Grassy Key vacation rentals

We found 1,871 vacation rentals — enter your dates for availability

Find spaces that suit your style

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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
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Delight in the beachside landscape of Grassy Key

The beaches and surrounding scenery provide a peaceful ambiance to your vacation home in Grassy Key. This city is well-known for its dolphin watching and seafood restaurants. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Exploring the beaches and other natural features in Grassy Key

Travelers enjoy Grassy Key for its seaside and sunsets. Whether you're looking for exciting outdoor activities or just want to take in the scenery, Grassy Key is a great spot to appreciate mother nature. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Coco Plum Beach (3.8 mi / 6.1 km)
  • Sombrero Beach (9.7 mi / 15.6 km)
  • Vaca Key (11.3 mi / 18.1 km)
  • Fiesta Key (11.4 mi / 18.4 km)
  • Anne's Beach (14.6 mi / 23.5 km)
  • Curry Hammock State Park (2.5 mi / 4 km)

Frequently asked questions

What is the most popular type of vacation rental accommodation in Grassy Key?
Houses are the most popular style of vacation rental in Grassy Key, according to our data. Even if you’ve got a different idea in mind, Vrbo has vacation homes in all sizes and shapes. Take a look at our options to find your perfect match.
How much does it cost to rent a vacation rental in Grassy Key?
The average price for a vacation home in Grassy Key can vary based on factors such as property type, length of stay and season. Whether you’re thinking about a sprawling villa with room to move around or a comfy cabin just enough for two, just enter your travel dates to discover some great-value stays.
How much does it cost to rent a beach house in Grassy Key?
Prices for beach houses in Grassy Key vary depending on the type and size of the property and when you plan to travel. Simply enter your travel dates into Vrbo and the number of guests to view vacation rental options and prices. From there you can use the filters to refine your search results by ratings, nearby activities and more.
Are there pet-friendly vacation rentals in Grassy Key?
Pack a suitcase and a bone for your canine companion because Grassy Key has 50 vacation rentals that throw open their doors to pets. Let your four-legged buddy have fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and travel dates, then check our “Pets allowed” filter box.
Can I rent a house with a pool in Grassy Key?
Add a whole new level of fun to your getaway by staying in one of the 35 houses with a private pool in Grassy Key. Use our search filter to find properties with pools on Vrbo, then spend lazy days splishing and splashing in a swimming pool that’s only for you.
What are popular rental amenities in Grassy Key?
Some of the most popular rental amenities people look for in Grassy Key are a nearby waterfront, an ocean view and a garden. Whether you’re vacationing with friends, family or even pets, Vrbo vacation properties have the best amenities for hanging out with the people you cherish the most.
Are there large group vacation rentals in Grassy Key?
You’ll discover eight vacation properties in Grassy Key that can accommodate a group of 10 or more guests. Whether you’re organizing a get-together with extended family or an event like a birthday party, there’s enough space to get your favorite people together under the same roof.
Are there vacation rentals in Grassy Key that welcome kids?
Grassy Key has 50 family-friendly vacation homes. And booking a stay that welcomes little ones is super easy with our “Properties good for families” filter. On top of having the whole place to yourselves, you’ll get perks and conveniences such as dining rooms, pools and kitchens.
What are the top attractions for families in Grassy Key?
You’ll find lots of awesome things to see and do with the family in Grassy Key, such as:

  • Coco Plum Beach
  • Florida Keys Aquarium Encounters
  • Crane Point Museum and Nature Center

Are there one-bedroom vacation rentals in Grassy Key?
Grassy Key has eight one-bedroom rentals available. Typically located in sought-after areas thanks to their smaller size, a one-bedroom vacation property is ideal if you’re getting away with a pal or your partner. And with comforts like air conditioning and more privacy than a standard hotel, you’ll be able to kick back and relax while exploring this amazing destination.
Can I find two-bedroom vacation rentals in Grassy Key?
Gather your loved ones and enjoy total privacy and comfort in one of the seven two-bedroom vacation homes Grassy Key has to offer.
Are there vacation rentals with WiFi in Grassy Key?
Whether you’d like to keep up with world events, reply to emails or surf your social networks, there are 18 vacation homes with WiFi in Grassy Key. Check the “WiFi” box when searching on Vrbo and stay connected on your getaway.
How can I find vacation rentals with air conditioning in Grassy Key?
You’ll find 50 vacation rentals with air conditioning in Grassy Key offering that gentle, cool breeze and extra comfort level. Simply enter your preferred dates of travel and then use our handy filters to find properties with air conditioning.
How old do you have to be to rent a vacation rental in Grassy Key?
The age limit can differ across properties on Vrbo, so be sure to check the rules of the vacation home in Grassy Key you want to book. But typically, it’s 16, 18 or 21.
How long can I rent a vacation rental in Grassy Key for?
It’s down to the Grassy Key property. To browse a list of options offering extended stays, just enter your dates and guest number into Vrbo’s search page. Look forward to having the entire property to yourself, along with home comforts like air conditioning, a kitchen and a yard where your little ones can play. Be on the lookout for any long-term stays that offer discounted weekly or monthly prices.

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