Islamorada Vacation Rentals



Please read about renting homes with pets:

Bringing your dog on your Islamorada vacation just adds to the fun and alleviates the worry of not knowing what's happening with you four-legged friend while your on the Islands. But finding homeowners that will take the risk of another families pet can be tough. We at Island Villa Rental Properties understand, and want to do all we can to find accommodations for all of our guests

However, homeowners in the Keys also accept risk when accepting pets they've never met into their homes for a week or month. We try it mitigate this risk while still assisting prospective guests. To help this, we've created our 'Pets Considered' policy. This policy creates a case-by-case basis for all pet owners. We've created a list of homes with two categories:

'Most Pets Considered' and 'Some Pets Considered.'

Ultimately every inquiry for pets must go to the owner of the estate who can either approve or reject. Rejection can be due to a number of factors so reservations with pets are in no way guaranteed.



'MOST Pets Considered' Rental Cottages and Estates


Four Bedroom/ Six Bath Ultra-Luxurious, Oceanfront estate with more than 6,000 square feet under air and 5500 square feet of covered terraces and deck. Featuring a gourmand's kitchen, home theatre, gym, tennis, pool, Jacuzzi, outdoor kitchen and more! Located on three secluded tropical acres on the Atlantic Ocean.

$12,500 weekly, $35,000 monthly



Ishmael's Watch

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Four Bedroom/ Six Bath Ultra-Luxurious, Oceanfront estate with more than 6,000 square feet under air and 5500 square feet of covered terraces and deck. Featuring a gourmand's kitchen, home theatre, gym, tennis, pool, Jacuzzi, outdoor kitchen and more! Located on three secluded tropical acres on the Atlantic Ocean.

$18,000 Monthly,$20,000 Holiday



Mile Marker 83. Five bedroom/four bath. Bayfront, with pool and dockage. Affordable vintage home with some of the best sunsets in Islamorada. Privately located.

$12,000 Monthly






'SOME Pets Considered' Rental Cottages and Estates


MM 76. Three bedrooms/four baths. Bayfront home with heated lagoon style pool, landscapes, Large Tiki hut with TV and bar, dockage, gameroom and more! Enjoy the Keys like intended, outdoors in the sun and breeze at the paradise playground. Sleeps 6.

$12,000 - $14,000 monthly



Mile Marker 83. Cottage 1: oceanfront, one bedroom/ one bath upstairs. One bedroom/one bath downstairs with separate entrance. Sleeps 4. Cottage 2: Two bedroom/one bath. Sleeps 4-6. Private beach, observing pier, wet bar, pool table & newly remodeled. #VR-123 Destination Wedding Location

$8,000 weekly, $24,000 monthly



Seaside Breezes

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MM 94. Three bedrooms/two baths. Sleeps 6. Located Ocean front with great sunrises. This two story rental home is great for older guests or Anglers. Located near popular restaurants and in proximity to John Pennekamp State Park.

$8,250 monthly



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!

$7,500 monthly