Vacation Condo Rentals By Owner In Key West, FL

$479.52

Island Breezes at the Truman Annex in Key West

Key West, Florida, United States

WEEKLY RENTAL - This property has the ability to be rented weekly.brThis charming second floor condominium features two bedrooms, and one full bath with views of the Truman Waterfront Park and the Florida Keys Eco Discovery Center.... | Located in the Shipyard within the award wining gated community of the Truman Annex, includes a community pool, off street parking and all of the amenities of home, including a laundry center. | The Truman Annex is conveniently located 2 blocks from Duval Street and Fort Zachary Taylor State Park and Beach and all of the Old Town Key West attractions. brPlease note: This property can be rented for a minimum of 7 nights.

Bed

Bath

Sleeps

$448.82

/ Nightly

Condo

A Harbour Roost at The Truman Annex in Key West

Key West, Florida, United States

This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water and sunset views from the large and luxurious pool area and large terraces. This beautifully decorated two bedroom, two and a half bath stately condo has wonderful views of the Atlantic Ocean and Sunset Key along the length of the Outer Mole pier which is adjacent to the beautiful Truman Waterfront Park... This community is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located 1 mile from one of the best beaches on the island. This unique property is outfitted with washer/dryer, pots & pans, towels; linens, central air conditioning, WIFI, off street parking and a gorgeous waterfront pool four comfortably...brbrPlease note: This property has a 28 night minimum stay

Bed

Bath

Sleeps

$185.5

/ Nightly

Condo

Almost Paradise at The Truman Annex in Key West

Key West, Florida, United States

Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The condos are located 2 blocks from Duval Street and all the Old Town Key West attractions. The properties are also ¼ mile from Fort Zachary Taylor State Park. This Shipyard home is a single level 2nd floor property with balconies. The property is outfitted with washer/dryer, pots/pans, towels, linens, have central air conditioning, off street parking, and pool access. brPlease note: This property has a 28 day minimum stay

Bed

Bath

Sleeps

$191.84

/ Nightly

Condo

**SERENITY ON SOUTHARD @ THE ANNEX** Condo Near Duval & Beach + LAST KEY SERVICE

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrSERENITY ON SOUTHARD is a beautifully renovated 1 bedroom second floor condo with a full kitchen and washer and dryer. This condo is located in the Truman Annex, a gated community located in the heart of the island - just steps from Mallory Square, Duval Street and all the attractions Key West has to offer. Yet, you'll have a peaceful retreat within a private gated community. Combined with Last Key Realty’s renowned Five-Star Guest Services, SERENITY ON SOUTHARD is an idyllic home base for your stay in paradise.brbrTHE LOCATION...brbrTruman Annex is a private, gated community right in Old Town, Key West. You'll be just a few blocks from Mallory Square, Duval Street and all the restaurants, shopping, and attractions of Old Town, yet you'll benefit from the peace and quiet that Truman Annex is known for. Although you won't need a car to get around from this excellent location, there is a reserved off-street parking space.brbrTHE LIVING AREA...brbrThe living room of has a large set of French doors so you can enjoy those wonderful tropical breezes, and a large flat screen TV for those evenings when you need a break from the excitement of Old Town. The kitchen has everything you’ll need to prepare meals at home. Across from the kitchen is a versatile multi-level counter with bar seating and a work space with an office chair. You'll be able to dine outside on the sunny back deck using the outdoor dining set with seating for four.brbrTHE COMMUNITY POOL & FORT ZACHARY TAYLOR STATE PARK...brbrThe community pool is located just around the corner, with chaises and a cabana with restrooms. Or you can walk to Fort Zachary Taylor State Park, with the prettiest beach in Key West, just a half mile from your front door. The entrance to Truman Annex is secured by a 24-hour staffed guard gate and you can use the residential entry gate keys to come and go on foot at night.brbrCompliance with Truman Annex Community Rules & Regulations is expected of all Last Key guests. This includes “Quiet Time” in all outdoor areas, public and private, after 10PM.brbrTHE ACCOMMODATIONS...brbr** Master Suite: King bed, flat screen TV, and access to the hall bathroom with a shower and tub combo.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchen (no dishwasher)br** 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** Community Pool Accessbr** Assigned Off-street Parking for 1 Car (with vehicle restrictions - no vehicle over 18’ long or 80’’ wide)brbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 2 adultsbr** No Pets Allowed

Bed

Bath

Sleeps

$393.37

/ Nightly

Condo

Atlantic Parrot | Oceanfront Condo w/ Pool

Key West, Florida, United States

This vibrant beachfront condo is the perfect home base for soaking up the sun and sea breezes of Key West. Located directly along the shoreline, this colorful coastal escape pairs relaxed island style with unbeatable ocean views, creating an inviting retreat just moments from beaches, bike paths, and iconic island attractions. With resort-style amenities and a private balcony overlooking the water, this condo sets the tone for a memorable Florida Keys getaway.brbrThe Ambiance:brDesigned with an open and airy layout, this fourth-floor condo offers plenty of space to unwind after a day in the sun. Step out onto your private ocean-view balcony to enjoy morning coffee or sunset skies over the Atlantic. Inside, the living area is bright and welcoming, complemented by a fully equipped kitchen and updated furnishings. The cheerful décor and beachy palette reflect the laid-back rhythm of island living.brbrGuest Perks:brGuests enjoy access to a variety of shared resort amenities, including a large outdoor pool, relaxing hot tub, fitness center, and on-site tennis courts. A digital E-lock provides secure, contactless entry with a unique code for each stay. The condo includes air conditioning, WiFi, and one designated parking space in the building's garage (parking fees apply). Whether you're lounging poolside or heading out for a day of adventure, convenience is built into every detail.brbrNeighborhood Highlights:brWith the Florida Keys Overseas Heritage Trail right outside the building, exploring the island is effortless. Bike or walk to Smathers Beach just steps away, or head west to the popular spots at Higgs Beach, including the pier and historic West Martello Tower. Old Town Key West attractions like the Ernest Hemingway Home and Museum and Mallory Square are just a short drive away, offering endless dining, shopping, and cultural experiences.brbrGetting Around:brOne vehicle parking is available on-site for an additional fee, making day trips and excursions simple. Explore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the property. This area is ideal for biking and walking, with direct access to scenic paths along the beach. Guests can easily reach beaches, parks, and attractions without needing to drive far. Feel free to ask for local recommendations!brbrOther Things to Note:br- This home is located in a noise-sensitive area and participates in a Good Neighbor programbr- Quiet hours are enforced from 10:00 p.m. to 8:00 a.m.br- No smoking is permitted anywhere on the premisesbr- No pets are allowedbr- Guests must be 25 years of age or older to rentbr- This rental is located on the 4th floorbr- One parking space is available for a feebrbrCheck-in time is 3:00 PMbrCheck-out time is 11:00 AMbrbrBook your stay today and enjoy beachfront living with resort-style amenities in one of Key West's most scenic coastal locations. Whether you're here to relax by the pool, bike along the shoreline, or explore the island's historic charm, this colorful oceanfront condo offers the perfect blend of comfort, convenience, and coastal adventure.brbrAt Colocada Vacation Rentals, we're committed to providing a smooth, relaxing, and unforgettable Key West experience. Have questions or need local tips We're always happy to help make your stay

Bed

Bath

Sleeps

$448.82

/ Nightly

Condo

Sunset Dalite at The Truman Annex in Key West

Key West, Florida, United States

Enjoy the breathtaking views of the Atlantic Ocean and the Gulf of Mexico from your front row seat! This gorgeous condominium has been tastefully updated with newer countertops, appliances, furniture, and linens. Both bedrooms enjoy waterfront views, one features a king sized bed and the other can be 2 twins or converted to a king. There is a relaxing balcony off of the living room and primary suite to take in the famous Key West sunsets. The inviting waterfront pool complex and gardens are unrivaled in Key West! There is covered parking for one vehicle. This Harbour Place condo is conveniently located in award-winning Truman Annex in the Heart of Old Town Key West, about 3 blocks from fabulous activities, shops and restaurants on Duval Street.brPlease note: This property has a 28 night minimum stay

Bed

Bath

Sleeps

$624.61

/ Nightly

Condo

A Gulfstream Drift at The Truman Annex in Key West

Key West, Florida, United States

Imagine yourself watching the sunset over the ocean from the huge penthouse balcony. This tropical retreat in Paradise has 2000 square feet of living space providing plenty of room for comfort and entertaining. The three large bedrooms have ocean views with en suite bathrooms in the master and king guest bedrooms. The third bedroom has a queen & one twin bed. The property is fully furnished and professionally decorated in a tropical theme complete with central AC, kitchenware, linens, TV, radio, cable internet with wifi, and a work desk in each bedroom. Other amenities are an elevator, covered private parking, nearby community pool and local professional management. This Harbour Place condo is conveniently located in prestigious Truman Annex in the Heart of Old Town, about 3 blocks from fabulous activities, shops and restaurants on Duval Street and about 1/4 mile from Fort Zachary Taylor State Park. This is Key West living at its finest for a vacation you will treasure.brPlease note: This property has a 28 night minimum stay

Bed

Bath

Sleeps

$448.82

/ Nightly

Condo

Aqua Breeze at the Truman Annex in Key West

Key West, Florida, United States

This two bedroom condo is located in the Truman Annex, Key West's premier residential community in Harbour Place on the Atlantic Ocean front. All major rooms and the balcony have a great view of the ocean and Westin Marina. Harbour Place has a large heated swimming pool directly on the ocean exclusively for Harbour Place residents. These are the largest condos in Truman Annex, and this unit has one assigned covered parking spot in case you have a car, which is not needed with the perfect location within Old Town Key West, as it is only a couple of blocks to Duval Street, Mallory Square, and very close to the world famous natural Fort Zachary Taylor State Park Beach. There is one King bed, and the guest room twins can be converted to a King bed if desired. Just let us know and the cleaner will have it set up for you prior to arrival. Complimentary wireless internet provided for your convenience. Each bedroom has TV's and there is a nice flat screen TV in the living room. All kitchen amenities included, so just pull some ice from freezer and make up a nice pitcher of tea while relaxing and watching the sailing ships along the island filled horizon.brPlease note: This property has a 28 night minimum stay

Bed

Bath

Sleeps

$411.18

/ Nightly

Condo

Royal Poinciana >>WEEKLY RENTAL! Truman Annex in Key West

Key West, Florida, United States

WEEKLY RENTAL - This property has the ability to be rented weekly all year long.brNestled in the heart of Old Town Key West within the sought-after Shipyard community, this inviting second-floor condo offers the perfect blend of comfort, privacy, and island charm. Featuring one bedroom and one bath, this custom unit boasts beautiful built-in cabinetry, a well-equipped kitchen, and two private balconies ideal for enjoying morning coffee or evening breezes.brThe properties are also located ¼ mile from one of the best beaches on the island. The Shipyard units in the Truman Annex are single level condominiums which have private courtyards on the first level or balconies on the second level. This property is fully outfitted with washer/dryer, pots and pans, towels and linens, has central air-conditioning, off-street parking and community pool access. brSurrounded by lush tropical landscaping, the Shipyard is a gated community offering residents a peaceful retreat with amenities like a shared swimming pool and designated parking. Just steps from world-famous Duval Street, the Historic Seaport, restaurants, shops, and galleries, this condo is perfectly positioned for enjoying all that Key West has to offer.

Bed

Bath

Sleeps

$866.68

/ Nightly

Condo

An Ocean Serenity at the Truman Annex in Key West

Key West, Florida, United States

A luxury, ocean front, 2 bedroom, (king in master, queen in guest bedroom) 2.5 bath condo at Harbour Place in the award winning Truman Annex in Old Town Key West. This second-floor condominium features spectacular Key West sunsets. Overlooking the Atlantic Ocean, and the Gulf of Mexico, it is a short walk to The Truman Waterfront Park, Duval Street and all the venues Key West is famous for. Dishwasher, washer, dryer, pots, tableware, towels and linens, central air, covered assigned parking and pool access. Wall mounted flat screen TV's in each bedroom. Walk or bike anywhere in Key West. Only two blocks from Duval Street and still enjoy the quiet atmosphere of the luxury condo. A quarter mile to one of the best beaches in Key West.brPlease note: This property has a 28 night minimum stay

Bed

Bath

Sleeps

$764.04

/ Nightly

Condo

American Shoal Light Suite

Key West, Florida, United States

Summary:brbrLuxury 2BD/1BA Suite with Two Oasis Pools, Pergola, Outdoor Bar and Grill and Private Patio.brbrbrbrThe Space:brbrEscape the Ordinary....brbrbrbrThe American Shoal Lighthouse Suite offers separate King and Queen bedrooms and was completely refurbished in 2024 that can sleep up to 6 guests. This beautifully appointed ground floor suite, located in a renovated 1930’s Historic Key West building, offers a private exterior entrance and a spacious private outside patio area offering Key West Lighthouse views tucked away on a quiet Key West Lane. The Suite is located steps away from the two brand new oasis pools and brand-new amenities on the property.brbrbrbrSuite Amenities:brbrbrbr• Luxury king and queen beds with premium linensbrbr• Full sized sectional couch with pull out bedbrbr• Fully equipped kitchen with granite countertopsbrbr• Spa quality stone rain shower bathroombrbr• Hardwood flooring throughout the suitebrbr• Spacious back porch with dining tablebrbr• Smart TVs with the latest Roku device for apps and streamingbrbr• High-speed Fiber Wi-Fibrbr• Washer and dryerbrbr• Luxury well-appointed furnishing and artworkbrbr• Reserved parking space for one vehiclebrbr• Luggage hut to store luggage and belongings in before check in or after check outbrbrbrbrLocation:brbrThe American Shoal Lighthouse Suite offers the perfect blend of convenience and tranquility, located just a half-block from world-famous Duval Street. While you’re steps away from the vibrant energy of Key West’s best shops, restaurants, and nightlife, the resort is tucked away on a peaceful, picturesque lane, providing a quiet retreat. The iconic Hemingway House Museum, just behind the property, is only a 2-minute walk away, and Fort Zachary Taylor Park and Beach are also within easy walking distance. Experience the best of both worlds—close to the action, yet an oasis of peace and quiet.brbrbrbrAbout the Property:brbrWelcome to The Lighthouse Suites Collection, an exclusive six-unit luxury vacation rental resort offering in the heart of historic Old Town Key West. Just steps from Duval Street and a short walk to Fort Zachary Taylor Park beach, our location places you at the center of Key West’s most iconic attractions and vibrant nightlife.brbrbrbrThe Lighthouse Suites Collection is truly one of a kind. This mini resort is defined by its luxurious suites, on-site parking, and exceptional location. Our immaculate 5-star accommodations are enhanced by a unique outdoor experience featuring two tropical oasis pools with spacious pool decks, a pergola with a cozy seating area and fire pit, and a fully equipped outdoor kitchen and BBQ grill with a Brio filtered water and ice maker station.brbrbrbrWhether you’re planning a romantic escape, a memorable family vacation, or an unforgettable group retreat, the Lighthouse Suites Collection offers the ultimate Key West experience, blending luxury, comfort, and first-class amenities.brbrbrbrIn March 2025, we completed a full renovation of our outdoor common areas, exclusively accessible to guests of our six suites.brbrbrbrThe property now features two brand-new oasis plunge pools, each with its own sundeck, offering the perfect spot to sunbathe or unwind by the pool. Guests can relax on our teak chaise loungers or indulge in one of our two luxury double chaise cabanas. We also added a 200-square-foot pergola, separated into two areas: one half features a cozy seating area with a swing and fire pit, perfect for enjoying an elegant evening cocktail. The other half houses a fully equipped outdoor kitchen, complete with a BBQ, sink and two refrigerators. To top it off, the kitchen includes a Brio filtered water and ice maker system to keep you hydrated on warm Key West days.brbrbrbrProperty Amenities:brbrbrbr• Two brand-new heated oasis plunge pools, each with waterfalls and pool showerbrbr• Brand-new spacious pool decks around each poolbrbr• Six luxury teak chaise loungers with umbrellas and pillowsbrbr• Two brand-new double chaise luxury resort cabanas seating two guests eachbrbr• Two in-pool chaise ledge loungers to sunbathe and cool off simultaneouslybrbr• A brand-new 200 SF teak pergola with a louvered open or closed ceilingbrbr• Luxury couch and daybed swing under the pergola with an elegant fire pitbrbr• Fully equipped outdoor bar, BBQ grill with a sink and fridge under the pergolabrbr• Covered bar kiosk for enjoying a cocktailbrbr• Key West tropical foliage throughout the property with lighted step-stone pathsbrbr• Exclusive on-street parking spaces with room for six vehicles and 1 per suitebrbr• Schlage smart lock security on all Suites and gate access to the propertybrbrbrbrGroup Accommodation:brbrIf you need more room for your party, contact us about renting one or more suites for your stay. We have 3, two-bedroom suites, 2, one-bedroom suites, 1, one-bedroom bungalow accommodating a maximum of 30 guests. The property is perfect for weddings, other large gatherings, and events.brbrbrbrFrequently Asked Questions:brbr1. Are the pools and amenities shared brbrYes, the 6 Suites share all the amenities above which are exclusive to only guests staying with us on property and is secured with smart locks on the gate access to the property common areas.brbrbrbr2. What is the parking situation Can I bring more than one vehicle brbrParking in Key West can be challenging, but we’ve made it easier for our guests. Our property includes five reserved parking spaces and one exclusive off-street parking space for the Carysfort Light Suite, all conveniently located on Eanes Lane, right next to the Suites. Each space is clearly marked with signage along the buildings.brbrbrbrWe can accommodate one vehicle per suite. If you rent multiple suites, you’ll be assigned the corresponding number of parking spaces. For your convenience, a property map showing the location of all six parking spaces is included in the photos. Additionally, we will send the property and parking map in your welcome packet for easy reference.brbrbrbr3. Where is my Suite located brbrPlease refer to the property map in the pictures, which will show you the location of your Suite on the property. All three properties are adjacent to each other and the property is fenced in with smart lock gates.brbrbrbr• The Alligator Reef (2BD, 1BA), American Shoal (2BD/1BA), Sombrero Reef (1BD/ 1BA), and Tortugas Harbor Suites (1BD/ 1BA) are located at 419 Truman Avenue in the same historic building, with Sombrero Reef and Tortugas Harbor Suite located upstairs.brbrbrbr• The Key West Lighthouse Suite is a separate individual queen bungalow with a loft featuring a queen bed, located at 215 Eanes Lane.brbrbrbr• The Carysfort Light Suite is a separate individual 2BD/ 2BA with its own exclusive off-street parking space, located at 217 Eanes Lane.brbrbrbr4. Do I need a vehicle or transportation brbrIf you have a vehicle, we have rare parking available that most lodging on the island cannot offer but you do not need a vehicle to enjoy your stay with us. The property is located one-half block off Duval Street on quaint and quiet Eanes Lane delivering one of the best lodging locations on the Island close to everything but in a peaceful and quiet location. Here are the distances to some Key West Landmarks:brbrbrbr• Key West Lighthouse Museum, 2-minute walkbrbr• Ernest Hemingway Home and Museum, 2-minute walkbrbr• Blue Heaven Restaurant, 5-minute walkbrbr• Southernmost Point Buoy, 8-minute walkbrbr• Key West Butterfly Conservatory, 8-minute walkbrbr• Sloppy Joe’s Bar, 12-minute walkbrbr• Key West Amphitheater and Park, 12-minute walkbrbr• Mallory Square Sunset, 12-minute walkbrbr• Fort Zachary Taylor State Park & Beach, 12-minute walkbrbrbrbrWe look forward to welcoming you to paradise!

Bed

Bath

Sleeps

$576.66

/ Nightly

Condo

TortugasHarbor Light Suite

Key West, Florida, United States

Bed

Bath

Sleeps

$464.64

/ Nightly

Condo

WINTER WEEK - KEY WEST - 2 Bedroom 2 Bathrooms Sleeps 6

Key West, Florida, United States

The Coconut Mallory Marina Resort - KEY WEST 2 Bedrooms 2 Bathroom Sleeps 6 Total. brbrThe Coconut Mallory Marina and Resort is located in the southernmost city in the continental United States. Key West, Florida was originally known as the primary base of operation against pirates many years ago.brbrAmenities at the Coconut Mallory Resort in the Conch Republic include seaside resort amenities, such as two swimming pools, Jacuzzi and BBQ area. In addition, the resort features a marina with a limited number of boat slips available for rent during your stay. If you are looking to sightsee, Coconut Mallory Resort s guest services desk is onsite to help arrange all island activities.brbrToday you can visit historic Fort Jefferson, the largest brick building in the Western Hemisphere, and the Dry Tortugas National Park. The Key West Shipwreck Historeum recreates the wreck and salvage of artifacts from ships long since past. There are a wide array of museums and attractions in Key West, including the Key West Aquarium, the Lighthouse Museum, the Audubon House and Gardens, and the Ernest Hemingway Home and Museum. Also, do not forget to take a Conch Tour Train for an informative narration about the area history throughout the old and new Key West.brbrDELUXE 2 BEDROOM CONDObrbrThis is a 2 bedroom, 2 bathroom condo unit that features a full kitchen and a flat panel television. All newly refurbishment and decorated in an island inspired elegance. The unit also has a private balcony, access to both resort pools, and the resort marina. Maximum occupancy of six.brbrEach unit features:brbrFull size kitchen ( Two Bedroom Units) with oven, stove, refrigerator/freezer, dishwasher, microwave, coffee pot, blender, toaster, pots/pans, dishes/silverware; everything you need to prepare your favorite gourmet meal…just add groceries!brbrLiving room with comfortable seating, TV with cable, & DVD player.brbrBalconies or patios to enjoy the natural surroundings.brbrTelevision with cable & alarm clock in each bedroombrbrHigh quality linens & towelsbrbrTelephonebrbrIronbrbrIroning BoardbrbrAccess to both resort poolsbrbrFree Wireless Internet in the public areas of the resortbrbrMarina, boat slips available for rental onsite at Average $55. Per week. Need to be reserved with the resort front desk in advance to guarantee your spot.brbrAll units Non-SmokingbrbrLinens & Towels ProvidedbrbrPaper productsbrbrBath soap, shampoo, & lotionbrbrView less

Bed

Bath

Sleeps

$687.34

/ Nightly

Condo

Luxury Waterfront at Galion Resort in Old Town

Key West, Florida, United States

This condo is a 2BR/2BA Penthouse Loft on the 5th floor overlooking the marina. On the first floor is a full sized, fully equipped kitchen, breakfast area, dining room, living room and the master bedroom & bath. The second floor has an open loft which overlooks the living room, the second bedroom & bath. This unit will sleep a total of 8, with a king bed in the master, a queen bed in the second bedroom and loft & a queen pullout in the living room. The balcony is accessible through French doors from both the living room and the master bedroom. Also included for your convenience are 4 TVs with cable, DVD player, washer/dryer, iron & ironing board, in room safe, wet bar and free wireless Internet. During September, this condo received a new kitchen, wet bat and entertainment center in both the living room and the master bedroom.

Bed

Bath

Sleeps

$219.08

/ Nightly

Condo

Pierre's Perch: Discover Charm and Convenience, Perfect Studio Retreat in Key West with Shared Pool

Key West, Florida, United States

Welcome to Pierre's Perch, a beautiful second-floor studio that blends modern design with tropical charm! brbr brbrLocated in the historic Galleria, once a haven for Key West’s traveling artists, this tranquil oasis includes a peaceful pool area and a spacious sundeck perfect for unwinding. Nestled in the heart of Bahama Village, a vibrant, residential neighborhood just blocks from Duval Street, you’ll be surrounded by Bahamian-inspired charm and within walking distance to iconic attractions like the Southernmost Point, Key West Lighthouse, and the Earnest Hemingway Museum. Whether you’re here to relax, explore, or find inspiration, Pierre's Perch offers the perfect home base for your Key West adventure! brbr brbrSLEEPS MAXIMUM OF 2 GUESTS: brbr brbrBedroom: Queen Bed, Flat Screen TV brbr brbrKitchenette: Lightly Equipped (mini refrigerator/freezer, sink, two-burner stove, microwave and Keurig) brbr brbrAMENITIES: brbr brbr- Shared Heated (Nov-Apr) Pool brbr brbr- Shared Laundry brbr brbr- Shared Bike Rack brbr brbr- Shared Propane BBQ Grill brbr brbr- Keurig brbr brbr- Linen's and Bath/Beach Towels Provided brbr brbr- Street Parking available, no off-street/designated parking available brbr brbr- 2.5 blocks to Duval Street brbr brbr- 0.4 miles to Southernmost Point brbr brbr- 0.7 miles to Fort Zachary Taylor State Park/Beach brbr brbr- 1.1 miles to Mallory Square Sunset Pier brbr brbr- 1.2 miles to Key West Historic Seaport brbr brbr- 2.6 miles to Smathers Beach brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrUnit Size: Please be aware, this unit is a cozy 115 sq. ft. studio—while compact, it provides all the essentials for a comfortable and enjoyable stay. brbr brbrAge and Occupancy Requirements: Booking tenant must be 25 years of age or older and must occupy the property for the entire duration of the booking. Furthermore, this property is exclusively available as a vacation rental and is not available for worker housing. brbr brbrNo Smoking: Smoking is strictly prohibited within the property to maintain a smoke-free environment for all guests. brbr brbrNo Pets: Pets are strictly prohibited within the property to maintain a pet-free environment for all guests. 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. brbr brbrSecurity Cameras: For the safety and security of guests and property, exterior security cameras monitor all exterior areas of the complex. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.

1

Bath

2

Sleeps

Exceptional(20)

$448.82

/ Nightly

Condo

Ocean Breeze at The Truman Annex in Key West

Key West, Florida, United States

Gorgeous open water views from this 2-bedroom, 2.5 bath condominium in Harbour Place in the award-winning Truman Annex! | Directly facing the ocean, where the Gulf of Mexico and Atlantic Ocean meet, this nicely furnished condominium enjoys a large waterfront plaza with chaise lounges and front row seating for sunset. | There is a beautiful community pool, covered off street parking and convenient access to Mallory Square! | The Truman Annex is a gated community, in the heart of Old Town with a quick walk to Duval Street, shopping, dining and watersports!brbrPlease note: This property has a 28 night minimum stay

Bed

Bath

Sleeps

$608.86

/ Nightly

Condo

Catch of the Day at The Truman Annex in Key West

Key West, Florida, United States

View passing ships and sunsets from your own first floor, large deck with plenty of seating for a large family in the Truman Annex's most prestigious building, the former U.S. Naval Headquarters in Key West. brTake in the sunshine from the refreshing pool overlooking the ever-changing waterfront. Just steps from the sights and sounds of Mallory Square, downtown tourist attractions, Key West's best beaches, and Old Town's fabulous restaurants. brThe three large bedrooms have ocean views with ensuite bathrooms in the primary and guest bedrooms. The property is fully furnished and professionally decorated complete with central AC, kitchenware, linens, cable TV & WIFI. brThis Harbour Place condo is conveniently located in prestigious Truman Annex in the Heart of Old Town, about 3 blocks from fabulous activities, shops and restaurants on Duval Street and about 1/4 mile from Fort Zachary Taylor State Park. brThis is Key West living at its finest for a vacation you will treasure for a lifetime.brbrPlease note: This property has a 28 night minimum stay.

Bed

Bath

Sleeps

$192.25

/ Nightly

Condo

SOUTHARD COMFORT at The Truman Annex in Key West

Key West, Florida, United States

LOCATION, LOCATION, LOCATION! Southard Comfort is on Southard Street in the TRUMAN ANNEX, which is one of the most beautiful peaceful retreats and uniquely close to everything, Key West. We are only two blocks from the main Duval Street with it’s bustling shopping, bars, restaurants, & nationally renowned entertainment spots. Southard Comfort is one block from the infamous Green Parrot and is walking and biking distance to everything you will require for a comfortable stay. There is the Truman Waterfront Park for the children with beautiful sunset and water views just a hop away.brAs one of our first guests to enjoy value and comfort in our refreshed, 2 bedroom 1 bath, 2nd floor condominium. You can enjoy televisions in every room, unlimited WIFI, USB charging stations, Keurig and drip coffee makers, washer and dryer, dual balconies and even a front porch. Southard Comfort comes equipped with a light and bright queen bedroom and twins (or King if combined) in the guest room. The condo has been freshly painted, updated and fully air-conditioned and all rooms have tropical ceiling fans. The balconies are situated to provide a wonderful open-air feel and cross breeze. The linens are new, including beach and pool towels. The full kitchen has a large refrigerator, stove with oven, microwave, blender, pots, pans and all the dishes necessary to enjoy a long stay. brKey West boasts an average daily temperature of 82 degrees keeping the ocean water temps at around 80. The Truman Annex SHIPYARD is a clean and safe hideaway, with parking for one car, near all the fun in Key West. Southard Comfort is directly on the parade route for Fantasy Fest and is ideal for couples, families, and seniors. 28 night stay minimum.

Bed

Bath

Sleeps

$183.48

/ Nightly

Condo

Sailor's Sanctuary - A Renovated Condo in Old Town

Key West, Florida, United States

Renovated ground floor apartment in Truman Annex. Steps from Duval Street! Enjoy all that the beautiful gated community has to offer including a large pool with lounge chairs and sitting areas. This two bedroom unit is a private, 1st floor entry that boast tons of natural light. The unit was just completed renovated and includes a large Samsung washer and dryer, Keurig Coffee Maker, Secure Keyless Entry, a parking spot specific to the unit, and more! Walking distance to Truman Waterfront Park. brbrThis unit is in a gate community with 24 hour security. In addition to being just steps from the heart of Duval Street and Truman Waterfront park, you are also walking distance to Mallory Square, Fort Zachary Taylor, Hemingway Home, Historic Waterfront Seaport, the Southernmost Point of the United States and all of the best Key West attractions. You really can't find a better location in Old Town Key West!

Bed

Bath

Sleeps

$167.37

/ Nightly

Condo

Atlantic Escape Luxury Oceanview Key West Condo resort style amenities

Key West, Florida, United States

Atlantic Paradise Escape | Luxury Oceanfront Condo in Key WestbrbrMonthly Rental | Unit MC322 | 2BR, 2BA | Direct Ocean Views | Assigned ParkingbrbrWelcome to Atlantic Paradise Escape—your private island sanctuary nestled within the exclusive 1800 Atlantic Condominiums in Key West. This elegantly renovated 2-bedroom, 2-bath oceanfront condo offers all the luxuries of a boutique hotel with the comforts of home, designed for extended monthly stays.brbrEnjoy direct ocean views, two spacious King Suites, and resort-style amenities, just steps from Smathers Beach. Tropical Luxury, Thoughtfully Designedbrbr Expansive Ocean Views from the living room and both bedrooms through floor-to-ceiling sliding glass doorsbr Private Balcony with outdoor seating—perfect for morning coffee or sunset cocktailsbr Two King Suites with high-thread-count linens, blackout curtains, and generous closet spacebr Spa-Inspired Bathrooms with upscale finishes, rainfall showerheads, and custom tilebr Curated Artwork & Designer Touches throughout the homebr Gourmet Kitchen with quartz countertops, stainless appliances, and fully stocked dishware and cookwarebr Smart TVs in Every Room, high-speed Wi-Fi, and streaming-ready cablebr In-Unit Washer & Dryer for convenience during long staysbr Accommodates up to 6 guests comfortablybr Assigned Parking Space includedbrbr Luxury Amenities at 1800 Atlanticbr Olympic-Size Heated Pool overlooking the Atlantic Oceanbr Jacuzzi, Sauna & Modern Fitness Centerbr Three Lighted Tennis Courts, including a professional-grade clay courtbr Racquetball Court, sun decks, and tropical garden pathwaysbr 400 ft. of Private Oceanfront Access with sun loungers and palm-shaded spotsbr Direct Beach Access to Smathers Beach (just a 5-minute walk)br Outdoor BBQ Grills & Picnic Areas for al fresco diningbr Secure Building with elevator access and on-site managementbrbrYour Private Retreat AwaitsbrWhether you're a snowbird escaping the winter chill, a remote worker in need of serenity, or a family ready for a coastal recharge, Atlantic Paradise Escape is your perfect home base in Key West.brbrContact us today to reserve your month in paradise.

2

Bed

2

Bath

6

Sleeps

Vacation Condo Rentals By Owner In Key West, FL

$479.52

$448.82

$185.5

$191.84

$393.37

$448.82

$624.61

$448.82

$411.18

$866.68

$764.04

$576.66

$464.64

$687.34

$219.08

$448.82

$608.86

$192.25

$183.48

$167.37

Rent a place that suits your needs

Most popular vacation rentals in Key West

$2606.88

$2168.85

$2179.76

$2193.75

$2377.08

$2433.36

$2489.04

$2519.19

$4253.21

$3363.07

Most Popular Cities in Florida