Pet-friendly holiday rentals in Stock Island

Sandra’s conch cottage was comfortable and beautiful and very clean. Provided all the necessary items for the week. The location of the house in Marathon is perfect to all amenities. I would definitely come again.

Plenty of room for all the family and their families. We enjoyed all the backyard amenities with pool, kyacks, boat dockage and fish cleaning station. There was sufficient seating for everyone and a great area to hangout. The only things we struggled with was TVs didn’t work properly in some of the rooms, no washcloths or kitchen towels available. With that being said, we will definitely consider renting Ryan’s place again in the future!

Incredible property. Perfect gathering space for my entire family of 6. Private yet close to commerce like Publix and local gym to work out. Great memories made.

The location and access to the beach and canal was amazing! We had such a fun time with the kayaks while being able to see all the wildlife and sail boats. The house was exactly what we needed. Jose was very helpful and flexible throughout our stay.

We had a great stay at Loretta’s place. The location offered a good jumping off point to explore the keys. The beach nearby along with canal access and kayaks was a huge plus. The garden area was nice though the mosquitos were intense. The place accommodated our group of 7 ppl well and everything was clean and well furnished. Overall, the place worked great for our group and we’d stay again!

Our gals trip was wonderful. The pool, ping pong table, corn hole, kayaks, nice bikes, and paddle boards were great amenities to have. The home is located just a couple blocks from Sombrero Beach. All of the outdoor patio furniture was great quality. Nice appliances all around. The beds were very comfortable.

Jorge’s place was super beautiful! We loved staying in key colony. Charming little neighborhood. The windows give you a beautiful view of the canal, everything was clean, we had everything we needed! We loved keeping the boat right there on the canal. We fit our large truck and trailer at the place. The patio provided lots of coverage through some rainy and windy weather. Jorge was always friendly and responsive. Also super close to the cabana club! He even left us champagne and chocolates which we enjoyed for our anniversary! Looking forward to booking our stay next year.

We thoroughly enjoyed our stay at the Catherine house and it was a perfect location to explore Key West. Beautiful space and well thought out. Perfect for two couples! A welcome retreat when you wanted to get out of the Key West hustle and bustle. We loved our time there!

Loved our stay here! Very private pool and the tiki bar/outside ice maker, was amazing. The house was clean and comfortable with the most comfortable beds ever! The only down side was the location for boating. The dock was excellent and the trip to the 7 mile bridge to fish was conveniently close, however, to do any ocean boating or fishing, the distance thru the sailboat/houseboat harbor was long and we encountered some not so friendly types through there. Over all, to stay and enjoy the privacy of the canal and pool, this was top notch!!!

Incredible for a family vacation. 🏝️The property feels very private, clean, well decorated, and many amenities. We tried out the paddle boards and spent a lot of time in the pool. When going to the beach, Aileen already had chairs and towels to bring! This property really is a gem. Thank you Aileen!

Beautiful ocean views and great local recommendations from the host! Some aspects of the interior were a bit dated, but with multiple areas to enjoy the outdoors (offering full shade to full sun and everything in between), we didn't do much inside except sleep. Kids spent hours per day in the pool and adults most enjoyed lounging on the jetty with 345 degrees of ocean views. Board games (and a ps3) were available for the occasional down time. The location allows for a feeling of privacy on the ocean while offering many hidden gems for dining and activities nearby.

This place was absolutely amazing from the second we walked in. The location was perfect with easy navigable water ways and plenty of dock space for larger boats. The pool was a hit for the younger kids, communication with Michel was fast and easy. We 100% will be staying here again.

Beautiful, well appointed home in the middle of the keys within driving distance to all the tourist attractions and restaurants. We are a 3 generation trip with grandparents and kids, and this house had it all! 3 bedrooms, each with excellent ocean views, great kitchen, kayaks and bikes in the garage, and incredible outdoor seating area! Highly recommended for families.

This place was absolutely beautiful! It gave you the perfect vacation vibe! The little area we were in was great and felt very safe even when walking around at all times of the day and night! The house had great beds/ bedrooms, great bathrooms and the living room and kitchen were perfect! The location was amazing , was walkable to everything, the beach, restaurants, bars, island tours and many stores and attractions and landmarks! It was amazing to stay and Joe was very helpful with everything when it came into the check in process and all the way to the end with check out! If we are ever in Key West again we DEFINITELY be staying here!!

The Grouper house was fabulous. I stayed there with my wife and kids for a week. Everything about this place was top notch. From booking to check in and check out. Her staff is nothing short of superb. Sean makes sure every need or question is answered promptly. The best place I have ever stayed. Highly recommend.

Our aqua lodge was very clean & cozy. Our mattress had just the right amount of firmness & was extremely comfortable. The RV park/dock area is well kept & is well lit in the evening. We felt very safe during our stay. (It's worth the walk to the end of the park to watch the sunset.) Despite seeing several young families in residence, the space is quiet & our neighbors were not intrusive.

The cabin was cozy and super cute. It was impeccably clean. I only stayed one night but wish I stayed longer. She had all the necessary amenities. I didn’t get to use the patio since I mostly stayed out on the boat but wish I had more time to do so. Kristin had board games, shampoo, conditioner, body wash, blow dryer, washer, dryer and everything you would want in an AirBNB. There are plenty of restaurants nearby and the supermarket wasn’t too far. I felt safe in the neighborhood. I hope to come back and stay here again!

We stayed from Sunday to Friday and had an incredible time! The location was perfect—just a short drive to all the excitement of Key West, yet tucked away enough to feel peaceful and relaxing. The houseboat was spotless, cozy, and a perfect fit for our family of four. It had everything we needed for a comfortable stay. The resort itself was stunning, and the pool was the perfect way to unwind after a full day of exploring. The neighbors were so friendly, and the entire community had such a welcoming vibe. We would absolutely recommend this spot to anyone looking for a unique and relaxing getaway—and we’re already planning our next visit!

Had a great week at Yunis place! Her house was extremely clean and had everything we needed and more especially for cooking which was nice. She had probably the most comfortable bed, sheets and pillows I’ve ever used. I loved how it was clutter free and didn’t have any breakable decorations down low around since we had our two toddlers with us. The pool was the perfect size for us and it was great to relax outdoors. We even saw Manatees swim up to the dock. 10/10 would recommend this spot.

A fantastic experience with a very friendly, responsive, and accommodating host team! Definitely think about this as a glamping experience. The boat is comfortable and climate controlled but it's not as large as a hotel room or beach condo. The boat has a bathroom and shower, but you'll need to mostly use the marina facilities for these. They are near the boat. The marina and hotel where the boat is docked is excellent. You have access to the hotel common spaces including two pools plus the lobby and multiple bars and restaurants. Always seemed to be live music happening. Great spaces to relax and stretch your legs if you want to get off the boat for a bit. If you have any sort of mobility issues, this is probably not a good option for you. My partner and I didn't have any difficulty boarding or getting off the boat, but it's something to consider. Not too difficult to get downtown and plenty of places to rent bikes or carts. Overall - it was rad!

My parents, wife, and I booked a three day run at this spot. It was awesome! The location was perfect and Leila recommended a lot of places around to visit and eat. Fishing is active off of the back dock and most of the surrounding areas have lights set up, so there were plenty of fish to target all day. It is a quick drive to Key West and had some nice beaches within a 5 minute drive. One big plus is that the cut that this home is located on had minimal seaweed compared to most of the other areas. Overall, this is the perfect spot. We will definitely be back.

Great place. Walk-able to all attractions in the historic district, Duval Street, Sunset Pier and Bahama village.

This is our 2nd time staying here. Great location and super clean. We love it here and look forward to booking again for next year! It is a nice and familiar place for us.

We spent four amazing days aboard the Shelly Kay with Blue Ocean Yacht Charters, and it was truly an unforgettable experience. From the moment we arrived, Cassey made sure we felt welcome and taken care of. She was incredibly attentive, quick to help with any questions or small issues, and always available when we needed her. The boat itself was in top shape—immaculate, well-maintained, and surprisingly spacious. Our quarters were very comfortable and had everything we needed to relax and enjoy the trip. It felt like our own private floating resort! Our excursion was the highlight of the stay—stunning views, smooth sailing, and such a peaceful way to explore the beauty of Key West. We couldn’t have asked for a better experience. If you’re looking for a unique and luxurious way to enjoy the Keys, this is it. We’ll definitely be back!