Vacation Rentals By Owner In Key West, FL

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.

Island Breezes at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$448.82

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

A Harbour Roost at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$2373.48

Summary:brbrCurry House provides three stories full of historic charm that take you back in time. Best of all, when you book the entire home, you have a large private pool to yourself as well as space to entertain outdoors. With 9 bedrooms and sleeping room for up to 18 people, entertain your large group with this rare find in the center of Old Town Key West.brbrbrbrThe Space:brbrEach of the home's nine rooms is historically decorated and includes a mini-fridge and a flatscreen cable TV and wifi. brbrEight of the rooms have attached verandas, perfect for enjoying a morning cup of coffee along with Key West sunshine.brbrBedroom 1 - Queen & en suite full bathroombrbrBedroom 2 - King & en suite full bathroombrbrBedroom 3 - Queen & shared full bathroom with room 4brbrBedroom 4 - Queen & shared full bathroom with room 3brbrBedroom 5 - King & en suite full bathroombrbrBedroom 6 - King & en suite full bathroombrbrBedroom 7 - king & en suite full bathroombrbrBedroom 8 - King & en suite full bathroombrbrBedroom 9 - queen & en suite full bathroombrbrThe property sleeps up to 18 total guests.brbrbrbrGuest Access:brbrGuest will receive 2 unique access codes upon check-in. One code will be used to access the front door of the home. The second, will be used to access the room.brbrbrbrThe Neighborhood:brbrThe quiet mornings on the front porch or balcony are the perfect way to start your day. Walk to attractions, restaurants, stores, and bars or make your way towards the Historic Seaport for a day on the water. Perfectly situated between Downtown Key West & the Historic Seaport the Curry House places our guests within 3 blocks of Duval Street and 2 blocks from the waterfront. Steps from award-winning restaurants, coffee and sandwich shops, wine bars, craft cocktail bars, a local grocery store and all of your favorite Key West attractions.brbrbrbrGetting Around:brbrPark your car for the weekend and walk or bike your way around this completely accessible location. Or use the fenced in patio for parking your bike to get around town for the day. Unfortunately, no parking is included with your stay but Fleming Street is filled with free and pay-to-park spots. Key West is the best for all types of transportation including bikes, scooters, golf carts and more! Feel free to as us for recommendations!brbrbrbrOther Things to Note:brbr- Complimentary Coffee in the lobby & keurig in each roombrbr- Family friendly for property buyout or reserve individual rooms!brbr- There is no access to the kitchen.brbr- This property is not pet friendly. brbr- Pool is heated and exclusive to Curry House guests.brbr- There is no on-site washer/dryer.brbr- Pool towels are included with your stay.

Private Heated Pool & Near Duval - The Curry House

Key West, Florida, United States

Bed

Bath

Sleeps

$245.23

Summary:brCurry House provides three stories full of historic charm that take you back in time. This guesthouse has private rooms to maximize comfort but allows for conversation with fellow guests in the common areas. Each guest of Curry House has access to a large shared pool as well as space to entertain outdoors. With sleeping space for up to 2 guests and a private bathroom, this rare find in Old Town Key West is perfect for your solo travel or couples getaway.brbrThe Space:brSleep comfortably in a king size bed for two with wood paneled walls, sloped ceilings and veranda over looking the pool. The shared balcony is perfect for sipping your morning coffee or enjoying a glass of wine under the moonlight. Located on the 3rd floor this unit has a private en-suite bathroom and is stair access only. Put your leftovers in the fridge, relax with cable TV and free wifi in the entire home.brbrGuest Access:brGuest will receive 2 unique access codes upon check-in. One code will be used to access the front door of the home. The second, will be used to access the room.brbrThe Neighborhood:brThe quiet mornings on the front porch or balcony are the perfect way to start your day. Walk to attractions, restaurants, stores, and bars or make your way towards the Historic Seaport for a day on the water.brPerfectly situated between Downtown Key West & the Historic Seaport the Curry House places our guests within 3 blocks of Duval Street and 2 blocks from the waterfront. Steps from award-winning restaurants, coffee and sandwich shops, wine bars, craft cocktail bars, a local grocery store and all of your favorite Key West attractions.brbrGetting Around:brPark your car for the weekend and walk or bike your way around this completely accessible location. Or use the fenced in patio for parking your bike to get around town for the day. Unfortunately, no parking is included with your stay but Fleming Street is filled with free and pay-to-park spots. Key West is the best for all types of transportation including bikes, scooters, golf carts and more! Feel free to as us for recommendations!brbrOther Things to Note:br- This guest room is apart of the larger Curry House Guesthouse that sleeps up to 18 guests. br- Complementary Coffee in the lobby.br- There is no access to the kitchen.br- This property is not pet friendly. br- Pool is heated and exclusive to Curry House guests.br- There is no on-site washer/dryer.br- This unit is located on the 3rd floor with stair access only. br- Must be 18+ to stay at this property.

Balcony, Pool, & Near Duval - Curry House Room 8

Key West, Florida, United States

Bed

Bath

Sleeps

$217.85

Summary:brbrCurry House provides three stories full of historic charm that take you back in time. This guesthouse has private guest rooms & bathrooms as well as common areas allowing for conversation with fellow guests. Each guest of Curry House has access to a large heated pool as well as space to entertain outdoors. This quirky room with a sharply sloped ceiling and a skylight to open in the shower, allows the very small space to feel larger.brbrbrbrThe Space:brbrThe room itself small, bright and airy, with low sharply sloped ceilings and a private en suite bathroom. This small suite is ideal for one to two guests. Please note this room has low, slanted ceilings and is located on the 3rd floor with stair access only. Perfect for a quick place to hang your hat for a night or 2, this room has a queen size bed, flat screen TV with cable and wifi. Several seating areas are around the property for lounging and relaxing.brbrbrbrGuest Access:brbrGuest will receive 2 unique access codes upon check-in. One code will be used to access the front door of the home. The second, will be used to access the room.brbrbrbrThe Neighborhood:brbrThe quiet mornings on the front porch or balcony are the perfect way to start your day. Walk to attractions, restaurants, stores, and bars or make your way towards the Historic Seaport for a day on the water. Perfectly situated between Downtown Key West & the Historic Seaport the Curry House places our guests within 3 blocks of Duval Street and 2 blocks from the waterfront. Steps from award-winning restaurants, coffee and sandwich shops, wine bars, craft cocktail bars, a local grocery store and all of your favorite Key West attractions.brbrbrbrGetting Around:brbrPark your car for the weekend and walk or bike your way around this completely accessible location. Or use the fenced in patio for parking your bike to get around town for the day. Unfortunately, no parking is included with your stay but Fleming Street is filled with free and pay-to-park spots. Key West is the best for all types of transportation including bikes, scooters, golf carts and more! Feel free to as us for recommendations!brbrbrbrOther Things to Note:brbr- This guest room is apart of the larger Curry House Guesthouse that sleeps up to 18 guests. brbr- Complementary coffee in the lobby.brbr- There is no access to the kitchen.brbr- This property is not pet friendly. brbr- Pool is heated and exclusive to Curry House guests.brbr- There is no on-site washer/dryer.brbr- Please note this room has very low ceilings and may not be suited for taller guests. It is located on the 3rd floor with stair access only.brbr- Must be 18+ to stay at this property.

Shared Pool & Near Duval - Curry House Room 9

Key West, Florida, United States

Bed

Bath

Sleeps

$259.01

Summary:brCurry House provides three stories full of historic charm that take you back in time. This guesthouse has private rooms to provide comfort but allows for conversation with fellow guests in the common areas. Each guest of Curry House has access to a large shared pool as well as space to entertain outdoors. With sleeping space for up to 2 guests and a private bathroom, this rare find in Old Town Key West is perfect for your solo travel or couples getaway.brbrThe Space:brLocated on the top floor of the house, this room has vaulted ceilings, large windows overlooking the city, and a private en suite bathroom. Sleeping up to 2 guests this king suite, has a mini-fridge to store leftovers from your many meals out, a flatscreen TV and WiFi throughout the home.brbrGuest Access:brGuest will receive 2 unique access codes upon check-in. One code will be used to access the front door of the home. The second, will be used to access the room.brbrThe Neighborhood:brThe quiet mornings on the front porch or balcony are the perfect way to start your day. Walk to attractions, restaurants, stores, and bars or make your way towards the Historic Seaport for a day on the water.brPerfectly situated between Downtown Key West & the Historic Seaport the Curry House places our guests within 3 blocks of Duval Street and 2 blocks from the waterfront. Steps from award-winning restaurants, coffee and sandwich shops, wine bars, craft cocktail bars, a local grocery store and all of your favorite Key West attractions.brbrGetting Around:brPark your car for the weekend and walk or bike your way around this completely accessible location. Or use the fenced in patio for parking your bike to get around town for the day. Unfortunately, no parking is included with your stay but Fleming Street is filled with free and pay-to-park spots. Key West is the best for all types of transportation including bikes, scooters, golf carts and more! Feel free to as us for recommendations!brbrOther Things to Note:br- This guest room is apart of the larger Curry House Guesthouse that sleeps up to 18 guests. br- Complementary Keurig Coffee maker in the lobby.br- There is NO access to the kitchen.br- This property is not pet friendly. br- There is no on-site parking for this property. However, there is street parking available on a first-come first-serve basis as well as pay to park spots. br- Pool is heated and exclusive to Curry House guests.br- There is no on-site washer/dryer.br- Room is located on the top floor of the house (3rd floor) with stair access only.br- Must be 18+ to stay at this property.

Balcony, Pool, & Near Duval - Curry House Room 7

Key West, Florida, United States

Bed

Bath

Sleeps

$247.93

Summary:brbrCurry House offers three stories of historic Conch house charm, perfect for your getaway. This guesthouse features private rooms for comfort, with shared common areas for connecting with others. Guests enjoy access to a spacious pool and outdoor entertainment space. Sleeping up to 2 guests with a private bathroom, it’s a rare find in Old Town Key West, ideal for solo travelers or couples looking for a peaceful retreat.brbrbrbrThe Space:brbrRoom 6 at Curry House offers a comfortable retreat with a king-size bed, a private bathroom, a flat-screen cable TV, and a mini-fridge for added convenience. This charming suite also boasts a private en-suite door that opens directly onto the side porch, where you can unwind and enjoy a peaceful moment with your morning coffee. It’s the perfect spot to start your day while taking in the tranquil surroundings of the property.brbrbrbrGuest Access:brbrGuest will receive 2 unique access codes upon check-in. One code will be used to access the front door of the home. The second, will be used to access the room.brbrbrbrThe Neighborhood:brbrStart your day with peaceful mornings on the front porch or balcony. From there, take a short walk to nearby attractions, restaurants, shops, and bars, or head toward the Historic Seaport for a day on the water. Ideally located between Downtown Key West and the Historic Seaport, Curry House is just 3 blocks from Duval Street and 2 blocks from the waterfront. You’ll be steps away from award-winning restaurants, coffee shops, wine bars, craft cocktail spots, a local grocery store, and all your favorite Key West attractions.brbrbrbrGetting Around:brbrPark your car for the weekend and walk or bike your way around this completely accessible location. Or use the fenced in patio for parking your bike to get around town for the day. Unfortunately, no parking is included with your stay but Fleming Street is filled with free and pay-to-park spots. Key West is the best for all types of transportation including bikes, scooters, golf carts and more! Feel free to as us for recommendations!brbrbrbrOther Things to Note:brbr- This guest room is apart of the larger Curry House Guesthouse that sleeps up to 18 guests. brbr- Bathroom & shower are small.brbr- Complementary Coffee in the lobby.brbr- There is no access to the kitchen.brbr- This property is not pet friendly. brbr- Pool is heated and exclusive to Curry House guests.brbr- There is no on-site washer/dryer.brbr- Must be 18+ to stay at this property.brbr- This unit is located on the first floor.

Curry House Room 6 - Balcony & Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$358.51

Summary:brbrCurry House offers three stories of historic charm, transporting you back in time. The guesthouse features private rooms for comfort, along with common areas for socializing, including access to a large shared pool and outdoor entertaining space. With room for up to 4 guests and a one bathroom, this unique Old Town Key West gem is perfect for a family or couples getaway.brbrbrbrThe Space:brbrTwo rooms at Curry House are combined for your ideal Key West getaway! Each bedroom is furnished with a queen-sized bed, comfortably accommodating up to 4 guests. One room includes a private bathroom with a charming walk-in shower. Perfect for small groups, both rooms feature a mini fridge, balcony, and TV for added convenience and comfort.brbrbrbrGuest Access:brbrGuest will receive 2 unique access codes upon check-in. One code will be used to access the front door of the home. The second, will be used to access the room.brbrbrbrThe Neighborhood:brbrStart your day with peaceful mornings on the front porch or balcony. From there, take a short walk to nearby attractions, restaurants, shops, and bars, or head toward the Historic Seaport for a day on the water. Ideally located between Downtown Key West and the Historic Seaport, Curry House is just 3 blocks from Duval Street and 2 blocks from the waterfront. You’ll be steps away from award-winning restaurants, coffee shops, wine bars, craft cocktail spots, a local grocery store, and all your favorite Key West attractions.brbrbrbrGetting Around:brbrPark your car for the weekend and walk or bike your way around this completely accessible location. Or use the fenced in patio for parking your bike to get around town for the day. Unfortunately, no parking is included with your stay but Fleming Street is filled with free and pay-to-park spots. Key West is the best for all types of transportation including bikes, scooters, golf carts and more! Feel free to as us for recommendations!brbrbrbrOther Things to Note:brbr- This guest room is apart of the larger Curry House Guesthouse that sleeps up to 18 guests. brbr- Complementary Coffee in the lobby.brbr- There is no access to the kitchen.brbr- This property is not pet friendly.brbr- Pool is heated and exclusive to Curry House guests.brbr- There is no on-site washer/dryer.brbr- Must be 18+ to stay at this property.brbr- This unit is located on the second floor with stair access only.

Curry House Room 3 & 4 - Near Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$256.55

Summary:brbrCurry House provides three stories full of historic charm that take you back in time. This guesthouse has private rooms to maximize comfort but allows for conversation with fellow guests in the common areas. Each guest of Curry House has access to a large shared pool as well as space to entertain outdoors. With sleeping space for up to 2 guests and a private bathroom, this rare find in Old Town Key West is perfect for your solo travel or couples getaway.brbrbrbrThe Space:brbrRoom #5, located on the first floor is nicely decorated and includes a mini-fridge and a private en suite bathroom. Lounge on the comfortable king-size bed while you browse the cable channels on the flatscreen TV, or use the free WiFi to search for nearby activities to fill your vacation days. In the evenings, enjoy a glass of wine on the semi-private wraparound porch.brbrbrbrGuest Access:brbrGuest will receive 2 unique access codes upon check-in. One code will be used to access the front door of the home. The second, will be used to access the room.brbrbrbrThe Neighborhood:brbrThe quiet mornings on the front porch or balcony are the perfect way to start your day. Walk to attractions, restaurants, stores, and bars or make your way towards the Historic Seaport for a day on the water.brbrPerfectly situated between Downtown Key West & the Historic Seaport the Curry House places our guests within 3 blocks of Duval Street and 2 blocks from the waterfront. Steps from award-winning restaurants, coffee and sandwich shops, wine bars, craft cocktail bars, a local grocery store and all of your favorite Key West attractions.brbrbrbrGetting Around:brbrPark your car for the weekend and walk or bike your way around this completely accessible location. Or use the fenced in patio for parking your bike to get around town for the day. Unfortunately, no parking is included with your stay but Fleming Street is filled with free and pay-to-park spots. Key West is the best for all types of transportation including bikes, scooters, golf carts and more! Feel free to as us for recommendations!brbrbrbrOther Things to Note:brbr- This guest room is apart of the larger Curry House Guesthouse that sleeps up to 18 guests. brbr- Complementary Coffee in the lobby.brbr- There is no access to the kitchen.brbr- This property is not pet friendly. brbr- Pool is heated and exclusive to Curry House guests.brbr- There is no on-site washer/dryer.brbr- Must be 18+ to stay at this property.brbr- Unit is located on the first floor located next to the front door.

Curry House Room 5 - First Floor

Key West, Florida, United States

Bed

Bath

Sleeps

$251.33

Summary:brbrCurry House provides three stories full of historic charm that take you back in time. This guesthouse has private rooms to maximize comfort but allows for conversation with fellow guests in the common areas. Each guest of Curry House has access to a large shared pool as well as space to entertain outdoors. With sleeping space for up to 2 guests and a private bathroom, this rare find in Old Town Key West is perfect for your solo travel or couples getaway.brbrbrbrThe Space:brbrThis room is warm and inviting, with touches of historic charm and a convenient private bathroom.brbrSleeping up to 2 guests this room has a king size bed for your comfort. The room includes a flatscreen TV with cable and wifi for connecting your own devices.brbrbrbrGuest Access:brbrGuest will receive 2 unique access codes upon check-in. One code will be used to access the front door of the home. The second, will be used to access the room.brbrbrbrThe Neighborhood:brbrThe quiet mornings on the front porch or balcony are the perfect way to start your day. Walk to attractions, restaurants, stores, and bars or make your way towards the Historic Seaport for a day on the water.brbrPerfectly situated between Downtown Key West & the Historic Seaport the Curry House places our guests within 3 blocks of Duval Street and 2 blocks from the waterfront. Steps from award-winning restaurants, coffee and sandwich shops, wine bars, craft cocktail bars, a local grocery store and all of your favorite Key West attractions.brbrbrbrGetting Around:brbrPark your car for the weekend and walk or bike your way around this completely accessible location. Or use the fenced in patio for parking your bike to get around town for the day. Unfortunately, no parking is included with your stay but Fleming Street is filled with free and pay-to-park spots. Key West is the best for all types of transportation including bikes, scooters, golf carts and more! Feel free to as us for recommendations!brbrbrbrOther Things to Note:brbr- This guest room is apart of the larger Curry House Guesthouse that sleeps up to 18 guests. brbr- Complementary Coffee in the lobby.brbr- There is no access to the kitchen.brbr- This property is not pet friendly. brbr- Pool is heated and exclusive to Curry House guests.brbr- There is no on-site washer/dryer.brbr- Must be 18+ to stay at this property.brbr- This unit is on the second floor and requires stairs to access.

Curry House Room 2 - Near Duval, Pool & Balcony

Key West, Florida, United States

Bed

Bath

Sleeps

$252.41

Summary:brbrCurry House provides three stories full of historic conch house charm that take you back in time. This guesthouse has private rooms to maximize comfort but allows for conversation with fellow guests in the common areas. Each guest of Curry House has access to a large shared pool as well as space to entertain outdoors. With sleeping space for up to 2 guests and a private bathroom, this rare find in Old Town Key West is perfect for your solo travel or couples getaway.brbrbrbrThe Space:brbrThis little suite is one of nine rooms within Curry House. Sleeping up to 2 - this unit features a queen size bed, a private quaint en suite bathroom, a mini-fridge, and shared balcony overlooking the pool. There's also a flatscreen cable TV and free WiFi.brbrbrbrGuest Access:brbrGuest will receive 2 unique access codes upon check-in. One code will be used to access the front door of the home. The second, will be used to access the room.brbrbrbrThe Neighborhood:brbrThe quiet mornings on the front porch or balcony are the perfect way to start your day. Walk to attractions, restaurants, stores, and bars or make your way towards the Historic Seaport for a day on the water.brbrPerfectly situated between Downtown Key West & the Historic Seaport the Curry House places our guests within 3 blocks of Duval Street and 2 blocks from the waterfront. Steps from award-winning restaurants, coffee and sandwich shops, wine bars, craft cocktail bars, a local grocery store and all of your favorite Key West attractions.brbrbrbrGetting Around:brbrPark your car for the weekend and walk or bike your way around this completely accessible location. Or use the fenced in patio for parking your bike to get around town for the day. Unfortunately, no parking is included with your stay but Fleming Street is filled with free and pay-to-park spots. Key West is the best for all types of transportation including bikes, scooters, golf carts and more! Feel free to as us for recommendations!brbrbrbrOther Things to Note:brbr- This guest room is apart of the larger Curry House Guesthouse that sleeps up to 18 guests. brbr- Complementary Coffee in the lobby.brbr- There is no access to the kitchen.brbr- This property is not pet friendly. brbr- Pool is heated and exclusive to Curry House guests.brbr- There is no on-site washer/dryer.brbr- Must be 18+ to stay at this property.brbr- This unit is on the second floor and requires stairs to access.

Curry House Room 1 - Near Duval, Pool & Balcony

Key West, Florida, United States

Bed

Bath

Sleeps

$247.45

This charming 2 story 2 bedroom with loft, two bath cottage in the Shipyard Condominiums is located just off the pool and gorgeous park. Both bathrooms have been recently updated! The first floor bedroom and bath are conveniently located just off the kitchen. Enjoy the very comfortable living room with a dining area that enjoys view through two sets of French doors to the rear deck and garden. The primary suite on the second floor enjoys a queen bed, plus a sitting area which includes a murphy bed. The large covered rear deck features out door dining and lounging and a back gate which provides quick access to the rest of the community and the park.brThe Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s Old Town area. These condos are located just 2 blocks from Duval Street and all the Old Town Key West attractions including Fort Zachary Taylor State Park and Beach and the Truman Waterfront park. This property is outfitted with washer/dryer, pots/pans, towels, linens, central air conditioning, assigned off street parking, and access to a refreshing community pool. brPlease note: This property will require a minimum of a 28 night stay.

A SUNRISE COTTAGE at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$629.69

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrStep into VOGUE VILLA, a stylish island escape where timeless Key West charm meets a confident dose of modern luxury. Behind its classic Old Town exterior and welcoming porch, the home has been fully reimagined into a chic retreat layered with curated comforts, designer touches, and a fabulously eclectic aesthetic that feels both relaxed and runway-ready. Teamed with Last Key Realty’s Five-Star Guest Services & Complimentary Concierge, your month in VOGUE VILLA will be the perfect blend of island living and contemporary luxury.brbrTHE LOCATION…brbrVOGUE VILLA is located on Southard St, a half block from the entrance to Truman Annex and the Green Parrot. (Worry not, part of the renovation includes soundproofing in the walls - you won’t hear a thing!) This location is truly the heart of Old Town, steps from all of the shops, restaurants, and sites of Duval Street and the Historic District. Take a short stroll or ride your bike to Duval and experience the best of Key West, such as local favorites like Green Parrot, Sloppy Joe’s, and Virgilio’s. Although you won’t need a vehicle to get around from this prime location, there is off-street parking available in the private driveway for up to 3 vehicles.brbrTHE LIVING AREA…brbrThis home was completely rebuilt from the ground up and it shows in every carefully chosen detail. The tasteful decor perfectly blends island life with modern luxury. The open floor plan and high ceilings in the living room and kitchen make the room feel even grander than it is. There’s comfortable seating and a large flat screen TV waiting for you in the living room.brbrThe kitchen is outfitted with everything you need, including all modern appliances and seating for 8 at the large kitchen table. The beautiful kitchen island has seating for 6 and is the perfect spot for an evening cocktail or a little remote work!brbrTHE BACKYARD OASIS…brbrVOGUE VILLA checks all the boxes, including having an absolutely incredible outdoor space. Step outside to your stunning private pool, framed by lush tropical surroundings providing both ambience and privacy. Whether you’re lounging poolside with a morning coffee or hosting sunset cocktails in your private tiki, this home was designed to make memories. There is a full bath that opens directly onto the pool area, perfect for rinsing off after a refreshing dip.brbrTHE ACCOMMODATIONS…brbr** Master Suite - Located on the First Floor with a King bed, flat screen TV, closet, and en-suite bathroom with walk-in shower and soaker tubbrbr** Bedroom 2 - Located on the First Floor with a King bed, large flat screen TV, closet, access to the hallway bathbrbr** Bedroom 3 - Located on the Second Floor with a King bed, large flat screen TV, en-suite bathroom with a walk-in showerbrbr** Full-sized Sleeper Sofa for 1 in the upstairs DenbrbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Air Conditioningbr** Ceiling Fansbr** Flat Screen Cable TVs in Living Room & All Bedroomsbr** Fully-Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access and full cable is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced & Landscaped Private Yardbr** Private Heated Poolbr** Propane BBQ Grillbr** Off-Street Parking in Driveway for up to 2 Full-size SUVsbrbrOther notes:brbr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 7 adultsbr** Pets Allowed

**VOGUE VILLA @ OLD TOWN** Fully Renovated Home & Pool + LAST KEY SERVICES...

Key West, Florida, United States

Bed

Bath

Sleeps

$185.5

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

Almost Paradise at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$219.79

Receive 1 FREE night for booking for booking a minimum of 30 nights!! Total renovation completed in 2020! This 4-bedroom contemporary home is waiting for your arrival! The Guava Duff (named after the delicious Bahamian dessert my Grandmother Yvonne used to make) was my grandparents’ home, and the renovation was done with the same tender love and care that Mama Yvonne used to make Guava Duff, by my friends and family, and the result is stunning. We took the walls down to the studs, replaced all the plumbing electrical, and windows, then finished it with contemporary flooring, fixtures, appliances and furnishings. It has an open floor plan for the Living room, dining area and new kitchen and boasts 4 separate bedrooms and two full baths. brbrEnjoy a great night’s sleep in our beautifully appointed main bedroom with King sized bed, sumptuous pillows, ensuite bathroom complete with a walk-in full body shower and double sinks. Chest of drawers/tv/two closets and with brand new soundproof windows throughout the house, central air as well as ceiling fans will have you sleeping like a baby! The other end of the house has two bedrooms with queen beds and one bedroom with a twin bed and foldaway bed if needed. Hall bathroom conveniently located near the bedrooms with a walk-in shower. The family area is ample for watching TV, discussing your day in Key West or just sitting back and enjoying on-line content with free Wi-Fi. Head out onto the extra-large front porch to chill, grill, watch people go by, or to watch a rugby or soccer game happening at the brand-new Monroe County Bernstein Park right across the street. Hungry The gourmet kitchen is well equipped with everything you need to create island meals. Dishwasher for easy clean up! Tile throughout the home. Good sized laundry room with full-sized front-loading washer and dryer as well as a laundry sink and door to the side porch. Beach towels also included. Unlike many rental properties on the island, we offer lots of parking at no extra charge. If you have your own boat, there is space to park in front of the house. There are also inexpensive boat slips within 1/2 mile. brbrThis convenient location gives you breathing room from all of the hustle and bustle on the island with a large fully fenced yard. Less than a mile away from great local restaurants and convenience stores including El Siboney, Hogfish Bar and Grill, Hurricane Hole, Roostica, Dolphin Cafe, El Mocho, Dion’s Quick Mart, Jolly’s Liquor Store and CVS. We are also within walking distance of three fine dining great restaurants located at the Perry Hotel and the Stock Island Marina Village- one of the top 50 marina’s in the nation! 10 minutes to Old Town Key West, 14 minutes to Duval St. and 9 minutes to Smather’s Beach!brbrSo welcome to the Guava Duff where you will feel both at home and comfortable and have your own space to enjoy that sweet Key West chill. brbrFeatures of this Property:br• Fully renovated with modern 1100 sq ft of living space/100sq ft front porchbr• Sleeps 8: 1 K, 2 Q, 1 Twin, 1 Foldaway Bedbr• 2 Designer bathrooms with walk-in showersbr• Family Room with sofa/loveseat/ TV- basic cable br• Full gourmet kitchen with dishwasherbr• Parking is FREE- can accommodate at least 4 vehiclesbr• Walking Distance to local Restaurants, Convenience Storesbr• Brand New City Park Across the Street with a Walking Track and Playgroundbr• Free Wi-Fibr• Washer/Dryer/Laundry Sinkbr• Boat Slip with full service just up the street

The GUAVA DUFF - Beautiful KW home with space to chill & lots of FREE PARKING!!

Key West, Florida, United States

4

Bed

2

Bath

8

Sleeps

$2062.13

Listing descriptionbrYou won’t forget your time aboard this romantic 60' Hatteras yacht, including 30 Catamaran tender with Captain taking you on water adventures, 2023 SUV with driver, to take you on land adventures a private chef and stewardess to pamper you. An exclusive dock to relax and enjoy the scenery. Floating in natures beauty while enjoying a cocktail watching a majestic Sunset as your chef prepares your delious dinner. You will have an opportunity only a few get experience and it will be unforgettable.

House Boat

Yacht Hatteras 60'

Key West, Florida, United States

Bed

Bath

Sleeps

$191.84

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

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

Key West, Florida, United States

Bed

Bath

Sleeps

$393.37

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

Atlantic Parrot | Oceanfront Condo w/ Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$624.61