Vacation Villa Rentals By Owner In Key West, FL

This gorgeous townhouse has 4 bedrooms, 4 full Bathrooms, and 2 half bathrooms. It is unique in that it has 2 of everything, 2 kitchens, 2 living rooms, 2 dining areas, and back patios. Two of the bedrooms have queen size beds, two bedrooms have 2 twin beds,which can be converted to King beds with a converter kit upon request and there are 2 sleeper sofas. The community pool is just out your back door. brbrPlease note: This property has a 28 night minimum stay

Archipelago at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$420

Two Bedroom and 2 and Half Bath beautiful condo in great private Coral Hammock community, close to Golf Course and short Bike ride to beaches and Key West famous downtown. Access to pool in private Coral Hammock community.brHouse has all new bedding, 3 flat screen tv's with cable and internet (wireless), access to pool, rental bikes available close by, bike ride to town and all nightlife and beaches, marina and of course golf. Perfect for family and friends to visit. Full kitchen, quiet and clean. One Bedroom has two twin beds, one bedroom has a queen bed, the couch in living room pulls out for a full size bed.

Key West - Stock Island

Key West, Florida, United States

Bed

Bath

Sleeps

$448.82

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

Aqua Breeze at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$459.16

Welcome to Be Still – Your Private Island Oasis in Key WestbrbrNestled on an oversized corner lot just a few blocks from White Street Pier and Higgs Beach, Be Still is a beautifully gated home offering the perfect blend of privacy, luxury, and island charm. With ample parking—including gated off-street spaces—this spacious retreat is ideally positioned between Old Town and New Town, making every part of Key West easily accessible.brbrMAIN HOUSE – 3 Bedrooms | 2 BathroomsbrbrPrimary SuitebrKing-size bed, 43” smart TV, en-suite bathroom with Jacuzzi tub, spacious closet, and private access to the pool deck.brbrGuest Bedrooms (2 & 3)brEach features a queen-size bed, 43” smart TV, and large closets.brbrBATHROOMSbrBoth bathrooms include whirlpool/Jacuzzi tubs and modern fixtures.brbrGOURMET KITCHEN & LIVING SPACEbrbrSolid wood cabinets, Corian countertops, and fully stocked with kitchen essentialsbrbrBuilt-in work station—ideal for remote work or e-learningbrbrSpacious dining area and laundry room conveniently located off the kitchenbrbrBright and open living room with large windows, lush garden views, and a 55” smart TVbrbrSunroom with vaulted clear heart pine ceilings, wall-to-wall windows, and French doors that open to the garden—perfect for relaxing with a book or winebrbrOUTDOOR LIVING & ENTERTAINMENTbrbrStep through the atrium doors from the primary suite or living area into your private pool deck and entertainment space:brbrHeated pool with waterfall (available Nov 16 – May 1, $20/day upon request)brbrWet bar with wine coolerbrbrGrill area with lighting for evening cookingbrbrSurrounded by mature trees, lush tropical landscaping, and a full privacy fencebrbrGUEST COTTAGE – 1 Bed | 1 Bath + LoftbrbrThe charming 1.5-story guest cottage features:brbrPrivate street entrance and two dedicated parking spotsbrbrBrick walkways, private deck, and separate washer/dryerbrbrLoft sleeping area with twin beds (convertible to king upon request)brbrFull kitchen, bathroom, dining and sitting areabrbrCentral HVAC and eco-smart water heaterbrbrIdeal for weekend visitors or additional family during your staybrbrADDITIONAL FEATURESbrbrLED lighting throughout the homebrbrEcoSmart point-of-use water heatersbrbrRecently updated high-efficiency central A/C unitsbrbrVaulted ceilings and premium wood finishesbrbrFully enclosed for total privacy and tranquilitybrbrExperience Key West LivingbrbrBe Still is the perfect setting for families, couples, or friends to gather and enjoy the laid-back, beautiful lifestyle Key West is known for—whether you're here to unwind or entertain.brbrLOCATION HIGHLIGHTS:brbrA short walk to Higgs Beach, White Street Pier, galleries, and cafésbrbrQuick drive or bike ride to Duval Street, Mallory Square, and historic Old TownbrbrWe invite you to relax, recharge, and create unforgettable memories at Be Still, your personal slice of paradise in Key West.

BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage

Key West, Florida, United States

Bed

Bath

Sleeps

$266.4

This charming unit has a whimsical nautical feel with the blue and white décor. There are two master suites, one on the second floor featuring a queen bed and one on the third floor which offers 2 twins that can be converted to king on request. This historic 3 level Bostonian style town home is located in the red brick Foundry building in the Truman Annex community. There is a refreshing community pool just across the street. This property also includes one assigned parking space. Conveniently located just 2 blocks from Duval Street and 1/4 mile from Ft Zachary Taylor State Park and beach. Also within walking distance is Mallory Square, known for its breathtaking sunsets and celebration, the Harry Truman Little White House Museum and the beautiful Truman Waterfront park with a splash zone, workout paths and gorgeous views of the harbor.brbrPlease note: This property has a 28 night minimum stay

Life in the Slow Lane at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$411.18

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.

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

Key West, Florida, United States

Bed

Bath

Sleeps

$866.68

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

An Ocean Serenity at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$537.46

VERY LUXURIOUS water front home located in the heart of downtown Key West within walking distance to all downtown attractions and the famous Fort Zachary Taylor Beach. This home has 2 master ensuites with king beds, and there is a total of 4 bedrooms and 3 baths. The second level offers open living and kitchen area, master bedroom with ensuite bath and a great view of the ocean. From the second floor you can enjoy the fantastic view of the harbor and sunsets from the balcony that also has a spiral staircase that leads to the private pool area. Downstairs you have the 2nd king master bedroom with ensuite bath that leads directly to the pool and 2 additional guest bedrooms and full bath. The first guest room has a queen bed and the second guest room has two twin beds that can be converted into a king. Don't miss out on this home as it is one of the few Private Homes in Key West that has a view of the water and located in the Prime Location area here at the Truman Annex Community! brbrPlease note: This property has a 28 night minimum stay

DOLPHIN WATCH at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$576.66

TortugasHarbor Light Suite

Key West, Florida, United States

Bed

Bath

Sleeps

$764.04

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!

American Shoal Light Suite

Key West, Florida, United States

Bed

Bath

Sleeps

$681.27

Summary:brbrLuxury queen bungalow suite with twin beds in the loft and a private porch with amazing views. Share two oasis pools, pergola, outdoor bar and grill.brbrbrbrThe Space:brbrEscape the Ordinary...brbrbrbrThe Key West Lighthouse Suite is a cozy queen bungalow home with a double twin loft that sleeps up to 4 guests. This beautifully appointed stand-alone suite remodeled in 2024 is a perfect romantic retreat or ideal for those traveling with children. The suite is directly in front of one of our two new oasis pools with rear pool views. There is also a private front porch with Key West Lighthouse and partial Duval Street views on a quiet Key West Lane.brbrbrbrSuite Amenities:brbrbrbr• Luxury queen-size bed with premium linensbrbr• Upstairs loft with 2 twin beds - can be set up as king upon request - with premium linensbrbr• Luxury well-appointed furnishings and artworkbrbr• Private bathroom with a glass showerbrbr• Private secure entrancebrbr• Spacious front porch with views of the Key West Lighthouse and Duval Streetbrbr• Smart TVs with the latest Roku device for apps and streamingbrbr• High-speed Fiber Wi-Fibrbr• Well-equipped kitchen with refrigerator and icemakerbrbr• Parking space for one vehiclebrbr• Hardwood flooring throughout the suitebrbr• Washer and dryer combo unitbrbr• Luggage hut to store luggage and belongings in before check in or after check outbrbrbrbrLocation:brbrThe Key West 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!

Key West Lighthouse Suite

Key West, Florida, United States

Bed

Bath

4

Sleeps

$1590.72

This listing is for a room within a hotel.brbr✦ Your room is 900 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 21 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.brbr✦ Pool is available.brbr✦ Street parking – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $45.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. extra charge of $50 per nightbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Hotel

Stunning 2 Floor Loft in Vibrant Key West Ideal for Romantic Weekends - Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$533.29

This listing is for a room within a hotel.brbr✦ Your room is 270 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 21 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.brbr✦ Pool is available.brbr✦ Street parking – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $45.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. extra charge of $50 per nightbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Hotel

Elegant Boutique Room w/ Private Patio & Garden - Duval Street steps away

Key West, Florida, United States

Bed

Bath

Sleeps

$710.94

This listing is for a room within a hotel.brbr✦ Your room is 450 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 21 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.brbr✦ Pool is available.brbr✦ Street parking – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $45.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. extra charge of $50 per nightbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Hotel

Vibrant 2 Floor Loft Ideal for Relaxing Escape in Key West - Near Duval St

Key West, Florida, United States

Bed

Bath

Sleeps

$464.64

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

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

Key West, Florida, United States

Bed

Bath

Sleeps

$346.28

Summary:brbrPerfectly Appointed 2BDR/2BA Conch Style HomebrbrbrbrThe Space:brbrWelcome to Your Old Key West Oasis! Experience the charm of Old Key West in this stunning traditional Conch-style home. The spacious downstairs living area boasts a large entertainment space with soaring 12-foot ceilings, creating an airy and inviting atmosphere. The fully equipped kitchen flows seamlessly into the dining and living areas, perfect for gathering with friends and family. Step through the back kitchen door to discover your oversized garden, a tranquil retreat shaded by a beautiful Poinciana tree—ideal for relaxation or casual outdoor dining. Upstairs, you'll find two comfortable bedrooms that provide a peaceful escape after a day of exploring. This property showcases the distinctive features of Conch architecture, including exquisite stained glass details, adding character and charm to your stay. Enjoy the outdoors on one of the two porches on each floor, where you can soak up the vibrant Key West lifestyle. Whether you're sipping coffee in the morning or enjoying a sunset cocktail, this home is a perfect blend of comfort, style, and authentic local flavor. Embrace the spirit of Old Key West—your slice of paradise awaits!

Key Lime Hideaway

Key West, Florida, United States

Bed

Bath

6

Sleeps

Select Dates for Price

Your home away from home in Key West with 3 bedrooms. This adorable townhome features a cozy sofa bed, a comfortable queen bed, and a luxurious king bed. Enjoy the convenience of AC, WiFi, and a washing machine during your stay. Relax in the tranquil atmosphere of this property, complete with a fitness room and two beautiful swimming pools for your use. We look forward to welcoming you to our place.

Charming 3-bedroom townhome with WiFi, AC in fantastic Key West Golf Course

Key West, Florida, United States

Bed

Bath

Sleeps

$310.28

Recently refurbished throughout in a fun, tropical theme, Amberjack is situated on Southard Street in the exclusive gated community of Truman Annex, very near Harry Truman’s Little White House and right in the heart of Old Town Key West; a great spot to watch the October Fantasy Fest Parade as it weaves its way past the front door. Amberjack is within easy walking distance of Mallory Dock, where the sunset is celebrated everyday: Duval Street with its shops, restaurants and entertainments, and Fort Zachary Beach where there is a beachside café and awesome snorkelling. In less than a 2 minute walk there is a deli/convenience store, Coffee Tea Café, Green Parrot Bar and Eaton Bikes where you can hire bikes daily or weekly at a reasonable rate. If cycling is not for you and you don’t want to hire a car, Pirate Scooters (located opposite the Green Parrot Bar) will hire you an electric car. The property does have an allocated off street parking space. Amberjack provides everything for a relaxing vacation. Fully air conditioned throughout with ceiling fans in all rooms. Downstairs there is a large living/dining/kitchen area and a half bathroom. The living area boasts a Cozy sofa that opens in to a luxurious queen bed with a ceiling fan above, two further comfy chairs, a Flatscreen TV/DVD, CD stereo, I Pod docking station and Wi Fi Broadband. There is a fully equipped kitchen and a dining table that seats four with two comfortable stools at the kitchen bar. The patio is furnished with table, chairs, parasol and electric grill; perfect for Al Fresco dining on a balmy Key West evening. Outdoor Grill. The shared pool is just 25 footfalls from the patio gate. Upstairs you will find the laundry area, with stackable washer/dryer, and two bedrooms, one queen and one twin (that can be easily converted in to a king) both with en suite bathrooms, TV’s and balconies with tables and chairs. brbrPlease note: This property has a 28 night minimum stay

Amberjack at The Truman Annex in Key West

Key West, Florida, United States

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Bath

Sleeps

$687.34

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.

Luxury Waterfront at Galion Resort in Old Town

Key West, Florida, United States

3

Bed