Holiday rentals in Rockland Key

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Popular amenities for Rockland Key holiday rentals

Other great holiday rentals in Rockland Key

Home in Summerland Key
4.82 out of 5 average rating, 57 reviews

Kelly’s Kabin - Private FL Keys Cottage

LadyRating, 5 stars3 weeks ago
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!
Top guest favourite
Private room in Big Pine Key
4.97 out of 5 average rating, 36 reviews

Sweet Spot - Kayak and SUP launch

JuleeRating, 5 stars1 month ago
We had a wonderful time. I took my daughter down to the Keys because well she’s 17 and growing up too fast so we got some us time. Our love for the ocean is deep. Staying here was perfect to get to Key West to do some adventures and was so peaceful to hangout and chill. Once you walk into the Airbnb it smelled so good and was very clean. Our room and bathroom was perfect. The Big Pine Rooster was our favorite place to eat. The breakfast and dinner was amazing and my daughter said they had great key Lime pie. We used the kayaks and just wished we would have been able to go out into the ocean instead of having to stay in the “slipway area” would have been amazing. Lili the owners sister was there and was great. She made sure the house always smelled great and made sure we were doing good and comfortable. She gave us a couple free passes for put out golf and unfortunately we couldn’t use them. Overall it was such a great stay and would recommend to everyone!
Home in Marathon
5 out of 5 average rating, 4 reviews

The Roseate House at Grassy Key

MollyRating, 5 stars3 weeks ago
I don’t even know where to begin. From start to finish, our stay was absolute perfection. The views could not be beat. There are kayaks to venture out into the gulf and the mangroves, a pool that’s COOLED (you know how hot pools can get during the summer. It was so refreshing) and a garden oasis full of some of the most beautiful foliage I’ve ever seen. I’m from Charleston, SC. I’m used to waterfront living, but this was just something more magical than I could’ve ever predicted. I’m already planning my trip back for next year. Heidi left a great list of recs for restaurants and activities to do, but the property was so incredible, I only left to eat really. If you’re looking for a relaxing place to stay, with on site water days this is the place for you. The house is nice, but also has that old school beach vibe which is my absolute favorite. I just can’t say enough good things. Thank you so much, Heidi, for sharing your stunning home with us.
Boat in Key West
5 out of 5 average rating, 4 reviews

Luxurious 40' Sailing Yacht!

ChristianRating, 5 stars1 week ago
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!
Tiny home in Key West
4.85 out of 5 average rating, 415 reviews

Downtown Studio half block from Duval w parking

JenniferRating, 5 stars3 weeks ago
The location of this house was perfect for our trip, close enough to walk to almost everything we wanted to do and having a parking place was a great bonus.
Boat in Key West
4.92 out of 5 average rating, 12 reviews

Yacht Just Chillin': Anchored Out on the Ocean!

CindyRating, 5 starstoday
We loved our stay! We enjoyed grilling out and eating all our meals on the deck with the constant ocean breeze. The sunrise and sunset were amazing! We spent hours in the water - the boat swings around to the light green clear water where you can stand or float around with noodles (get some from Publix’s). Bathrooms smelled fresh and water pressure was great. We slept well with the AC. Captain Kevin is a friendly and responsive host, even for the small things.
Bungalow in Cudjoe Key
4.8 out of 5 average rating, 10 reviews

Oceanfront Bungalow Venture Out

DanaRating, 5 stars1 week ago
I can surely say that this location had everything we were looking for. The view was incredible and the kids enjoyed fishing and snorkeling right off the dock. We saw many lobsters, tarpon, a nice sized shark, parrot fish, mangrove snapper and a grouper within the canal right at the house dockage. We chummed the water and had a blast catching smaller fish. There was a boat rental right across the bay and we made use of the house’s dock for 3 days. Extremely quiet street. We rarely saw neighbors from the porch. The community pool was nice, clean and cool. The house was clean and inviting. Great location and an overall great stay!
Boat in Key West
4.71 out of 5 average rating, 7 reviews

Elegant Sailboat Stay

JulietRating, 5 stars3 weeks ago
Airbnb at it's best! So glad to have chosen this experience over a hotel alternative. We loved her charm and character and wished to have sailed the oceans on her!

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