Monroe County, FL Homes for Rent

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  $15,000 Per Month

  • 4 Beds
  • 3 Baths
  • 2,638 Sq Ft
  • House for Rent

  108 W Plaza Del Lago, Islamorada, FL 33036

  Waterfront Islamorada Home with Private Beach Access & 75' Dock Experience the best of the Florida Keys in this waterfront home in Islamorada, accommodating up to 12 guests and perfect for family vacations, multigenerational gatherings, fishing adventures, or extended stays.Located on Lower Matecumbe Key, this 4-bedroom, 3-bath home offers 2,638 square feet of comfortable indoor-outdoor

  

  Victor Ruiz

  Move Miami, LLC.

  108 W Plaza Del Lago, Islamorada, FL 33036
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  /34

  Starting at $2,699 Per Month

  • 1 - 3 Beds

  96 Coco Plum Dr, Marathon, FL 33050

  CoCo Vista

  

  96 Coco Plum Dr, Marathon, FL 33050
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  /36

  $6,500 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,080 Sq Ft
  • House for Rent

  121 Long Key Lake Dr, Layton, FL 33001

  Beautifully redesigned and fully furnished waterfront home available for seasonal rental in Layton. Available starting October 2026 till May 2027. Recently renovated from top to bottom, this canal-front retreat feels like a brand new home while offering the peaceful, natural setting that makes this part of the Keys so special. Boaters will love the 50 feet of dockage, 15,000-pound boat lift, and

  

  Megan Jones

  Coldwell Banker Schmitt Islamorada

  121 Long Key Lake Dr, Layton, FL 33001
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  /35

  Starting at $2,670 Per Month

  • 1 - 3 Beds

  10 Betty Rose Dr, Key West, FL 33040

  Welcome to The Quarry, a residential community in Key West, FL featuring one, two, and three bedroom apartments. Spacious layouts welcome you home, along with exceptional service and an ideal location close to shopping, dining and entertainment.

  The Quarry

  

  10 Betty Rose Dr, Key West, FL 33040
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  $5,000 Per Month

  • 3 Beds
  • 3 Baths
  • 1,380 Sq Ft
  • House for Rent

  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

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  59 Palm Dr, Key West, FL 33040
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  /35

  Starting at $2,451 Per Month

  • Studio - 3 Beds

  3900 S Roosevelt Blvd, Key West, FL 33040

  Ocean 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

  

  3900 S Roosevelt Blvd, Key West, FL 33040
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  /38

  $3,800 Per Month

  • 2 Beds
  • 1.5 Baths
  • Townhouse for Rent

  96000 Overseas Hwy Unit U1, Key Largo, FL 33037

  Annual rental available in this beautiful end unit townhome with a 32' boat slip in Buttonwood Bay Club. This fully furnished, beautifully updated home has granite countertops, an open-concept living and dining area, and screened in patio that looks out to your back patio where you can chill or entertain. This is a true boater's dream, complete with a 32' boat slip in a deep-water, protected

  

  Karol Marsden

  Langley Knight Gardner Islamorada

  96000 Overseas Hwy Unit U1, Key Largo, FL 33037
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  /20

  Starting at $3,299 Per Month

  • 2 - 4 Beds

  28501 Channel View Dr, Little Torch Key, FL 33042

  In Little Torch Key, near Mile Marker 28 on US Highway 1, Little Torch Cottages features 48 homes for those looking for something special. This beautiful property has 400 feet of open water views on Pine Channel, and also offers 22 foot boat slips at a discounted monthly rate for community residents. You will also be able to enjoy a community Clubhouse, park, BBQ areas, Paddle Board and Kayak

  Little Torch Cottages

  

  28501 Channel View Dr, Little Torch Key, FL 33042
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  $4,250 Per Month

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Property for Rent

  136 Sable Palm Ln, Tavernier, FL 33070

  Seasonal furnished rental, available October through April. This fully remodeled double-wide sits on a finger canal with no fixed bridges — quick, unrestricted boat access to open water. Inside, the home flows effortlessly for entertaining, anchored by a stunning blue quartz waterfall island with bar seating, stainless appliances, and a wine fridge. The open living area spills out to a large

  

  Ashley Kettner

  Compass Florida LLC

  136 Sable Palm Ln, Tavernier, FL 33070
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  /20

  $14,421

  Total Monthly Price

  • 3 Beds
  • 4 Baths
  • 3,595 Sq Ft
  • Condo for Rent

  45 Mutiny Place Unit SI ID1546436P, Key Largo, FL 33037

  The advertised rate of $14,421/month is the lowest available price, based on a 1 month(s) stay with a move-in date of April 18, 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

  45 Mutiny Place Unit SI ID1546436P, Key Largo, FL 33037
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  /34

  $5,000 Per Month

  • 3 Beds
  • 3 Baths
  • 1,380 Sq Ft
  • House for Rent

  37 Palm Dr, Key West, FL 33040

  Turnkey Waterfront Living in Saddlebunch Key - $5,500/monthThis 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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  /23

  $7,322

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 775 Sq Ft
  • Condo for Rent

  28 Merganser Ln Unit SI FL1-ID1545971P, Key West, FL 33040

  The advertised rate of $7,322/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 29, 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

  28 Merganser Ln Unit SI FL1-ID1545971P, Key West, FL 33040
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  /47

  $5,500 Per Month

  • 2 Beds
  • 2 Baths
  • 932 Sq Ft
  • House for Rent

  24 Beach Dr, Key West, FL 33040

  Enjoy the best of both worlds with this completely remodeled oceanfront home, located just fifteen minutes from downtown Key West. Quiet mornings and breathtaking sunsets make this the ideal spot for a relaxing island retreat.Start and end your day with incredible views of the ocean from the comfort of your home. Includes a master bedroom with a king-size bed, smart TV, and private bathroom,

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  24 Beach Dr, Key West, FL 33040
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  /20

  $8,009

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,431 Sq Ft
  • Condo for Rent

  886 Loggerhead Ln Unit SI ID1297829P, Summerland Key, FL 33042

  The advertised rate of $8,009/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 23, 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

  886 Loggerhead Ln Unit SI ID1297829P, Summerland Key, FL 33042
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  /30

  $5,300 Per Month

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • House for Rent

  932 Tropical Ln, Key Largo, FL 33037

  Furnished seasonal rental, available October through March. Perched at the tip of its own peninsula in Key Largo's Cross Key Waterways, this 3-bed, 2-bath, 1,440 sq ft canal-front retreat is surrounded by water on nearly every side. Boats dock steps from the door, and even the kitchen sink looks out over palm trees and passing boats — do the dishes with a view you won't want to look away from. A

  

  Ashley Kettner

  Compass Florida LLC

  932 Tropical Ln, Key Largo, FL 33037
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  /19

  $4,174

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 990 Sq Ft
  • Condo for Rent

  29179 Rose Dr Unit SI ID1545784P, Big Pine Key, FL 33043

  The advertised rate of $4,175/month is the lowest available price, based on a 1 month(s) stay with a move-in date of April 27, 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

  29179 Rose Dr Unit SI ID1545784P, Big Pine Key, FL 33043
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  /39

  $5,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,598 Sq Ft
  • House for Rent

  9 Blue Water Dr, Key West, FL 33040

  Spacious 3 bedroom and 2 bathroom home for long term rental. High and dry Single family residence with extraordinary water views. This lot has ample off street parking, storage, a workshop, enclosed garage, Laundry room, and flex spaces. There is a large air conditioned shed in the back yard, perfect for an office or art studio.Landscaping and garbage service included.Applicants are

  

  Dustan Carpenter

  Berkshire Hathaway HomeServices Knight & Gardner Realty

  9 Blue Water Dr, Key West, FL 33040
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  /20

  $5,993

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 990 Sq Ft
  • Condo for Rent

  205 Pirates Dr Unit SI ID1546154P, Key Largo, FL 33037

  The advertised rate of $5,993/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 23, 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

  205 Pirates Dr Unit SI ID1546154P, Key Largo, FL 33037
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  /24

  $6,000 Per Month

  • 3 Beds
  • 4 Baths
  • 2,012 Sq Ft
  • House for Rent

  129 N Indies Dr, Duck Key, FL 33050

  Brand new construction for rent in the heart of Duck Key, FL, between Marathon and Islamorada. This newly built, single story 3 bedroom, 4 bathroom home features a split floor plan and a dedicated pool bathroom, with 10.8 foot ceilings, 8 foot solid doors, impact rated windows and doors, a one car garage, and a gourmet kitchen with marble countertops and premium finishes, plus a heated saltwater

  

  Joseph Suarez

  Trustpoint Realty, LLC

  129 N Indies Dr, Duck Key, FL 33050
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  /11

  $2,250

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft
  • Condo for Rent

  6800 Maloney Ave, Key West, FL 33040

  Furnished. Nicely renovated. Fresh paint. New ductless AC units. Entryway. Bedroom with closet. Open kitchen onto large living space. WD hookups. Back unit with one parking space (duplex). Quiet residential area. No pets. Smoke free dwelling. Utilities included $1850 monthly. F/L/S.

  6800 Maloney Ave, Key West, FL 33040
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  /43

  $6,500 Per Month

  • 3 Beds
  • 2 Baths
  • 2,129 Sq Ft
  • House for Rent

  273 W Seaview Dr, Duck Key, FL 33050

  Available for annual lease, 273 W Seaview Dr is a private retreat in the heart of Duck Key, home to Hawks Cay Resort and some of the best boating and fishing waters in the Florida Keys. Built in 2020 on a 15,247 SF lot, this concrete home is elevated on concrete pilings and engineered to withstand hurricane force winds, with impact windows and doors throughout for lasting peace of mind. The main

  

  Joseph Suarez

  Trustpoint Realty, LLC

  273 W Seaview Dr, Duck Key, FL 33050
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  /20

  $1,800 Per Month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  101 Caloosa St Unit 3, Tavernier, FL 33070

  Property Id: 1167998 1 bed 1 bath furnished apartment in Islamorada (mm89.5), on desirable Plantation Key, available for annual lease. $1800 per month includes electric, water, sewer, trash removal and monthly pest control. Tenant responsible for comcast/internet if desired. Laundromat nearby. Perfect for 1 person, no smoking inside. 1 assigned off-street parking space. $2000 security

  101 Caloosa St Unit 3, Tavernier, FL 33070
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  /20

  $6,789

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,044 Sq Ft
  • Condo for Rent

  201 E Ocean Dr Unit SI FL3-ID1545795P, Key Colony Beach, FL 33051

  The advertised rate of $6,789/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 23, 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

  201 E Ocean Dr Unit SI FL3-ID1545795P, Key Colony Beach, FL 33051
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  /20

  $6,617

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,388 Sq Ft
  • Condo for Rent

  31 Palm Dr Unit SI FL1-ID1546457P, Key West, FL 33040

  The advertised rate of $6,618/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 23, 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

  31 Palm Dr Unit SI FL1-ID1546457P, Key West, FL 33040
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  /20

  $19,354

  Total Monthly Price

  • 5 Beds
  • 4.5 Baths
  • 5,198 Sq Ft
  • Condo for Rent

  59720 Overseas Hwy Unit SI FL3-ID1531779P, Marathon, FL 33050

  The advertised rate of $19,354/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 24, 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

  59720 Overseas Hwy Unit SI FL3-ID1531779P, Marathon, FL 33050
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  /29

  $9,499

  Total Monthly Price

  • 4 Beds
  • 2 Baths
  • 1,496 Sq Ft
  • Condo for Rent

  59753 Paradise Place Unit SI ID1602727P, Marathon, FL 33050

  The advertised rate of $9,499/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 10, 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

  59753 Paradise Place Unit SI ID1602727P, Marathon, FL 33050
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  /20

  $6,690

  Total Monthly Price

  • 4 Beds
  • 3 Baths
  • 1,797 Sq Ft
  • Condo for Rent

  1315 Whitehead St Unit SI ID1297834P, Key West, FL 33040

  The advertised rate of $6,690/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

  1315 Whitehead St Unit SI ID1297834P, Key West, FL 33040
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  /20

  $11,220

  Total Monthly Price

  • 2 Beds
  • 3 Baths
  • 1,345 Sq Ft
  • Condo for Rent

  629 Elizabeth St Unit SI ID1297833P, Key West, FL 33040

  The advertised rate of $11,220/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 3, 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

  629 Elizabeth St Unit SI ID1297833P, Key West, FL 33040
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  /21

  $3,350

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 1,250 Sq Ft
  • Townhouse for Rent

  594 W Shore Dr, Summerland Key, FL 33042

  Enjoy the laid-back Florida Keys lifestyle in this spacious upstairs 2-bedroom, 1-bath waterfront duplex located on beautiful Summerland Key. With approximately 1,180 square feet of living space, this home offers a comfortable, open layout in a convenient location near Key West, Big Pine Key, and Marathon.Inside, you'll find a bright open-concept living and dining area with plenty of room to

  594 W Shore Dr, Summerland Key, FL 33042
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  /11

  $5,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Condo for Rent

  1800 Atlantic Blvd, Key West, FL 33040

  Property Id: 2136484 Fully 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

  1800 Atlantic Blvd, Key West, FL 33040
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  /20

  $7,229

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Condo for Rent

  343 Oleander Dr Unit SI FL1-ID1539598P, Tavernier, FL 33070

  The advertised rate of $7,229/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 23, 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

  343 Oleander Dr Unit SI FL1-ID1539598P, Tavernier, FL 33070
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  /20

  $5,681

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 839 Sq Ft
  • Condo for Rent

  398 Burton Dr Unit SI ID1545789P, Tavernier, FL 33070

  The advertised rate of $5,681/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 23, 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

  398 Burton Dr Unit SI ID1545789P, Tavernier, FL 33070
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  /18

  $4,500 Per Month

  • 3 Beds
  • 2.5 Baths
  • House for Rent

  480-490 90th Street Ocean, Marathon, FL 33050

  Property Id: 1581244 Enjoy comfortable Florida Keys living in this spacious 3-bedroom, 2.5-bath single-family home with approximately 1,918 sq. ft. of living space in Marathon. This elevated home offers the privacy and space of a single-family residence, with plenty of room both inside and out. Enjoy a spacious partially fenced yard, screened outdoor living space, large covered area

  480-490 90th Street Ocean, Marathon, FL 33050
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  /50

  $9,796

  Total Monthly Price

  • 4 Beds
  • 4 Baths
  • 2,292 Sq Ft
  • Condo for Rent

  841 Copa D Oro W Unit SI ID1608714P, Marathon, FL 33050

  The advertised rate of $9,797/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 24, 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

  841 Copa D Oro W Unit SI ID1608714P, Marathon, FL 33050
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  /13

  $3,300

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 792 Sq Ft
  • Condo for Rent

  3312 Northside Dr Unit 111, Key West, FL 33040

  Available NOW !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, shopping, dining, downtown

  3312 Northside Dr Unit 111, Key West, FL 33040
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  /20

  $3,335

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 1,119 Sq Ft
  • Condo for Rent

  97652 Overseas Hwy Unit SI FL2-ID1546120P, Key Largo, FL 33037

  The advertised rate of $3,335/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 19, 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

  97652 Overseas Hwy Unit SI FL2-ID1546120P, Key Largo, FL 33037
• 

  

  /24

  $19,530

  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

  The advertised rate of $19,530/month is the lowest available price, based on a 30 day(s) stay with a move-in date of March 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

  536 Fleming St Unit SI FL2-ID1297611P, Key West, FL 33040
• 

  

  /14

  $2,200

  Total Monthly Price

  • Studio
  • 1 Bath
  • 495 Sq Ft
  • Condo for Rent

  88500 Overseas Hwy Unit 433, Tavernier, FL 33070

  88500 Overseas Hwy Unit 433, Tavernier, FL 33070
• 

  

  /18

  $3,250 Per Month

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft
  • House for Rent

  1635 Pandorea Ln, Big Pine Key, FL 33043

  Welcome to your ideal rental in Big Pine Key, Florida! This charming property offers a perfect environment for those seeking a peaceful lifestyle close to nature and conveniences. Key Property Features include a spacious living area designed for comfort, ensuring you have plenty of room to relax and entertain. Enjoy the benefit of central heating and air conditioning, complemented by ceiling

  1635 Pandorea Ln, Big Pine Key, FL 33043
• 

  

  /23

  $3,650

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft
  • Townhouse for Rent

  596 W Shore Dr, Summerland Key, FL 33042

  Enjoy the laid-back Florida Keys lifestyle in this spacious downstairs 3-bedroom, 2-bath waterfront duplex located on beautiful Summerland Key. With approximately 1,392 square feet of living space, this home offers a comfortable, open layout in a convenient location near Key West, Big Pine Key, and Marathon.Inside, you'll find an open-concept living and dining area with plenty of room to

  596 W Shore Dr, Summerland Key, FL 33042

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