Lagoons Canals & Waterway Vacation Rentals Florida Keys

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

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

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

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

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

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

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

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

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


$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

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

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

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

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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