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

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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

    Agent Photo

    Stephanie Herrmann

    Truman & Co. Real Estate

    (645) 230-1832

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

    $69,000

    • 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

    Agent Photo

    Stephanie Herrmann

    Truman & Co. (KW)

    (645) 231-4457

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

    Agent Photo

    Stephanie Herrmann

    Truman & Co. Real Estate

    (833) 427-4068

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

    Agent Photo

    Stephanie Herrmann

    Truman & Co. (KW)

    (645) 231-3562

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

    Agent Photo

    Stephanie Herrmann

    Truman & Co. (KW)

    (645) 230-4415

    617 Front St Unit B-24 Week 45, Key West, FL 33040
  • /44

    $69,000

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

    617 Front St Unit C-54 Penthouse Wk 36, 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

    Agent Photo

    Stephanie Herrmann

    Truman & Co. Real Estate

    (645) 236-8896

    617 Front St Unit C-54 Penthouse Wk 36, Key West, FL 33040
  • /66

    $31,000

    • 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

    Agent Photo

    Stephanie Herrmann

    Truman & Co. (KW)

    (645) 233-3593

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

    Agent Photo

    Stephanie Herrmann

    Truman & Co. (KW)

    (855) 450-7168

    617 Front St Unit E-43 AB Week 46 Lock, Key West, FL 33040
  • /59

    $31,000

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

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

    Welcome to your dream coastal retreat, where breathtaking Gulf and Marina views await you from this desirable PENTHOUSE, top-floor end-unit deeded Timeshare week 37! 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.Enjoy front-row views as Coast Guard

    Agent Photo

    Stephanie Herrmann

    Truman & Co. Real Estate

    (645) 238-9517

    617 Front St Unit D-54 Week 37 Penthou, Key West, FL 33040
  • /8

    $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.

    Agent Photo

    Matthew Sheehan

    Ocean Sotheby's International Realty

    (786) 400-2812

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

    Agent Photo

    Stephanie Herrmann

    Truman & Co. Real Estate

    (645) 400-9393

    617 Front St Unit B41 Week 1, Key West, FL 33040
  • /18

    $4,195

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft

    1916 Staples Ave, Key West, FL 33040

    ANNUAL RENTAL! Available JUNE 1st. The perfect Key West classic cottage with all the modern features! Perfectly located just short bike ride to Old Town or distance to the island's major shopping centers. Gated entry and fenced in. Large storage area in backyard, Gas BBQ grill for cookouts and sundeck. Has Washer/dryer in rear utility room. Nicely appointed interior fully furnished with a coastal

    Agent Photo

    Christian Loffreno

    Loffreno Real Estate

    (786) 686-9482

    1916 Staples Ave, Key West, FL 33040
  • /13

    $3,350

    • 1 Bed
    • 1 Bath
    • 450 Sq Ft

    828 Fleming St, Key West, FL 33040

    Some addresses offer more than a place to stay, they offer a lifestyle. This brand-new Old Town studio is one of them: a refined pied-à-terre in the heart of Key West's Historic District, designed for those who appreciate effortless luxury. Completely reimagined from the ground up, the space blends clean, modern lines with warm, natural finishes. Wide-plank white oak floors, a bright, airy

    Agent Photo

    Damian Vantriglia

    Berkshire Hathaway HomeServices Knight & Gardner Realty

    (786) 822-7030

    828 Fleming St, Key West, FL 33040
  • /41

    $59,000

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

    617 Front St Unit A52 Penthouse Week 3, 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

    Agent Photo

    Stephanie Herrmann

    Truman & Co. Real Estate

    (645) 215-6438

    617 Front St Unit A52 Penthouse Week 3, Key West, FL 33040
  • /42

    $69,000

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

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

    On the Gulf of Mexico this 4th floor end unit Timeshare is on the water and overlooks the Key West Marina. 2 bed 2bath with sofa couch sleeps 6. Week 50 is a very sought after week that offers ideal winter weather, a relaxed island atmosphere and peak rental demand. Enjoy the decorative Christmas boat parades from your own personal view balconies and experience Key West all dressed up for the

    Agent Photo

    Stephanie Herrmann

    Truman & Co. Real Estate

    (645) 300-5987

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

    $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 Celebrations, including live music, fireworks, and iconic Duval Street events.

    Agent Photo

    Stephanie Herrmann

    Truman & Co. Real Estate

    (645) 215-8159

    617 Front St Unit A-52 Penthouse Week, Key West, FL 33040
  • /21

    $2,975

    • 1 Bed
    • 1 Bath
    • 365 Sq Ft

    904 Terry Ln Unit 4, Key West, FL 33040

    Ideal Island Retreat, this adorable, furnished 2nd floor condo with central AC has everything you need in order to fully enjoy Old Town KW living. A designated parking spot (golden asset!) on quiet Terry Lane, which is bordered by Whitehead, Thomas, Olivia Sts & Truman Ave, is steps away from famous Duval St, the Hemingway & Lighthouse, as well as iconic restaurants Blue Heaven & Moon Dog Cafe.

    Jimmy Lane Island Life Realty Experts

    904 Terry Ln Unit 4, Key West, FL 33040
  • /21

    $2,900

    • 1 Bed
    • 1 Bath
    • 533 Sq Ft

    1420 Petronia St Unit 2, Key West, FL 33040

    1420 Petronia St. Apt. #2 available June 1. Cozy 533 sf. 1bd/1bath apartment on second floor with private tree top deck in back. Located in the Meadows on a quiet, one way street with ample street parking. The entire duplex was totally renovated in 2024 including the 2nd floor apartment. This apartment has all new plumbing and electric, impact windows and door with treatments, LED ceiling lights,

    Curtis A. Skomp, CCIM RE/MAX Keys Connection (KW)

    1420 Petronia St Unit 2, Key West, FL 33040
  • /14

    $3,900

    • 2 Beds
    • 1 Bath
    • 738 Sq Ft

    1420 Petronia St Unit 1, Key West, FL 33040

    Recently totally renovated and restored 1st floor apartment. Located in the highly desirable Meadows neighborhood on quiet, one way street. Unfurnished 738 sf. 2bedroom/1bath with inviting front porch and large private outdoor rear deck. Tropically landscaped around the entire property and mostly fenced in backyard. Inside has Mitsubishi ductless AC system with remote controls and 4 air handlers.

    Curtis A. Skomp, CCIM RE/MAX Keys Connection (KW)

    1420 Petronia St Unit 1, Key West, FL 33040
  • /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 LoKation Real Estate - Pompano Beach

    1124 Eaton St, Key West, FL 33040
  • /21

    $4,800

    • 3 Beds
    • 3 Baths
    • 1,216 Sq Ft

    1207 William St Unit 3, Key West, FL 33040

    Contact the owner Andy to inquire: 954-650-7217 Spacious 3-bedroom, 3-bath home offers a layout you simply don't see often in Key West. Each LARGE bedroom has its own en-suite bath, giving everyone their own private space. What really makes this property stand out are the three separate entrances, including private exterior access to two of the bedrooms. A hallway door can be closed to fully

    Sarah Bixby eXp Realty LLC

    1207 William St Unit 3, Key West, FL 33040
  • /19

    $5,900

    • 3 Beds
    • 3 Baths
    • 1,533 Sq Ft

    1215 Grinnell St Unit D, Key West, FL 33040

    Experience the charm of Old Town Key West in this beautifully renovated home located in the gated community of Grinnell Gardens. Featuring 3 bedrooms and 3 full bathrooms, this property offers modern updates throughout, including impact windows and doors, Hardie board siding, and a metal roof. Enjoy two private landscaped outdoor spaces, off-street parking, and a prime location just a short walk

    Justyn Ewald Expert Realty LLC

    1215 Grinnell St Unit D, Key West, FL 33040
  • /16

    $3,200

    • 1 Bed
    • 1 Bath
    • 754 Sq Ft

    2601 S Roosevelt Blvd Unit 404B, Key West, FL 33040

    FULLY FURNISHED 1 bed 1 bath condo overlooking Smathers Beach is now available for long term rental.. This unit has a newly remodeled kitchen, with new stove-top, Quartz Counters, and it has a Quartz Lunch Counter. The Ocean View balcony has a small bar with stools and is perfect for evening drinks.The furnishings include a living room couch with a hide-a-bed feature. end-tables with lamps,

    Mark Peterson Mark F. Peterson Licensed Real Estate Broker

    2601 S Roosevelt Blvd Unit 404B, Key West, FL 33040
  • /21

    $6,500

    • 3 Beds
    • 2 Baths
    • 1,321 Sq Ft

    1420 Petronia St Unit 1 & 2, Key West, FL 33040

    Recently totally renovated and restored two story Duplex in the Meadows. Both units #1 and #2 are available June 1. Rental rate is for both units.Located in the highly desirable neighborhood on quiet, one way street. Downstairs is 788 sf. 2 bedroom/1bath with inviting front porch, private outdoor rear deck with lush, tropically landscaping. Gated and mostly fenced in backyard. Upstairs is 533

    Curtis A. Skomp, CCIM RE/MAX Keys Connection (KW)

    1420 Petronia St Unit 1 & 2, Key West, FL 33040
  • /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
  • /7

    $2,400

    • 1 Bed
    • 1 Bath
    • 450 Sq Ft

    742 Windsor Ln Unit 1, Key West, FL 33040

    Wonderful 1 bedroom / 1 bathroom unit in the heart of Old Town! Unit has hardwood flooring and ceiling fans throughout, and features custom cabinets and lighting, and large windows. Open living and kitchen area and private bedroom. Bathroom is custom-tiled. Spacious front porch faces out to a tranquil fenced front yard surrounded by trees. A true Old Town gem! Pets considered on case by case

    Jimmy Lane Island Life Realty Experts

    742 Windsor Ln Unit 1, Key West, FL 33040
  • /19

    $6,000

    • 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 trash and internet. One small dog is allowed upon approval by the owner and for a

    Jessica Prescott Coastal Collection Real Estate Inc.

    1002 Thomas St, Key West, FL 33040
  • /18

    $3,450

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

    Unlisted Address

    Fully furnished La Brisa condo available through December 15, 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
  • /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
  • /14

    $4,500

    • 3 Beds
    • 1 Bath
    • 1,079 Sq Ft

    1704 Duncan St, Key West, FL 33040

    Enjoy island living in this charming 3-bedroom, 1-bath home located in the desirable Newtown neighborhood of Key West. Conveniently situated near shopping, dining, beaches, and local attractions, this home offers both comfort and accessibility. Inside, you'll find a bright living area, functional layout, and well-sized bedrooms. The spacious backyard provides plenty of room to relax and enjoy the

    Justyn Ewald Expert Realty LLC

    1704 Duncan St, Key West, FL 33040
  • /26

    $4,900

    • 3 Beds
    • 2 Baths
    • 912 Sq Ft

    2401 Patterson Ave Unit 101, Key West, FL 33040

    Spacious 3BD/2BA - Renovated First-Floor Duplex in Midtown This fully renovated 3-bedroom, 2-bath apartment offers everything you need for comfortable long-term living in Key West's Midtown neighborhood. Located on the first floor of a freshly updated duplex, this home features a large open-concept living area and kitchen with all new appliances and high-end finishes. The unit includes a

    Jody Clark Key West Luxury Real Estate Inc (KW)

    2401 Patterson Ave Unit 101, Key West, FL 33040
  • /5

    $3,300

    • 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
  • /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
  • /15

    $2,775

    • 1 Bed
    • 1 Bath
    • 368 Sq Ft

    1318 Duncan St Unit 3, Key West, FL 33040

    AVAILABLE JULY 1st. Lease at $2775 per month for a yearly lease. Renovated detached pool view cottage with stainless range and fridge/freezer close to vibrant White St with its cafes and restaurants, gourmet food stores, galleries and yoga studios. A short walk or bike ride to the beaches and the heart of Old Town, the Historic Seaport and Duval Street.....The compound has a large pool shared

    Rob Severin Rob Severin Real Estate Co

    1318 Duncan St Unit 3, Key West, FL 33040
  • /9

    $2,050

    • 1 Bed
    • 1 Bath
    • 300 Sq Ft

    1120 Washington St Unit SU, Key West, FL 33040

    Studio available at the lower end of Washington Street, for one person. No pets permitted. Water is included. First month, last month, and security deposit required upfront. Please note, there is no washer or dryer on site.

    Hana Tomita Berkshire Hathaway HomeServices Knight & Gardner Realty

    1120 Washington St Unit SU, Key West, FL 33040
  • /21

    $5,900

    • 3 Beds
    • 2 Baths
    • 2,018 Sq Ft

    3817 Duck Ave, Key West, FL 33040

    Furnished 3-bedroom, 2-bath single-level home available for a one-year lease after June 10th. First, last, and security deposit required. Small pets may be considered with an additional deposit. The property features a beautiful tropical garden and a two-car carport for convenient parking.

    Hana Tomita Berkshire Hathaway HomeServices Knight & Gardner Realty

    3817 Duck Ave, Key West, FL 33040
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