33040, Florida, United States Vacation Rental Condos By Owner

This is a great OCEANFRONT unit with large balcony to watch sunsets. Hyatt Sunset Harbor is perfectly located in downtown Key West next to Mallory Square and the Mel Fisher Museum. Walk along the boardwalk, shop in the local stores, or head to Duval Street only a couple blocks away. The resort has pool, hot tub, and grills for use during your stay.brbrHyatt Sunset Harbor is a 40 unit Hyatt Residence Club Resort. There are laundry facilities on site free of charge. There are NO daily resort fees, but parking is extra.brbrEach unit has a King sized bed in master and a Queen sized bed in second bedroom. In addition, there is a pull out couch in the living room. Max occupancy 6 guests.brbrCheck-ins and Check-outs are Sunday to Sunday.

DOWNTOWN KEY WEST 2BED OCEANFRONT!

Key West, Florida, United States

Bed

Bath

Sleeps

$178.42

PLEASE BE ADVISED IF BOOKING THIS UNIT FOR AUGUST 2026: The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. The HOA expects the project to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. There is no other pool available at the Shipyard, so we have adjusted our rates to offset the inconvenience.brbrCOMFORT AND VALUE IN TRUMAN ANNEX…brThis newly renovated 2nd floor two bedroom condo is located in The Shipyard, a neighborhood of Truman Annex in the heart of Old Town Key West! Colorful, fun patterns fill the rental with life while the furnishings provide a comfortable gathering space for your group. The sunny deck overlooks the distance views of the ocean through the lush trees but can also be a shady retreat with the help of an awning. This unit is accessed via one flight of stairs.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrFURNISHINGS…brThe Quarterdeck’s open floor plan and ample seating provides the perfect space for your group to enjoy together. Curl up on the couch and watch a movie on the flat screen, gather around the dining table to play a game or cook together in the fully equipped kitchen!brbrSLEEPING ARRANGEMENTS…brBoth guest rooms have a comfortable queen bed with extra drawers built into the bed frames for maximum storage space! Each room has a closet with lots of hanging space a flat screen TV, tile throughout and new paint for a fresh, clean feel. brbrDETAILS AND AMENITIES…brSettled in the manicured, gated community of The Shipyard, this location offers guests a peaceful spot to relax just a block from all the action! You will be in walking distance from Fort Zachary’s gorgeous beach and picnic area, Duval Street, Mallory Square and more! The Shipyard also offers a beautiful community pool lined with lounge chairs perfect for soaking up the sun. Parking is always an issue in Old Town, but this condo comes with its own designated parking space (vehicle cannot exceed 18 ft.)brbrOUTDOOR LIVING…brOpen the French doors to the back deck letting in the great breezes and sun rays that fill the space throughout the day. This wonderful extension to the living space has a table for two where you can have your morning coffee or enjoy a cocktail after a long day of exploring. On hot summer days pull out the awning to push back the sun so you can enjoy the views without sitting in the direct sunlight.brbrPETS...brThe is not a pet friendly home.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrbrBOOKING 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. brbrPARKING!brThis home does offer parking for one vehicle (cannot exceed 18 ft), but oversized trucks and extra large SUV's are not permitted and will have to park outside of this community.brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.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!brbrCOME STAY A WHILE...

THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Shipyard Unit!

Key West, Florida, United States

Bed

Bath

Sleeps

$396.45

Your Peaceful Key West Escape Awaits! brbrWelcome to this comfortably appointed 2-bedroom, 2-bath condo located in the desirable Sunrise Suites complex—a quiet, well-maintained community offering privacy and relaxation away from the hustle of Old Town Key West, yet close enough to enjoy it all. brbrCOMFORTABLE & THOUGHTFULLY DESIGNED INTERIORbrStep inside and feel right at home in this bright and welcoming space. The condo features:br- Primary bedroom with a king bed and private en-suite bathroombr- Second bedroom with a queen bed, also with its own en-suite bathroombr- Spacious living room with a sofa sleeper for extra guestsbrEach bathroom is well stocked and includes a bathtub and hair dryer for added convenience. brbrFULLY EQUIPPED KITCHEN & DININGbrThe efficient kitchen is perfect for preparing meals or light snacks and includes:br- Standard appliancesbr- Breakfast bar seatingbr- Keurig / drip coffee maker combobrPlenty of cookware, utensils, bowls, pots, and pansbrWhether you’re enjoying a quick breakfast or winding down with dinner, you’ll have everything you need.brbrPRIVATE LANAIbrThe open living room leads to your private lanai overlooking the tennis courts—a great spot to enjoy your morning coffee or unwind after a day at the beach .brbrPRIME END LOCATIONbrThis condo is an end unit on the 3rd floor, offering extra privacy and convenience. You’ll be just steps away frombr- Shared swimming poolbr- Tennis courtsbr- Fitness facilitybr- Shared laundry areabrbrIDEAL LOCATIONbr- Close to the beach and Key West International Airport brJust a quick Uber or drive to downtown Key West (approximately 2 miles) br- A small convenience store located within the Seaside complex, perfect for quick essentialsbr-Parking & ComfortbrParking for one vehicle includedbr-Central air conditioning and heating ensure year-round comfortbrbrRELAX, RECHARGE & ENJOYbrWhether you’re exploring the island, lounging by the pool, or savoring peaceful mornings on the lanai, this gorgeous condo offers the perfect blend of comfort, location, and tranquility.brbrWe look forward to hosting you and hope you enjoy your stay in beautiful Key West!

SEASIDE ESCAPE- 2 Bed/2 Bath Condo With Shared Pool & Parking

Key West, Florida, United States

Bed

Bath

Sleeps

$444.38

Welcome to the Hyatt Beach House, a Hyatt Residence Club, your own private sanctuary in Key West with crystal-clear water views and direct beach access. Enjoy the private beach, furnished with thick-cushioned chairs, picnic tables, barbeque grills and a private dock. Soak up the sun in the zero-entry lagoon shaped pool and hot tub.brbrWalk down stairs and enjoy the complimentary kayaking, gorgeous beach area and pool. Spend a wonderful week in the sunny Florida Keys!brbrThe space:brThis condo is 2 bedroom, 2 bathrooms and comes with a full kitchen, dining area and living room with balcony. The master bedroom has a King bed and the guest bedroom has a Queen bed. There is also a sleeper sofa in the living room. Max occupancy is 6 guests per unit.brbrComplimentary Wi-Fi access, in room washer and dryer, and on-site parking are also included.brbrHyatt typically offers complimentary, freshly brewed Starbucks coffee and an assortment of teas from 7:00 to 9:00 AM each morning in the lobby.brbrSpend your days relaxing by the lagoon-shaped pool with zero-entry end for easy access, or on Hyatt's private on-site beach. The heated pool is wheelchair accessible and open year-round.brbrThe Hyatt Beach House’s convenient location puts you just minutes from the free-spirited art, music and entertainment scene of Old Town. Or head over to nearby Smathers Beach, the biggest white sand beach in Key West to rent windsurfers or go parasailing. The keys are also a haven for anglers - shallow flats, mangrove islands, inland channels and open blue waters offer world-class fishing opportunities.brbrWhether you choose to spend your days simply relaxing by the lagoon pool or setting off on a diving adventure, Key West delivers a dream vacation of your own design. Your island home is just minutes away from celebrating the sunset each evening at Mallory Square and taking in the renowned dining, shopping and nightlife of Duval Street.brbrComplementary onsite parking is available at the Hyatt Beach House. Hyatt will issue a parking permit to you at Check-in. Parking is limited to one car per reservation. Reservations of less than 7 nights will be charged a fee of $80 payable to the resort for split week cleaning.brbrTrailer parking is available for a fee if you reserve a boat dock. The boat dock and trailer parking must be reserved directly with Hyatt Beach House in advance. I am not involved with the boat docks and/ or trailer parking.brbrThe Hyatt Beach House is located about 3 Miles from Key West's Historic Seaport District, Duval Street, Mallory Square, and the Sunset Pier. You can drive downtown and park. Alternately, you can take a taxi, Uber, or Lyft or you can rent a scooter or an electric vehicle.

2 bedroom Beach House Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$669.38

WEEK 39 PENTHOUSE UNIT D-51 ! 9/26--10/3/26.brEnjoy 7 nights in downtown Key West at The Galleon Resort!brbrThe Galleon Resort is located in the heart of Old Town Key West in the Historic Seaport District. This resort overlooks the Gulf of Mexico with a private marina, private beach, pool, hot tub, with a restaurant and tiki bar. Relax in the hot tub or workout in the onsite fitness center. Enjoy fishing off the dock, or rent bicycles and take in all that Old Town Key West has to offer.brbrMel Fisher Museum, Mallory Square and Duval St are just a 5 minute walk from this conveniently located resort. The Ernest Hemingway Home & Museum is 1 mile away.br.brWe have one week to offer in 2026 with guaranteed unit number as follows:brWeek 39, 9/26--10/3 is Unit D51 PENTHOUSE marina side unit. The 2nd bdrm here has two twins that can be pushed together to make a queen.brbrOverlooking the marina and historic seaport. This two bedroom condo sleeps six, and features a fully equipped kitchen. The primary suite has a king size bed, jetted tub, shower, two vanity sinks and large closets. The guest bedroom features either two twins and has access to the full guest bathroom with a shower. The living room has a TV with cable, dining area for six, and a queen sleeper sofa. Large balcony from the living room overlooking all of the boats & restaurants in the marina.brbrOther than the rent paid to VRBO, there will be a $80 resort fee to be collected by the front desk upon check in. This is in addition to the rent already paid. A $150 refundable security deposit is also secured on your credit card and is released by resort after checkout as long as no damages occur during your stay.brbrOne free mid week cleaning! Housekeeping changes linens and towels on Wednesday only at no additional charge. If daily housekeeping is desired, there is an additional fee imposed by the resort.brbrParking for one vehicle, per unit only. No oversized vehicles, RV's or trailers are allowed to park on property. Parking is extremely limited and multiple vehicles are not able to be accommodated.brbrMinimum Age: 21 years oldbrPet Policy: No PetsbrAn ID and credit card for a refundable security deposit will be required.brCheck-in is after 4 pm;brcheck-out by 10 am.brNo Smoking. Penalties will apply.brNon-Refundable Cancellation and Refund Policy:br$80 Resort Fee Due at Check-in *Pricing Subject to changebrGuest check-in certificate will be email to you directly from the resort once VRBO releases full payment to me, the owner.brPlease look over the lease document uploaded in VRBO.brbrNote that we do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service. Trip/Vacation insurance is highly recommended and may be included as part of VRBO's fees.brbrPictures are representative of the unit, layout and decor may vary.

WATERFRONT PENTHOUSE! Galleon Resort Key West, Sleeps 6, Private Beach

Key West, Florida, United States

Bed

Bath

Sleeps

$531.78

Open the door to Villa Serena and find yourself transported to a peaceful sanctuary. Villa Serena is the perfect space for your relaxing Key West vacation. Duval Square is located in the heart of Old Town Key West, yet is secluded away upstairs from the crowds. Delicious restaurants and unique shops are located in the quaint bricked courtyard below. A bright and sunny rooftop pool and pavilion area are just few steps from your front door. This home also offers one reserved parking space in the gated garage. brbrThe downstairs living area is decorated in soothing cobalt and beachy sand tones and provides plenty of space for entertaining. French doors lead out to a covered and private patio area. The kitchen features modern appliances and granite countertops.brbrUpstairs, the main bedroom is a calming oasis of dramatic wood tones and Caribbean blue accents. A spa-like ensuite bath features a large step in, pebble-tiled shower and generous vanity. A second balcony provides a private outdoor space to enjoy your morning coffee. The second bedroom features a queen size bed and another ensuite bath.brbrBedding: 1 King, 1 Queen.brbrElevator access from ground level to the first floor of the condos. Stairs to the unit's second floor bedrooms.brbr**Construction Disclaimer** From mid May through the month of June, 2026, the pool area will be under construction. This will create noise and dust that could impact your stay and may lead to pool closure as well.

VILLA SERENA@DUVAL SQUARE - A peaceful retreat in the heart of Old Town.

Key West, Florida, United States

Bed

Bath

Sleeps

$512.75

Open the door to Paradise Place and find yourself transported to a peaceful sanctuary. brbrThe downstairs living area is decorated with warm wood floors, blue and sand accents and provides plenty of space for entertaining. French doors lead out to a large covered and private patio area. The kitchen features modern appliances, clean white cabinets and a dramatic granite countertop that seats four for dining.brbrUpstairs, the main bedroom is a calming oasis of ocean blue green accents. A spa-like ensuite bath features a large step in shower and generous vanity. A second balcony provides a private outdoor space to enjoy your morning coffee. The second bedroom features a queen size bed and another ensuite bath.brbrDuval Square is located in the heart of Old Town Key West, yet is secluded away upstairs from the crowds. Delicious restaurants and unique shops are located in the quaint courtyard below. A bright and sunny rooftop pool and pavilion area are just few steps from your front door. This home also features one reserved parking space in the secure, gated garage.brbrBedding: 1 King, 1 Queen.brbrDuval Square Retreat is In the heart of Old Town. Duval Square is located at the artistic and quieter end of Duval Street. This recently upgraded unit is tastefully decorated with design elements from around the world. The first floor offers a well- equipped kitchen, and an open living and dining concept, French doors to a private balcony and a half bath powder room. brbrUpstairs, the main bedroom suite has a private balcony and ensuite bath. The second second bedroom also has an ensuite bath. brbrThere is central air conditioning and Wi-Fi internet. The complex's shared pool and sunning area overlooks world famous Duval Street. On the street level you will find a unique tree lined courtyard with restaurants and shops. While gated garage parking is provided here, all you really need is a bicycle for your main mode of transportation as you can walk or bike everywhere from Duval Square. brbrBedding: 2 QueenbrA shared, sun-drenched, rooftop pool and pavilion are just steps from your door.brbrThis is an unbeatable location offering easy pedestrian access to dozens of shops and restaurants, the Ernest Hemingway Home Museum and other notable local attractions, and of course the serene, turquoise ocean that the island is famous for. brbrGather your friends and family together and book a Key West vacation you will never forget at Duval Square Penthouse.brbrBeds: 3 Kings, 2 Twins, 1 Sleeper SofabrDuval Square is a charming community with shops and restaurants downstairs and secure, quiet, private residences, pool and pavilion upstairs. Although the condo includes one assigned parking space in the gated garage, you can stroll anywhere from this conveniently located condo. All of the shops, galleries, restaurants, and attractions on and around Duval Street and nearby beaches are just a leisurely stroll away. brbrWhen you enter the home you will find a fully equipped kitchen, dining area, spacious living room and a convenient half bath. French doors let in the natural sunshine and open to the private back deck with dining table and chairs perfect for outdoor entertaining. brbrOn the second floor, you will find 2 bedroom suites, each with their own private bathroom and an additional private balcony off the main suite.brbrBedding: 1 king, 1 queen, 1 queen sleeper sofa.brbrElevator access from ground level to the first floor of the condos. Stairs to the unit's second floor bedrooms.brbr1 Reserved Parking Space in the Gated Garage.brbr**Construction Disclaimer** From mid May through the month of June, 2026, the pool area will be under construction. This will create noise and dust that could impact your stay and may lead to pool closure as well.

PARADISE PLACE:A tastefully decorated space in the heart of Old Town Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$358.41

A Duck on the Green --This lovely, fully furnished, townhouse has two and a half bedrooms that sleeps up to five and two full baths . The two spacious upstairs bedrooms offer queen beds, dressers, and closet areas with a shared full bath. One full bath with shower and den/single bedroom are conveniently located downstairs. Wrap around screened porches overlooking the golf course and pond offer tranquil nature and wildlife views. This home offers a fully equipped new kitchen with dishwasher and microwave. Flat screen Smart TVs in the living room and each bedroom with cable and complimentary Wi-Fi service for access to Netflix, Amazon Prime, Hulu and Google Play, in addition to live TV. The upstairs bedrooms have privacy shades and room darkening drapes for napping/sleeping in on lazy mornings while on vacation. The screened in back porch from the living room is furnished with dining table and seating for six people for al fresco dining anytime to enjoy the tropical breezes. The brick paved back yard offers lush, tropical landscaping. Additional outdoor seating is located on the front porch. This home is located within the Key West Golf Club Community and offers a private gated entrance with 24 hour security services providing a safe environment for an evening neighborhood walk or use of the large waterfall pool and the exercise room/gym. These complimentary amenities are located just a short walk from your porch. An additional pool is located across the street from the home. Both pool locations offer complimentary Wi-Fi access.

A Duck on the Green at the Key West Golf Club

Key West, Florida, United States

Bed

Bath

Sleeps

$192.25

Southernmost Sanctuary is a beautiful two bedroom, one bath condominium has recently been updated located in the Shipyard Condominiums in the award winning Truman Annex. The charming master bedroom has a queen bed, flat screen tv and plenty of storage. | The guest bedroom has twin beds which can easily be converted to a king. | Enjoy the lovely granite counter tops and stainless steel appliances in the open theater style kitchen. | Relax and enjoy the rear covered deck which is just steps away from the refreshing community pool. | There is assigned off-street parking for one vehicle. brPlease note: This property will require a minimum of a 28 night stay.

Southernmost Sanctuary at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$495.96

Imagine waking up every morning to the sun rising over the Atlantic Ocean. That's what you will experience with this beautifully furnished three bedroom condo right on the ocean at Oceanside Marina. With direct views of the ocean from the living room, master bedroom and of course, your private balcony, you will never want to leave this quiet and peaceful enclave. There are touches of tropical whimsy everywhere, a constant reminder that you have arrived in America's Paradise. And it goes without saying that there are overhead fans in every room.brbrThe living area is bright and airy, with plenty of room to entertain. The kitchen is completely equipped with everything you would need to prepare the most ambitious meal. The dining area is surrounded by windows on three sides, with light shining in from all angles. French doors open onto the spacious ocean view balcony, which has comfortable seating as well as an outdoor dining set.brbrThe master bedroom has a queen size bed, walk-in closet and french doors to the balcony, with an in-suite bathroom furnished with twin vanities and a separate room for the toilet and oversize shower. The second bedroom has two twin beds, and the second bathroom also has an extra large shower. The third bedroom has a queen bed. All linens are provided, along with beach towels. brbrThe large pool and hot tub are situated right on the oceanfront; you'll have those cooling ocean breezes almost all the time. There are a generous number of chaises and tables with umbrellas. When you want to be on the ocean instead of just looking at it, you'll be glad to know that Oceanedge Marina is considered the best deep water marina in Key West. If you have brought your own boat, you'll be able to keep it at one the many dry slips or wet slips available. Stand Up Paddleboard, Kayak, Jetski rentals are available. Contact the Dockmaster @ 305-360-2909.brThe Yellowfin bar and restaurant is across the parking lot.br28 Day Min. RentalbrbrbrbrbrbrKeywords: Condominium

'Oceanside Oasis' Direct Ocean Views & 3 BR'S

Key West, Florida, United States

3

Bed

Bath

Sleeps

$141.37

Pool & Jacuzzi Resurfacing NoticebrbrPlease be advised that the pool and jacuzzi area will be closed for resurfacing beginning:brJuly 6th – August 30th (weather permitting)brbrThe entire pool and jacuzzi area will be fully closed off during this time to allow the contractor to safely complete the work.brThis project is part of our ongoing efforts to maintain and improve our community amenities for everyone’s enjoyment.brbrBeautiful top floor ocean front 2 bedroom 2 bath condo at La Brisa in Key West.brThe property has a queen bed in each bedroom and the master has an en suite bathroom. brTotally renovated Kitchen and a balcony with amazing Sunrise Views across Smathers Beach.brThe living room has a flat screen smart TV with streaming services and access to your ocean front balcony.brLa Brisa is a premier complex in Key West across A1A from Smathers Beach our large city beach.brJust about 1.5 mile to Downtown Key West and the Historic District. Perfect for a relaxing stay in paradise.brThe complex has a pool, jacuzzi, steam room, tennis court and BBQ facilities and your property has an assigned covered parking space.

The Crown Jewel of La Brisa 2 bdrm Monthly Spectacular ocean views.

Key West, Florida, United States

Bed

Bath

4

Sleeps

$356.73

STEPS TO DUVAL ST…brTake advantage of this premier opportunity to indulge in all your desired Key West bucket list items at this crisp condo centered in the heartbeat of Duval St. Located in the upbeat and lively district of Key West, this home is just steps to high end art galleries, museums, The Southernmost Point of the U.S. and all best nightlife action yet tucked away above the action for a peaceful evening's rest.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brThis island retreat resides on a second-floor level off Duval St. for incredible convenience to everything. Tile floors and a vaulted, open Great Room with a flat screen TV create a welcoming space for your happy hour before hitting the town. Enjoy an updated and fully equipped kitchen featuring granite counters, stainless steel appliances and bar seating for 3. brbrSLEEPING ARRANGEMENTS…brTotaling 2 bedrooms, this condo is equipped with 2 guest bedrooms to accommodate 4 people. Both rooms come with queen beds, closet space, ceiling fans and a shared bathroom featuring a shower/tub combination. One bedroom opens up to the outdoor balcony to catch your island breeze! brbrOUTDOOR LIVING…brStart your morning perched above an attractive, tropical courtyard area with your cup of coffee at the table for 2 while you plan the day’s activities. Make the most out of your vacation by being located in the heart of it all! brbrParking...brParking in the downtown area is a rarity but this gem features a parking space for a small to medium sized vehicle! Oversized SUVs and trucks will not fit. brbrPETS...brPets are considered except for puppies or barking dogs. A pet fee is required.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 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrTHE ULTIMATE KEY WEST EXPERIENCE!

JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!

Key West, Florida, United States

Bed

Bath

Sleeps

$867.37

Experience a tropical getaway designed in classic Key West style, o ering manicured gardens and panoramic views of the Gulf of Mexico. Luxurious touches include a magnificent free-form pool, white-sand beach and lush surroundings, with water sports, boating and shing just minutes away at private marinas nearby.brbrLush tropical beauty welcomes you to a spacious residential-style condominium featuring a master bedroom suite with king-size bed and adjoining bath with walk-in shower and jetted spa tub, and guest suite with king-size bed and full bath. Lavish amenities include fully equipped kitchen, dining area, living room, sofa bed, screened-in balcony, stereo, brbrDVD player and high-speed Internet. brRoom AmenitiesbrFlat Screen televisionbrBlue Ray/DVD PlayerbrSpa tubbrWalk-in showerbrHairdryerbrIron/ironing boardbrMakeup mirrorbrWasher and dryerbrDining areabrRefrigeratorbrMicrowavebrCoffee makerbrOvenbrDishwasherbrAdditional TV(s) in bedroom(s)brCable/satellite TV channelsbrStereo systembrRadio alarm clockbrVoicemailbrComplimentary WiFi Internet accessbrDataportbrTwo telephonesbrIndividual heat controlbrIndividual air conditioning controlbrCeiling fansbrWindows that openbrConcierge during regular hoursbrIn-room safebrSeparate sitting areabrFully equipped kitchenbrMaximum guests per room: 6brNon-Smoking Room & Balcony

Hyatt Residence Club - Key West, FL - 2 Bedroom Unit - Beach House Location!!!

Key West, Florida, United States

Bed

Bath

Sleeps

$588.58

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 Aqua is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway.brbrThe 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.

Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West

Key West, Florida, United States

Bed

Bath

4

Sleeps

$409.44

Escape to Above The Horizon, a stunning 3-bedroom retreat in the exclusive gated Truman Annex — just one block from the energy of Duval Street and moments from the waterfront at Truman Waterfront Park and beautiful Fort Zachary Taylor State Beach. Enjoy tropical garden views, two balconies, and a heated pool next to your garden patio in the heart of Old Town.brbrAbove The Horizon blends island charm, comfort, and history, offering the perfect sanctuary for an extended stay along one of the most beautiful streets in Key West. This lovely 3‑bedroom, 2 bath, multi‑level condo is just moments away from live music, waterfront sunsets, farmers markets, dining, and beach adventures — yet worlds away in your own peaceful oasis.brbrInside, the condo feels bright and open with vaulted ceilings, elegant island décor, and breezy tropical views. The main level features a king‑size master suite, a twin bedroom, laundry facilities, a spacious living and dining area, and a fully equipped kitchen. Upstairs, the aery spacious queen loft suite offers a private balcony surrounded by lush scenery, with a peek of the ocean — the perfect spot to sip wine as the sun fades into the horizon. brbrStart your day with coffee surrounded by blooming orchids in your private bistro garden, enjoy a refreshing dip in the heated pool just steps from your patio, or bike a few minutes to Fort Zachary Taylor Beach, known as Key West’s best. In the evenings, watch the sunset from the the Truman Waterfront, explore local restaurants and live entertainment, or simply unwind on your balcony under a blanket of stars.brbrPart of the original 1844 U.S. Naval Base Hospital, Above The Horizon offers an authentic connection to Key West’s storied past while providing every modern comfort — including parking, multiple verandas, and serene garden views.brbrWhether you’re here to relax, explore, or reconnect, Above The Horizon is more than a vacation rental — it’s your home in paradise.brbrPlease note: This property will require a minimum of a 28 night stay.

Luxury Truman Annex Condo I 3BDR I Pool & Parking I Walk to Duval & Beach

Key West, Florida, United States

3

Bed

Bath

Sleeps

$540.0

Welcome to Our Home Away from home. Our condo is located in the LaBrisa complex which is a GATED COMMUNITY across from Smather's Beach.brALL PHOTOS ARE CURRENT AND ACCURATELY DEPICT OUR SPOTLESS HOME.brRENTAL CALENDAR SHOWS NIGHTLY RATES- discount given for 7 or more nights.brbrOur tropical oasis is waiting for you to kick back and enjoy. Perfect for large families (the master bedroom has 2 full sized beds (that could accommodate 4 people), second bedroom has a queen sized bed, living room has a sleeper sofa. brbrFully equipped kitchen makes dining out an option rather than a necessity (gas grill bron site for barbeques). Wi-fi (bring your lap top), 3 flat screen TV's keep you in touch. You don't have to leave the property to enjoy the heated pool, whirlpool spa, sauna, tennis court, lounges and covered patio. Pool and whirlpool are available to guests 24 hours a day, great to take a midnight swim! brbrStep across the street and onto famous Smather's Beach (voted #6 of Florida's 10 best beaches by the travel channel)where you can relax in the shade of a palm tree or join in the many activities available. Smather's Beach is the largest in Key West; it boasts chair and raft rentals, food vendors, snorkeling, sailing, parasailing, paddleboarding and kayaking.brbrKeywords: Condominium, La Brisa Community, Sanitized

GATED OCEANFRONT CONDO AT SMATHER'S BEACH

Key West, Florida, United States

Bed

Bath

Sleeps

$200.11

This is an amazing second floor two bedroom TWO BATH condo over by the gorgeous pool. Fully equipped for you to enjoy your time away from it all. Enjoy mornings out on the rear deck overlooking the refreshing community pool. Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and close to 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. All properties are outfitted with washer/dryer, pots & pans, towels & linens, condo has central air conditioning, off street parking and community pool access. brPlease note: This property is monthly rental - the minimum rental period is 28 nights

Poolside Hangover at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$160.44

CONSTRUCTION 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.brbrLocated facing the tranquil lush courtyard at 1800 Atlantic. This spacious family retreat features a renovated kitchen. Both bedrooms and the living room open onto the expansive private balcony facing the tropical oasis.brFull size washer dryer & wireless. Guest bedroom features a queen bed. The Master Suite is set up more family style with a king, double and twin bed. Come and relax in this retreat and enjoy all the amenities of 1800 Atlantic. There is an olympic size heated pool. 20 person jacuzzi out by the pool. 3 Tennis courts one of which is clay. Fitness center and much more. We have secure parking and security. brWe have a small sunning beach area on property and are literally a 5 minute walk to Smathers Beach , Key West's largest beach. 2 miles from Downtown Key West and the Historic district.

Smith Families Southernmost 2 Bedroom retreat, Key West style beach vacation

Key West, Florida, United States

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Bath

Sleeps

$633.91

Welcome to the perfect location in old town Key West. Situated on the western side of the island, this resort is located near the Gulf of Mexico. Outside the property enjoy the charms of Duval Street and a nightly sunset celebration at Mallory Square. There are also many activities like diving, scuba or snorkeling, parasailing, fishing charters, boat tours, and more.brbrProperty amenities include: onsite washer and dryers, wireless internet access, pool, hot tub, and excellent location. Take a stroll or bike ride and enjoy the Truman Annex, The harbor, Mallory Square, Duval street and much more.brbrBike rentals available just outside the property on the Harbor walkwaybr.brWelcome to the perfect location in old town Key West. Situated on the western side of the island, this property overlooks the Gulf of Mexico. Outside the property enjoy the charms of Duval Street and a nightly sunset celebration at Mallory Square. There are also many activities like diving, scuba or snorkeling, parasailing, fishing charters, boat tours, and more.brbrThis 2 Bedroom, 2 Bath Condo sleeps 6, the primary suite has a king bed and connecting bath. The guest suite has a queen bed and full bath. This two-bedroom unit offers a fully-equipped kitchen, dining area, seating area with TV. The living room also features a sleeper sofa.brProperty amenities include: onsite washers and dryers, wireless internet access, pool, hot tub, and excellent location. Take a stroll or bike ride and enjoy the Truman Annex, The harbor, Mallory Square, Duval street and much more.brbrNearby attractions include Mallory Square - 4 minute walk, The Green Room - 4 minute walk, and Tree House - 5 minute walk.brbr- Parking is approximately $27 per day, or approximately $55 per week (subject to change)br- An ID and a credit card are required upon arrival for a refundable security deposit.brbr*Fees are subject to change.brbrStays of less than 1 week may require additional housekeeping for a fee.brbrWe do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service.

Sunset Harbor - Old Town Key West Location - Beautiful Property

Key West, Florida, United States

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