Ocean Side Vacation Rentals Florida Keys

Sea Ranch $9,000 weekly ~ Call for holiday rates

Sea Ranch

$9,000 weekly ~ Call for holiday rates

Mile Marker 83 – Oceanfront Two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada! 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…

4 beds 4 baths
4 beds 4 baths

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

The Beach House

$7,000 Weekly - Call for holiday rates

Mile Marker 80 – Oceanfront   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….

4 beds 4 baths
4 beds 4 baths

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

Leila’s Beach House $4,750 / weekly

Leila’s Beach House

$4,750 / weekly

Miles Marker 81 – Oceanfront   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…

3 beds 2 baths
3 beds 2 baths

Mile Marker 81. NEWLY DONE POOL and HOT TUB! This 4 bedrooms, 4.5 bath home is brand new to 2019.  Watch perfect sunrises off the balcony that overlooks the pool and Atlantic Ocean.   Grounds feature a white sand beach, new observation pier, pool, hot tub,…

4 beds 4.5 baths
4 beds 4.5 baths

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

Ishmael’s Watch

$18,000-$20,000 / monthly

Mile Marker 77 – Oceanfront – 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…

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 – Oceanfront   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…

3 beds 2.5 baths
3 beds 2.5 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

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

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

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

Seaside Breezes $14,000/ monthly

Seaside Breezes

$14,000/ monthly

Mile Marker 94. Three bedrooms/two baths.   Ocean front in South Key Largo– this private gated home has dockage and beautiful sunrises.   Enjoy the Atlantic Ocean how a local sees it…  Sleeps 6.  

3 beds 2 baths
3 beds 2 baths

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

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

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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