Title: Pet-friendly Vacations in Islamorada 2026 | Expedia.ca ![](https://images.trvl-media.com/place/10768/fc4588ee-e7f3-44af-8fce-e7aa6a494cda.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # 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](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Siesta Resort & Villas Matecumbe CA $933 per person May 2 - May 5 found 1 day ago Roundtrip flight included Detroit (DTT) 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](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Islander Resort Matecumbe CA $3,066 per person Apr 17 - Apr 24 found 1 day ago Roundtrip flight included Toronto (YYZ) 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 Don't see what you're looking for? See all available trips from Columbus to Islamorada [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-09/2026-03-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Pet-friendly holidays in Islamorada Price found within the past 48 hours. Click for updated prices. ![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Siesta Resort & Villas Matecumbe CA $933 per person May 2 - May 5 found 1 day ago Roundtrip flight included Detroit (DTT) 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](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Islander Resort Matecumbe CA $2,645 per person Mar 19 - Mar 22 found 18 hours ago Roundtrip non-stop flight included Ottawa (YOW) 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 Don't see what you're looking for? See all available trips from Columbus to Islamorada [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-09/2026-03-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Pet-friendly holidays in Islamorada Price found within the past 48 hours. Click for updated prices. ![Fisher Inn Resort & Marina](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fisher Inn Resort & Marina CA $1,244 per person Mar 14 - Mar 18 found 1 day ago Roundtrip non-stop flight included Detroit (DTW) 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 ![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Siesta Resort & Villas Matecumbe CA $1,597 per person Mar 15 - Mar 19 found 20 hours ago Roundtrip flight included Detroit (DTW) 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 ![Bayside Villas by Islander Resort](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/70514579_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bayside Villas by Islander Resort Matecumbe CA $2,890 per person Mar 14 - Mar 18 found 1 day ago Roundtrip non-stop flight included Detroit (DTW) to Miami (MIA) 8.8/10 Excellent! (395 reviews) Staff was very responsive. Great location Reviewed on Jan 25, 2026 Don't see what you're looking for? See all available trips from Columbus to Islamorada [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-09/2026-03-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Pet-friendly Hotels in Islamorada ![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 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 [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 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! (143 reviews) Spotless room, friendly staff, excellent food Reviewed on Feb 6, 2026 [](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 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! (1,005 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 [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) [See all 2,218 properties in Islamorada](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=10768) 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 ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## More Vacations Ideas [Flights to Islamorada ](https://expedia.ca/Cheap-Flights-To-Islamorada.d10768.Travel-Guide-Flights)[ Islamorada Hotels ](https://expedia.ca/Islamorada-Hotels.d10768.Travel-Guide-Hotels)[ Islamorada Vacation Rentals ](https://expedia.ca/Islamorada-Vacation-Rentals.d10768.Travel-Guide-VacationRentals)[ Islamorada Car Rentals ](https://expedia.ca/Car-Rentals-In-Islamorada.d10768.Car-Rental-Guide)[ Islamorada Vacations ](https://expedia.ca/Islamorada.d10768.Destination-Travel-Guides)[ Things to do in Islamorada ](https://expedia.ca/Things-To-Do-In-Islamorada.d10768.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app