast Includedbr* Parking by Reservation ($15/night plus tax)br* 200 Feet from Duval Street

Villa

Poolside Studio Villa Steps from Duval!

Key West, Florida, United States

Bed

Bath

Sleeps

$1036.13

A contemporary island gem that was formerly used as a bottling plant, this modern and spacious home is now a desirable tropical retreat loctated in the heart of Key West. Having received a prestigious Ceramic Star for Architectural Preservation Excellence, Casa Amor captivates historic essence while luring you in with the finest of amenities.brbrStep into an open and bright space boasting high ceilings and natural lighting flowing into this island getaway. Polished concrete floors on the lower level and rosewood and travertine marble on the upper level keeps you cool on a steamy summer afternoon. The updated and fully equipped kitchen comes with granite counters and bar seating for 4 with an indoor dining table to seat 6 for group mealtime. Adjoining the kitchen is an open concept living area featuring cozy furnishings, a flat screen TV, and views through the floor to ceiling sliding doors of the lush backyard area, making this a great indoor/outdoor space to be enjoyed for entertaining. An additional table for 4 is located in the center of the home for card games or a happy hour before a night out on the town. Youtube TV service is available in this home.brbrTwo large guest rooms occupy the first level with comfortable king beds and flat screen TVs, and one of these rooms also includes a bunk bed. There is a nearby full bathroom with a shower and another half bathroom on this level making it convenient for those utilizing the sofa sleeper. Travel up the spiral staircase to the master suite that comes with a king size bed, a flat screen TV, walk in closet and an ensuite full bathroom with a soaking tub and shower.brbrThe lush backyard oasis is the epitome of Key West living! The covered and airy patio has plenty of room for lounging on a lazy day overlooking the lap pool which can be heated during the winter months and features a waterfall. Enjoy the convenience of your own outdoor shower and high walls outlining the home creating ideal privacy. An outdoor gas grill is available for your fresh catch of the day! Located blocks from all the fun Key West has to offer, you're sure to experience the true island lifestyle at Casa Amor.brbrOff street parking is available for one vehicle.brbrEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!

A contemporary island gem that was formerly used as a bottling plant,

Key West, Florida, United States

4

Bed

Bath

8

Sleeps

$419.61

Slack Tide Sunset : Location, location, location! Small Balcony looking towards the sunset, just 2 blocks from the beach and Southernmost Point, with lively Duval Street nightlife down the street and the Hemingway House nearby. Enjoy a beautifully newly decorated interior and a central Key West stay with free parking for 1 car plus washer and dryer—everything you need for life at slack tide sunset, that calm, perfect moment between the tides.brbrThe bedroom has a queen bed, and the living room has a queen sleeper sofa.brbr2 Blocks from the beach, and 2 blocks from Hemingway house VERY CENTRALbrbrYou get an exclusive 20% discount at Minty’s Golf Cart Rental in Key West if you rent a golf cart and book it online. And we have parking for you on premise.brRegistered Guests Only: Only guests included in your reservation may stay overnight. No unregistered visitors.brbrRespect the Property: Please treat the home, furnishings, and amenities with care. Damages or missing items will be charged.brbrQuiet Hours: Quiet hours are 10:00 PM – 7:00 AM in compliance with Key West ordinances. Please respect our neighbors.

Two blocks from Southernmost Beach! Cozy One Bedroom Apartment.

Key West, Florida, United States

Bed

Bath

Sleeps

$367.88

Summary:brbrWelcome to the Bartlum, a historic and luxurious studio apartment just steps to Duval Street. brbrbrbrThis studio, located on Caroline St, has been designed with comfort in mind, offering large windows for natural sunlight and plenty of space to spread out. Enjoy an updated kitchen, spacious bathroom, open concept layout, and all the hot spots of Key west within walking distance!brbrbrbrThe Space:brbrThis studio apartment is attached to a grand historic conch home and enjoys private access through a street-front courtyard. Enjoy the updated chef's kitchen with stainless-steel appliances that’s fully stocked with everything you need! Sip coffee in the morning from your Keurig coffee maker and take in the fresh Florida air in the outdoor seating area.brbrbrbrHave an extra guest or 2 No worries! The queen sized pull out sleeper sofa allows for comfortable sleeping for 2 and, allowing for a total of 4 occupants in the unit as a whole.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guest will receive a personalized access code prior to arrival.brbrbrbrThe Neighborhood:brbrPlaced perfectly in-between Downtown and the Historic seaport, enjoy attractions like Mallory Square at sunset, Brightwild Adventures for a day out at the sandbar, Dante's Pool Bar and the Shipwreck and Mel Fisher Maritime Museum for some Key West History.brbrbrbrHalf a block from Duval Street, The Bartlum, is steps away from Key Wests most famous bars and kitchens. Local’s favorite restaurants such as Fat Tuesdays, Irish Kevin's, Sloppy Joe's, Bagatelle and Two Friend’s patio are less than a 5 minute walk from your front door. Got a sweet tooth Keep an eye out for Kermit’s Key Lime pie shop in the Historic Seaport known for the best Key Lime Pie in Key West, or grab some homemade fudge and candy from River Street Sweets.brbrbrbrForgot something and or need a quick fix Shorty’s Market has your last minute necessities for your weekend getaway. Just 2 blocks away you can also find Fausto’s food market for locally sourced groceries.brbrbrbrGetting Around:brbrOne of the best parts of staying in Key West is how close in proximity you are to everything. Don’t feel like walking Peddle your way to breakfast, or take a bike ride along the water at sunset. Rent your bikes from Fury or Island Bicycles who offer both pick up & drop off services to your home! Feel like you’re on island time when you rent from Minty’s where you can enjoy exploring Key West on a scooter or golf cart. In addition to these non-traditional modes of transportation, you can also Uber, Lyft or Taxi to your next destination. Pink Taxi is an easy, reliable and affordable way for getting to your rental from the airport.brbrbrbrUnfortunately, there is no on-site parking for this unit.brbrFor overnight parking here are some parking lots:brbr• 204 Simonton Street (This is right around the corner from your unit and the most affordable on the island!)brbr• Caroline Street Outdoor Parking Lotbrbr• Park N Ride Old Town GaragebrbrStreet parking information:brbr• Street parking varies, from metered spots to free spots to residential. Please note: do not park in any spots marked residential they are for Key West Residents only and you can get a ticket.brbrbrbrOther Things to Note:brbrFree WiFibrbrNo pets allowedbrbrNo parking includedbrbrNo smoking

The Bartlum - Steps to Duval Street

Key West, Florida, United States

Bed

Bath

Sleeps

$239.96

*This condo is available for 28+ day stays only, and the pool area is shared with 3 other condos.*brbrLocated at 906-2 Truman Avenue, Blue Heron is a charming two-bedroom, two-bath condo nestled in the vibrant heart of Key West. Just steps from the island’s most beloved attractions, this cozy retreat combines comfort, convenience, and a touch of island flair—perfect for your next sun-soaked escape.brbrInside, the living room features two plush sofas and board games for rainy days. Whip up meals in the fully equipped kitchen, and make your morning brew with the Keurig coffee maker. The primary bedroom features a king bed, TV, and direct access to the patio and pool area, while the second bedroom offers a plush queen, making it easy for everyone to unwind in privacy. brbrStep outside to the serene shared patio, where lush landscaping sets the scene for total island relaxation. Take a dip in the sparkling pool and soak up the sun with plenty of poolside lounge space, or opt for the shady hammock. An outdoor kitchenette and grill await for the perfect evening BBQ.brbrWhen you're ready to explore, you're just steps away from Duval Street, the Hemingway House, beaches, and a local grocery store. Whether you're here to explore Old Town’s rich history, sip cocktails at sunset, or simply recharge in paradise, Blue Heron puts you in the perfect place to experience it all!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrLocal Attractions: Key West Shipwreck Treasure Museum, Hemingway Home and Museum, Mel Fisher Maritime Museum, Harry S. Truman Little White House, Conch Tour Train, Dry Tortugas National Park, Lazy Dog Adventures, Dolphin encounters, Ghosts & Gravestones Tour, Old Town Trolley, Sloppy Joe’s Bar, Audubon House & Tropical Gardens, Florida Keys Eco-Discovery Center, Bike Tours, Seaplane adventures, Key West Aquarium, Sebago Day Tours, Private boat charters, Sportfishing, Rick’s Entertainment Complex, Duval Street (shop strips, shops, bar, and cafes), Mallory Square (waterfront plaza), Key West Garden Club, Sunset Pier, Grand, Cafe Key West, Island House, El Meson de Pepé, Cafe Sole.brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbrHome Truths:br- Please note that all bookings 28 days or longer will require a security deposit of $2000 which will be collected after the booking has been made. Multiple months reservations might be subject to a higher security deposit fee.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- Unfortunately, pets are not allowed in this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- Please note that the pool and outdoor area are shared with 3 other condos. This home does not have a balcony. The balcony seen in the photo gallery belongs to another unit.br- The hammock, bbq, and laundry facilities are private amenities for this unit.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:brNo onsite parking.brStreet parking only.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bed brBedroom 2 / Queen bedbrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Prime Old Town Location w/ Pool, Walk to Duval Steet | Blue Heron by AvantStay

Key West, Florida, United States

Bed

Bath

Sleeps

$452.2

Summary:brbrA beautiful oceanfront suite located at the best marina in the Keys. Situated on the glistening Atlantic Ocean, our Grand Marina Suite is a tranquil respite with on-site access to boat dockage and world-class fishing charters. Located minutes away from downtown Key West, known for its quaint boutiques, historic landmarks, sight-seeing, sunsets and dancing. Our condominium will provide you with an intimate lodging experience unlike any hotel.brbrbrbrThe Space:brbrGrand Marina Suite is a full two-bedroom suite, with a full kitchen, living room and outdoor lanai. Each of the two bedrooms feature luxurious king sized beds and en suite bathrooms. There is a sleeper sofa in the living room. Outside of the Suite, our guests are encouraged to take advantage of our on-site pool, beach, sauna and fitness center.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival.brbrbrbrThe Neighborhood:brbrOur property is secluded and private yet minutes away from the excitement of Key West. This condo is located at the private Key West Harbour Marina, in Stock Island, the authentic and revitalized fishing and arts community located directly east of downtown Key West.brbrbrbrGetting Around:brbrArrive by boat, plane or car. On-site golf cart rentals are available, or take advantage of the many taxi and ride-sharing services available for short trips around Key West.brbrbrbrThere are assigned parking spots in front of the Harbour Residences marked as Condo 1, Condo 2, or Condo 3. You have 2 private parking spots located in front of your unit included with your stay.brbrbrbrOther Things to Note:brbr-For the purpose of creating a safe environment for our guests, the exterior of the building is monitored by security cameras.brbr-Please note the onsite restaurant is no longer open.brbr- Not pet friendly

Grand Marina Suite - Poolside & Waterfront Condo

Key West, Florida, United States

Bed