Handpicked vacation homes across South Florida. Book directly with owners for the best rates, personalized service, and unforgettable experiences.
From beachfront villas to cozy mountain retreats — every property is owner-managed for a truly personal experience.
Our properties come fully equipped with thoughtfully curated amenities to make your Caribbean getaway unforgettable.
Booking directly through our site saves you up to 20% versus major platforms — and puts you in direct contact with owners who truly care about your stay.
Booking directly is simple, secure, and completely stress-free. Here is exactly how the process works.
Thousands of verified guests have enjoyed unforgettable stays with us. Read their authentic stories.
"Best vacation rental experience I have ever had. Direct booking saved us $340 compared to Airbnb! The owner was incredibly responsive and the beachfront villa exceeded every single expectation."
"The Downtown Miami flat was absolutely perfect for our anniversary trip. Stunning views, immaculate, and the owner left fresh mangoes and a local rum welcome basket. Cannot beat that personal touch."
"We compared prices on three platforms and IslaStays was $60 per night cheaper for the same property. The owner answered every question within minutes. We will only ever book direct from now on."
"The rainforest treehouse was a bucket-list experience. Woke up to El Yunque mist every morning. The owner gave us a full hiking guide and even arranged a kayak tour. Absolutely magical."
"Rented the Key Biscayne villa for a family reunion of 10 people. Private beach, infinity pool, outdoor kitchen. The owner personally welcomed us on arrival. A 10 out of 10 in every category."
"Best vacation rental experience I have ever had. Direct booking saved us $340 compared to Airbnb! The owner was incredibly responsive and the beachfront villa exceeded every single expectation."
"The Downtown Miami flat was absolutely perfect for our anniversary trip. Stunning views, immaculate, and the owner left fresh mangoes and a local rum welcome basket. Cannot beat that personal touch."
"We compared prices on three platforms and IslaStays was $60 per night cheaper for the same property. The owner answered every question within minutes. We will only ever book direct from now on."
"The rainforest treehouse was a bucket-list experience. Woke up to El Yunque mist every morning. The owner gave us a full hiking guide and even arranged a kayak tour. Absolutely magical."
"Rented the Key Biscayne villa for a family reunion of 10 people. Private beach, infinity pool, outdoor kitchen. The owner personally welcomed us on arrival. A 10 out of 10 in every category."
No hidden fees. No booking commissions. No surprises. What you see is exactly what you pay.
Everything you need to know about booking directly with IslaStays.
Quality solutions tailored to every need
Nightly rate for stays under one week. Includes linens, Wi-Fi, and concierge support.
1-6 nights
Discounted weekly rate with mid-stay cleaning, airport pickup, and local guidebook.
7 nights
Long-term rate with weekly housekeeping, utilities included, and flexible checkout.
30 nights
Round-trip private transfer between SJU airport and your rental property.
45 min
Guided full-day tour covering rainforests, beaches, and local cuisine stops.
Full day
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