$3,900 - $4,650 per month
NAS Key West Homes
3 Beds
800 Sigsbee Rd, Key West, FL 33040
42
Homes for Rent near Monroe County Detention Center
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800 Sigsbee Rd, Key West, FL 33040
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$4,500 per month
- 2 Beds
- 2 Baths
- 1,416 Sq Ft
- Property for Rent
728 Ashe St, Key West, FL 33040
728 Ashe St, Key West, FL 33040Charming Historic Home in Old Town Key West - Annual Lease RequiredStep into the charm of Old Town Key West with this spacious and beautifully maintained historic home. This two-bedroom, one-and-a-half-bath residence blends classic island character with modern comfort.Both bedrooms are generously sized, each offering ample closet space. The primary bedroom features direct access to the full bath
Jody Clark Key West Luxury Real Estate Inc (KW)
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$2,389 - $4,210 per month
3900 S Roosevelt Blvd, Key West, FL 33040Ocean Walk
Studio - 3 Beds
3900 S Roosevelt Blvd, Key West, FL 33040
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$4,100 per month
- 3 Beds
- 2 Baths
- 1,071 Sq Ft
- Condo for Rent
3930 S Roosevelt Blvd Unit N304, Key West, FL 33040
3930 S Roosevelt Blvd Unit N304, Key West, FL 33040Experience the easygoing charm of island life in this thoughtfully updated 3-bedroom, 2-bath condo, in the desirable resort-style living in Las Salinas. Fully Furnished, Light pours into the open-concept living space, creating a warm and inviting atmosphere that feels like home. The primary suite includes a private balcony that overlooks the pool and steps away from the newly updated fitness
Kayley Arn Coldwell Banker Realty - Aventura
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$3,300 - $3,800 per month
5555 College Rd, Key West, FL 33040Sunset Marina Apts
2 Beds
5555 College Rd, Key West, FL 33040
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$3,750 per month
- 1 Bed
- 1 Bath
- 475 Sq Ft
- Property for Rent
621 Whitehead St, Key West, FL 33040
621 Whitehead St, Key West, FL 33040Charming 1-Bedroom Home in Old Town with Bonus Loft Space! Fully renovated 1-bedroom, 1-bathroom rental home in the heart of Old Key West, featuring a bonus loft, one off-street parking space and a washer/dryer inside. Fully furnished, the property includes a cozy sitting room, a well-equipped kitchen, large bedroom, and updated bathroom with new shower. Relax on the porch, surrounded by lush
Damian Vantriglia Berkshire Hathaway HomeServices Knight & Gardner Realty
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$2,854 - $3,961 per month
750 Fort St, Key West, FL 33040Lofts at Bahama Village
1 - 3 Beds
750 Fort St, Key West, FL 33040
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$5,000 per month
- 3 Beds
- 2 Baths
- Property for Rent
1010 17th Terrace, Key West, FL 33040
1010 17th Terrace, Key West, FL 33040This house has three bedrooms and two baths with a fenced in yard and off street parking.The back yard has a big pool with waterfall plus a outdoor shower.
Danny Sanchez Century 21 All Keys Inc (KW)
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$5,500 per month
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
- Condo for Rent
1800 Atlantic Blvd, Key West, FL 33040
1800 Atlantic Blvd, Key West, FL 33040Property Id: 2136484Fully furnished two bedroom, two bath. It can sleep six with a pull out couch. Very quiet and picturesque ocean view from the west facing balcony. The sunsets are amazing. All condominium amenities included Jacuzzi spa sauna
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$4,000 per month
- 2 Beds
- 1 Bath
- 775 Sq Ft
- Property for Rent
1116 Truman Ave Unit 1, Key West, FL 33040
1116 Truman Ave Unit 1, Key West, FL 33040Beautifully renovated Old Town second floor condo, furnished. High ceilings, freshly painted, and a wonderful front porch to relax on. Walk or Bike to everything Old Town, local restaurants, steps to Sandy's Cafe for your morning cuban coffee, Walk on White event, food store, and more! This unit has a beautiful kitchen with a dish washer, an in unit washer and dryer, and access to a shared pool.
Elaine Coyle Keller Williams Key West Compass Realty
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$4,150 per month
- 2 Beds
- 2 Baths
- 1,265 Sq Ft
- Condo for Rent
1700 Flagler Ave Unit 1, Key West, FL 33040
1700 Flagler Ave Unit 1, Key West, FL 33040Property Id: 1485104This 2 bed / 2 bath ensuite unit offers comfort and convenience in a charming setting. Enjoy generous living areas, ample closets, in unit washer/dryer, and a spacious yard with decks and spa. Onsite parking. The property's traditional Key West style exterior creates a welcoming home in a prime Midtown location. A must see! F/L/S required. Background checks on all
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$3,950 per month
- 2 Beds
- 1 Bath
- 504 Sq Ft
- Property for Rent
614 Whitehead St, Key West, FL 33040
614 Whitehead St, Key West, FL 33040Fully Renovated, fully furnished 2-Bedroom in Prime Old Town Key West. Available November 1stLive the Key West dream in this beautifully renovated two-bedroom, one-bathroom apartment located in the heart of Old Town--right across from the iconic Green Parrot. This furnished rental is move-in ready--just bring your toothbrush!Worried about parking? Don't be. You'll have space for two cars right in
Everett Watkins Keller Williams Key West Compass Realty
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$4,000 per month
- 2 Beds
- 2 Baths
- 1,339 Sq Ft
- Condo for Rent
1800 Atlantic Blvd Unit 220C, Key West, FL 33040
1800 Atlantic Blvd Unit 220C, Key West, FL 33040Property Id: 2208861This beautiful 2-bedroom, 2-bath condo is located in the desirable 1800 Atlantic complex with a private beach in Key West. It is situated on the second floor, offering ocean and garden views. The condo has a spacious open floor plan, high ceilings that create a light and airy feel, and a private balcony accessible from the living room and both bedrooms, ensuring a
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$5,200 per month
- 3 Beds
- 2 Baths
- 1,320 Sq Ft
- Property for Rent
28 Whistling Duck Ln, Key West, FL 33040
28 Whistling Duck Ln, Key West, FL 33040Bright and spacious 3-bedroom, 2-bathroom home perfectly situated in the Key West Golf Club community. Overlooking the 9th hole, this property offers a peaceful setting in one of the most desirable parts of the neighborhood, with plenty of parking available.The home is offered unfurnished, with no utilities included, giving you the flexibility to make it your own. One bedroom is downstairs with
Everett Watkins Keller Williams Key West Compass Realty
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$1,600 per month
- 1 Bed
- 1 Bath
- House for Rent
3045 Flagler Ave, Key West, FL 33040
3045 Flagler Ave, Key West, FL 33040Property Id: 1577811Available 11/01/2025 Small 1/1 Cottage in New TownAlright, here's what you're looking at: a small, straightforward 1-bedroom, 1-bathroom cottage in my backyard. It's just right for one person who appreciates simplicity. Now, there's no full kitchen, but you've got a small refrigerator, a microwave, and a nifty air fryer/oven combo that'll cover your
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$5,000 per month
- 3 Beds
- 3 Baths
- 1,216 Sq Ft
- Property for Rent
1207 William St Unit 3, Key West, FL 33040
1207 William St Unit 3, Key West, FL 33040Step inside this exceptional 3-bedroom condo, where modern living meets unmatched versatility. Each of the three bedrooms features its own en-suite bathroom, ensuring comfort and privacy for all. But the true standout feature? Three separate entrances, with two bedrooms featuring private exterior access. There is a door in the hallway that can be closed to separate the front and back of the house
Sarah Bixby eXp Realty LLC
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$9,600 per month
- 2 Beds
- 3 Baths
- 1,345 Sq Ft
- Condo for Rent
629 Elizabeth St Unit ID1297833P, Key West, FL 33040
629 Elizabeth St Unit ID1297833P, Key West, FL 33040Casa Azul is a luxurious modern cottage featuring an open-concept living area that is bathed in natural sunlight. Enjoy a dip in the heated saltwater plunge pool with a waterfall feature and night lighting. Located in Old Town Key West, just two blocks from Duval Street, this pet-friendly home offers private parking and is perfect for your next extended stay.Casa Azul perfectly blends comfort
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$2,500 per month
- 2,244 Sq Ft
- Property for Rent
2001 Flagler Ave, Key West, FL 33040
2001 Flagler Ave, Key West, FL 33040Prime 2,244 SQFT Vacant Lot Available for Rent.A rare opportunity to lease a centrally located vacant lot in the heart of New Town! Whether you're looking to advertise your business, operate a food truck, start a new venture, or create a space uniquely your own--this versatile lot offers endless potential. Multiple possible uses (tenant to verify).Please do not walk the property without prior
Everett Watkins Keller Williams Key West Compass Realty
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$13,200 per month
- 4 Beds
- 3.5 Baths
- 1,797 Sq Ft
- Condo for Rent
1315 Whitehead St Unit ID1297834P, Key West, FL 33040
1315 Whitehead St Unit ID1297834P, Key West, FL 33040Southernmost View is a modern and luxurious waterfront home located in a private seven-home gated community, just steps from the beach and the Southernmost Point of the continental USA. Enjoy turquoise blue waters from the rooftop sundeck, perfect for tanning, reading, and sipping your morning coffee. Relax under the southernmost stars or watch the sunset over the horizon.This upscale beach
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$4,000 per month
- 4 Beds
- 2 Baths
- 1,593 Sq Ft
- Property for Rent
1608 Venetian Dr, Key West, FL 33040
1608 Venetian Dr, Key West, FL 33040Ground level single family home with living room, dining area, new kitchen and appliances, four bedrooms, two new baths, laundry room, central AC, tile floors, in Key West's New Town. Available for a yearly lease. Would consider rent-to-own offers at sales price of $995,000.
Dave Lewis Key West Real Estate Sales & Rentals, LLC (KW)
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$10,584 per month
- 2 Beds
- 2 Baths
- 2,023 Sq Ft
- Condo for Rent
536 Fleming St Unit FL2-ID1297611P, Key West, FL 33040
536 Fleming St Unit FL2-ID1297611P, Key West, FL 33040Experience the allure of this luxurious 2,000+ square foot penthouse, The Maloney, which occupies the entire second story of a historic red brick building at the corner of Fleming and Simonton. Originally constructed in 1908 as Key West's first pharmacy, this building now features two penthouse units and a first-floor boutique. The Maloney is available exclusively for monthly rentals, requiring a
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$7,000 per month
- 4 Beds
- 2 Baths
- Property for Rent
417 Southard St Unit A, Key West, FL 33040
417 Southard St Unit A, Key West, FL 33040Long term rental, 4 bedroom, 2-bathroom furnished apartment is conveniently located just steps away from Duval Street, Mile Marker 0, and within walking distance to the Southernmost Point, Fort Zachary Taylor Historic State Park. The apartment boasts Beautiful bathrooms with walk-in showers, spacious kitchens equipped with upgraded stainless steel appliances, a stunning waterfall kitchen counter
Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty
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$6,378 per month
- 3 Beds
- 3 Baths
- 2,518 Sq Ft
- Condo for Rent
8 Floral Ave Unit ID1297832P, Key West, FL 33040
8 Floral Ave Unit ID1297832P, Key West, FL 33040The Haven House is a truly heavenly retreat nestled on the quiet residential canals in Key Haven. This home boasts a modern waterfront private backyard with a dock and boat lift. With space-maximizing and luxury island touches from top to bottom, this monthly rental has it all. Stay just 15 minutes from downtown Duval Street in this one-of-a-kind island home.Seamless indoor-outdoor
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$2,800 per month
- 2 Beds
- 1 Bath
- 620 Sq Ft
- Property for Rent
6440 2nd St Unit 9, Key West, FL 33040
6440 2nd St Unit 9, Key West, FL 33040Half of a Duplex, unfurnished, tenant pays for all utilities, instant on demand tankless water heater saves on your electric bill. Approx. 600 Sq.Ft. 2 units per building so only 1 shared wall for a typical duplex layout with fenced gravel yard, landscaping with palm trees. Has hookups for a clothes washing machine or the new combination models that wash and dry in the same drum. Kitchen has a
Dave Lewis Key West Real Estate Sales & Rentals, LLC (KW)
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$6,762 per month
- 3 Beds
- 2 Baths
- 1,399 Sq Ft
- Condo for Rent
2026 Seidenberg Ave Unit ID1297830P, Key West, FL 33040
2026 Seidenberg Ave Unit ID1297830P, Key West, FL 33040Welcome to Hidden Oasis, a luxurious three-bedroom, two-bathroom home nestled in the heart of Midtown, Key West. This stunning property offers contemporary luxury with an open floor plan, situated on a private fenced-in yard on a corner lot with lush tropical landscaping. Feel at home as you step through French doors to the backyard, featuring a private heated pool, lounge seating, a TV, a grill,
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$12,000 per month
- 3 Beds
- 2.5 Baths
- 2,400 Sq Ft
- House for Rent
1623 Venetian Dr, Key West, FL 33040
1623 Venetian Dr, Key West, FL 33040WATERFRONT!! EXITS TO THE OCEAN. FULLY FURNISHED HOME, READY TO MOVE IN. ONE OF THE FEW CANALS LEADING TO OCEAN INSIDE KEY WEST.Completely remodeled Oceanfront 3 bedrooms, 2 bathrooms, 2 car garage, completely furnished dream home on the water with game room and a 50ft dock on a very private neighborhood. This home is move in ready. UPSTAIRS- This home has a brand new top of the line kitchen with
Esney Diaz Premier Real Estate Associates
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$4,065 per month
- 1 Bed
- 1 Bath
- 419 Sq Ft
- Condo for Rent
817 Terry Ln Unit ID1297837P, Key West, FL 33040
817 Terry Ln Unit ID1297837P, Key West, FL 33040"Lil Bit" is a rare find in the historic Bahama Village neighborhood. This classic "conch" home is modern and renovated to have an elevated feel but retains the charm and character of old Key West. Perfect for a couple or visitors looking for a monthly stay, this home is equipped with everything you need. While it is a "Lil Bit," the space feels large, open, and fresh, and is a short walk to Fort
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$13,000 per month
- 4 Beds
- 4 Baths
- Property for Rent
2214 Seidenberg Ave, Key West, FL 33040
2214 Seidenberg Ave, Key West, FL 33040Welcome to your luxurious oasis in Key West, where modern comfort meets tropical paradise. This stunning new construction home features four spacious bedrooms, each with an en suite bathroom. Lushly landscaped grounds, this 5,700 square foot property offers plenty of room to unwind and enjoy the beauty of the island.Imagine starting your day with a refreshing swim in the large, private, heated
Paige Bethel Island Home Realty Inc.
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$3,900 per month
- 2 Beds
- 1.5 Baths
- 800 Sq Ft
- House for Rent
6800 Maloney Ave, Key West, FL 33040
6800 Maloney Ave, Key West, FL 33040Property Id: 1805361Oceanfront house for long term rental w/in the 1st 5 miles of Key West w/ seawall for boat or just enjoy the view! 2 & 2. $3,900/ month for 12 month lease + electric, water & internet. Includes sewer, trash, basic cable & landscaping. 1st, last & $2500 deposit. Available Nov. 15. Mostly unfurnished. 1 bedroom comes w/ murphy bed w/ ocean view & built in closets. Small
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$5,250 per month
- 4 Beds
- 2 Baths
- 1,572 Sq Ft
- House for Rent
1735 Bahama Dr, Key West, FL 33040
1735 Bahama Dr, Key West, FL 33040Escape to paradise with this charming fully furnished rental in the heart of Key West, FL! Experience the ultimate getaway with all the comforts of home in this roomy 4-bedroom, 2-bathroom retreat with a large private backyard and backyard Tiki cottage. Can accommodate/sleep up to 10 people with 5 full-sized beds. Relax in the spacious landscaped area in the large backyard and the Tiki Cottage.
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$4,300 per month
- 2 Beds
- 2.5 Baths
- 1,225 Sq Ft
- Condo for Rent
1075 Duval St Unit R28, Key West, FL 33040
1075 Duval St Unit R28, Key West, FL 33040Live where others vacation! Spacious 2/2.5 two story townhome located above the cozy shops and restaurants of Duval Square. Balconies overlook Virginia Street and the open parking area, providing a very light and airy feel. Appliances include Washer/Dryer, Stove with over-the-range Microwave, Refrigerator and (brand new) Dishwasher. First floor parking garage is close to the home with space for
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$2,875 per month
- Studio
- 1 Bath
- 425 Sq Ft
- Condo for Rent
922 Eaton St Unit 922C, Key West, FL 33040
922 Eaton St Unit 922C, Key West, FL 330401 FLETCHER’S LANE, KWFREE-STANDING COTTAGE AVAILABLE 1/1/26. Stand alone, PRIVATE COTTAGE, near Old Town Bakery. Nice rooms and storage. Ample room for scooter and bike. W/D coin-operated 1 block away. PRIVATE FRONT PORCH wonderful bonus.Main living area + loft; 2 can easily live and sleep comfortably.Refrigerator, stovetop, dishwasher, and microwave in galley
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$5,500 per month
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
- Condo for Rent
1800 Atlantic Blvd Unit 302A, Key West, FL 33040
1800 Atlantic Blvd Unit 302A, Key West, FL 330401800 Atlantic blvd. Has so much to offer, quiet location, fantastic apartment views, and a long list of amenities.
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$2,500 per month
- 1 Bed
- 1 Bath
- 528 Sq Ft
- Condo for Rent
3312 Northside Dr Unit 712, Key West, FL 33040
3312 Northside Dr Unit 712, Key West, FL 33040Beautiful sunset views 7th floor 1bd/1b apt, open kitchen, large bedroom with closet, Central AC, balcony, impact sliding door, impact windows, shutters. Laundry facility on every floor, very large pool, gated parking. Elevators. Walking distance to shopping malls, movie theater and school.
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$1,975 per month
- Studio - 1 Bed
- 1 Bath
- 300 Sq Ft
- Condo for Rent
1703 Johnson St, Key West, FL 33040
1703 Johnson St, Key West, FL 33040Do not disturb tenants, 300 SF studio unit, small kitchenette, AC, Washer/Dryer connection, large living/bedroom area with closet, large bathroom with glass shower enclosure. New Tile flooring. Renovated in last five years. First floor unit, with rear fenced deck . On site parking, 24 hour notice to show. Please text me if interested in seeing the unit, available November 20th, 6 months or
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$3,950 per month
- 2 Beds
- 1 Bath
- 1,000 Sq Ft
- Condo for Rent
1017 White St Unit 1, Key West, FL 33040
1017 White St Unit 1, Key West, FL 33040Light filled two bedroom one bath with private pool and garden. Excellent location. Newly renovated kitchen.
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$2,100 per month
- Studio
- 1 Bath
- 252 Sq Ft
- Condo for Rent
908 Elizabeth St Unit 4, Key West, FL 33040
908 Elizabeth St Unit 4, Key West, FL 33040Very cute little garden studio available Early August. Small but in the very HEART of it all! Walk to everything Old Town has to offer! Tenant pays electric and cable/internet. F/S/S. Sorry No Pets!
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$1,975 per month
- Studio - 1 Bed
- 1 Bath
- 300 Sq Ft
- Condo for Rent
1703 Johnson St, Key West, FL 33040
1703 Johnson St, Key West, FL 33040Do not disturb tenants, 300 SF studio unit, small kitchenette, AC, Washer/Dryer connection, large living/bedroom area with closet, large bathroom with glass shower enclosure. New Tile flooring. Renovated in last five years. First floor unit, with rear fenced deck . On site parking, 24 hour notice to show. Please text me if interested in seeing the unit, available November 20th, 6 months or
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$2,500 per month
- 1 Bed
- 1 Bath
- 550 Sq Ft
- Condo for Rent
1005 Flagler Ave Unit 4, Key West, FL 33040
1005 Flagler Ave Unit 4, Key West, FL 33040BUILDINGS ARE CURRENTLY FOR SALE; Occasional showings may be required; Proper notice will be given. Lease will NOT have a ‘kick out clause’ in it so once under lease any potential new owner would be required to honor it.AVAILABLE NOW!! This 1/1 is located in the heart of the Casa Marina District. Features a shared balcony and On-site shared coin operated laundry. Lawn care and
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$2,950 per month
- 2 Beds
- 2 Baths
- 1,070 Sq Ft
- Condo for Rent
3930 S Roosevelt Blvd Unit N303, Key West, FL 33040
3930 S Roosevelt Blvd Unit N303, Key West, FL 33040This is one of 12 large two bedroom units in the Las Salinas community. Very large kitchen with many cabinets, accordion hurricane shutters on living room doors, each bedroom has walk in closet, baths updated. An assigned covered parking area is included. New carpet in bedrooms Condo management requires background check. Applications require credit check, employment, rent references. NO PETS
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