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Plantation Key, FL Homes for Rent

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  • /39

    $2,850 per month

    • 2 Beds
    • 1.5 Baths
    • 981 Sq Ft
    • Townhouse for Rent

    87465 Old Hwy Unit 224, Islamorada, FL 33036

    LONG TERM RENTAL in desirable Islamorada at Plantation By The Sea Condominiums. 6 Mos and 1 day ; 1 year; or 2 years. See below for details. Ocean front complex. During your free time lounge by the pool and gaze at the Atlantic Ocean or walk out on the long pier and catch your dinner! Wonderful two-story townhouse style condo completely furnished. Linens, dishes, pots and pans - everything,

    Agent Photo

    Andrea (Andi) Saylor

    Paradise Florida Keys Real Estate, a Luxury Brand

    (888) 430-3847

    87465 Old Hwy Unit 224, Islamorada, FL 33036
  • /27

    $8,759 per month

    • 6 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Condo for Rent

    87200 Overseas Hwy Unit E4, Islamorada, FL 33036

    Enjoy your 2026 winter, come immerse your body, mind, and soul in soothing waters that surround our Florida Keys paradise. Amazing sandy beaches, sunset fishing pier, new heated pool, and moderized clubhouse.Best community for fun activities! We offer as is bikes, kayaks, and many more amenities. Semi-private backyard. Sleep in 2.5 separate bedrooms, and loft. Nice bedding & towels. 2

    87200 Overseas Hwy Unit E4, Islamorada, FL 33036
  • /16

    $5,500 per month

    • 2 Beds
    • 2 Baths
    • 1,016 Sq Ft
    • House for Rent

    87455 Old Hwy 229 Hwy Unit 87455, Plantation Key, FL 33036

    Beautifully maintained 2-bedroom, 2-bath townhouse-style condo located oceanside in the heart of Islamorada. This fully turn-key residence offers effortless island living—just arrive and enjoy. Featuring a newer A/C system (2022), updated appliances (2024), and fully replaced air ducts (2024) for optimal comfort and efficiency. Impact windows provide peace of mind, while electric blackout blinds

    Jose Medina Main Assets Corp

    87455 Old Hwy 229 Hwy Unit 87455, Plantation Key, FL 33036
  • /27

    $35,000 per month

    • 4 Beds
    • 4.5 Baths
    • 5,348 Sq Ft
    • House for Rent

    133 Severino Dr, Islamorada, FL 33036

    Experience luxury living at its finest in this completely renovated four-bedroom, four-bathroom home nestled in one of the most prestigious neighborhoods in the upper Keys. This stunning residence showcases exceptional craftsmanship by a renowned local builder, creating an extraordinary retreat where sophisticated design meets tropical paradise. The home features two separate living areas and

    Pete Riveiro The Firm Realty Group

    133 Severino Dr, Islamorada, FL 33036
  • /21

    $2,800 per month

    • 2 Beds
    • 3 Baths
    • Townhouse for Rent

    87200 Overseas Hwy Unit 5, Islamorada, FL 33036

    Available for annual rental only starting November 1st. Beautifully renovated and fully furnished, this 2 bedroom, 3 bath townhouse is ready to move right in. The loft has been thoughtfully set up with two twin beds, making it a great spot for extra guests. More interior photos to come!Executive Bay Club offers everything you could want - tennis courts, a pool, and a private beach with incredible

    Courtney Jeffers Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

    87200 Overseas Hwy Unit 5, Islamorada, FL 33036
  • /20

    $5,500 per month

    • 2 Beds
    • 2 Baths
    • Townhouse for Rent

    87200 Overseas Hwy Unit 1, Islamorada, FL 33036

    Prestigious Executive Bay Club corner townhouse in Islamorada. Offering 2BD/2Bth and loft. Spacious, updated & completely furnished. Beach front private community with 24 manned gate entrance, private beach to enjoy beautiful sunsets, pool, tennis courts, club house, first come first serve dock. Next door to Founder's Park offering many activities including the famous Nautical flee market. Assoc

    Isabel Ruiz Coldwell Banker Realty

    87200 Overseas Hwy Unit 1, Islamorada, FL 33036
  • /30

    $20,000 per month

    • 5 Beds
    • 4.5 Baths
    • House for Rent

    128 Leoni Dr, Islamorada, FL 33036

    SPECTACULAR VENETIAN SHORES HOME! 70' concrete dock on deep water canal which opens directly to Snake Creek for quick and easy access to bay or ocean; Furnished; 5 bedrooms/4.5 baths; private master retreat with gorgeous bath on third level; marble floors throughout; elevator; FABULOUS chef's kitchen with Wolf gas range and huge island; large terraces and fantastic entertaining spaces; Sonos

    Emily Romberg Real Estate Sales Force - Coral Gables

    128 Leoni Dr, Islamorada, FL 33036
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