Grassy Key villas
We found 100 villas — enter your dates for availability
Explore Grassy Key villa rentals
"Casa Azul Villa" - Beautiful Spacious Home with Private Pool, Dock, kayaks
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
30 reviews(30 reviews)
Villa IKI -Private Dock & Pool - Oceanfront 8 guests
Sleeps 10 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Beachfront 8-bedroom villa
Sleeps 20 · 8 bedrooms · 5+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
92 reviews(92 reviews)
Waterfront Beauty 8-guests, Dock, Kayaks and more
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
Relax by Sombrero Beach 21 mins away at our 2-bedroom Marathon Villa
Sleeps 6 · 2 bedrooms · 2+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
71 reviews(71 reviews)
I HATE THIS PLACE! 3/3 GULF FRONT~ELEVATOR~TIKI BAR~BOAT SLIP, MOON DECK-POOL!!!
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
131 reviews(131 reviews)
Top rated villa rentals - Grassy Key
Perfect getaway from winter
1010 out of 10
Exceptionalexceptional
50 reviews(50 reviews)
Great location. Comfortable property.
1010 out of 10
Exceptionalexceptional
204 reviews(204 reviews)
beautiful property
1010 out of 10
Exceptionalexceptional
89 reviews(89 reviews)
Perfect Vacation
1010 out of 10
Exceptionalexceptional
123 reviews(123 reviews)
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All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
How much does it cost to stay in a villa rental in Grassy Key?
Where you stay, when you plan to travel and the length of your trip will influence how much you pay for a villa rental in Grassy Key. Enter your travel details on Vrbo to easily compare options and then book one that’s right for you.
Where can I rent a Grassy Key villa with great views?
One of the easiest ways to look for a Grassy Key villa with views is to use our convenient filter tool. Narrow down your search by “Location” or select “Guest rating” to see accommodations other guests love. After all, why book a room with a view when you can have a villa rental with beautiful vistas?
Can I book a luxury villa in Grassy Key?
Featuring an array of amenities such as private pools, beautiful courtyards and modern technology features, our luxurious villa rentals in Grassy Key offer a high-end travel experience. Look forward to enjoying the best in comfortable furnishings, ample space and a setting that guarantees privacy and tranquility for both you and your guests.
What are the top things to do in Grassy Key?
Spend your days visiting Grassy Key’s prominent attractions like Sombrero Beach and your evenings unwinding in the cozy comforts of your inviting villa rental. If you’re on a family vacation, Coco Plum Beach and Fiesta Key are a couple of other places you can experience together.
Why should I book my villa vacation with Vrbo?
When you stay in a Vrbo villa rental, the only people you have to share your living space with are the people you take with you. It will just be you, your closest companions and the whole property to yourselves. Our flexible cancellation policies also mean you can book your villa with peace of mind if you need to change your plans.