Islamorada Vacation Homes

A beach with white lounge chairs, a covered pavilion, and palm trees.

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Our top choices for Islamorada holiday homes

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

1. Little Peace of Haven

Key Largo

Mitchel R.

HK$3,443 total

includes taxes & fees

16 Nov - 17 Nov

A modern living room with a flat-screen TV, a black leather sofa, and a white ottoman.

2. Charming Home in Key Largo

Key Largo

JOHN P.

HK$2,857 total

includes taxes & fees

19 Oct - 20 Oct

A two-story building with a pool, a boat dock, and a table set for dining.

3. Waterfront / Ocean Access Canal / Kamp Key / Homes

Matecumbe

"Excellent house. Very clean. We had a little trouble with the check in code and we were immediately contacted and the code was changed and we were in within minutes. The maintenance guy stopped by to make sure we got in and everything was good. EXCELLENT Customer Service!!!!!House was very well stocked with pots and pans and misc things needed for a week stay! Right on a nice little canal with plenty of room for our boat."

Mike H.

HK$6,957 total

includes taxes & fees

20 Oct - 21 Oct

A waterfront patio with a view of the sunset, a pool, and lounge chairs.

4. 4. Cozy Key Largo Waterfront Studio | Dive

Key Largo

Brittany M.

HK$3,057 total

includes taxes & fees

9 Nov - 10 Nov

A beach with a wooden structure and a signpost indicating directions to various locations.

5. FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

Key Largo

Aaron G.

HK$4,822 total

includes taxes & fees

19 Oct - 20 Oct

A beach setting with white chairs arranged around a fire pit, a thatched-roof structure, and a view of the ocean.

6. Key Largo Kawama Villa L1, 3/3

Key Largo

Dayanis

HK$4,445 total

includes taxes & fees

18 Oct - 19 Oct

A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

7. Oceanside Retreat w/Rooftop, Pool & Kayaks

Key Largo

HK$6,251 total

includes taxes & fees

26 Oct - 27 Oct

A beach setting with white chairs arranged around a fire pit, overlooking the ocean.

8. Key Largo Villa, Kawama K5, 3/3

Key Largo

Susan S.

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Top Islamorada Hotel Reviews

Chesapeake Beach Resort

10/10 Excellent

"Super el hotel"

Hadley Resort and Marina

8/10 Good

"Lovely gem of a place and in a great location to explore either direction in the Keys! Helpful and friendly staff! I stayed in the room units closer to the road and next to the main lobby, so I can't compare them to the larger suites or ocean-view spots--which I'm guessing are fancier. The room was decently clean and comfy! Just noting (not complaining), the bathroom was tiny, but it worked fine for 1 person. Had a nice little kitchenette with a mini fridge, microwave, large sink, and coffee pod maker, so it was easy to save restaurant leftovers or keep a few groceries. There's a sweet little spot to sit in loungers or chairs at the end of the marina and soak up some ocean views (east-facing for sunrise is nice). It's just a quick walk to the backside of the property. It wasn't busy during my stay in early Oct., so it was easy to get a chair anytime, but note that there isn't space for more than a few people at a time. There are kayaks and other things you can use (I didn't have the time)."

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