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Top Pet-friendly vacation packages in Islamorada

Price found within the past 48 hours. Click for updated prices.

La Siesta Resort & Villas

Matecumbe

Save 100% on your flight

$1,042

per person

Apr 13 - Apr 17

found 1 day ago

Roundtrip non-stop flight included

Harlingen (HRL) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

excellent location very nice simple breakfast close to liz’s of activities great poool

Reviewed on Feb 2, 2026

Islander Resort

Matecumbe

Save 100% on your flight

$1,365

per person

Apr 12 - Apr 16

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Miami (MIA)

9.2/10 Wonderful! (1,005 reviews)

My husband and I stayed 3 nights and we absolutely loved the resort. Beautiful, quiet and serene and with so many amenities. Our room was amazing with a wonderful huge patio that had a path right out to the beach. Breakfast and dinner at the two restaurants was fabulous with excellent food and great service. Would definitely stay here again!

Reviewed on Jan 30, 2026

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3 Night Pet-friendly vacations in Islamorada

Price found within the past 48 hours. Click for updated prices.

Islander Resort

Matecumbe

$1,110

per person

Apr 13 - Apr 16

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Miami (MIA)

9.2/10 Wonderful! (1,005 reviews)

My husband and I stayed 3 nights and we absolutely loved the resort. Beautiful, quiet and serene and with so many amenities. Our room was amazing with a wonderful huge patio that had a path right out to the beach. Breakfast and dinner at the two restaurants was fabulous with excellent food and great service. Would definitely stay here again!

Reviewed on Jan 30, 2026

La Siesta Resort & Villas

Matecumbe

Save 100% on your flight

$1,172

per person

Mar 12 - Mar 15

found 1 day ago

Roundtrip flight included

Nashville (BNA) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

excellent location very nice simple breakfast close to liz’s of activities great poool

Reviewed on Feb 2, 2026

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4 Night Pet-friendly vacations in Islamorada

Price found within the past 48 hours. Click for updated prices.

Casa Morada

Matecumbe

Save 100% on your flight

$1,004

per person

Apr 12 - Apr 16

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Miami (MIA)

9.4/10 Exceptional! (410 reviews)

Very nice resort, beautiful sunset’s. Staff were wonderful, housekeeping excellent

Reviewed on Feb 8, 2026

La Siesta Resort & Villas

Matecumbe

Save 100% on your flight

$1,042

per person

Apr 13 - Apr 17

found 1 day ago

Roundtrip non-stop flight included

Harlingen (HRL) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

excellent location very nice simple breakfast close to liz’s of activities great poool

Reviewed on Feb 2, 2026

Fisher Inn Resort & Marina

$1,113

per person

Mar 12 - Mar 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,003 reviews)

Wish we had this place our entire time in the Keys instead of just one night! It was definitely the best accommodations we had. The room was updated nicely, clean and comfortable. It had an unusually large flat screen tv, a long counter with a sink for preparing food or whatever, and a balcony (ours overlooked an empty lot - but there was a large gull bird nest that was interesting to watch). The outdoor space was nice - picnic tables and adirondack chairs overlooking the water. Continental breakfast provided.

Reviewed on Feb 9, 2026

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Top Pet-friendly Islamorada Hotels

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

22 min walk from Theater of the Sea

Book a stay at this 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! (1,665 reviews)

We loved this place. It’s small and easy to get around. Beautiful setting, watched the sunrise from bed, and the best hotel breakfast we’ve ever had.

Reviewed on Feb 3, 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

84001 Overseas Hwy Islamorada FL

10 min walk from Theater of the Sea

This family-friendly, oceanfront resort welcomes dogs (fees apply) with pet-friendly perks such as food and water bowls. While you're here, explore nearby hiking ...

8.8/10 Excellent! (141 reviews)

Location cannot be beat and amenities were perfect we can’t wait to go back

Reviewed on Feb 3, 2026

Islander Resort

82100 Overseas Highway Islamorada FL

7 min drive from Theater of the Sea

Hiking and biking trails are ready for you to explore near this oceanfront hotel, where dogs and cats can stay for an additional fee.

9.2/10 Wonderful! (1,005 reviews)

My husband and I stayed 3 nights and we absolutely loved the resort. Beautiful, quiet and serene and with so many amenities. Our room was amazing with a wonderful huge patio that had a path right out to the beach. Breakfast and dinner at the two restaurants was fabulous with excellent food and great ...

Reviewed on Jan 30, 2026

See all 2,114 properties in Islamorada

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.