Lagoons Canals & Waterway Vacation Rentals Florida Keys

  • Oceanista $6,500 / monthly


    $6,500 / monthly

    Mile Marker 75. Very Private – Two Bedrooms / Two Baths. Sleeps 6. Private waterfront lagoon to accommodate deep water boaters. Oceanfront ‘Walking Beach’ just steps away!   Virtual Tour

    2 beds 2 baths
    2 beds 2 baths
  • Sunset Lagoon $5,500 / weekly $7,500 Holiday

    Sunset Lagoon

    $5,500 / weekly $7,500 Holiday

    MM 90.  5 BR. One of the best homes for families, Sunset Lagoon has 5 bedrooms nestled on the Florida Bay in Islamorada, Florida Keys.   Let the kids hang out at the pool while you launch your boat out the convenient dockage to the back country or Atlantic Ocean.

    This home is complete with beautiful Sunset views and a game room for the kids.

    5 beds 5 baths
    5 beds 5 baths
  • Little Biscuit $7,500 / monthly

    Little Biscuit

    $7,500 / monthly

    MM 74. Three bedrooms/1 bath. Canal front home with beach access.

    3 beds 1 bath
    3 beds 1 bath
  • Seas the Day $8,000 / Month *SPECIAL*

    Seas the Day

    $8,000 / Month *SPECIAL*

    Mile marker 77. Ocean side canal. Straight shot to the Atlantic Ocean and Alligator Light House. Sunny Patio and splash Pool. 4 Bedrooms/4 Baths. Sleeps 8. Two private bedroom suits in addition to the two bedrooms with living area.      

    4 beds 4 baths
    4 beds 4 baths
  • Morada Breeze in Venetian Shores $8,000 / Month *NEW*

    Morada Breeze in Venetian Shores

    $8,000 / Month *NEW*

    Located in Venetian shores, this lower level 2 bedroom unit is complete with pool and dockage.   Dockage has great access to Ocean via Snake Creek where you’ll find the blue green water and the fishing that made Islamorada famous.   Inside, you have a comfortable…

    2 beds 2 baths
    2 beds 2 baths
  • Holly’s Hideout $9,000 / Month

    Holly’s Hideout

    $9,000 / Month

    MM 91. Situated on a clean, clear canal with deep water access to either the bay or ocean via Tavernier Creek! Enjoy your island time in this bright and breezy hideaway … Two bedrooms/Two baths upstairs along with open living, dining and kitchen. Two bedrooms/One…

    4 beds 3 baths
    4 beds 3 baths
  • Latitudes $14,000 / Monthly


    $14,000 / Monthly

    Large, modern 4 bedroom canal front home with pool in Lower Matecumbe Key in Islamorada, Florida Keys. This gorgeous home overlooks the pool and canal and is just minutes away from the FAMOUS Port Antigua Neighborhood beach, one of the BEST beaches in Islamorada. Port…

    4 beds 2.5 baths
    4 beds 2.5 baths
  • Villa Paraiso $16,000 / monthly

    Villa Paraiso

    $16,000 / monthly

    The extravagant Villa Paraiso boasts 6.5 bedrooms, with an 88’ dock, two Jacuzzis, veranda, and canal and bay views.  Located Bayside at mm 90, the large, custom built, villa would be perfect for large families or groups.    A large 10 person heated 16’x7′ swim spa…

    7 beds 4.5 baths
    7 beds 4.5 baths
  • Barefoot Elegance $27,500 / monthly

    Barefoot Elegance

    $27,500 / monthly

    Mile Marker 75, 5 bedrooms, 4 baths, sleeps 10, luxurious, heated pool, deep water dockage. Boathouse with slip.  

    5 beds 4 baths
    5 beds 4 baths

Reservation Procedure

A 30% security deposit is required along with the rental agreement and application within 24 hours to insure your booking.  The security deposit is payable by credit card.  A $75.00 reservation fee, cleaning fee and 12.5% sales and county tax are additional to the rental amount.  The balance due is payable by check or wire transfer within 90 days prior to check in  Cancellations will be refunded in full 90 days prior to check in.  The 30% security deposit will be refunded within 30 days after your departure if the property is found in satisfactory condition.  


Please be advised that during the event of a hurricane, your deposit is fully refundable without penalty. You may also use your deposit toward a future rental at a different date.


Status of properties and prices are subject to change. If owner changes status of property, a substitution will be made or refund given. Check-in is 4 PM. Check-out is 10 AM.

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