Islamorada Pet-friendly Vacations
Book a Pet-friendly Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to $1,045 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
Top Pet-friendly vacation packages in Islamorada
Price found within the past 48 hours. Click for updated prices.
Islander Resort
Matecumbe
Save 100% on your flight
Price was $638, price is now $437 per person
$437
per person
Nov 16 - Nov 19
found 16 hours ago
Roundtrip flight included
Orlando (ORL) to Miami (MIA)
9.2/10 Wonderful! (1,002 reviews)
We loved staying at the Islander! The staff was very welcoming and responded instantly to texts. It was nice that they offered a shuttled so we could experience other places close to the resort. The rooms were beautiful along with the beach and pool areas! So many seating/lounging options with the cutest furniture. I would highly recommend this resort, well done!
Reviewed on Oct 14, 2025
3 Night Pet-friendly vacations in Islamorada
Price found within the past 48 hours. Click for updated prices.
Islander Resort
Matecumbe
Save 100% on your flight
Price was $638, price is now $437 per person
$437
per person
Nov 16 - Nov 19
found 16 hours ago
Roundtrip flight included
Orlando (ORL) to Miami (MIA)
9.2/10 Wonderful! (1,002 reviews)
We loved staying at the Islander! The staff was very welcoming and responded instantly to texts. It was nice that they offered a shuttled so we could experience other places close to the resort. The rooms were beautiful along with the beach and pool areas! So many seating/lounging options with the cutest furniture. I would highly recommend this resort, well done!
Reviewed on Oct 14, 2025
4 Night Pet-friendly vacations in Islamorada
Price found within the past 48 hours. Click for updated prices.
Hadley Resort and Marina
Matecumbe
Price was $577, price is now $431 per person
$431
per person
Nov 18 - Nov 22
found 18 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Miami (MIA)
7.8/10 Good! (1,003 reviews)
Loved the rooms very spacious. Ocean view was amazing very close to restaurants
Reviewed on Sep 18, 2025
Islander Resort
Matecumbe
Save 100% on your flight
Price was $1,253, price is now $933 per person
$933
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Miami (MIA)
9.2/10 Wonderful! (1,002 reviews)
We loved staying at the Islander! The staff was very welcoming and responded instantly to texts. It was nice that they offered a shuttled so we could experience other places close to the resort. The rooms were beautiful along with the beach and pool areas! So many seating/lounging options with the cutest furniture. I would highly recommend this resort, well done!
Reviewed on Oct 14, 2025
Top Pet-friendly Islamorada Hotels
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Enjoy hiking or biking trails near this oceanfront resort, where dogs are treated to pet-friendly amenities, like food and water bowls. Fees apply for pets.
8.8/10 Excellent! (1,254 reviews)
"Room was spacious, clean with a great balcony."
Reviewed on Oct 7, 2025
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. ...
9.2/10 Wonderful! (1,543 reviews)
"Love this place. Great beach/pool. Lovely room with great bathroom. Unbelievable view of the sunrise over the water from our balcony"
Reviewed on Oct 14, 2025
Islander Resort
82100 Overseas Highway, Islamorada, FL
Hiking and biking trails are ready for you to explore near this oceanfront hotel, where dogs and cats can stay for an additional fee.
9/10 Wonderful! (1,009 reviews)
"Amazing property! We’ve been going for years!!"
Reviewed on Oct 11, 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.
