• Blue Heaven Bahamas $5,600 / weekly

    Blue Heaven Bahamas

    $5,600 / weekly

    Blue Heaven is a recently renovated open and airy cottage with three bedrooms, and three baths. With views of the bright blue ocean with pinks sandy beaches on one side and Hope Town harbor with the historic lighthouse and anchored sailboats on the other. Get…

    3 beds 3 baths
    3 beds 3 baths
  • Bayview Villas $4,600 - $5,600 weekly

    Bayview Villas

    $4,600 - $5,600 weekly

    3 Bedrooms & 3.5 bathrooms Villas 7-9 $3,960 – $7,000 Weekly depending on dates   Mile Marker 81.6 — Bayside Villas   Bayview Villas are named because they are… bayside! The closest villas to the pool, water and dockage, these villas are a set of…

    3 beds 3.5 baths
    3 beds 3.5 baths
  • 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
  • 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
  • The Beach House $7,000 - $8,400 weekly ~ Call for holiday rates

    The Beach House

    $7,000 - $8,400 weekly ~ Call for holiday rates

    3 bedroom home with a one bedroom guest house, totaling 4 bedrooms.  Located on the Ocean side with lovely pool and dock.  Located near Morada way in the ‘Heart of Islamorada.’ Quietly located on the old road, walk or ride bikes to breakfast, lunch, dinner…

    4 beds 4 baths
    4 beds 4 baths
  • 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
  • Green Turtle Beach $9,950 / week ~ $13,140 Holidays

    Green Turtle Beach

    $9,950 / week ~ $13,140 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 security. Optional separate cottage, additional $1,000 weekly. #VR-082    

    5 beds 5.5 baths
    5 beds 5.5 baths
  • Little Bay $2,500 weekly/unit

    Little Bay

    $2,500 weekly/unit

    Mile Marker 82, duplex (up and downstairs). Each unit has 2 bedrooms, 1.5 bath, sleeps 6, basin, dockage, snorkeling. Vacation Rental License #VR-084, & 85.    

    2 beds 1.5 baths
    2 beds 1.5 baths
  • Little Bay Cottage $2,500 weekly

    Little Bay Cottage

    $2,500 weekly

    Mile Marker 82. One bedroom/two bath with Florida room. Newly remodeled. Vacation Rental License #VR-086.  

    1 bed 2 baths
    1 bed 2 baths
  • 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
  • Conch Villas $3,600 - $4,200 Weekly

    Conch Villas

    $3,600 - $4,200 Weekly

    3 Bedrooms & 3.5 bathrooms Villas 4-6 $3,600 – $4,200 Weekly depending on dates Mile Marker 81.6 — Bayside Villas Conch Villas, aptly named for the famous large snails that inspired the Keys to be called the ‘Conch Republic,’ are a set of three brand…

    3 beds 3.5 baths
    3 beds 3.5 baths
  • 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
  • Osprey Bay $5,700-$6,500 Weekly

    Osprey Bay

    $5,700-$6,500 Weekly

    Mile Marker 82.7, 5 bedrooms, 3 baths, sleeps 10-12, dockage, pool, spa, and beautiful sunsets. Located in heart of Islamorada. VR-171  

    5 beds 3 baths
    5 beds 3 baths
  • Key Lime Villas $3,600 - $4,200 / weekly

    Key Lime Villas

    $3,600 - $4,200 / weekly

    3 Bedrooms & 3.5 bathrooms Villas 1-3 $3,300 – $3,850 Weekly depending on dates Mile Marker 81.6 — Bayside Villas   Key Lime Villas, aptly named for the famous Key’s citrus fruit, are a set of three brand new villas located in the heart of…

    3 beds 3.5 baths
    3 beds 3.5 baths
  • 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
  • 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
  • Captains Quarters- 4 Plex $1,250 weekly - $4,750 monthly

    Captains Quarters- 4 Plex

    $1,250 weekly - $4,750 monthly

    Mile Marker 81. Two bedroom/one bath $1,450 weekly, $4,750 monthly One bedroom/one bath $1,250 weekly, $3,500 monthly Sleeps 4-6. Dockage, Wireless Internet, New A/C. #VR-127 & #VR-128  

    2 beds 1 bath
    2 beds 1 bath
  • Futura Yacht club #302 $1,400 weekly, $1,600 Holidays

    Futura Yacht club #302

    $1,400 weekly, $1,600 Holidays

    MM 88.5. 2 bedrooms, 2 baths, sleeps 4. 3rd floor. King in master W/ queen size bed in guest. Heated pool, beautiful sunsets, and lit tennis, basketball, and volleyball courts. Optional deeded dock for boats. #VR-178

    2 beds 2 baths
    2 beds 2 baths
  • Futura Yacht Club #403 $1,400 / Week, $1,600 Holidays

    Futura Yacht Club #403

    $1,400 / Week, $1,600 Holidays

    MM 88.5. 2 bedroom, 2 baths, sleeps 4. 4th Floor. King in master w/ 2 twins in guest. Heated pool, screened Lanai, tennis courts, basketball and volleyball courts. Optional dock for boats up to 33′. Beautiful sunsets. #VR-17

    2 beds 2 baths
    2 beds 2 baths
  • Sunset Lagoon $6,500 / weekly $7,500 Holiday

    Sunset Lagoon

    $6,500 / 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