Holiday Rentals in Grassy Key

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Our top choices for Grassy Key holiday rentals

Houseboat in Marathon

Yacht Haven Marina
3.5 star property
9.8 out of 10, Exceptional, (245)
"Friendly staff and extremely clean."
United States
Travis
Yacht Haven Marina

Aparthotel in Marathon

Knight's Key Suites
3.0 star property
9.0 out of 10, Wonderful, (1161)
"Nice shower and great location room was clean and comfortable"
United States
Bruce
The price is €120
includes taxes & fees
8 Jan - 9 Jan
Knight's Key Suites

Aparthotel in Marathon

Skipjack Resort & Marina
3.0 star property
8.6 out of 10, Excellent, (1218)
"Beautiful location clean rooms friendly staff "
United States
Tiffany
Skipjack Resort & Marina
3.5 star property
9.6 out of 10, Exceptional, (201)
"A unique and interesting place to vacation. Relaxing yet close enough to things to do. I highly recommend the Aqua Loge rentals as a place to stay."
United States
Keith
Aqua Lodge Rentals At Coconut Cay

Cottage in Marathon

Tropical Cottages
3.0 star property
8.6 out of 10, Excellent, (915)
"Decent stay, easy check in and contactless checkout. Very quiet and nice place! "
United States
Swastik
The price is €129
includes taxes & fees
8 Jan - 9 Jan
Tropical Cottages
The price is €1,412
includes taxes & fees
2 Feb - 3 Feb
Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available
The price is €287
includes taxes & fees
4 Jan - 5 Jan
Tropical Escape | King Room w/ Resort Perks
8.0 out of 10, Very good, (1)
"The property is excellent, rooms are very nice but the check-in was disappointing. Room was not ready at 4 pm and we had flown in early. We were not able to enter our room until 4:40. "
United States
Linda C.
The price is €616
includes taxes & fees
6 Jan - 7 Jan
Marathon Oceanfront | 2 King Beds + Balcony
10.0 out of 10, Exceptional, (2)
"We were the first guests to this villa, Fantastic villa great service from the host and swift response to messages. Amazing location, very clean and tidy, great furniture. Amazing private pool deck. My only negative would be the aircon is very very noisy in the master bedroom. To sum up. Amazing "
United Kingdom
John W.
The price is €750
includes taxes & fees
4 Jan - 5 Jan
Charming 3-bedroom house featuring a heated private pool.
9.6 out of 10, Exceptional, (46)
"Clean property! Great views! Great communication with owner! Perfect location- close to marathon and key west! "
United States
candi b.
The price is €517
includes taxes & fees
5 Jan - 6 Jan
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
9.0 out of 10, Wonderful, (8)
"Property was clean and comfortable with an excellent sunset view each evening."
United States
william d.
The price is €664
includes taxes & fees
2 Feb - 3 Feb
Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA
10.0 out of 10, Exceptional, (13)
"We enjoyed our stay here! It was perfect for a family of 4!"
United States
Amy S.
Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun
10.0 out of 10, Exceptional, (1)
"The location was perfect, house was very clean, and the view was breathtaking. We will 100% return."
United States
Gina A.
The price is €619
includes taxes & fees
2 Feb - 3 Feb
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA
9.2 out of 10, Wonderful, (18)
"Property was very nice, everything as expected based on listing. Very good place for families."
United States
Nicholas H.
The price is €545
includes taxes & fees
12 Jan - 13 Jan
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
9.2 out of 10, Wonderful, (5)
"The villa is in a great location, and has a very private and secluded feeling to it when inside and around the pool. We had a great time, the villa met and exceeded or expectations, there were 6 of us staying there and the age ranges were from 27 to 64, we rented a charter boat out of marathon so the villa location was perfect.Thank you very much for such a great place to stay, we will try and stay here again if we come back down."
United States
Kevin J.
The price is €1,188
includes taxes & fees
21 Jan - 22 Jan
4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request
The price is €994
includes taxes & fees
2 Feb - 3 Feb
Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA
10.0 out of 10, Exceptional, (159)
"We enjoyed our weekday stay! Please note the Cabana Club pool is 10 - 15 minutes away from the property, it’s not in Hawk’s Cay. Otherwise we enjoyed our stay. We ended up using the cabana pool everyday on our trip. "
United States
Rachel A.
The price is €1,067
includes taxes & fees
11 Jan - 12 Jan
Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!
10.0 out of 10, Exceptional, (13)
"Beautiful views. Very nice accommodations. Wonderfull location!"
United States
michael h.
The price is €566
includes taxes & fees
7 Jan - 8 Jan
Tiny Villa, Big Ocean Views| Breathtaking Sunsets
9.4 out of 10, Exceptional, (9)
"Convenient location to our needs. Store right around the corner as well as Sombrero beach "
United States
Brian D.
The price is €360
includes taxes & fees
6 Jan - 7 Jan
Sombrero Beach Tropical Getaway in the Heart of Marathon
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Grassy Key Hotel Reviews

Find out more about Grassy Key

Everything you need to know about Grassy Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Grassy Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Grassy Key holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Grassy Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Grassy Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Grassy Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Grassy Key holiday rentals we have selected for you start as low as €120 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Grassy Key rentals

At Expedia, we put the best Grassy Key holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Grassy Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Grassy Key holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Grassy Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.