Seas the Day $11,000-$13,000 Monthly, Call for Holiday rates

Seas the Day

$11,000-$13,000 Monthly, Call for Holiday rates

Mile marker 77. Deep Water ocean side canal with direct access to the Atlantic Ocean and a straight shot to Alligator Light House. Sunny Patio and splash Pool. 4 Bedrooms/4 Baths. Sleeps 8.  There is no cable package with this home so please bring your…

4 beds 4 baths

Morada Breeze in Venetian Shores $6,900 - $8,000 / Month

Morada Breeze in Venetian Shores

$6,900 - $8,000 / Month

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 1 bath

Holly’s Hideout $12,500 / Month

Holly’s Hideout

$12,500 / Month

Mile Marker 91 – Ocean Side 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…

4 beds 3 baths

Seaside Breezes $18,000-$20,000 Monthly

Seaside Breezes

$18,000-$20,000 Monthly

Mile Marker 94. Three bedrooms/two baths.   Ocean front in South Key Largo– this private gated home has dockage and is known for the soft breezes & beautiful sunrises.   Enjoy the Atlantic Ocean how a local enjoys it… Enjoy mornings on the wrap around patio watching…

3 beds 2 baths

Ocean Terrace Currently Under Construction

Ocean Terrace

Currently Under Construction

Mile Marker 81.5, This 3 bedroom, 3 bath home is complete with den, breezes and sunrises.   Featuring a jacuzzi and splash pool located right next to the sandy beach, this home comfortable sleeps 6-8 people. Currently Under Construction Vacation Rental License #VR-047.  

3 beds 3 baths

Kahiki Creek $20,000 / Monthly Call for holidays

Kahiki Creek

$20,000 / Monthly Call for holidays

🌴 Kahiki Creek – Tropical Paradise Getaway in Islamorada, Florida Keys 🌴 Welcome to the exquisite rental home nestled on a quiet natural canal in Islamorada… A picturesque oasis in the enchanting Florida Keys. Immerse yourself in the ultimate blend of luxury, comfort, and stunning…

4 beds 3 baths

Madeira Villa $20,000 / Monthly

Madeira Villa

$20,000 / Monthly

Fantastic for entertaining, Madeira Villa features a large and partially covered pool and deck area with plenty of activities for entertaining guests!  Multiple decks and patios overlook a heated pool and dockage on a canal with easy access to the world famous Florida Keys waters. …

3 beds 2 baths

Latitudes $20,000 - $25,000 / Monthly

Latitudes

$20,000 - $25,000 / Monthly

Mile Marker 75 – Bayside 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. The main selling point of Latitudes is the home’s awesome outdoor area. Pool, Tiki Hut,…

4 beds 2.5 baths

Tropical Villa $19,000 / Monthly

Tropical Villa

$19,000 / Monthly

Mile Marker 77 – Waterway – Ocean side Immaculately designed and landscaped home with heated pool and dockage located in a quiet neighborhood in Lower Matecumbe Key.  Built in 2019, the 2900 sq. ft. home features a large, covered outdoor kitchen, pool area, dockage and…

4 beds 3.5 baths

Bella Del Mar $12,000 - $15,000 / Monthly

Bella Del Mar

$12,000 - $15,000 / Monthly

3 bedroom, 3 bath home on an immaculately updated and maintained canal front home in  the famous Port Antigua neighborhood, Islamorada, Florida Keys. Excellent dockage and access to Port Antigua Beach, one of the best white sand beaches in the Florida Keys. Inside the home,…

3 beds 3 baths

Palm Cottage South $15,000 / Monthly

Palm Cottage South

$15,000 / Monthly

Mile Marker 75 – Bayside 4 bedroom 3 bath   Palm Cottage South, is a charming, modern home directly on the canal with a heated, private pool, dockage, and access to the Port Antigua community sandy beach.  Dockage for 24′ boat max on the lift…

4 beds 3 baths

Sweet Escape $20,000 - $24,000 / Monthly

Sweet Escape

$20,000 - $24,000 / Monthly

Sweet Escape is an exquisite, canal front home located in Islamorada in the Florida Keys. This impeccable 5 bedroom villa benefits from having wide, clear dockage in front of the house, a secluded pool & tiki area, and access to the famous and gated Port…

5 beds 5 baths

Paradise Found- w/ neighborhood beach! $18,000 / Monthly Call for off season pricing

Paradise Found- w/ neighborhood beach!

$18,000 / Monthly Call for off season pricing

Mile Marker 75 – Bayside 🏖️ Luxurious 4 Bedroom, 4 Bath Vacation Rental Home with Dockage and Beach Access in Islamorada, Florida Keys 🏖️ Nestled in the heart of the enchanting Islamorada, known as the “Village of Islands,” this exquisite 4-bedroom, 4-bath vacation rental home…

4 beds 4 baths

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

Nautica $20,000 / monthly

Nautica

$20,000 / monthly

Mile Marker 83 – Bayfront Welcome to your dream waterfront rental home in Islamorada, located in the heart of the Florida Keys. This stunning 4 bedroom, 4 bathroom home sits on the bay and offers breathtaking views of the water and world class sunsets.  …

4 beds 4 baths

Seagrape Cottage $7,500 / Month

Seagrape Cottage

$7,500 / Month

MM 81 – Heart of Islamorada 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! ***Optional Add on Dockage available at weekly rates,…

2 beds 2 baths

Little Bay Cottage $3,000 weekly

Little Bay Cottage

$3,000 weekly

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

1 bed 2 baths

Little Bay $3,000 weekly/unit

Little Bay

$3,000 weekly/unit

Mile Marker 82 – Bayfront Multiple units available, including the Duplex (up and downstairs).  Located bayside, Little Bay has some of the best sunsets in Islamorada.   Great dockage, wildlife, and snorkeling makes this property even more beautiful. Each unit has 2 bedrooms, 1.5 bath, sleeps…

2 beds 2 baths

Oasis At Tavernier $20,000 Monthly ~ Call for Holiday Rates

Oasis At Tavernier

$20,000 Monthly ~ Call for Holiday Rates

$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 boaters.  …

6 beds 7 baths

Ishmael’s Watch $20,000 / Monthly Call for Holiday rates

Ishmael’s Watch

$20,000 / Monthly Call for Holiday rates

Mile Marker 77 – Oceanfront – Lower Matecumbe Key.   Six 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…

6 beds 4 baths

Venetian Villa – Brand New $25,000 / monthly

Venetian Villa – Brand New

$25,000 / monthly

Mile Marker 74 – Bayfront observation pier / Boat basin dockage 5 bedroom and 5.5 bath with Pool and Dockage surrounded by natural beauty. The sparkling pool features a spa and waterfall overlooking the deep-water natural beauty and secluded portion basin and canal..  Just a…

5 beds 5.5 baths

Sunrise Lookout $10,000 / monthly

Sunrise Lookout

$10,000 / monthly

Mile Marker 82 – Open Ocean front *Upstairs only for rent, Sunrise Lookout looks out on the world famous blue green waters of the Florida Keys.  Spend every morning greeted by a beautiful sunset, and every evening enjoying cool ocean breezes.   Up the stairs, the…

2 beds 1 bath

Gulfview $13,000-$15,000 Monthly Call for holiday rates

Gulfview

$13,000-$15,000 Monthly Call for holiday rates

The private home features 3 modern bedrooms and 2 updated baths and sleeps 6 adults.  The master bedroom features a king size bed and stunning bay and sunset views.  Two guest bedrooms, one with a king bed and one with a queen bed makes this house ideal for friends or family.  An additional bunk room with a bunk and day bed provides plenty of room for accompanying children.  

3 beds 2 baths

Sea Breeze Villa $12,000 Monthly, call for off season

Sea Breeze Villa

$12,000 Monthly, call for off season

Mile Marker 81 – Heart of Islamorada

A magical, modern, Island-style Villa with the ideal location!  This newly renovated Villa, in Green Turtle Beach Neighborhood, features 2 bedrooms, 2.5 baths, and a custom pool featuring a private sandy area around pool.

3 beds 3 baths

Happy Ours $30,000 / monthly

Happy Ours

$30,000 / monthly

Mile Marker 74.5 – Open Bayfront Six Bedroom/ Six Bath Ultra-Luxurious, Open water front estate with more than 5,000 square feet under air and 4,500 of covered terraces and deck.  Walk out the back door to the world famous Port Antigua gated community beach!  The…

6 beds 6 baths