Islamorada Pet-friendly Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Flight and Pet-friendly hotel deals in Islamorada
Price found within the past 48 hours. Click for updated prices.
La Siesta Resort & Villas
Matecumbe
Price was CA $827, price is now CA $784 per person
CA $784
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
8.6/10 Excellent! (1,008 reviews)
Wonderful Southern Florida type cottages. Super quiet and well kept grounds. The rooms show some wear but otherwise a great stay.
Reviewed on Aug. 21, 2025
3 Night Pet-friendly holidays in Islamorada
Price found within the past 48 hours. Click for updated prices.
La Siesta Resort & Villas
Matecumbe
Price was CA $827, price is now CA $784 per person
CA $784
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
8.6/10 Excellent! (1,008 reviews)
Wonderful Southern Florida type cottages. Super quiet and well kept grounds. The rooms show some wear but otherwise a great stay.
Reviewed on Aug. 21, 2025
4 Night Pet-friendly holidays in Islamorada
Price found within the past 48 hours. Click for updated prices.
Pet-friendly Hotels in Islamorada
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Stay at this 3.5-star beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9/10 Wonderful! (1,499 reviews)
"Fresh new rooms. Location was right on the ocean. Great breakfast, made for you. Front desk staff was amazing. Super accommodating and great communication. The only thing I would have recommended is that during construction they should have instated a bathroom vanity. Would return there again!!"
Reviewed on Aug. 24, 2025
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Stay at this 4-star beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the bar in our reviews. ...
8.8/10 Excellent! (1,240 reviews)
"Beautiful and the smell is wonderful"
Reviewed on Aug. 25, 2025
Islander Resort
82100 Overseas Highway, Islamorada, FL
Stay at this 4-star beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9/10 Wonderful! (1,001 reviews)
"We loved the resort atmosphere. It was peaceful and relaxing--just what we were looking for. The drinks are pretty expensive, but that was literally the only downside to the whole trip. It is close to anything you want to do in the Keys."
Reviewed on Aug. 22, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.