• 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
  • Sunset Dream $12,000 / monthly

    Sunset Dream

    $12,000 / monthly

    Mile Marker 83. Five bedroom/four bath. Bayfront, pool and dockage.  

    5 beds 4 baths
    5 beds 4 baths
  • Nautica $20,000 / monthly

    Nautica

    $20,000 / monthly

    Mile Marker 83. Four bedroom/four bath. Sleeps 8-10. Bayfront, pool, dockage.  

    4 beds 4 baths
    4 beds 4 baths
  • Virga Limbo $17,000 / monthly

    Virga Limbo

    $17,000 / monthly

    MM 76. Five bedrooms/four baths. Charming bay front home. Hammocks, outdoor bar, and dockage all with views of uninhabited islands that dot the Keys. Sorry, no pets.  

    5 beds 4 baths
    5 beds 4 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
  • Villa Terra Carroll $9,000 Monthly

    Villa Terra Carroll

    $9,000 Monthly

    New home with pool and beach access– This 4 bedroom, 4 bath house was completed in 2014 and its located near shops and entertainment in the heart of Islamorada. Relax by the heated pool while the rest of the family heads down to the beach,…

    4 beds 4 baths
    4 beds 4 baths
  • 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
  • Seaside Breezes $8,250/ monthly

    Seaside Breezes

    $8,250/ monthly

    Mile Marker 94. Three bedrooms/two baths. Sleeps 6. Ocean front, dockage, and beautiful sunrises.  Located conveniently in Key Largo, Florida Keys.

    3 beds 2 baths
    3 beds 2 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
  • 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
  • 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
  • Treehouse $5,000 / monthly

    Treehouse

    $5,000 / monthly

    Mile Marker 96, 1 bedroom, 1 bath, sleeps 4, dock, beach, and sunsets.  

    1 bed 1 bath
    1 bed 1 bath
  • 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
  • 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
  • Grey Heron Cottage $24,000/ Monthly ~ Call for holiday rates

    Grey Heron Cottage

    $24,000/ Monthly ~ 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
  • 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
  • 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
  • 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
  • Sea Shore Drive $7,200 / monthly

    Sea Shore Drive

    $7,200 / monthly

    Mile Marker 80.5. 2 BR – 2BA Large master & bath. Walk to Morada Way festivals and restaurants. Fantastic location! W/ access to neighborhood beach.  

    2 beds 2 baths
    2 beds 2 baths
  • The Cove South $3,000 / monthly

    The Cove South

    $3,000 / monthly

    Mile Marker 801. 1 BR – 1BA Villa on Old Hwy. Short bike ride to Morada Way festivals and restaurants. Fantastic location! Large walk in shower.   This is for the South side of the Duplex.  

    1 bed 1 bath
    1 bed 1 bath
  • The Cove North $3,000 / monthly

    The Cove North

    $3,000 / monthly

    Mile Marker 801. 1 BR – 1BA Villa on Old Hwy. Short bike ride to Morada Way festivals and restaurants. Fantastic location! Large walk in shower. This is for the North side of the duplex.

    1 bed 1 bath
    1 bed 1 bath
  • 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
  • Seagrape Cottage $7,500 / Month

    Seagrape Cottage

    $7,500 / Month

    MM 81. 2 bedroom & 2 bath, set in the heart of Islamorada, near restaurants and shopping, great location for walking/biking to cultural areas! Newly renovated and now with a newly installed POOL!  

    2 beds 2 baths
    2 beds 2 baths
  • 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
  • Latitudes $16,000 / Monthly

    Latitudes

    $16,000 / 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 White Marlin Neighborhood beach, one of the BEST beaches in Islamorada. White…

    4 beds 2.5 baths
    4 beds 2.5 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
  • 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
  • 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
  • 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
  • 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
  • Oceanista $6,500 / monthly

    Oceanista

    $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