Grassy Key rentals with pool

We visited this beautiful property in early May 2025. Our part consisted of two couples and two kids, 3 and 5. We wanted for nothing during our stay! The property is big and feels very private, which we loved. That’s incredibly rare in the Keys! We thoroughly enjoyed the wrap around porch and the multiple seating options around the house. The pool is perfection, and we loved that it was gated for extra security for the kids. There’s sooo many toys for kids, including beach toys. The amount of kayaks and paddle boards is incredible, even though we only used one tandem kayak. For larger parties, this option is amazing. The view is unreal, and you can watch the sunsets from the comfort of the private dock (another rare find in the Keys). We brought a 22ft skiff and were able to put in just down the street from where we were staying and dock it at the dock. The water levels do get low, but if your boat floats skinny, it’s no issue. We spent the majority of our time outside, either boating, kayaking, swimming in the pool or enjoying the shade and breeze under the house. But inside is also so nice. 5 bedrooms! The beds, we all agreed, were so comfortable! The kitchen is incredibly well-stocked. There’s a Publix about 15 minutes away, so groceries and cooking in were very easy. The restaurant that neighbors the property was also very good. We throughly enjoyed our time here and are already discussing the next time we can return.

The home and property were amazing! Better than the pictures. We enjoyed every minute. Kayaking and paddle boarding, fishing from the dock, the pool and hot tib

This was a very nice property in a quiet neighborhood. Very clean and nicely decorated. Everything worked well, we had no issues with any of the amenities. The view from the living room was really beautiful, and the sunset from the end of the dock spectacular!The two extra bedrooms do not have direct access to the main living area, which was a bit inconvenient. The "pool" is not actually for swimming, also disappointing.However, we had a great week. 6 adults had plenty of room and enjoyed our vacation!The rental agency was very accommodating and answered all our questions prompty.

We loved everything about this property. We can't wait to come back and stay again!!

Large house on huge property. Gulf front with private pool and tennis court. Could just stay on property with lots of activities—putting green, basket ball goal. Nice grill and in door and out door eating space. Property manager came by to check several times. Family gave it 10 out of 10–including teenager!

I have experience with vacation renting a property and know first hand that this place was exceptional. First off the owner was completely accessible and responsive to my many questions. The property had absolutely everything you could ever need. We were celebrating a milestone birthday and there was a mixer and baking pans, which is not always available in vacation rental properties. The was a little problem with the Keurig coffee machine that was resolved in less than 24 hours with a new machine. The beds were comfortable. The place was immaculate, the linens were a high quality, we didn't need to bring beach towels, there were kayaks and pool toys...I could go on and on. The screened in porch was massive and allowed us to be outside but shaded from the sun. The dock was so long and wonderful. We enjoyed hours and hours of family time in the heated pool. My family has memories that will last a lifetime. I will recommend this property to anyone wanting to spend some time in the Florida Keys. Thank you Alida for sharing your wonderful home with my family.

The host thought of everything when designing this property! Roman and Karen went out of their way to make sure our stay was perfect!!!! And The view in the photos do not do the property Justice. The spectacular windows in every room made you feel as though you were next to the ocean at all times. So RELAXING. Our family enjoyed so much fun at the home we rarely left the property except to escape to the beach or eat at a restaurant. We spent hours playing family tournaments of corn hole and ping pong. And then there were countless hours soaking and playing in the probate pool. Other than the activities my favorite little personal heaven was that each room had its own shower/bathroom! It made it nice to get a relaxing shower after a long fun day. We are definitely booking this property again. Because we loved this so much we are planning a trip in December to try out another one of their properties. After staying here I’m certain we will not be disappointed!

Property is as listed and is in a great location. You are minutes from marathon and grocery stores. The SS wreck and galley grille and the Dolphin research center are a short walk from the home. We fished from the dock and caught plenty of fish. The pool and hot tub are amazing and the enclosure makes it a perfect spot to relax all day. There was a large Iguana that hangs out by the dock that we saw daily. It was an amazing family vacation and I would highly recommend.