Ocean Side Vacation Rentals Florida Keys

  • 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
  • The Beach House $6,500 - $8,400 weekly ~ Call for holiday rates

    The Beach House

    $6,500 - $8,400 weekly ~ Call for holiday rates

    3 bedroom home with a one bedroom guest house, rents all as one.  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,…

    3 beds 3 baths
    3 beds 3 baths
  • Sea Ranch $8,000 weekly - $24,000 monthly ~ Call for holiday rates

    Sea Ranch

    $8,000 weekly - $24,000 monthly ~ 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
  • Grey Heron Cottage $6,000 / weekly ~ Call for holiday rates

    Grey Heron Cottage

    $6,000 / 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
  • 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
  • Ishmael’s Watch $18,000-$20,000 / monthly

    Ishmael’s Watch

    $18,000-$20,000 / monthly

    Mile Marker 77 — Lower Matecumbe Key. Seven bedroom/ five 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 and Jacuzzi. Catch palm tree shade or…

    7 beds 4 baths
    7 beds 4 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
  • 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
  • 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
  • Unit 309 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, oceanside unit with beautiful sunrise views! #VR-027

    3 beds 3 baths
    3 beds 3 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
  • 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
  • Seaside Breezes $8,250/ monthly

    Seaside Breezes

    $8,250/ monthly

    Mile Marker 94. Three bedrooms/two baths. Sleeps 6. Ocean front, dockage, sunrises.

    3 beds 2 baths
    3 beds 2 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

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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