Stay well, then step out and discover Islamorada.
Best Stays by Sonder Islamorada
Find places to stay in Islamorada. Choose from apartment-style stays and boutique hotels for weekend breaks, business trips, and longer city stays.
Travelers
Where to Stay in Islamorada
Islamorada Popular Stays
Choose your perfect stays
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Oceanfront -
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Ocean View
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Oceanfront
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Parking
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Pool
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Ocean View
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Oceanfront
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Parking
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Ocean View
Good for the Weekend
Easy in-and-out for quick Islamorada gateway.
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Oceanfront
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Parking
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Pool
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Ocean View
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Oceanfront
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Parking
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Pool
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Ocean View
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Oceanfront
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Parking
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Ocean View
Work-friendly stays
Desks, fast Wi-Fi, and a kitchen for work trips that run long, with dinner a short walk away.
Sonder hasn't arrived in Islamorada yet. You may like these stays from trusted partners
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Oceanfront
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Parking
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Pool
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Ocean View
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Oceanfront
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Parking
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Pool
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Ocean View
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Oceanfront
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Parking
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Pool
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Ocean View
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Parking
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Ocean View
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Balcony/Terrace -
View
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Private Pool -
Oceanfront
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Parking
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Pool
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Oceanfront
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Parking
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Pool
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Ocean View
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Oceanfront
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Parking
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Pool
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Ocean View
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Private Pool
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Parking
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Pool
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Ocean View
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Parking
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Pool
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Ocean View
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Balcony/Terrace
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Oceanfront
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Parking
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Pool
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Ocean View
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Oceanfront
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Hot Tub -
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Pool
Explore neighborhoods in Islamorada.
Explore different parts of Islamorada and find the setting that suits your trip.
Islamorada travel questions, answered.
Quick answers to the questions travelers ask most.
There are 243 vacation rentals with private pools near Islamorada. Top-rated homes that have access to a swimming pool include:
If you are looking for a family-friendly vacation home in Islamorada, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Islamorada:
Currently, the total number of properties listed in 2026 is over 1584 in the Islamorada area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Islamorada.
Go with curiosity. Come back with stories.
The best trips rarely go exactly as planned. Sonder keeps you closer to the neighborhoods, kitchens, and small moments that make a city worth remembering.