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Flight and Pet-friendly hotel deals in Islamorada

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

La Siesta Resort & Villas

Matecumbe

CA $1,847

per person

Jul 25 - Aug 1

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

8.6/10 Excellent! (1,003 reviews)

We stayed for mother’s day and we had a good time there. Staff were very friendly

Reviewed on May 12, 2026

Islander Resort

Matecumbe

CA $2,007

per person

Jul 16 - Jul 23

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Miami (MIA)

9.2/10 Wonderful! (1,004 reviews)

Everything about this property was excellent, from the wonderful staff to the kid-friendly atmosphere. We loved the breakfast brunch and the overall vibe of the place. However, dinner at The Drift was a letdown. For the price, the quality just wasn't there. I’d highly recommend the stay, but I suggest looking for other dinner options nearby. We will definitely be back!

Reviewed on May 10, 2026

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4 Night Pet-friendly holidays in Islamorada

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

Islander Resort

Matecumbe

CA $1,241

per person

Jun 13 - Jun 17

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

9.2/10 Wonderful! (1,004 reviews)

Everything about this property was excellent, from the wonderful staff to the kid-friendly atmosphere. We loved the breakfast brunch and the overall vibe of the place. However, dinner at The Drift was a letdown. For the price, the quality just wasn't there. I’d highly recommend the stay, but I suggest looking for other dinner options nearby. We will definitely be back!

Reviewed on May 10, 2026

Bayside Villas by Islander Resort

Matecumbe

CA $1,370

per person

Jun 13 - Jun 17

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

8.8/10 Excellent! (421 reviews)

La propiedad me encantó, muy limpia y bonita. Para el precio está muy bien, sin duda volvería

Reviewed on May 10, 2026

Casa Morada

Matecumbe

CA $1,566

per person

Jun 13 - Jun 17

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

9.4/10 Exceptional! (433 reviews)

Easily accessible from the highway - but tucked away in quiet corner - Casa Morada is a peaceful retreat. Good parking. Clean beautiful room/suite. Easy access to pool and lounging area. No beach.

Reviewed on Mar 22, 2026

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Pet-friendly Hotels in Islamorada

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! (1,740 reviews)

The Villas are great! Nice and clean/ modern We had an amazing time with my elderly parents and my litte kids.

Reviewed on May 12, 2026

Islander Resort

82100 Overseas Highway Islamorada FL

7 min drive from Theater of the Sea

Book a stay at this 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. ...

9.2/10 Wonderful! (1,014 reviews)

Everything about this property was excellent, from the wonderful staff to the kid-friendly atmosphere. We loved the breakfast brunch and the overall vibe of the place. However, dinner at The Drift was a letdown. For the price, the quality just wasn't there. I’d highly recommend the stay, but I suggest ...

Reviewed on May 10, 2026

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

84001 Overseas Hwy Islamorada FL

10 min walk from Theater of the Sea

Book a stay at this beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...

9/10 Wonderful! (194 reviews)

The resort, staff and facilities are excellent. The location in Islamorada is great either for a few days in the keys or as a stopping point to or from Key West. We didn’t get time to use all of the facilities but there are restaurants on site, kayaks, pools, a lively beach and breakfast so you don’t ...

Reviewed on May 10, 2026

See all 2,174 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.