Vacation Condo Rentals By Owner In Key West, FL

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrLA PETITE PENTHOUSE is a jewel-like second-story condo in the Shipyard at the Truman Annex, a gated community located in the very heart of Old Town Key West. You'll be just steps from Mallory Square, Duval Street and all the attractions Key West has to offer. Yet, you'll have all of the peace and quiet that comes with a gated community.brbrTHE LIVING AREA...brbrThe living room of LA PETITE PENTHOUSE has double French doors that open to the balcony so you can enjoy those wonderful tropical breezes, and a large Hi-Def flat screen TV for those evenings when you need a break from the excitement of Old Town. The rear balcony looks out on the lush tropical trees that surround the community pool. Inside, there's a dining table that seats 4, and there is also dining for four on the balcony. The kitchen is fully equipped to satisfy the most demanding chef, and has a French door to the front balcony.brbrTHE ACCOMMODATIONS...brbr• Master Bedroom: Queen bed, flat screen TV and overhead fan. brbr• Second Bedroom: Two Twins OR One King bed, flat screen TV, and overhead fan. brbrThe shared hall bathroom has a glass shower and stacked washer/dryer.brbrTHE COMMUNITY POOL and FORT ZACHARY TAYLOR STATE PARK...brbrThe community pool is right around the corner from LA PETITE PENTHOUSE, with plenty of chaises. There is a cabana with restrooms for your convenience. Fort Zachary Taylor Park is less than a half mile away, with the prettiest beach in Key West.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.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr• Washer and Dryerbr• Central Heat and A/Cbr• Ceiling Fansbr• Flat Screen 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 & 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 4 adultsbr• Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**LA PETITE PENTHOUSE @ THE ANNEX** Elegant Condo & Pool + LAST KEY SERVICES...

Key West, Florida, United States

Bed

Bath

Sleeps

$281.46

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrSUNSET POINT has everything you could want in a vacation home: it is close to Old Town, so you'll be able to enjoy everything that Key West has to offer. Yet, you'll be in your own world at SUNSET POINT with a very large balcony overlooking the Florida Bay and the Gulf of Mexico beyond.brbrTHE PRIVATE GATED COMMUNITY...brbrSunset Marina is a gated community located on Stock Island, right off the entrance to Key West. The location is a great balance between being secluded in a private community yet still only a short Uber ride into the best of Old Town Key West. With your rental home at Sunset Marina you'll have plenty of space for parking, both covered garage space and visitor space, as well as access to the private waterfront community pool.brbrTHE LIVING AREA...brbrThis beautiful condo is an end unit with commanding views of the Florida Bay, located right at the point of the marina. SUNSET POINT is a 1658 square foot condo that has been meticulously designed and furnished to a level you seldom see in a vacation home. You'll have plenty of room to spread out, with the large main balcony and open living area. The kitchen is completely equipped, with everything a good chef would need to prepare the most ambitious meals and even room for some sous-chefs.brbrTHE ACCOMMODATIONS...brbr• Master Bedroom: King bed, flat screen TV, direct access to the main balcony, large walk-in closet, and an en-suite bathroom with twin vanities, an oversized shower and a Jacuzzi tub. brbr• Second Bedroom: Two Twin beds OR One King bed, flat screen TV, private balcony and access to the shared full bathroom in the hall.brbr• Third Bedroom: Two twin beds (or convert to a king), flat screen TV, private balcony, and direct access to the shared full bathroom. brbrTHE COMMUNITY POOL and JACUZZI...brbrThe community pool area is a beautiful place to spend the day, with its setting right on the waterfront facing the marina and Florida Bay beyond. There are plenty of chaises and sitting areas in the sun and in the shade.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr• Washer and Dryerbr• Central Heat and A/Cbr• Ceiling Fansbr• Flat Screen TVs in Living Room and All Bedroomsbr• Fully Equipped Kitchenbr• Basic stock of spicesbr• Starter supply of paper productsbr• Starter set of cleaning productsbr• Linens and Towels providedbr• Wireless high-speed Internet access and full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr• Community Pool Accessbr• Community Jacuzzi Accessbr• Assigned off-street covered parking for 1 carbrbrOther 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 6 adultsbr• No Pets Allowed

**SUNSET POINT @ SUNSET MARINA** Condo / Pool & Spa + LAST KEY SERVICES...

Key West, Florida, United States

Bed

Bath

Sleeps

$227.61

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrSALTWATER HARMONY is a cozy and beautifully furnished first-floor condo in the Shipyard at the Truman Annex, an exclusive gated community located in the heart of Old Town Key West. You'll be just steps from Mallory Square, Duval Street and all of Key West's major attractions, and yet you'll have all of the peace and quiet that comes with a gated community.brbrTHE LIVING AREA...brbrThe living room of SALTWATER HARMONY has large French doors that open to your own back porch so you can enjoy those wonderful tropical breezes, and a Hi-Def flat screen TV for those evenings when you need a break from the excitement of Old Town. The back porch is surrounded by lush tropical foliage. There's a dining table on the porch that seats 4, and there is also dining for four inside at the kitchen bar. The kitchen is fully equipped with top of the line appliances and will satisfy the most demanding chef.brbrTHE ACCOMMODATIONS...brbr• Master Bedroom: King bed, flat screen TV and overhead fan. brbr• Second Bedroom: Two Twins OR One King bed, flat screen TV, and overhead fan. brbrThe shared hall bathroom has a glass shower.brbrTHE COMMUNITY POOL and FORT ZACHARY TAYLOR STATE PARK...brbrThe community pool is right around the corner, with plenty of chaise lounges. There is a cabana with restrooms for your convenience. Fort Zachary Taylor Park is less than a half mile away, with the prettiest beach in Key West.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.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr• Washer and Dryerbr• Central Heat and A/Cbr• Ceiling Fansbr• Flat Screen 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 & 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 4 adultsbr• Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**SALTWATER HARMONY @ THE ANNEX** Charming Condo & Pool + LAST KEY SERVICES...

Key West, Florida, United States

Bed

Bath

Sleeps

$833.44

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrImagine a home with floor-to-ceiling panoramic views of the Atlantic Ocean from every room. WINDSWEPT PALMS has been thoughtfully decorated and furnished. The modern, upscale furniture is complemented with splashes of color throughout the home. The balcony wraps 270 degrees around the condo, with seating for everyone in your group. WINDSWEPT PALMS is located within an upscale private community within walking or biking distance to all of your favorite Key West spots, including beaches, restaurants, shopping, and the beautiful waters surrounding the island.brbrTHE LIVING AREA...brbrThe living room of WINDSWEPT PALMS is filled with light. There's a large flat screen TV, for those times you aren't marveling at those breathtaking Key West sunsets. The kitchen features butcher block counters and has everything a good chef would need to prepare any meal, including upgraded appliances. There's a dining table with seating for six.brbrTHE POOL, THE BEACH & TENNIS...brbr1800 Atlantic offers Resort-style amenities, including an extra large Community Pool right downstairs. There are chaise lounges surrounding the pool for your comfort, and a cabana with restrooms for your convenience. Please note this is a shared pool with set rules, such as no music and no coolers. We ask that our guests be mindful of their neighbors and respect the rules.brbrFrom the pool, there's a walking path that leads to the on-site beach. The on-site beach offers a relaxing setting, with chaise lounges and soft sand. There is no direct water access from this beach, but Smathers Beach, Key West's largest public beach, is located within walking distance right next door. There is also an oversized Jacuzzi and a picnic area with BBQs available for guest use. You'll also have access to the newly built fitness center and Key West's only clay tennis courts, both located on-site.brbrTHE ACCOMMODATIONS...brbr** Master Bedroom: a King bed, two large closets, a large flat screen TV, direct access to the balcony with stunning views, and an en suite with an oversized shower. brbr** Second Bedroom: Two Twin beds or One King bed, a flat screen TV, direct access to the balcony, and access to the full second bathroom. brbr** Third Bedroom: Two Twin beds or One King bed, a flat screen TV, direct access to the balcony, and access to the full second bathroom. brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen 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 & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Community Pool Accessbr** Community Jacuzzi Accessbr** Assigned off-street carport for 1 car (Parking Garage has a low clearance of 6'2)br** Key West's only clay tennis courtsbr** Handball courtsbr** Fitness Centerbr** Dry Saunasbr** Picnic areas with BBQsbr** Recreation rooms available for private partiesbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** This complex has both visitors and locals living here, we expect our guests to be mindful & respectful of the posted rulesbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**WINDSWEPT PALMS @ THE BEACH** Oceanfront / Pool & Jacuzzi + LAST KEY SERVICE

Key West, Florida, United States

4

Bed

Bath

6

Sleeps

$350.33

This unit has a king in both bedrooms.brbr1800 Atlantic is directly on the Atlantic ocean in Key West, adjacent to Smathers Beach the City Beach with a variety of watersports activities available.brbrThe property itself features assigned secure parking spaces, 3 lighted tennis courts, one of which is the only clay court in Town. There are beautiful botanical gardens with picnic and BBQ areas.brbrThe Olympic size heated pool sits on the edge of the Atlantic Ocean, There is also a 20 person bubbling Jacuzzi tub by the pool, a Sauna also if you so desire.brbrThe pool is the envy of many of our island visitors.brAssigned parking is one of our many amenities. brbrThe historic area is less than a 5 minute drive or 10 minute bike ride.brFish, snorkel, dive, dine, jet ski, theater or simply just relax, it is your vacation and we are to help. We will share our island secrets and you will be back. brbrHigh speed internet access.brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Botanical Island Delight Key West fantastic discounts for Summer & Fall

Key West, Florida, United States

Bed

Bath

4

Sleeps

$610.0

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrThis Old Town condo is perfect for anyone who can't get enough of Key West's famous nightlife scene. CASITA ANGELITA is located right in Old Town, half a block away from Duval Street and smack dab in the center of the entertainment district. You couldn't be any closer to the late-night scene and attractions of downtown. Fair warning... It can get a little noisy out there! This tropical two-bedroom retreat is hidden within a renovated Old Town home, with all of the charm of the famous conch houses of Key West. You won't need a car, but should you decide to bring one you will have one spot in the driveway.brbrTHE LIVING AREA... brbrCASITA ANGELITA is the first floor of this converted Old Town home. As you enter the apartment through the front door of the house, you'll be greeted with a light-filled living area with a modern tropical feeling. Don't let the name fool you, this 'casita' has lofty ceilings and feels quite spacious. A large flat screen TV on the wall overlooks the spacious living area with plenty of seating. The sofa pulls out to a queen sized bed to sleep 2 extra guests. brbrTHE KITCHEN...brbrOff of the living area, the open kitchen is fully equipped with all the high-end tools and appliances you'll need to whip up a meal at home (if you can resist the temptation of all of the famous Key West restaurants within walking distance, that is.) A dining nook by the windows is the perfect place for a morning coffee. Additional seating at the bar is convenient for a quick bite. brbrTHE ACCOMMODATIONS... brbr• Master Bedroom: King bed, flat screen TV, full closet, and an en-suite with a glass shower. brbr• Second Bedroom: Two Twins OR One King, flat screen TV, full closet, private back patio, and direct access to the second bathroom with a glass shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr• Washer and Dryerbr• Central Heat and A/Cbr• Ceiling Fansbr• Flat Screen TVs in Living Room and All Bedroomsbr• Fully Equipped Kitchenbr• Basic stock of spicesbr• Starter supply of paper productsbr• Starter set of cleaning productsbr• Linens and Towels providedbr• Wireless high-speed Internet access & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr• Private Gated and Landscaped Outdoor Patiobr• Off-street Parking in DrivewaybrbrOther notes:brbr• Interim housekeeping provided upon requestbr• This property will accommodate up to 6 adultsbr• Max of 2 Pets Allowed with Additional Fee of $200 per petbr• Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**CASITA ANGELITA @ OLD TOWN** Historic Condo by Duval + LAST KEY SERVICES...

Key West, Florida, United States

Bed

Bath

Sleeps

$1022.11

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrA stay in Key West calls for a light and airy oasis, with breathtaking water views and an easy beach location to fully enjoy the ultimate of island life in America. RIVIERA AMERICANA is located in an upscale private community within walking or biking distance to all of your favorite Key West spots, including beaches, restaurants, shopping, and the beautiful waters surrounding the island.brbrTHE LIVING AREA & KITCHEN... brbrRIVIERA AMERICANA is lovingly decorated to reflect the ambiance of an upscale coastal destination with a modern feel. The living room is filled with light. There's a large flat screen TV, for those times you aren't marveling at the view beyond your balcony. The living room of has plenty of comfortable seating for the group to gather, and the sofa pulls out to a Queen sized sleeper for extra guests. The kitchen is fully appointed and has everything a good chef would need to prepare any meal, including upgraded appliances. There's a dining table with seating for six inside, or an outdoor dining set on the breezy balcony of Riviera Americana for a meal overlooking the gorgeous waters of Key West.brbrTHE POOL, THE BEACH & TENNIS... brbr1800 Atlantic offers Resort-style amenities, including an extra large Community Pool right downstairs. There are chaise lounges surrounding the pool for your comfort, and a cabana with restrooms for your convenience. Please note this is a shared pool with set rules, such as no music and no coolers. We ask that our guests be mindful of their neighbors and respect the rules.brbrFrom the pool, there's a walking path that leads to the on-site beach. The on-site beach offers a relaxing setting, with chaise lounges and soft sand. There is no direct water access from this beach, but Smathers Beach, Key West's largest public beach, is located within walking distance right next door. There is also an oversized Jacuzzi and a picnic area with BBQs available for guest use. You'll also have access to the newly built fitness center and Key West's only clay tennis courts, both located on-site.brbrTHE ACCOMMODATIONS... brbr** Master Bedroom: King bed, large flat screen TV, direct access to the balcony with panoramic views, and an en suite with an oversized shower. brbr** Second Bedroom: Queen bed, flat screen TV, direct access to the balcony, and access to the full second bathroom.brbr** Third Bedroom: Two Twin beds or One King bed, direct access to the balcony, and access to the full second bathroom. brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen 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 & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Community Pool Accessbr** Community Jacuzzi Accessbr** Assigned off-street carport for 1 car (Parking Garage has a low clearance of 6'2)br** Key West's only clay tennis courtsbr** Handball courtsbr** Fitness Centerbr** Dry Saunasbr** Picnic areas with BBQsbr** Recreation rooms available for private partiesbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 8 adultsbr** This complex has both visitors and locals living here, we expect our guests to be mindful & respectful of the posted rulesbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...

Key West, Florida, United States

Bed

Bath

Sleeps

$923.53

Summary:brbrRooftop Penthouse- Luxury Penthouse in prime Downtown locationbrbrbrbrThe Space:brbrThe high-end sophisticated Rooftop Penthouse is located directly above the famous Wyland Gallery on Duval Street. Enjoy Dining, Shopping, and Entertainment in the heart of Key West. Once you enter the property through your private entrance, you would be captivated by its expansive space. The oversized living room with a high 15 FT ceiling has an abundance of natural light coming from the French doors and floor to ceiling windows. Florida is all about outdoor living; we have the pleasure to offer you a private rooftop terrace where you can enjoy the dazzling view of Duval street from the front row seat. Open your living room with french doors and combine the indoor and outdoor spaces. There’s nothing better than feeling like you’re on top of the world.brbrbrbrOpen floor plan living room has comfortable couches and a flat-screen Tv to help relax after all day sightseeing and shopping.brbrbrbrFor those who love to entertain and cook, we offer a fully equipped chef kitchen with new stainless steel appliances, granite countertops, and dark wood cabinets.brbrbrbrMaster Bedroom has a King bed and comfortable seating area, couch can convert into queen sleeper sofa nad can sleep additional 2 guests. Plush towels and high-end linens are available for the most discerning guests. The second bedroom is open to a living room, has a King size bed, and can be closed off ONLY with blackout curtains. There are no walls.brbrbrbrThe great news is that your furry friends are all welcome to enjoy Key West with you. A newly constructed park, Truman Waterfront, is just 10 min walk away as well as the most beautiful beach and a state park Ft. Zachary Taylor.brbrbrbrRooftop Penthouse featuresbrbr- Two bedrooms with king bedsbrbr- 1 full bathroom with stand up showerbrbr- 0.5 powder room accessible from Outdoor terrace only, no ACbrbr- Laundry/utility room with powder roombrbr- Rooftop private entertaining terracebrbr- One free off Street parking behind the buildingbrbrbrbrWasher & Dryer Central Heat and A/C Ceiling Fans Flat Screen TVs in Living Room & Master Bedroom Fully Equipped Kitchen Starter supply of paper products Starter set of cleaning products Linens and Towels provided Wireless high-speed Internet access & full cable includedbrbrInterim housekeeping provided upon request This property will accommodate up to 6 adults No Pets

Rooftop Penthouse

Key West, Florida, United States

Bed

1

Bath

6

Sleeps

$632.01

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrFormerly La Bonne Vie, SMOOTH SAILING has been meticulously furnished with a modern coastal feel, and the only beauty that competes with the interior is the spectacular views from your private oceanfront balcony. You'll be able to enjoy quiet afternoons with those balmy Key West breezes wafting through the floor-to-ceiling glass doors from the living room, and sunrise shadows from your bedroom balconies in the morning. This home is located in an upscale private community within walking or biking distance to all of your favorite Key West spots, including beaches, restaurants, shopping, and the beautiful waters surrounding the island. You'll be hard pressed to find a more stunning mix of upscale furnishings and water views than SMOOTH SAILING.brbrTHE LIVING AREA...brbrThe living room of SMOOTH SAILING is modern and bright, with plenty of light streaming in from the floor-to-ceiling glass doors. There's a large flat screen TV, for those times you aren't marveling at the breathtaking Key West sunsets from your private balcony. The living room sofa pulls out into a Queen sleeper to accommodate two extra guests. The kitchen has everything a good chef would need to prepare any meal. There's a dining table for six when you decide to heat leftovers and stay in. Your dining set on the balcony is the ultimate sunset dinner locale.brbrTHE POOL, THE BEACH & TENNIS...brbr1800 Atlantic offers Resort-style amenities, including an extra large Community Pool right downstairs. There are chaise lounges surrounding the pool for your comfort, and a cabana with restrooms for your convenience. Please note this is a shared pool with set rules, such as no music and no coolers. We ask that our guests be mindful of their neighbors and respect the rules.brbrFrom the pool, there's a walking path that leads to the on-site beach. The on-site beach offers a relaxing setting, with chaise lounges and soft sand. There is no direct water access from this beach, but Smathers Beach, Key West's largest public beach, is located within walking distance right next door. There is also an oversized Jacuzzi and a picnic area with BBQs available for guest use. You'll also have access to the newly built fitness center and Key West's only clay tennis courts, both located on-site.brbrTHE ACCOMMODATIONS...brbr** Master Bedroom: a King bed, a large flat screen TV, direct access to the balcony, and an oversized shower. brbr** Second Bedroom: Two Twin beds OR One King bed, a flat screen TV, direct access to the balcony, and access to the full second bathroom.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen 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 & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Community Pool Accessbr** Community Jacuzzi Accessbr** Assigned off-street carport for 1 car (Parking Garage has a low clearance of 6'2)br** Key West's only clay tennis courtsbr** Handball courtsbr** Fitness Centerbr** Dry Saunasbr** Picnic areas with BBQsbr** Recreation rooms available for private partiesbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** This complex has both visitors and locals living here, we expect our guests to be mindful & respectful of the posted rulesbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..

Key West, Florida, United States

Bed

Bath

Sleeps

$443.86

Come relax or play while enjoying the spectacular sunsets and blue waters of Key West! brbrYou’ll want to take pictures at the Southernmost Point in the continental United States (only 3.5 blocks away), and fulfill all of your shopping desires at the dozens--if not hundreds--of shops and stores distributed along Duval and the adjoining streets. One block away is Banana Cafe, a fantastic French restaurant for breakfast with crepes, baguettes, and croissants. The sandy shores of South Beach are just three blocks away, with the Southernmost Cafe right there for lunch. The best sushi in town is served at Origami, also located one block away. It’s all there for you, so come and enjoy!brbrPLEASE NOTE THAT THIS PROPERTY DOESNT HAVE A POOL.brbrYou may use the pool at Dante’s if you utilize their food and beverage services or you may purchase a day pass using the link below at any of the hotels located near your rental. br brhttps://www.resortpass.com/s/us/fl/key-west/pool search_term=Key+West%2C+Florida&city_alias_id=26brbrThis spacious ground-level two-bedroom, two-bathroom property is located in the heart of Key West right off of Duval Street. A private, enclosed patio beckons you to relax in peaceful seclusion. The primary bedroom features a king-sized bed, a 32 flat-screen TV, and two nightstands with reading lamps. The second bedroom has a queen bed and full bath. A queen-sized sleeper sofa graces the living room, as well as another 32 flat-screen TV. The kitchen features a full-sized refrigerator, oven, toaster, microwave, and coffee maker to do all or none of the cooking while enjoying the island life. This property comes equipped with a private porch, air conditioning, free wi-fi, and an in-unit washer/dryer.

La Casa de Luces 2 Bed condo off Duval

Key West, Florida, United States

Bed

Bath

4

Sleeps

$397.73

Oceanfront Oasis in Key West – Steps from Smathers BeachbrbrEscape to paradise in this spacious 2-bedroom, 2-bath condo with breathtaking tropical ocean views, just 20 yards from the sandy shores of Smathers Beach. This 1,350 sq. ft. retreat offers the ultimate blend of comfort, convenience, and island charm.brbrThe master suite features a luxurious King Memory Foam bed, while the second bedroom includes a plush Queen pillow top and an additional Twin bed—perfect for families or groups. Need more space A Queen sleeper sofa in the living room accommodates extra guests with ease.brbrEnjoy Key West’s famous sunsets from your private 35-foot balcony, or relax indoors with floor-to-ceiling windows and flat-screen TVs with Wi-Fi in every room.brbrIdeally located just two miles from lively Duval Street, you're minutes from top restaurants, nightlife, and adventure activities like scuba diving, jet skiing, and deep-sea fishing.brbrOn-site amenities include:brbr Olympic-sized poolbr 20-person Jacuzzibr Picnic areas nestled in lush tropical gardensbr Easy access to water sports and snorkelingbrbrWhether you're seeking relaxation or adventure, this oceanfront condo is your perfect Key West getaway.brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$375.03

Welcome to Caribbean Conch – Your Island Retreat AwaitsbrbrEscape to the serene beauty of Caribbean Conch, a spacious and stylish island rental just steps from the pool and moments from the sparkling Atlantic. With a generous floor plan and elegant coastal decor, this tropical haven is the perfect backdrop for your next unforgettable getaway.brbrStep through impact-resistant sliding glass doors in the living room and both bedrooms to access a wrap-around deck that overlooks lush, tropical landscaping. Enjoy your morning coffee or evening cocktail with gentle ocean breezes and glimpses of the sea through swaying palms.brbrInside, you'll find comfort and convenience at every turn. The fully tiled interior includes a modern kitchen with full-sized appliances, two full bathrooms, and a full-sized washer and dryer—ideal for extended stays or family vacations.brbrResort-Style Amenities:brGuests of Caribbean Conch enjoy access to an array of premium amenities, including:brbr An Olympic-size swimming poolbr A 20-person hot tubbr Three tennis courtsbr Saunas for relaxing after a day of sun and sandbr A small fitness area to keep up your routinebr A cozy library for quiet reading or unwinding indoorsbrbrSleeping Arrangements:brbr Master Bedroom: King-sized bedbr Guest Bedroom: Queen-sized bedbr Living Room: Commercial-grade sleeper sofabrbrStay connected and entertained with free Wi-Fi and a large smart TV in the living area, plus additional TVs in each bedroom. Your stay also includes an assigned parking spot for a standard-sized vehicle.brbrWhether you're lounging poolside, enjoying a match on the tennis courts, or exploring the nearby attractions, Caribbean Conch offers everything you need for a relaxing, resort-style stay in paradise.brbrBook your stay and discover your own piece of island luxury at Caribbean Conch.brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value

Key West, Florida, United States

Bed

Bath

Sleeps

$520.07

Summary:brbrSea Breeze is the perfect location for your tropical getaway. This two bedroom condo is located in the heart of Old Town Key West, just steps away from the world famous Duval Street's shops, bars and restaurants! With off-street parking and just one block from Duval, this property has everything you need and more.brbrbrbrThe Space:brbrThis quaint two bedroom condominium has two queen beds and one queen sofa bed allowing for a maximum occupancy of six. brbrbrbrWith this rental you will find a a private covered porch, private off-street parking space, central A/C, and free wifi. The kitchen is fully equipped for all you may need during your stay!brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to check-in to enter the unit.brbrbrbrThe Neighborhood:brbrLocated on Whitehead St which is one block from world famous Duval St, Sea Breeze is walking distance to nearly everything you will want to experience during your escape to Key West. Walk to popular spots like The Southernmost Point, Key West Lighthouse, Blue Heaven, Firefly, Green Parrot and the Earnest Hemingway Home which are all just right down the street. Want to hit the beach Head down to Ft Zach State Park & Beach and enjoy the crystal clear waters and beautiful quiet beaches for a small admission fee.brbrbrbrGetting Around:brbrParking Information: There is one off-street private parking space assigned and included in your stay.brbrbrbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance.brbrbrbrOther Things to Note:brbr- Property includes onsite washer/dryer (located in the outside closet).brbr- This property is 1 of 4 units in a house, however has a private entrance, and patio.brbr- This property is not pet friendly.

Sea Breeze - One Block from Duval Street

Key West, Florida, United States

Bed

Bath

Sleeps

$850.46

Summary:br- Located on the south end of Duval Street steps from the Southernmost Point!br- Large open-concept condo with private balconies overlooking Duval Square restaurants & shops.br- On the intersection of Truman Avenue and Duval Street, just a 10 minute walk to downtown bars, restaurants and Key West's famous attractions.br- Private off-street parking included with your stay along with access to the rooftop pool overlooking Duval Street.brbrThe Space:brCasa Key West is an open-concept 3 bedroom, 2 bathroom condo. The bedroom layout consists of the following: brBedroom 1: Master suite with ensuite bath balcony and king bedbrBedroom 2: Queen size bed with balcony brBedroom 3: Two twin beds brExtra Sleeping: Queen size fold out sofa couch in the living room. brThis unit has a maximum occupancy of 8.brbrThere is a full kitchen as well as free WiFi, cable TV, and a private washer and dryer.brbrGuest Access:brOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to check-in to enter the unit.brbrShared community features: A shared rooftop pool with lounge chairs is located along the walkway of the Duval Square rooftops.brbrHow to Access: Unit is located on 2nd floor (no elevator access) above Duval Square restaurants.brbrThe Neighborhood:brOn the 1000 Block of Duval Street located in Duval Square this second story condo is in close proximity all of your Key West favorites. Explore local restaurants directly below the complex, such as New York Pasta Garden and Origami Sushi or make your way to Duval Street for art galleries, more food, shopping and nightlife. Casa Key West is also walking distance to the Southernmost Point!brbrGetting Around:brParking Information: There is one private parking spot for this unit in the Duval Square garage. Key to garage is provided at check in. The Duval Square parking garage is on Simonton Street.brbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance. Feel free to ask us for recommendations!brbrOther Things to Note:br- Unit features a private washer/dryer.br- This unit is not pet friendly.

Parking & Shared Pool - Casa Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$425.48

Summary:brbr1 bed, 1 bath condo w/shared pool at The Bayview HousebrbrbrbrThe Space:brbrExperience the charm of historic Key West with a stay at The Elizabeth Suite, a recently renovated 1 bedroom, 1 bathroom nightly vacation rental located in The Bayview House, a beautifully restored 1928 home in the heart of Old Town Key West. One of just four private suites on the property, this ground-floor unit offers a peaceful and convenient home base for your tropical getaway.brbrbrbrThe suite sleeps up to 4 guests comfortably with a queen bed in the bedroom and a queen sleeper sofa in the tastefully furnished living room. The living area is perfect for relaxing after a day of exploring the island. A fully equipped kitchenette — with a refrigerator, small cooktop, microwave, sink, and coffee maker — makes it easy to prepare light meals, snacks, or breakfast in the comfort of your suite.brbrbrbrEnjoy all the essentials for a relaxing stay, including:brbrbrbr- Shared swimming poolbrbr- Shared on-site laundry facilitiesbrbr- Modern bathroom with updated fixturesbrbr- Air conditioning, high-speed Wi-Fi, and flat-screen TVbrbr- First-come, first-served off-street parking (2 spaces) + additional street parkingbrbr- Unmatched location near Duval Street & Key West’s top attractionsbrbrbrbrThe Elizabeth Suite places you just steps away from everything that makes Key West a world-famous destination:brbrbrbr- Duval Street – Bars, restaurants, art galleries and nightlifebrbr- Mallory Square – Enjoy unforgettable sunset celebrationsbrbr- Key West Historic Seaport – Stroll the waterfront or hop on a boat tourbrbr- Ernest Hemingway Home, Fort Zachary Taylor Beach, Southernmost Point and morebrbrbrbrWhether you're in town for romance, relaxation or adventure, The Elizabeth Suite offers the perfect blend of comfort, location and style.brbrbrbrBook your stay at The Elizabeth Suite today and enjoy a memorable Key West vacation from a beautifully updated suite in the center of it all.

The Elizabeth Suite | 1 bedroom condo, shared pool

Key West, Florida, United States

Bed

Bath

Sleeps

$159.07

Summary:brbr1 bed, 1 bath rental w/shared pool at The Bayview HousebrbrbrbrThe Space:brbrWelcome to The Fleming Suite, a 1 bedroom, 1 bathroom vacation rental located at The Bayview House in vibrant Key West. This charming second-floor suite offers modern amenities, classic island charm and a prime location just minutes from the best attractions in Old Town Key West.brbrbrbrThis stylish suite features a cozy queen-size bed in the bedroom and a queen sleeper sofa in the living area, comfortably accommodating up to 4 guests. The kitchenette includes essentials like a refrigerator, microwave, cooktop, sink and coffee maker — perfect for preparing light meals or quick snacks before heading out for the day.brbrbrbrGuests will also enjoy access to a shared pool, ideal for cooling off after sightseeing or lounging under the Florida sun. A shared laundry on-site adds extra convenience for longer stays.brbrbrbrAdditional amenities include:brbrbrbr- Free Wi-Fibrbr- Flat-screen TVbrbr- Air conditioningbrbr- 2 on-site parking spaces (first come, first served) + street parkingbrbrbrbrLocation, Location, Location! Situated in one of Key West’s most desirable neighborhoods, The Fleming Suite places you within walking distance of top attractions:brbrbrbr- Duval Street – Lively bars, restaurants, shops and nightlifebrbr- Mallory Square – Sunset celebrations and street performancesbrbr- Key West Historic Seaport – Dining, water excursions and charming marina viewsbrbr- Higgs Beach & Fort Zachary Taylor State Park – Relaxation, snorkeling and historybrbr- Whether you're planning a romantic getaway, a sightseeing adventure, or a work-from-paradise escape, The Fleming Suite offers the perfect blend of comfort, convenience and local flair.brbrbrbrBook your stay today at The Fleming Suite – your tropical home away from home in beautiful Key West.

The Fleming Suite | 1 bedroom condo w/shared pool

Key West, Florida, United States

Bed

Bath

Sleeps

$707.01

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrAs Neptune was known as the Roman God of the Sea, NEPTUNE'S PENTHOUSE is known as the crown jewel of the 1800 Atlantic complex overlooking the Sea. This Penthouse Condominium has a lavish wrap-around balcony that overlooks the Atlantic Ocean and Community Pool below. You'll be able to enjoy the refreshing Key West breezes from atop your own private balcony, with lofty vaulted ceilings surrounded by the palm tree tops. This home is located in an upscale private Community within walking or biking distance to all of your favorite Key West spots, including beaches, restaurants, shopping, and the beautiful waters surrounding the island. Have your breath taken away by the scenic views and seaside serenity of NEPTUNE'S PENTHOUSE.brbrTHE LIVING AREA...brbrTo experience the most unique feature of NEPTUNE'S PENTHOUSE, you'll only need to look up; the vaulted ceilings in a lovely white wood set the tone for your gorgeous beachside home. The neutral colors of the living area are a beautiful contrast to the natural bright light shining through the floor-to-ceiling glass doors. There's a large HD Smart TV to enjoy your favorite show if you can tear yourself away from the stunning views of your balcony. The living room sofa pulls out to an additional bed for extra guests. The kitchen is fully equipped with everything needed to prepare any meal. There's a dining table for six when you decide to heat leftovers and stay in. Your dining set on the balcony is the perfect sunset dinner spot.brbrTHE POOL, THE BEACH & TENNIS... brbr1800 Atlantic offers Resort-style amenities, including an extra large Community Pool right downstairs. There are chaise lounges surrounding the pool for your comfort, and a cabana with restrooms for your convenience. Please note this is a shared pool with set rules, such as no music and no coolers. We ask that our guests be mindful of their neighbors and respect the rules.brbrFrom the pool, there's a walking path that leads to the on-site beach. The on-site beach offers a relaxing setting, with chaise lounges and soft sand. There is no direct water access from this beach, but Smathers Beach, Key West's largest public beach, is located within walking distance right next door. There is also an oversized Jacuzzi and a picnic area with BBQs available for guest use. You'll also have access to the newly built fitness center and Key West's only clay tennis courts, both located on-site.brbrTHE ACCOMMODATIONS... brbr** Master bedroom: a King bed, a large flat screen TV, direct access to the balcony, and an oversized shower. brbr** Second bedroom: Two Twin beds OR One King bed, a flat screen TV, direct access to the balcony, and access to the full second bathroom.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen 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 & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Community Pool Accessbr** Community Jacuzzi Accessbr** Assigned off-street carport for 1 car (Parking Garage has a low clearance of 6'2)br** Key West's only clay tennis courtsbr** Handball courtsbr** Fitness Centerbr** Dry Saunasbr** Picnic areas with BBQsbr** Recreation rooms available for private partiesbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** This complex has both visitors and locals living here, we expect our guests to be mindful & respectful of the posted rulesbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**NEPTUNE'S PENTHOUSE @ THE BEACH** Oceanfront Condo / Pool + LAST KEY SERVICE.

Key West, Florida, United States

Bed

Bath

Sleeps

$1047.86

A shared, sun-drenched, rooftop pool and pavilion are just steps from your door.brbrThis is an unbeatable location offering easy pedestrian access to dozens of shops and restaurants, the Ernest Hemingway Home Museum and other notable local attractions, and of course the serene, turquoise ocean that the island is famous for. brbrGather your friends and family together and book a Key West vacation you will never forget at Duval Square Penthouse.brbrBeds: 3 Kings, 2 Twins, 1 Sleeper SofabrDuval Square is a charming community with shops and restaurants downstairs and secure, quiet, private residences, pool and pavilion upstairs. Although the condo includes one assigned parking space in the gated garage, you can stroll anywhere from this conveniently located condo. All of the shops, galleries, restaurants, and attractions on and around Duval Street and nearby beaches are just a leisurely stroll away. brbrWhen you enter the home you will find a fully equipped kitchen, dining area, spacious living room and a convenient half bath. French doors let in the natural sunshine and open to the private back deck with dining table and chairs perfect for outdoor entertaining. brbrOn the second floor, you will find 2 bedroom suites, each with their own private bathroom and an additional private balcony off the main suite.brbrBedding: 1 king, 1 queen, 1 queen sleeper sofa.brbrElevator access from ground level to the first floor of the condos. Stairs to the unit's second floor bedrooms.brbr1 Reserved Parking Space in the Gated Garage.brbr**Construction Disclaimer** From mid May through the month of June, 2026, the pool area will be under construction. This will create noise and dust that could impact your stay and may lead to pool closure as well.

DUVAL SQUARE PENTHOUSE! A gorgeous condo on Duval St with room for everyone!

Key West, Florida, United States

Bed

Bath

Sleeps

$323.74

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrGULFSIDE VISTAS is a beautiful penthouse condo and is the perfect place to spend your stay in Key West, with panoramic views of the Gulf and cruise ships as they dock nearby. You'll have ocean views on three sides of GULFSIDE VISTAS, and two spacious balconies as well.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 LIVING AREA...brbrYou can see the ocean from any point in the open plan living area, and it is full of light. Sunsets are especially breathtaking. The kitchen of GULFSIDE VISTAS has granite counter tops and upgraded appliances, including the Sub-Zero refrigerator. There's even a bar with seating for four. The 50 INCH flat screen TV and stereo are great for those nights you aren't out on the town. The living room has a couch that pulls out into a sleeper sofa that can accommodate an extra two guests. There's a powder room in the hall for the convenience of your guests.brbrTHE POOL and THE BEACH...brbrThe Community Pool is right downstairs, located directly on the waterfront. There are plenty of chaises for your comfort, and a cabana with restrooms for your convenience. Fort Zachary Taylor State Park is a half mile away, with the prettiest beach in Key West.brbrTHE ACCOMMODATIONS...brbr• Master Bedroom: King bed, direct access to the sundeck, large closets, and an en-suite bathroom with twin vanities, a tub, and a shower.brbr• Second Bedroom: Two Twins OR One King bed, a flat screen TV, large closets, and an en-suite bathroom with a shower and tub combination.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr• Washer and Dryerbr• Central Heat and A/Cbr• Ceiling Fansbr• Flat Screen 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 & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr• Fully Fenced and Landscaped Private Yard br• Large Community Pool Accessbr• Two Covered Off-street Parking SpacesbrbrOther notes:brbr• Interim housekeeping provided upon requestbr• This property will accommodate up to 6 adultsbr• Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**GULFSIDE VISTAS @ THE ANNEX** Condo & Pool + LAST KEY SERVICES...

Key West, Florida, United States

Bed