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Our top choices for Grassy Key holiday rentals

1. 🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets

🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets
Marathon
9.2 out of 10, Wonderful, (66 reviews)
"Location is fantastic. House needs some work on the bathrooms but overall we had a wonderful time! Would book again."
United States
Becky F.
The price is £899
includes taxes & fees
7 Nov - 8 Nov
🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets

2. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,013 reviews)
"The family running the food truck and tiki hut were great. Felt like we were guests in their home."
United States
Douglas
The price is £80
includes taxes & fees
4 Nov - 5 Nov
Tropical Cottages

3. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (238 reviews)
"Never stayed in a houseboat before. It was a novel experience!"
United States
Susan
The price is £183
includes taxes & fees
4 Nov - 5 Nov
Aqua Lodge Rentals At Coconut Cay

4. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,245 reviews)
"We had the pool view..Excellent!"
United States
Brandy
The price is £93
includes taxes & fees
29 Nov - 30 Nov
Knight's Key Suites

5. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (380 reviews)
"Loved staying in the aqua lodges, such a relaxing place."
United States
Lauren
The price is £185
includes taxes & fees
4 Nov - 5 Nov
Yacht Haven Marina

6. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,296 reviews)
"Great spot"
Canada
Justin
The price is £164
includes taxes & fees
4 Nov - 5 Nov
Skipjack Resort & Marina

7. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.2 out of 10, Wonderful, (147 reviews)
"It is an excellent place."
United States
Arianna
The price is £170
includes taxes & fees
2 Dec - 3 Dec
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

8. Aqua Lodges at 47th Street Gulfside

Aqua Lodges at 47th Street Gulfside
3.0 star property
Marathon
8.8 out of 10, Excellent, (61 reviews)
"Loved our stay at the aqua lodges 10/10 would do it again"
United States
Lauren
The price is £220
includes taxes & fees
17 Nov - 18 Nov
Aqua Lodges at 47th Street Gulfside

9. Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.6 out of 10, Exceptional, (55 reviews)
"Great location. Pretty views of Bay. Comfortable rooms. Enjoyed our brief stay for July 4th."
United States
Jorge D.
The price is £418
includes taxes & fees
4 Nov - 5 Nov
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

10. Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Tiny Villa, Big Ocean Views| Breathtaking Sunsets
Duck Key
10.0 out of 10, Exceptional, (24 reviews)
"This was without a doubt one of the nicest places we have ever stayed! Our hostess was PHENOMENAL and went above and beyond to be sure we were comfortable and had everything we needed for our stay. Literally the best vacation we’ve had!!!’ I suggest this place to everyone!"
United States
Stephanie
The price is £342
includes taxes & fees
19 Nov - 20 Nov
Tiny Villa, Big Ocean Views| Breathtaking Sunsets

11. Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
8.8 out of 10, Excellent, (9 reviews)
"Property was clean and comfortable with an excellent sunset view each evening."
United States
william d.
The price is £434
includes taxes & fees
17 Nov - 18 Nov
Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA

12. Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.4 out of 10, Exceptional, (23 reviews)
"Awesome place to stay"
United States
Takuma F.
The price is £434
includes taxes & fees
4 Nov - 5 Nov
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

13. Villa del Sol - Sunset Views, Kayaks, 2/2.5

Villa del Sol - Sunset Views, Kayaks, 2/2.5
Duck Key
10.0 out of 10, Exceptional, (10 reviews)
"Really enjoy the time there"
United States
Han W.
The price is £457
includes taxes & fees
7 Nov - 8 Nov
Villa del Sol - Sunset Views, Kayaks, 2/2.5

14. Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA
Duck Key
10.0 out of 10, Exceptional, (2 reviews)
"The location was perfect, house was very clean, and the view was breathtaking. We will 100% return."
United States
Gina A.
The price is £418
includes taxes & fees
4 Nov - 5 Nov
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA

15. Tropical Oasis on Sombrero Beach in the Heart of Marathon FL

Tropical Oasis on Sombrero Beach in the Heart of Marathon FL
Marathon
9.8 out of 10, Exceptional, (16 reviews)
"What a charming and beautiful property. Beautiful landscape and the room was clean and comfortable. (The only minor issue was the lack of electrical outlets , but we brought our own extension cords) We definitely recommend this place 👌"
United States
JOHN
The price is £277
includes taxes & fees
17 Nov - 18 Nov
Tropical Oasis on Sombrero Beach in the Heart of Marathon FL

16. Oceanfront Tiny Villa in the Heart of the FL Keys

Oceanfront Tiny Villa in the Heart of the FL Keys
Marathon
9.8 out of 10, Exceptional, (17 reviews)
"Great stay!"
United States
Nick E.
The price is £376
includes taxes & fees
8 Nov - 9 Nov
Oceanfront Tiny Villa in the Heart of the FL Keys

17. Canal Front Retreat with Pool + Free Breakfast

Canal Front Retreat with Pool + Free Breakfast
Marathon
9.8 out of 10, Exceptional, (30 reviews)
"Super easy check in, great location in the Keys and very quiet in the room."
United States
Eric
The price is £317
includes taxes & fees
8 Nov - 9 Nov
Canal Front Retreat with Pool + Free Breakfast

18. Waterfront Retreat

Waterfront Retreat
Duck Key
10.0 out of 10, Exceptional, (38 reviews)
"We had an amazing stay and couldn't have asked for a better place to spend the week in the Keys! The home was exactly as described—clean, comfortable, and in a beautiful location. We especially loved relaxing outside and taking in the gorgeous views. It truly felt like a home away from home.The host was wonderful, responsive, and made everything easy from check-in to check-out. We made so many great memories here and would absolutely stay again. Highly recommend this property to anyone looking...
United States
Katie B.
The price is £397
includes taxes & fees
5 Nov - 6 Nov
Waterfront Retreat

19. Waterfront Suite with Pool, Tiki Bar & Marina

Waterfront Suite with Pool, Tiki Bar & Marina
Marathon
10.0 out of 10, Exceptional, (1 review)
"The condo was super clean and nice very close to Publix, the beach, the flowrider! A great location along with a relaxing and beautiful place to come back to after fishing all day!"
United States
Grace K.
The price is £312
includes taxes & fees
4 Nov - 5 Nov
Waterfront Suite with Pool, Tiki Bar & Marina

20. Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.0 out of 10, Wonderful, (16 reviews)
"Everything was perfect. Great place to stay"
United States
Kirk r.
The price is £459
includes taxes & fees
4 Nov - 5 Nov
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
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 £80 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. 

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