Properties

  • 68

    Peace of Paradise $20,000 / monthly

    Peace of Paradise

    $20,000 / monthly

    MM 75. Four bedrooms/three and a half baths. Gorgeous house over 3 floors, with heated/cooled pool in quiet, private side street in Lower Matecumbe Key. Directly on the Atlantic with open 180-degree panoramic view. Upscale interior design, fully furnished. Glass elevator. Gorgeous views from every…

    4 beds 3.5 baths
    4 beds 3.5 baths
    Details
  • 20

    Ocean Terrace $4,500 weekly - $15,000 monthly

    Ocean Terrace

    $4,500 weekly - $15,000 monthly

    Mile Marker 81.5, 3 bedrooms, 3 baths with den, sleeps 6-8, Jacuzzi/splash pool and sandy beach. Vacation Rental License #VR-047.  

    3 beds 3 baths
    3 beds 3 baths
    Details
  • 59

    Aguazul $4,500 weekly - $14,000 monthly ~ Call for holiday rates

    Aguazul

    $4,500 weekly - $14,000 monthly ~ Call for holiday rates

    Mile Marker 88. Four bedroom/three baths. Sleeps 8. Ocean front estate with fantastic views, heated pool and deep water dockage. Exclusive Community. Vacation Rental License #VR-014.  

    5 beds 4 baths
    5 beds 4 baths
    Details
  • 46

    The Beach House $7,000 Weekly - Call for holiday rates

    The Beach House

    $7,000 Weekly - Call for holiday rates

    Indulge in the island lifestyle at this beautiful private estate located in the heart of islamorada. The gated property is lush in tropical landscaping that boost an oceanfront pool, boat dockage, brand NEW tennis court and sand volleyball net. Enjoy breathtaking panoramic ocean views from…

    4 beds 4 baths
    4 beds 4 baths
    Details
  • 61

    Sea Ranch $8,000 weekly ~ Call for holiday rates

    Sea Ranch

    $8,000 weekly ~ Call for holiday rates

    Two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada at mile marker 83. This stunning property is truly a tropical paradise with a private, sandy beach and observing pier. Relax at the beach or cool down in the beachside…

    4 beds 4 baths
    4 beds 4 baths
    Details
  • 32

    Green Turtle Beach $10,500 -$12,500 In season and holidays

    Green Turtle Beach

    $10,500 -$12,500 In season and holidays

    Mile Marker 81. Ocean front estate located on 4 acres, five bedroom/five 1/2 baths. Sleeps 10. Sandy beach and heated pool with jacuzzi. 24 hour caretaker overseas the property. #VR-082   In Season and Holiday Rate: $12,500 Weekly Off Season: $10,500 Weekly Add optional 1…

    5 beds 5.5 baths
    5 beds 5.5 baths
    Details
  • 21

    Oasis At Tavernier $18,000 - $20,000 Monthly ~ Call for Holiday Rates

    Oasis At Tavernier

    $18,000 - $20,000 Monthly ~ Call for Holiday Rates

    $18,000 – $20,000 monthly~ Call for holiday rates   Mile Marker 92.   This luxurious 6 bedroom estate is located in Tavernier, in the Upper Florida Keys. Conveniently located a short distance from the Atlantic Ocean, deep water dockage makes Oasis in Tavernier perfect for…

    6 beds 7 baths
    6 beds 7 baths
    Details
  • 9

    Angler’s Reef Garden Side $2,600 / weekly

    Angler’s Reef Garden Side

    $2,600 / weekly

    MM 85. 2 Bedroom & 2.5 Bath. Located on the quiet side of Angler’s Reef Village. A walk down quaint streets to pool, ocean and beach!

    2 beds 2.5 baths
    2 beds 2.5 baths
    Details
  • 56

    Ishmael’s Watch $18,000-$20,000 / monthly

    Ishmael’s Watch

    $18,000-$20,000 / monthly

    Mile Marker 77 — Lower Matecumbe Key. Seven bedroom/ four bath luxurious oceanfront premier rental estate on Lower Matecumbe Key in Islamorada. Enjoy a walk around the lush, native garden or take a dip in the oceanfront pool. Catch palm tree shade or sun on…

    7 beds 4 baths
    7 beds 4 baths
    Details
  • 63

    Grey Heron Cottage $6,500 Weekly ~ Call for holiday rates

    Grey Heron Cottage

    $6,500 Weekly ~ Call for holiday rates

    Mile Marker 89.  Grey Heron Cottage Estate (named after original owner) is located on the famous Millionaire’s Row. You’ll love the fantastic sun rises, ocean views, dockage and brand new pool that this property features!   After entering the gated grounds, a long driveway leads…

    3 beds 2.5 baths
    3 beds 2.5 baths
    Details
  • 64

    Leila’s Beach House $4,750 / weekly

    Leila’s Beach House

    $4,750 / weekly

    Cozy, stylish house located in the heart of Islamorada.  3 Bedrooms and 2 baths located right on the ocean with a heated pool, private beach and more!  Enjoy the large master bedroom with master bath and shower.  Located at the end of a quiet street…

    3 beds 2 baths
    3 beds 2 baths
    Details
  • 25

    Cabana Flat – Maison Matecumbe $3,800 / weekly

    Cabana Flat – Maison Matecumbe

    $3,800 / weekly

    Unit 301 located within Maison Matecumbe gated community. Mile Marker 81. NEWLY DONE POOL and HOT TUB! 3 bedrooms, 2 baths, sleeps 6, pool, sandy beach. Vacation Rental License #VR-111.  

    3 beds 2 baths
    3 beds 2 baths
    Details
  • 18

    Maison Matecumbe #304 $3,300 / weekly - $9,900 monthly

    Maison Matecumbe #304

    $3,300 / weekly - $9,900 monthly

    Unit 304 located within Maison Matecumbe gated community. Mile Marker 81. NEWLY DONE POOL and HOT TUB! 3 bedrooms, 3 baths, 2 stories sleeps 6, pool, sandy beach. New stainless steel appliances. Vacation Rental License #VR-021

    3 beds 3 baths
    3 beds 3 baths
    Details