• Sunset Dream $12,000 / monthly

    Sunset Dream

    $12,000 / monthly

    Mile Marker 83. Five bedroom/four bath home located on the Florida Bay.   Sunset Dream has an ideal view for Sunsets, dolphins, and a view of the Florida Bay Keys.  Heated pool gives plenty of fun for the family.   This home is older, but is in…

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

    Nautica

    $20,000 / monthly

    Mile Marker 83. Four bedroom/four bath clean home located directly on the Florida Bay.  Featuring fantastic sunset views, Nautica Sleeps 8-10 and has a heated pool and good dockage.   Monthly rental only.

    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
  • 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.   Ocean front in South Key Largo– this private gated home has dockage and beautiful sunrises.  Sleeps 6.   Monthly only.  

    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
  • 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
  • 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 $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
  • 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
  • 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 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
  • The Cove South $3,000 / monthly

    The Cove South

    $3,000 / monthly

    Mile Marker 801. 1 BR – 1BA Villa on Old Hwy.   This fantastic location is just a short bike ride to Morada Way festivals, the Art Walk, Full Moon Party and restaurants.   Grab breakfast and Coffee at Midway Cafe, lunch at Green Turtle Inn, dinner…

    1 bed 1 bath
    1 bed 1 bath
  • Tatenda Ishe Cottage 1 $3,500 / monthly

    Tatenda Ishe Cottage 1

    $3,500 / monthly

    Mile Marker 81.  A neat and cozy 2 bedroom flat located in the heart of Islamorada– Walk, bike, or ride two many of Islamorada’s restaurants, breweries, and festivals–

    Optional detached bedroom to add for $400/month.

    2 beds 1 bath
    2 beds 1 bath
  • Tatenda Ishe Cottage 2 $3,500 / monthly

    Tatenda Ishe Cottage 2

    $3,500 / monthly

    Mile Marker 81.   Cute and cozy two bedroom home located off the main streets, in the heart of Islamorada.  A full porch wraps around the front and back yard, for relaxing and entertaining in the Florida Keys weather.   Natural sunlight fills the main living space as you enter into the quaint cottage. The fully equipped kitchen is open to the dining and the newly renovated bathroom is conveniently located in the middle of the home. Multiple cozy sitting areas lead  you into the tv room, furnished with a flat screen tv and a large leather sofa. The back bedroom features french doors that extend out into a courtyard where you will find a covered sitting area and native landscaping.  The guest bedroom features two twins. Enjoy being a short distance from all the charming restaurants, marinas, shops, and galleries that makes Islamorada the perfect vacation destination.

    2 beds 2 baths
    2 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
  • 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 Port Antigua Neighborhood beach, one of the BEST beaches in Islamorada. Port…

    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
  • 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.  The upstairs will not be occupied during…

    2 beds 2 baths
    2 beds 2 baths
  • Seas the Day $8,000 / Month *SPECIAL* $10,000 July

    Seas the Day

    $8,000 / Month *SPECIAL* $10,000 July

    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
  • 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