Discover a selection of 1,500 vacation rentals in Grassy Key, Marathon that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $145 per night, and houses and villas are popular options for a stay in Grassy Key. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Grassy Key
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Destination guide

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.

Natural features

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:

  • 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)
  • Coco Plum Beach (3.8 mi / 6.1 km)

What are the top vacation rentals in or near Grassy Key?

Whatever vacation experience you're seeking, you'll find a rental property in or around Grassy Key that's right up your alley. Here are some of our faves:

  • Make use of amenities including air conditioning and a TV at "Sombrero Beach Home On Canal With Private Dock And Heated Pool". Situated around 8 miles from Grassy Key, this unique property has 3 bedrooms and good guest reviews.
  • Another appealing choice is "Kayak Boot Key Harbor, 75ft Canal Home", which is around 9 miles from Grassy Key. With 2 bedrooms, WiFi and nearby birdwatching activities, it has everything you need to make your visit comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Grassy Key vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Grassy Key?

Your working week will be a lot easier to bear if you've got something fabulous planned for the weekend. Give yourself something nice to look forward to by arranging a stay at one of these top weekend getaways in or near Grassy Key:

  • If spending time in nature is a priority for you, book a night or two at "Wow Private Pool, Ocean Front". Around 7 miles southwest of Grassy Key, it's close to Veterans Memorial Park & Beach and Great White Heron National Wildlife Refuge. Top amenities at this getaway include an ocean view and cable/satellite TV services.
  • Also look into "Coconut Sunsets And Open Water Views", which you'll find around 6 miles west of Grassy Key. After exploring nearby sights like Bahia Honda State Park and Beach and Anne's Beach, settle into your rental and make use of coffee and tea making facilities, an outdoor pool and more.

Can I find studio apartments for rent in and around Grassy Key?

Studio apartments are a simple yet stylish choice, ideally suited for traveling couples or solo stays. Spend your days checking out your new surroundings and your nights kicking back in your cozy hideaway. The following options in or near Grassy Key will tick all the boxes:

  • Get away on your own or take a few friends to "Waterfront Luxury Living Inside And Out". You'll have plenty of amenities to take advantage of, including a beach and an iron and ironing board.
  • Another fantastic property is "Ocean's Edge Spectacular Panoramic Ocean View Apartment". Don't let its modest size fool you — this comfy apartment is filled with convenient amenities like off-street parking options, an ice maker and plenty more.

Can I find short term rentals in or near Grassy Key?

Just because you only have a few days free doesn't mean you have to spend it in a dull hotel. Go on vacation but still have the comforts of home at one of these short-term rentals in or around Grassy Key:

  • "Waterfront Luxury Living Inside And Out" is close to the heart of Grassy Key, which means you'll have loads of things to do and see. Check out top attractions like The Turtle Hospital and Florida Keys Country Club when you're not kicking back in your cozy rental.
  • Hop out of bed, pour yourself a coffee and then plan what to see around "Life In Paradise With Boat Slip At #1 Rated Resort In Marathon". Captain Hooks Marina and Dive Center and Island Hoppers Aerial Adventures are must-do's if you choose to stay at this top-rated vacation rental.

What are the best romantic weekend getaways in or near Grassy Key?

Forget about flowers and chocolates. Sometimes all you need is to take off for the weekend, just you and your sweetie. At Vrbo, we've got romantic getaways in and around Grassy Key that would make Cupid swoon. Here are some we think you'll love:

  • Sneak away on Friday afternoon for a couple of passion-filled nights at "Sombrero Beach Home On Canal With Private Dock And Heated Pool". Located approximately 8 miles from Grassy Key, this property comes with lots of nice touches, like a restaurant dining guide and air conditioning.
  • Alternatively, spend your mini break enjoying each other's company at "Kayak Boot Key Harbor, 75ft Canal Home", around 9 miles from Grassy Key. Shopping facilities and beach sun loungers will help set the mood.

What are the best large group vacation rentals in or near Grassy Key?

Sneak a look at these large group vacation rentals in or near Grassy Key and forget about leaving anyone off your guest list:

  • You'll have loads of space to sprawl out at "Spectacular Waterfront Estate". Around 9 miles southwest of Grassy Key, this expansive property has 6 bedrooms and sleeps up to 14 guests. Top amenities include a kitchen and a water park.
  • Nothing's more important than being together with loved ones, and "Fall Weekly And Monthly Rates" makes it easy to do that. Located around 4 miles to the southwest of Grassy Key, as many as 12 guests can stay in this vacation rental which has 5 bedrooms. A swimming pool and a nearby waterfront are among the many amenities here.

What are the best houses for rent with a pool in or near Grassy Key?

Having access to a pool is always a plus when you're vacationing, especially if you have kids in tow. Stay, play and splash the days away at one of these houses with a pool in or near Grassy Key:

  • Pack your swimsuit and goggles and enjoy a fun stay with your guests at "Spacious Ground Level Gulf Side House W". Other amenities here include a kitchen island and a living room.
  • "Best Marathon House With Heated Pool And Spa" is another top option. After you've enjoyed a refreshing dip with the kids, make use of other conveniences like a TV and childrens activities.

What are the best large family vacation rentals in or near Grassy Key?

Every get-together with the family should be a memorable one. Whether you're organizing an action-packed escape with the kids or a party with relatives, Vrbo's large family vacation rentals in or near Grassy Key offer a comfy home away from home with plenty of space for everyone:

  • Get your nearest and dearest under the same roof at "Life In Paradise With Boat Slip At #1 Rated Resort In Marathon", which has 3 bedrooms that sleep up to 8 guests. This getaway is located 5 miles to the southwest of Grassy Key and comes with amenities such as a balcony and coffee and tea making facilities.
  • Another top choice is "Disinfecting And Sanitizing Measures On Gulf". This property is 7 miles west of Grassy Key and comes with coffee and tea making facilities, a kitchen and more. With 4 bedrooms accommodating up to 10 people, you won't need to leave anyone off your invitation list.

If you're eager to do some sightseeing, there are lots of family-friendly attractions nearby to put on your itinerary. Dolphin Research Center, The Turtle Hospital and Florida Keys Aquarium Encounters are excellent places to start.

What are the best large houses to rent with indoor pools in or near Grassy Key?

Go for a dip anytime the mood strikes when you book one of our large rental houses with an indoor pool. Slip on your swimsuit and check out these getaways in or near Grassy Key that feature this deluxe perk:

  • Invite your friends over for a leisurely paddle around at "Thanksgiving Week Available Beautiful Waterfront". This property has space to spare, with 4 bedrooms comfortably sleeping up to 10 guests. A swimming pool and a nearby waterfront are other things your squad will love about this place.
  • Another attractive option is "Sun Of A Beach 7bed/5bath Updated Single Family With Private Pool". With 7 bedrooms accommodating up to 16 people, you can invite the whole crew to stay with you and swim. A swimming pool and a kitchen are other amenities on offer here.

Chasing more options? Find the perfect pad among these the search bar at the top of the page. Simply adjust the filters to find the Grassy Key vacation rental that's perfect for you.

Are there one-bedroom vacation rentals in or near Grassy Key?

Absolutely. You'll find a good variety of one-bedroom vacation rentals in or near Grassy Key. If you only need a small space, one of these popular properties is sure to be a perfect fit:

  • Good things come in small packages, and "Ocean's Edge Spectacular Panoramic Ocean View Apartment" is no exception. This one-bedroom property can be found in a convenient central location and offers guests amenities like a nearby waterfront and a water view.
  • Or perhaps "Authentic And Charming Little Cottage 60 Ft From The Ocean" is better suited. Another central one-bedroom option, this place has a garden, an ocean view and more.