Title: Pet-friendly Vacations in Windley Key 2026 | Expedia.ca ![](https://images.trvl-media.com/place/553248635997958830/30b22f53-286f-436b-ae7a-d035c9062e6c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windley Key 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 Windley Key Price found within the past 48 hours. Click for updated prices. ![Solé Miami, A Noble House Resort](https://images.trvl-media.com/lodging/3000000/2810000/2803900/2803820/387d2cd6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Solé Miami, A Noble House Resort Ocean Four CA $1,019 per person Feb 19 - Feb 23 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8.4/10 Very Good! (1,935 reviews) Great hotel. Other than one elevator being broken we had a really great experience here :) Reviewed on Jan 12, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach CA $10,097 per person Mar 16 - Mar 20 found 24 hours ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8/10 Very Good! (1 review) ![Villas At Hawks Cay Resort](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920083/8638cc9f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Villas At Hawks Cay Resort Marathon Shores CA $2,583 per person Feb 25 - Mar 4 found 23 hours ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8.4/10 Very Good! (145 reviews) Villa had a great few; toilets don’t flush well; handle on showered were backwards. Never came to clean at all during 5 day stay; had to text number to get anything needed; resort was understaffed; did two fishing charters and caught fish, nothing to bring home; rented paddle boards off site bc ones on site can only used in small area. Pools and hot tubs close at sunset which was a bummer we always live night swimming; golf cart was fun to rent a drive around looking at houses; no where to eat on island besides resort. Have to drive at least 20mins in either directions to get anything so if you like a variety of restaurants or happy hours this is not the place. Front desk is very understaffed; the line was always so long. Lots of people complaining about charges that weren’t theirs. We had it also happen to use. We avoided charging anything to the room bc if it. Reviewed on Jan 4, 2026 ![Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton](https://images.trvl-media.com/lodging/2000000/1170000/1169600/1169583/16bbce87_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton CA $1,499 per person Feb 25 - Mar 4 found 23 hours ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8.8/10 Excellent! (1,275 reviews) The staff was amazing, but there just aren't enough people. The room had dust bunnies in corners, behind couches and doors. We saw housekeeping once in our five days, and regularly ran out of towels, tissues and toilet paper. When we arrived at 8:00 pm, our room wasn't ready yet. In fairness, this was the busy week between Christmas and New Years, so maybe it's cleaner and more organized when it's slower. I read a review (after the fact) that said this is really a two star hotel pretending to be a four star hotel, and nothing is further from the truth. There are four or five amazing staff who seem to run the whole place, but they can't keep up with it all. As a result, you run out of beach and room towels, trash is overflowing, etc. For the price we paid, I would have expected more. Reviewed on Jan 6, 2026 ![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/b1845555_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hawks Cay Resort CA $1,708 per person Feb 25 - Mar 4 found 23 hours ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8/10 Very Good! (1,003 reviews) The condition of the rooms, ie; air conditioning, humidity and heat where an ongoing issue, so much so the floors where wet everyday. The housekeeping staff was less than adequate. However on the upside Salt and Ash and Angler and Ale were great! I special shout out to the resturant staff, Johnny, Hendry and all the manangement were wonderful and selectively I would give 10 stars to each member! Reviewed on Jan 12, 2026 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-13/2026-02-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Pet-friendly holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![EAST Miami Residences](https://images.trvl-media.com/lodging/79000000/78580000/78570600/78570563/dca879fa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### EAST Miami Residences Downtown Miami CA $1,979 per person Feb 13 - Feb 16 found 21 hours ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 9/10 Wonderful! (84 reviews) Great location and hotel. Reviewed on Dec 8, 2025 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach CA $10,097 per person Mar 16 - Mar 20 found 24 hours ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8/10 Very Good! (1 review) ![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/w4800h3297x0y3-ab24f575_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel South Beach South Beach CA $3,836 per person Mar 15 - Mar 20 found 1 day ago Roundtrip non-stop flight included Detroit (DTW) to Miami (MIA) 9.4/10 Exceptional! (1,365 reviews) Hotel is great in every way. For all the money they charge it would be nice to have late checkout option Reviewed on Jan 12, 2026 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-13/2026-02-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Pet-friendly holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![The Shelborne By Proper, a Member of Design Hotels](https://images.trvl-media.com/lodging/1000000/30000/25500/25451/e49031f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shelborne By Proper, a Member of Design Hotels South Beach CA $1,088 per person Mar 15 - Mar 18 found 1 day ago Roundtrip non-stop flight included Detroit (DTW) to Miami (MIA) 9.4/10 Exceptional! (56 reviews) The holding fee is ridiculously high Reviewed on Jan 8, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach CA $7,785 per person Mar 3 - Mar 6 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8/10 Very Good! (1 review) ![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/w4800h3297x0y3-ab24f575_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel South Beach South Beach CA $3,525 per person Feb 13 - Feb 16 found 1 day ago Roundtrip non-stop flight included Detroit (DTW) to Miami (MIA) 9.4/10 Exceptional! (1,365 reviews) Hotel is great in every way. For all the money they charge it would be nice to have late checkout option Reviewed on Jan 12, 2026 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-13/2026-02-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Pet-friendly holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![Cavalier Hotel South Beach](https://images.trvl-media.com/lodging/1000000/20000/13600/13579/c0c3faa8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cavalier Hotel South Beach South Beach CA $746 per person Feb 16 - Feb 20 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8.4/10 Very Good! (1,001 reviews) Main road in front of hotel was closed. When we arrived, the concierge had no idea where to tell us to park. If they were transparent about it, ok. I would be ok. Then they said they are out of the 'free' wine, but could charge me $8 for a Heineken. Then couldn't get the elevator to work (we were on the 2nd floor thank God) The room was in good shape. The parking is what set off the chain for me. It's not hard to update a website. Or at least tell your staff what to say. Ended up parking in the City parking garage. I'd give it like a 75/100. Reviewed on Jan 6, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach CA $10,097 per person Mar 16 - Mar 20 found 24 hours ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8/10 Very Good! (1 review) ![Solé Miami, A Noble House Resort](https://images.trvl-media.com/lodging/3000000/2810000/2803900/2803820/387d2cd6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Solé Miami, A Noble House Resort Ocean Four CA $1,019 per person Feb 19 - Feb 23 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8.4/10 Very Good! (1,935 reviews) Great hotel. Other than one elevator being broken we had a really great experience here :) Reviewed on Jan 12, 2026 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-13/2026-02-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Pet-friendly Hotels in Windley Key ![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 ... 8.8/10 Excellent! (124 reviews) Amazing place - so much variety Reviewed on Jan 6, 2026 [](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![Fisher Inn Resort & Marina](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Fisher Inn Resort & Marina 84951 Overseas Hwy Islamorada FL - 6 min walk from Theater of the Sea Book a stay at this beach motel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ... 8.2/10 Very Good! (1,003 reviews) We loved this place! The staff was awesome and it looked unassuming but the rooms were big and clean and had everything we needed. We loved the kayak and paddleboard and other activities. We would definitely stay there again! Reviewed on Jan 9, 2026 [](https://expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information) ![Drop Anchor](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Drop Anchor 84959 Overseas Highway, 222 Islamorada FL - 8 min walk from Theater of the Sea Stay at this hotel in Islamorada. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ... 8.6/10 Excellent! (1,000 reviews) The staff was personable, great location, having the bicycles and kayaks were a great touch Reviewed on Jan 1, 2026 [](https://expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) [See all 2,745 properties in Windley Key](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=553248635976197663) 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 Windley Key ](https://expedia.ca/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[ Windley Key Hotels ](https://expedia.ca/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)[ Windley Key Vacation Rentals ](https://expedia.ca/Windley-Key-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals)[ Windley Key Car Rentals ](https://expedia.ca/Car-Rentals-In-Windley-Key.d553248635976197663.Car-Rental-Guide)[ Windley Key Vacations ](https://expedia.ca/Windley-Key.d553248635976197663.Destination-Travel-Guides)[ Things to do in Windley Key ](https://expedia.ca/Things-To-Do-In-Windley-Key.d553248635976197663.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. 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