$2,800
Total Monthly Price
- 1 Bed
- 1 Bath
- 650 Sq Ft
- Condo for Rent
400 Simonton St, Key West, FL 33040
92
Homes for Rent near Monroe County School District Virtual Instruction Program
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400 Simonton St, Key West, FL 33040
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Starting at $2,429 Per Month
- Studio - 3 Beds
3900 S Roosevelt Blvd, Key West, FL 33040
3900 S Roosevelt Blvd, Key West, FL 33040Ocean Walk apartments are located on the peaceful Atlantic side of the island, nestled among lush natural vegetation, just steps away from the beach. Ideally located just minutes from the best dining, shopping and entertainment Key West has to offer, Ocean Walk Apartment Homes boast spacious one, two, and three bedroom apartments, spectacular views, and first-rate amenities. Each recently
Ocean Walk
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$2,800
Total Monthly Price
- 1 Bed
- 1 Bath
- 650 Sq Ft
- Condo for Rent
400 Simonton St, Key West, FL 33040
400 Simonton St, Key West, FL 33040 -
Starting at $3,200 Per Month
- 2 Beds
5555 College Rd, Key West, FL 33040
5555 College Rd, Key West, FL 33040Sunset Marina Apts
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Starting at $3,145 Per Month
- 1 - 3 Beds
750 Fort St, Key West, FL 33040
750 Fort St, Key West, FL 33040Discover your place in the heart of Key West's most historic and vibrant neighborhood. The Lofts at Bahama Village offers affordable housing options designed for locals, where homeownership and rental opportunities meet the warmth of a close-knit community.Live steps away from iconic Key West landmarks, while enjoying the charm and cultural heritage that make Bahama Village truly one of a
Lofts at Bahama Village
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$7,920
Total Monthly Price
- 2 Beds
- 3 Baths
- 1,345 Sq Ft
- Condo for Rent
629 Elizabeth St Unit SI ID1297833P, Key West, FL 33040
629 Elizabeth St Unit SI ID1297833P, Key West, FL 33040The advertised rate of $7,920/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 31, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
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$3,800 Per Month
- 1 Bed
- 1 Bath
- Condo for Rent
2601 S Roosevelt Blvd, Key West, FL 33040
2601 S Roosevelt Blvd, Key West, FL 33040Property Id: 2585627 THIS IS A MONTHLY OFF SEASON VACATION RENTAL, DISCOUNT FOR 6 MO. RENTAL FULLY FURNISHED. Rent for one month or six. Subject to 12.5 tourist tax. All utilities included All new stainless appliances. Two mini-split AC units, tankless hot water heater, new countertops. New hurricane-soundproof doors and windows. Open the large slider and enjoy listening to the ocean
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$2,500 Per Month
- 1 Bed
- 1 Bath
- Condo for Rent
34G Miriam St Unit 34 Miriam st stock Island, Stock Island, FL 33040
34G Miriam St Unit 34 Miriam st stock Island, Stock Island, FL 33040Property Id: 2604250 Location : 34 Miriam st Stock Island 10 minutes to downtown Key West $2500 per month rent. Require security deposit and first month rent to move in. Total $5,000 to move in. All utilities are included. Furnished. Only good for 1 person and good background. Short or long term is ok. Contact # Grace thnaks.
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$9,148
Total Monthly Price
- 2 Beds
- 1 Bath
- 796 Sq Ft
- Condo for Rent
169 Golf Club Dr Unit SI FL1-ID1545690P, Key West, FL 33040
169 Golf Club Dr Unit SI FL1-ID1545690P, Key West, FL 33040The advertised rate of $9,149/month is the lowest available price, based on a 1 month(s) and 2 day(s) stay with a move-in date of February 23, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed
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$5,100 Per Month
- 2 Beds
- 2 Baths
- 1,311 Sq Ft
- Condo for Rent
1800 Atlantic Blvd Unit C127, Key West, FL 33040
1800 Atlantic Blvd Unit C127, Key West, FL 33040Property Id: 2599443 As one of the most coveted condominium properties in Key West, 1800 Atlantic is iconic for its oceanfront location, lush gardens, and spectacular pool setting overlooking the ocean. The heated, salt-water, Olympic-sized pool, jacuzzi hot-tub and lounge seating area is the centerpiece of this beautifully cared-for property. Tennis enthusiasts, will have access to 3 tennis
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$2,300 Per Month
- 1 Bed
- 1 Bath
- 1,000 Sq Ft
- Condo for Rent
4D 10th Ave Unit B units, Stock Island, FL 33040
4D 10th Ave Unit B units, Stock Island, FL 33040Property Id: 2725581 Location : D4 10th Ave Stock Island This is one bedroom Apt $2300 per month rent all utilities are included . Washer, dryer in the unit and fence up private yard. 10 minutes to Down town Key west . Require security deposit $2300 and first month rent $2300 to move in. Contact # Grace Thanks.
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$3,200 Per Month
- 2 Beds
- 2 Baths
- Condo for Rent
3625 Seaside Dr Unit 25110, Key West, FL 33040
3625 Seaside Dr Unit 25110, Key West, FL 33040Property Id: 2572967 Escape to Cat Island Suite, a serene, beautifully updated, and well-appointed 2-bedroom condo located in the peaceful Sunrise Suites community on the east side of Key West. Just a mile from the beach, this charming getaway provides the perfect combination of relaxation and adventure. Whether you're lounging by the pool, exploring nearby attractions, or enjoying the
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$4,200 Per Month
- 3 Beds
- 2 Baths
- 1,320 Sq Ft
- Townhouse for Rent
15 Whistling Duck Ln, Key West, FL 33040
15 Whistling Duck Ln, Key West, FL 33040Property Id: 2732485 This is a beautiful furnished three bedroom two bath townhome, 1320 sq. ft. Located on a cul-de-sac in the golf course community. Internet and cable tv is provided. Updated kitchen and bathrooms! The community offers a fitness center, butterfly garden and two pools.
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$2,300 Per Month
- Studio
- 1 Bath
- Condo for Rent
34G Miriam St Unit Studio for rent, Stock Island, FL 33040
34G Miriam St Unit Studio for rent, Stock Island, FL 33040Property Id: 2483336 Studio for rent with furnished. $2300 per month rent for a person, 2 people $2400, Pet $100 extra. Require security deposit and first month rent to move in. New renovation. 10 minutes to downtown Key West. Only good for good background and long term.
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$18,964
Total Monthly Price
- 2 Beds
- 2 Baths
- 2,023 Sq Ft
- Condo for Rent
536 Fleming St Unit SI FL2-ID1297611P, Key West, FL 33040
536 Fleming St Unit SI FL2-ID1297611P, Key West, FL 33040The advertised rate of $18,964/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 7, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
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$2,200 Per Month
- 1 Bed
- 1 Bath
- House for Rent
G34 Miriam St, Stock Island, FL 33040
G34 Miriam St, Stock Island, FL 33040Property Id: 2485763 Location: 34G Miriam St stock Island 10 minutes to down town. This is new renovation studio one person $2200 per month rent, 2 people $2400. All utilities are included. Require security deposit and first month rent to move in. Pet $100 extra. No stove, only hot plate, microwave, air fryer and refrigerator . 1 or 2 parking space. Only
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$1,400 Per Month
- 1 Bed
- 1 Bath
- House for Rent
2102 Staples Ave, Key West, FL 33040
2102 Staples Ave, Key West, FL 33040Property Id: 1785777 Key West, FL (Midtown) - available July 1 Private furnished bedroom and bathroom with private entrance for rent for a single person. Room comes furnished including microwave, refrigerator and window AC. Walking distance to the beach. Ready to move in! $1400/month for month-to-month. Month to month lease… First plus $1400 security deposit.
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$2,300 Per Month
- 1 Bed
- 1 Bath
- 1,000 Sq Ft
- Condo for Rent
D4 10th Ave Unit B unit, Stock Island, FL 33040
D4 10th Ave Unit B unit, Stock Island, FL 33040Property Id: 2725559 Location : 4D 10th Ave Stock Island $2200 per month rent, all utilities are included. Require security deposit $1000 and first month rent to move in. Pet friendly. Washer, dryer in the unit. 10 minutes to downtown Key West.
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$2,500 Per Month
- 2 Beds
- 1 Bath
- 1,200 Sq Ft
- Condo for Rent
D4 10th Ave Unit D4 10th Ave, Stock Island, FL 33040
D4 10th Ave Unit D4 10th Ave, Stock Island, FL 33040Property Id: 2682074 This unit located in D4 10th Ave Stock Island. This unit is 1200 Square Feet. 10 to 15 minutes to down town Key West. $2500 per month rent with washer, dryer in the unit. Private porch. Require security deposit $2000 and first month rent $2500 to move in. Pet friendly. All utilities are included You can call Grace any time to
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$2,875
Total Monthly Price
- 2 Beds
- 1 Bath
- 627 Sq Ft
- Condo for Rent
2406 Harris Ave Unit 2406, Key West, FL 33040
2406 Harris Ave Unit 2406, Key West, FL 33040AVAILABLE NOW, Charming, unfurnished 2-bedroom, 1-bathroom condo is now available for rent. Large open area, with living room, kitchen and dining. Nestled in a quiet and friendly neighborhood, this home offers everything you need for comfortable and convenient living. With off-street parking. Washer and dryer hook-up. Great yard. $45 Application fee (anyone 18 years of age and older
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$4,000
Total Monthly Price
- 2 Beds
- 2 Baths
- 850 Sq Ft
- Condo for Rent
710 Whitmarsh Ln Unit 2, Key West, FL 33040
710 Whitmarsh Ln Unit 2, Key West, FL 33040Old town Key West second floor apartment. Only a block and a half from Duval and six blocks to the Gulf, to the West or the Atlantic, to the East . Properly is on Solaris Hill, the highest point on the island. Parking for one car, balcony and a private side deck. Updated kitchen and bathrooms. Central A/C & Heat.
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$6,000
Total Monthly Price
- 5 Beds
- 2 Baths
- 3,372 Sq Ft
- House for Rent
3535 17th Terrace, Key West, FL 33040
3535 17th Terrace, Key West, FL 33040Private Oasis with Pool & 9,000 Sq. Ft. Yard! 4BR/2BA Furnished or Unfurnished. TESLA Charging Station ready for use!Live like a local in this spacious 5-bedroom, 2-bathroom home located on a quiet, residential terrace in Key West’s desirable New Town. Situated on a rare, oversized lot, this property offers the ultimate indoor-outdoor lifestyle for families and nature lovers.The Ultimate
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$3,400
Total Monthly Price
- 2 Beds
- 1 Bath
- 681 Sq Ft
- Condo for Rent
1624 Bertha St Unit Key West Apartment, Key West, FL 33040
1624 Bertha St Unit Key West Apartment, Key West, FL 33040Beautifully remodeled apartment with brand new hurricane impact windows, new central AC, stainless steel appliances, quartz countertops, and many other updated features. One designated parking spot off street for this unit. Just two blocks from smathers beach and a short walk to Duval.
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$3,250
Total Monthly Price
- 2 Beds
- 2 Baths
- 1,175 Sq Ft
- Condo for Rent
1901 S Roosevelt Blvd Unit 404N, Key West, FL 33040
1901 S Roosevelt Blvd Unit 404N, Key West, FL 33040This 2 bedroom, 2 bath fully furnished condo at La Brisa condominium is available for rent August 2, 2026 through September 30. 2026. Rent is $3,250 per month and includes $250 per month for water/sewer and electric. Wi-Fi also included. There's a covered parking space and adjacent storage space. Sorry, no pets and a background check is required. Exit cleaning fee of $250. La Brisa offers a
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$2,800
Total Monthly Price
- 2 Beds
- 2 Baths
- 792 Sq Ft
- Condo for Rent
3312 Northside Dr Unit 111, Key West, FL 33040
3312 Northside Dr Unit 111, Key West, FL 33040Available NOW through January 30,2027!Welcome to paradise in Santa Clara Condominiums — a beautifully renovated, fully furnished 2 Fully renovated kitchen & bathroomsHurricane-impact windows & doorsSpacious walk-in storage/closet spacePrivate patio & secluded yard areaDirect access to tennis courts & poolOn-site laundry & secure entryJust minutes from beaches,
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$2,950
Total Monthly Price
- 1 Bed
- 1 Bath
- 300 Sq Ft
- Condo for Rent
818 White St Unit 5, Key West, FL 33040
818 White St Unit 5, Key West, FL 33040Specials: Get 5% off for a month stay or a deep discount for 6-month bookings in 2026! Available May till October 2026Refundable Security Deposit: $1200.00 (Note: First month's rent, security deposit, and last month's rent are due upfront for long-term rentals.)Additional Features: pool access, porches, private entrance Rebuilt in 2005, this unique home offers modern
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$2,675
Total Monthly Price
- 1 Bed
- 1 Bath
- 368 Sq Ft
- Condo for Rent
1318 Duncan St Unit 3, Key West, FL 33040
1318 Duncan St Unit 3, Key West, FL 33040AVAILABLE JULY. 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 with
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$2,800
Total Monthly Price
- 2 Beds
- 2 Baths
- 1,099 Sq Ft
- Condo for Rent
1901 S Roosevelt Blvd Unit La Brisa, Key West, FL 33040
1901 S Roosevelt Blvd Unit La Brisa, Key West, FL 33040Sammy's Hideaway is located in a gated community with easy beach access. This 2 bedroom/2 bath condo faces the Atlantic Ocean offering wonderful ocean breezes and an oversized balcony with dining set. The open style living room has glass slider doors that invite in mother nature's hues. Full size kitchen with room for more than one cook. Master bedroom with queen size bed and en suite bathroom
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$3,000
Total Monthly Price
- 1 Bed
- 1 Bath
- 1,000 Sq Ft
- Condo for Rent
8 Hilton Haven Rd, Key West, FL 33040
8 Hilton Haven Rd, Key West, FL 33040This 1-bedroom, (with additional bonus room for office, workout equipment, art studio etc) 1 large bathroom with double sinks . canal property on Hilton Haven Rd offers 1,000 square feet of living space. The living room provides ample room for relaxation and features ceiling fans for comfort. The kitchen is equipped with a refrigerator, freezer, microwave, dishwasher, and includes a washer and
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$5,000
Total Monthly Price
- 2 Beds
- 2 Baths
- 900 Sq Ft
- House for Rent
1102 Pearl St, Key West, FL 33040
1102 Pearl St, Key West, FL 33040Totally restored historic conch furnished pool home. On site parking, one bedroom, den, one interior bath, one pool side bath, IPE deck, central AC, Exposed beam ceilings, loft and pool. Very High quality renovation. Available monthly or annually. Pool heater, central AC, Viking & Wolf appliances, sleeps 6. King bed in bedroom, den has a pull out couch, living room has a pull out couch, you
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$2,800
Total Monthly Price
- 1 Bed
- 1 Bath
- 550 Sq Ft
- Condo for Rent
1315 Laird St Unit C, Key West, FL 33040
1315 Laird St Unit C, Key West, FL 33040One bedroom apartment on the 2nd floor at 1315 Laird Street. 5 minute walk to White Street Pier. Located on a quiet street in the beautiful Casa Marina neighborhood. Reserved parking spot in front of apartment. Water, sewer, trash, and parking included in monthly rent. First/last/security needed for move in.
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$5,900
Total Monthly Price
- 2 Beds
- 1.5 Baths
- 850 Sq Ft
- Townhouse for Rent
634 Louisa St, Key West, FL 33040
634 Louisa St, Key West, FL 33040Newly Renovated, furnished Townhome in Prime Old Town Key West located just 3 blocks from the beach! Experience the best of island living in this beautifully renovated 2-bedroom, 1.5-bath end-unit townhouse, perfectly situated in one of Key West's most sought-after neighborhoods. Features include a stunning new kitchen with quartz countertops, custom cabinetry, stainless steel appliances, and a
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$2,875
Total Monthly Price
- 1 Bed
- 1 Bath
- 525 Sq Ft
- Condo for Rent
825 Eaton St Unit C, Key West, FL 33040
825 Eaton St Unit C, Key West, FL 33040OLD TOWN ACROSS FROM EATON BIKES - 1/1 AVAILABLE IMMEDIATELY. PAYMENT ARRANGEMENTS AVAILABLE.Second floor, PRIVATE entrance and apartment, across from Eaton Bikes. Nice rooms and storage. Ample room for scooters and bikes. W/D coin-operated on premises.Refrigerator, oven, stove and ceiling fans. A/C in living room and bedroom. Newer renovation last year. Just professionally
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$4,500 Per Month
- 2 Beds
- 2 Baths
- 1,032 Sq Ft
- Townhouse for Rent
3318 Harriet Ave, Key West, FL 33040
3318 Harriet Ave, Key West, FL 33040PRIVATE, LUSH TOWNHOUSE in New Town with 2 bedrooms and 2 baths available this month! Offers new hardwood floors, new appliance package, new ductless AC units, bright, spacious bedrooms w/ built-in closet systems, beautiful fixtures, ample storage inside and out and washer/ dryer. Close to dining, shopping, and great schools. Available for long term lease with F & S, credit and background check.
Regan Butler Truman & Co. (KW)
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$6,617
Total Monthly Price
- 2 Beds
- 1 Bath
- 775 Sq Ft
- Condo for Rent
28 Merganser Ln Unit SI FL1-ID1545971P, Key West, FL 33040
28 Merganser Ln Unit SI FL1-ID1545971P, Key West, FL 33040The advertised rate of $6,618/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 3, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can
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$1,650 Per Month
- 1 Bed
- 1 Bath
- 434 Sq Ft
- Condo for Rent
1411 Truman Ave, Key West, FL 33040
1411 Truman Ave, Key West, FL 33040WE ENCOURAGE ALL INTERESTED PARTIES TO CALL OUR OFFICE PHONE DIRECTLY FOR THE FASTEST ANSWER AND ASSISTANCE WITH THIS LISTING. Application required prior to scheduling a showing. Available September 10th. Steeped in rich island history and radiating classic Conch charm offers a rare opportunity to own a piece of Old Town Key West paradise. Nestled in the highly coveted and peaceful neighborhood
Maria Ottinger Maria Ottinger R.E Broker
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$5,715
Total Monthly Price
- 4 Beds
- 3 Baths
- 1,797 Sq Ft
- Condo for Rent
1315 Whitehead St Unit SI ID1297834P, Key West, FL 33040
1315 Whitehead St Unit SI ID1297834P, Key West, FL 33040The advertised rate of $5,715/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 17, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
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$4,550 Per Month
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
- Townhouse for Rent
2515 Staples Ave Unit A, Key West, FL 33040
2515 Staples Ave Unit A, Key West, FL 33040Long Term Rental (1 year lease) Fully renovated and offered furnished (if desired), this villa-style half-duplex offers a spacious 3-bedroom, 2-bath layout with two entrances, W/D, a private Porch and Patio with lawn. The property is fully enclosed with high-quality fencing, creating privacy, lovely tropical landscaping and a clean, finished look throughout the property.Positioned along Key
Michelle Blades Realty Executives Florida Keys Old Town
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$2,650 Per Month
- 2 Beds
- 1 Bath
- 760 Sq Ft
- 2 bed + Den 1 bath Single Family House in Bahama Village
210 Angela St, Key West, FL 33040
210 Angela St, Key West, FL 33040Located in Old Town Key West, this unfurnished 2-bedroom + den 1-bath single-family home offers central AC, washer/dryer hook up, off-street parking, fenced yard. Walk to Duval and Ft. Zachary beach. Pets considered. $2650/month plus water & electric. Available early October for 12 month lease. F/L/SAt Historic Key West Annual Rentals, we strive to provide an experience that is
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$3,400 Per Month
- 2 Beds
- 1.5 Baths
- 780 Sq Ft
- Townhouse for Rent
36 Merganser Ln, Key West, FL 33040
36 Merganser Ln, Key West, FL 33040Stunning 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
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