Key West, FL Homes for Sale under $100,000

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  /68

  $37,500

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  617 Front St Unit B-24 Week 45, Key West, FL 33040

  Experience deeded ownership of the same week, each year (Week 45) at the highly desirable Galleon Resort with this premier timeshare opportunity. This unit showcases a wonderful location and some of the most spectacular sunsets in all of Key West.Filled with natural light, the residence also features a private balcony perfectly positioned to capture the stunning waterfront scenery above the

  

  Stephanie Herrmann

  Truman & Co. (KW)

  617 Front St Unit B-24 Week 45, Key West, FL 33040
• Explore Key West

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  /44

  $65,000

  $4K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  617 Front St Unit C54 Penthaus Wk36, Key West, FL 33040

  Experience premium waterfront ownership with this deeded timeshare week 36 in the highly coveted Building C at the Galleon Resort. This PENTHOUSE, end-corner unit offers one of the most desirable locations in the resort, featuring unobstructed, straight-on views of the Gulf of Mexico. The residence boasts soaring vaulted ceilings, additional windows for abundant natural light, and multiple

  

  Stephanie Herrmann

  Truman & Co. Real Estate

  617 Front St Unit C54 Penthaus Wk36, Key West, FL 33040
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  /66

  $26,000

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  617 Front St Unit D-54 Week 37 Penthou, Key West, FL 33040

  Penthouse, top floor, end unit! Experience premium waterfront ownership with this deeded timeshare in the highly coveted building at the Galleon Resort. This unit delivers a truly unforgettable Key West sunset experience, among the finest views in Key West. The residence boasts windows for abundant natural light and a balcony that maximizes the breathtaking waterfront setting. Enjoy front-row

  

  Stephanie Herrmann

  Truman & Co. (KW)

  617 Front St Unit D-54 Week 37 Penthou, Key West, FL 33040
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  /70

  $49,900

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  617 Front St Unit E-43 AB Week 46 Lock, Key West, FL 33040

  Welcome to your dream coastal retreat, where breathtaking Gulf and Marina views await from this desirable 3rd-floor lock door unit - where 2 units can be combined into one or separate. Nestled within a secure, gated community, this resort-style property offers exceptional amenities, one unassigned parking space, a sauna, fitness center, and the on-site Pirates Cove Café--everything you need for a

  

  Stephanie Herrmann

  Truman & Co. (KW)

  617 Front St Unit E-43 AB Week 46 Lock, Key West, FL 33040
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  /58

  $32,500

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  617 Front St Unit B51 Week 36 Penthous, Key West, FL 33040

  Top floor Penthouse end unit! Experience premium waterfront ownership with this deeded timeshare week 36 in the highly coveted building at the Galleon Resort. This unit offers one of the most beautiful Key West Sunsets at the resort.The residence boasts windows for abundant natural light and a balcony that maximizes the breathtaking waterfront setting. Enjoy front-row views as Coast Guard

  

  Stephanie Herrmann

  Truman & Co. Real Estate

  617 Front St Unit B51 Week 36 Penthous, Key West, FL 33040
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  /68

  $65,000

  $4K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  617 Front St Unit C54 Penthouse Week 3, Key West, FL 33040

  Experience elevated waterfront ownership with this deeded timeshare in the highly desirable Building C at the Galleon Resort. This penthouse end-corner unit boasts one of the most sought-after spots in the resort, showcasing unobstructed, head-on views of the Gulf of Mexico.The residence features vaulted ceilings, extra windows for enhanced natural light, and multiple balconies designed to

  

  Stephanie Herrmann

  Truman & Co. (KW)

  617 Front St Unit C54 Penthouse Week 3, Key West, FL 33040
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  /58

  $49,900

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  617 Front St Unit E43-Ab Lockout Week, Key West, FL 33040

  Welcome to your dream coastal retreat, where breathtaking Gulf and Marina views await from this desirable 3rd-floor lockout unit deeded timeshare week 46- where 2 units can be combined into one or separate. Nestled within a secure, gated community, this resort-style property offers exceptional amenities, one unassigned parking space, a sauna, fitness center, and the on-site Pirates Cove

  

  Stephanie Herrmann

  Truman & Co. Real Estate

  617 Front St Unit E43-Ab Lockout Week, Key West, FL 33040
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  /66

  $32,500

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  617 Front St Unit B-51 Penthouse Week, Key West, FL 33040

  Top floor unit! Experience premium waterfront ownership with this deeded timeshare in the highly coveted building at the Galleon Resort. This unit offers one of the most beautiful Key West Sunsets at the resort.The residence boasts windows for abundant natural light and a balcony that maximizes the breathtaking waterfront setting. Enjoy front-row views as Coast Guard vessels and iconic pirate

  

  Stephanie Herrmann

  Truman & Co. (KW)

  617 Front St Unit B-51 Penthouse Week, Key West, FL 33040
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  /53

  $62,000

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  617 Front St Unit A-52 Penthouse Week, Key West, FL 33040

  PentHouse! What an incredible opportunity to own this fabulous penthouse at the Galleon Resort. Enjoy the unmatched appeal of owning a deeded Key West timeshare during the final week of the year (Week 52)--one of the most desirable weeks in the Florida Keys! This prime holiday week offers Key West's legendary New Year's Eve celebrations, including live music, fireworks, and iconic Duval Street

  

  Stephanie Herrmann

  Truman & Co. (KW)

  617 Front St Unit A-52 Penthouse Week, Key West, FL 33040
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  $6,000

  • 2 Beds
  • 2 Baths
  • 999 Sq Ft

  32 Beach Dr, Key West, FL 33040

  RENT ONLY!!!August 1st to November 1st, 2026. Stunning open water views from this beautiful oceanfront home. You can enjoy quiet mornings and spectacular sunsets.The home features 2 bedrooms 2 bathrooms and the main bedroom has a king and an en-suite. The guest bedroom is furnished with a queen size bed. Second bathroom can be accessed from the main living/kitchen area, as well as from

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  32 Beach Dr, Key West, FL 33040
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  /11

  $3,350

  • 2 Beds
  • 1 Bath

  1614 Dennis St Unit B, Key West, FL 33040

  Newtown annual rental is now available to RENT! 2 bed 1 bath large deck! Convenient location near Key West Highs and just a short ride to down town. Can be rented ASAP, comes with washer and dryer fro your unit! First Month and security deposit to get started. Tenant pays utilities.

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  1614 Dennis St Unit B, Key West, FL 33040
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  /32

  $5,500

  • 3 Beds
  • 3 Baths
  • 1,380 Sq Ft

  59 Palm Dr, Key West, FL 33040

  Enjoy the Keys lifestyle in this stunning canal-front 3-bedroom, 3-bathroom elevated modular home, located in the desirable Bay Point neighborhood, just behind Baby's Coffee. Available for $5,500 per month, this 2015-built home offers modern amenities and a spacious layout perfect for comfortable living. The lower level features a bedroom with a full bath, 9-foot ceilings, and access to a covered

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  59 Palm Dr, Key West, FL 33040
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  /41

  $42,000

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  617 Front St Unit B41 Week 1, Key West, FL 33040

  Views of the famous Key West Sunset, Gulf of Mexico and pool await you when you arrive at this 4th-floor end- deeded timeshare unit. The live music from the Tiki bar saunters up to the balconies. This highly desirable winter week is magical enjoy the warm weather and Christmas boat parades while Key West is all dressed up for the holidays. Enjoy the private beach, pool, hot tub, sauna, outdoor

  

  Stephanie Herrmann

  Truman & Co. Real Estate

  617 Front St Unit B41 Week 1, Key West, FL 33040
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  $5,500

  • 3 Beds
  • 3 Baths
  • 1,380 Sq Ft

  37 Palm Dr, Key West, FL 33040

  Turnkey Waterfront Living in Saddlebunch Key - $5,500/month This fully furnished 3 bed, 3 bath canal-front home offers the ultimate Keys lifestyle just behind Baby's Coffee. Enjoy quick access to open water with your own boat lift, perfect for fishing or sunset cruising. Spacious open-concept living, updated kitchen, and outdoor entertaining areas make this a perfect getaway or full-time

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  37 Palm Dr, Key West, FL 33040
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  /57

  $59,900

  $9K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  617 Front St Unit C41 Week 50, Key West, FL 33040

  Own a deeded 4th-floor Gulf and waterfront corner end unit at the highly desirable Galleon Resort in the heart of Old Town Key West! This beautifully maintained 2-bedroom, 2-bath condo sleeps six and features new 2026 furnishings, a king bed, two twins (convertible to a queen), sleeper sofa, two full baths, and a private balcony with marina, gulf, live-music, and sunset views. Everything you love

  

  Stephanie Herrmann

  Truman & Co. (KW)

  617 Front St Unit C41 Week 50, Key West, FL 33040
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  /41

  $59,000

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  617 Front St Unit A52 Penthaus Week 32, Key West, FL 33040

  PENTHOUSE! Beautiful straight-on views of the Gulf, Pool, Beach, Sunsets, and Tiki Bar. Enjoy week 32 in this Timeless Timeshare and celebrate Lobster Week and the Rum Festival. The Galleon resort has Elevators, a rooftop deck, a gated parking garage, a sauna, an exercise room, and the Pirates Cove Cafe and Outdoor gas grills, which are located on the Marina side of the Galleon. Stay or rent it

  

  Stephanie Herrmann

  Truman & Co. Real Estate

  617 Front St Unit A52 Penthaus Week 32, Key West, FL 33040
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  /41

  $62,000

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  617 Front St Unit A-52 Penthaus Week 5, Key West, FL 33040

  Penthouse! What an incredible opportunity to own this fabulous penthouse at the Galleon Resort. Enjoy the unmatched appeal of owning a deeded Key West timeshare during the final week of the year, Week 52- one of the most desirable weeks in the Florida Keys! This prime holiday week offers Key West's legendary New Year's Celebrations, including live music, fireworks, and iconic Duval Street events.

  

  Stephanie Herrmann

  Truman & Co. Real Estate

  617 Front St Unit A-52 Penthaus Week 5, Key West, FL 33040
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  /27

  $28,900

  $1K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  617 Front St Unit B54/42, Key West, FL 33040

  DEEDED ANNUAL TIMESHARE! Enjoy 7 nights PER YEAR in a large 2bd, 2ba PENTHOUSE condo at the Galleon Resort in Key West! Sleeps up to 6 adults. This Penthouse SWING FLOAT week is deeded as B54/42. Choose from the following 18 Swing Floating weeks every year: 18-23, 36-50. (excludes Fantasy Fest (usually week 42 and Boat Race weeks) A Penthouse 5th Top floor unit also GUARENTEED each year! Make

  Mary Bradford LIST FOR LESS, LLC

  617 Front St Unit B54/42, Key West, FL 33040
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  /15

  $5,500

  • 3 Beds
  • 2 Baths
  • 1,407 Sq Ft

  218 Whitehead St Unit Apartment, Key West, FL 33040

  Rare opportunity to lease a spacious 1,407-square-foot second-floor apartment in the heart of Old Town Key West. This 3-bedroom, 2-bath residence features an expansive open-concept floor plan, generous living and dining areas, and two private balconies overlooking one of the city's most iconic intersections. Filled with natural light and offering ample space for comfortable living, the apartment

  Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  218 Whitehead St Unit Apartment, Key West, FL 33040
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  /11

  $3,000

  • 1 Bed
  • 1 Bath
  • 400 Sq Ft

  513 Truman Ave Unit B, Key West, FL 33040

  Charming 1 bedroom, 1 bathroom upstairs apartment in the heart of Old Town Key West! Features include a full kitchen, impact windows, private balcony off the bedroom, and shared laundry. Located at 513 Truman Ave., just minutes from shops, restaurants, and the waterfront. Available for a 12 month lease. F/L/S and credit background check. No pets.

  Jenny Perry Preferred Properties (KW)

  513 Truman Ave Unit B, Key West, FL 33040
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  /2

  $15,000

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft

  323 Whitehead St Unit 702 wks 12, Key West, FL 33040

  Own Week 12 at The Banyan Resort and enjoy one of the most sought-after times of year in Key West. Nestled in the heart of Old Town, this charming one-bedroom loft suite offers the perfect island getaway just steps from the energy of Duval Street. Unit 702 comfortably accommodates up to four guests and features a unique loft-style design with a spiral staircase leading to a semi-private bedroom

  Monika Rydzak eXp Realty LLC KW Branch

  323 Whitehead St Unit 702 wks 12, Key West, FL 33040
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  /11

  $2,900

  • 1 Bed
  • 1 Bath
  • 642 Sq Ft

  1120 Elgin Ln Unit B, Key West, FL 33040

  Available August 1st, this 1/1 cottage in the heart of Old Town offers walkability to world class dining, shopping, and the world-famous Duval Street. Off street parking for up to 2 cars. First month's rent and security deposit due up front.

  Justyn Ewald Expert Realty LLC

  1120 Elgin Ln Unit B, Key West, FL 33040
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  /12

  $4,000

  • 2 Beds
  • 1.5 Baths
  • 780 Sq Ft

  36 Merganser Ln, Key West, FL 33040

  Stunning furnished two-bedroom Townhouse with tropical views, modern kitchen, and spacious living room available for a year-long lease. Pet-friendly community with security station, two community pools, gym, and butterfly garden. First-month rent, last month's rent, and security deposit are required at the lease signing. Utilities are not included. Background and financial screening also

  Hana Tomita Berkshire Hathaway HomeServices Knight & Gardner Realty

  36 Merganser Ln, Key West, FL 33040
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  /19

  $5,900

  • 2 Beds
  • 2.5 Baths
  • 728 Sq Ft

  1002 Thomas St, Key West, FL 33040

  Located in the heart of Old Town Key West! Walk, bike or drive your golf cart to famous restaurants, bars, tourist attractions and beaches. This 2 bedroom 2.5 bath home is being rented annually, fully furnished and includes two of street parking spaces, a rare find in Old Town! OWNER PAYS water, electric and trash. One small dog is allowed upon approval by the owner and for a non-refundable pet

  Jessica Prescott Coastal Collection Real Estate Inc.

  1002 Thomas St, Key West, FL 33040
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  /23

  $4,200

  • 2 Beds
  • 2.5 Baths
  • 1,120 Sq Ft

  202 Golf Club Dr, Key West, FL 33040

  Ready for immediate occupancy! This Spa home located in the Sanctuary at the Key West Golf Club features a private dip pool and carport. The first floor is an open floor plan with kitchen, living area and half bath. French doors open to the walled, private rear yard with your own dip pool. Upstairs feature the primary and guest bedroom ensuites. New impact windows and doors are scheduled to be

  Behmke The Compass Realty (KW)

  202 Golf Club Dr, Key West, FL 33040
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  /28

  $5,000

  • 2 Beds
  • 2.5 Baths
  • 1,288 Sq Ft

  1124 Eaton St, Key West, FL 33040

  Welcome to your Key West paradise at 1124 Eaton Street! Located in the heart of Old Town, this charming 2-bedroom, 2.5-bath home offers the perfect launchpad for your Key West adventure. Enjoy the luxury of a private off-street patio ideal for entertaining or a quiet retreat. Forget the hassle of parking with your own private parking space. Just a short walk to the Seaport, you'll have easy

  Lisa Karp Cashel Properties

  1124 Eaton St, Key West, FL 33040
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  /20

  $5,200

  • 3 Beds
  • 3 Baths
  • 1,344 Sq Ft

  1110 Truman Ave Unit UP, Key West, FL 33040

  Available now! Brand new 3 bedroom 3 bath in Old Town with off street parking for 2 cars! Second floor apartment is NEW and offers spacious bedrooms, designer baths, light filled spaces and a gorgeous kitchen. Washer/Dryer. Central AC. Close to dining, shopping, tennis courts, and just blocks to Duval Street. Available for an annual lease. Rent includes water/sewer and garbage. Owner is a Lic. RE

  Bascom Grooms Bascom Grooms Real Estate (KW)

  1110 Truman Ave Unit UP, Key West, FL 33040
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  /25

  $5,000

  • 2 Beds
  • 2.5 Baths
  • 1,216 Sq Ft

  101 Front St Unit 4, Key West, FL 33040

  Annual Rental Available in the Truman Annex Foundry Building! Enjoy the best of Key West living from this fully furnished 2 bedroom, 2.5 bath, 3 story townhome located in the highly desirable Truman Annex Foundry Building at 101 Front Street, Unit #4.This spacious residence is offered fully furnished and features multiple levels of living space, a private fenced yard area, and access to the

  Terri Spottswood Truman & Co. (KW)

  101 Front St Unit 4, Key West, FL 33040
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  /9

  $5,800

  • 3 Beds
  • 2 Baths

  14 Aster Terrace, Key West, FL 33040

  Available AUGUST 1st. NOT FURNISHED. This key haven home is on one of the nicest boating swimming canals in Key Haven, just a few houses from open water and less than a mile from Key West. Seawall and deck. There is a formal dining area, living room, kitchen and three bedrooms, the outdoor spaces ideal for entertaining or just relaxing. Large pergola and a partial in ground large hot tub with

  Daniel Coll Coll & Coll Inc

  14 Aster Terrace, Key West, FL 33040
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  /5

  $2,800

  • 2 Beds
  • 1 Bath

  6630 Maloney Ave Unit 7D, Key West, FL 33040

  Ernie Cruz Berkshire Hathaway HomeServices Knight & Gardner Realty

  6630 Maloney Ave Unit 7D, Key West, FL 33040
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  /9

  $20,000

  $5K PRICE INCREASE

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft

  3675 S Roosevelt Blvd Unit week 42, Key West, FL 33040

  Selling weeks 42 and 43. High Tourist season. Fantasy Fest and Halloween. 2 Bedroom Villa, Ocean view sunrise view, Princess balcony

  Jenny Murphy Keller Williams Key West Compass Realty

  3675 S Roosevelt Blvd Unit week 42, Key West, FL 33040
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  /2

  $2,500

  5950 Peninsular Ave Unit 640, Key West, FL 33040

  Prestigious boat slip for rent at Ocean's Edge Marina, suitable for boats up to 50FT located on the North pier with ample water access boasting a 6ft control depth. Features include a nearby fuel station and access to the hotel pool for tenants. Ideal for water enthusiasts seeking a premium marina experience. Daily, monthly or long term rentals available. Air bnb's or houseboats are not allowed.

  Hana Tomita Berkshire Hathaway HomeServices Knight & Gardner Realty

  5950 Peninsular Ave Unit 640, Key West, FL 33040
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  /18

  $3,450

  • 2 Beds
  • 2 Baths
  • 1,175 Sq Ft

  Unlisted Address

  Fully furnished La Brisa condo available through September 30, 2026. Electric, water and wi-fi included up to $200 per month. Washer and dryer in the unit. Covered carport, storage unit, central a/c, salt ponds view. Secured entry and building. La Brisa has an EV charging station, car wash area, tennis/pickleball court, barbecues, heated pool and hot tub and saunas No smoking, no pets, background

  Suzanne Washburn Coldwell Banker Schmitt Real Estate Co. (KW)

  Unlisted Address
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  /9

  $20,000

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft

  3675 S Roosevelt Blvd Unit week 43, Key West, FL 33040

  Selling week 42 and 43. High Tourist season. Fantasy Fest and Halloween. These weeks can be sold as deeded weeks or as points to add to an existing portfolio. Across from Smathers beach. There is an ocean view and amazing Sunrise views. Princess Balcony. 2 Bedroom Villa.

  Jenny Murphy Keller Williams Key West Compass Realty

  3675 S Roosevelt Blvd Unit week 43, Key West, FL 33040
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  /13

  $2,000

  • 1 Bed
  • 1 Bath
  • 396 Sq Ft

  55 Boca Chica Rd Unit 451, Key West, FL 33040

  Just 10 miles from downtown Key West! This Seaside resort mobile home has a covered deck that maximizes indoor-outdoor living with a relaxed space to take in the views. Added storage space can be found in the shed off the deck. Not only is it close to Key West, the 1 bedroom, 1 bath unit has a fantastic location inside the community, situated on Fantasy Island, just a short walk from the Seaside

  Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

  55 Boca Chica Rd Unit 451, Key West, FL 33040
• 

  

  /13

  $3,100

  • 2 Beds
  • 1 Bath

  1421 2nd St Unit 1425, Key West, FL 33040

  Ready for immediate occupancy, grab this 2/1 unfurnished apartment while it's still available. New kitchen, new flooring, central air, impact windows for safety. Washer/dryer hookups. Potential for a nice garden courtyard in front. No pets, please.

  Everett Watkins Keller Williams Key West Compass Realty

  1421 2nd St Unit 1425, Key West, FL 33040
• 

  

  /17

  $4,200

  • 3 Beds
  • 2 Baths
  • 642 Sq Ft

  1120 Elgin Ln Unit A, Key West, FL 33040

  Experience Old Town Key West living in this charming home tucked away on a quiet lane just steps from restaurants, shops, and attractions. Enjoy the convenience of off-street parking, a private outdoor sitting area, and plenty of space to relax and enjoy the island lifestyle. Located in one of Key West's most desirable neighborhoods, this property offers privacy, character, and an unbeatable

  Justyn Ewald Expert Realty LLC

  1120 Elgin Ln Unit A, Key West, FL 33040
• 

  

  /5

  $3,500

  • 2 Beds
  • 1 Bath

  1110 White St Unit 2, Key West, FL 33040

  2-bedroom,1-bath apartment in prime Key West location .Walking distance to Sandy's cafe ,Fausto's Food Palace ,and local shops ,and just minutes from the beach .Conveniently located near restaurants ,grocery stores ,and laundry facilities. Enjoy the convenience of having everything you need just steps away in one of Key West's most desirable areas

  Ernie Cruz Berkshire Hathaway HomeServices Knight & Gardner Realty

  1110 White St Unit 2, Key West, FL 33040
• 

  

  /17

  $3,995

  • 2 Beds
  • 1.5 Baths
  • 780 Sq Ft

  81 Golf Club Dr, Key West, FL 33040

  For Rent - Key West Golf Club Community Beautifully updated 2 bedroom, 1.5 bath townhome located in the highly desirable gated Key West Golf Club community on Stock Island. This 780 sq ft home offers a perfect blend of comfort, style and island living. This home features beautifully renovated kitchen and bathrooms, along with an open and inviting living space. Step outside to a spacious, private

  Nicole Gruenauer Key West Luxury Real Estate Inc (KW)

  81 Golf Club Dr, Key West, FL 33040
• 

  

  /19

  $3,975

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft

  1901 S Roosevelt Blvd Unit 404W, Key West, FL 33040

  Owners are licensed real estate brokers. Beautifully redecorated condo on 4th floor facing tranquil nature preserve. Hurricane shutters. One covered parking space and storage locker. Easy to show. Occupancy date negotiable. Newer appliances & HVAC including washer/dryer. BBQ pits on premises, along with pool, Jacuzzi, tennis court... (see supplement for full remarks). Across the street from

  Douglas Miller Amerirealty Corp (KW)

  1901 S Roosevelt Blvd Unit 404W, Key West, FL 33040

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