Grassy Key Vacation Rentals

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Our top choices for Grassy Key vacation 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 CA $706
CA $1,763 total
includes taxes & fees
Nov 9 - Nov 10
🌊 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, (1,014 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 CA $140
CA $157 total
includes taxes & fees
Nov 10 - Nov 11
Tropical Cottages

3. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (382 reviews)
"Loved staying in the aqua lodges, such a relaxing place."
United States
Lauren
The price is CA $160
CA $379 total
includes taxes & fees
Dec 8 - Dec 9
Yacht Haven Marina

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 CA $126
CA $172 total
includes taxes & fees
Nov 29 - Nov 30
Knight's Key Suites

5. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (239 reviews)
"Never stayed in a houseboat before. It was a novel experience!"
United States
Susan
The price is CA $137
CA $368 total
includes taxes & fees
Nov 15 - Nov 16
Aqua Lodge Rentals At Coconut Cay

6. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,297 reviews)
"Great spot"
Canada
Justin
The price is CA $225
CA $310 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $231
CA $300 total
includes taxes & fees
Nov 18 - Nov 19
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 CA $178
CA $399 total
includes taxes & fees
Nov 10 - Nov 11
Aqua Lodges at 47th Street Gulfside

9. Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.8 out of 10, Exceptional, (8 reviews)
"Great Location! The house was beautiful and clean We had a great time!"
United States
Andres
The price is CA $366
CA $829 total
includes taxes & fees
Dec 3 - Dec 4
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA

10. Seas the Keys Getaway with plunge pool/spa

Seas the Keys Getaway with plunge pool/spa
Marathon
9.6 out of 10, Exceptional, (15 reviews)
"Nice location "
United States
Gina W.
The price is CA $277
CA $674 total
includes taxes & fees
Nov 10 - Nov 11
Seas the Keys Getaway with plunge pool/spa

11. 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 CA $431
CA $898 total
includes taxes & fees
Nov 19 - Nov 20
Villa del Sol - Sunset Views, Kayaks, 2/2.5

12. 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 CA $291
CA $692 total
includes taxes & fees
Dec 1 - Dec 2
Tiny Villa, Big Ocean Views| Breathtaking Sunsets

13. 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 CA $348
CA $773 total
includes taxes & fees
Nov 9 - Nov 10
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

14. 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 CA $374
CA $838 total
includes taxes & fees
Nov 9 - Nov 10
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

15. 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, (3 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 CA $366
CA $793 total
includes taxes & fees
Nov 23 - Nov 24
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA

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 CA $463
CA $901 total
includes taxes & fees
Nov 26 - Nov 27
Oceanfront Tiny Villa in the Heart of the FL Keys

17. Charming 3-bedroom house featuring a heated private pool.

Charming 3-bedroom house featuring a heated private pool.
Duck Key
10.0 out of 10, Exceptional, (49 reviews)
"It was perfect for our girl trip!"
United States
Brandy
The price is CA $706
CA $1,303 total
includes taxes & fees
Nov 21 - Nov 22
Charming 3-bedroom house featuring a heated private pool.

18. Canal Front, 3 BR, Cabana Club, Sleeps 8

Canal Front, 3 BR, Cabana Club, Sleeps 8
Marathon
9.2 out of 10, Wonderful, (5 reviews)
"Place was perfect. Property manager was amazing and always answered questions within minutes. Definitely would stay again"
United States
lori p.
The price is CA $381
CA $1,293 total
includes taxes & fees
Nov 11 - Nov 12
Canal Front, 3 BR, Cabana Club, Sleeps 8

19. 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 CA $166
CA $523 total
includes taxes & fees
Nov 9 - Nov 10
Canal Front Retreat with Pool + Free Breakfast

20. Villa 4204 on Duck Key Boat Slip Available - 3BD 2BA

Villa 4204 on Duck Key Boat Slip Available - 3BD 2BA
Marathon
9.8 out of 10, Exceptional, (7 reviews)
"The property was very clean."
United States
Kelsey S.
The price is CA $468
CA $1,167 total
includes taxes & fees
Nov 9 - Nov 10
Villa 4204 on Duck Key Boat Slip Available - 3BD 2BA
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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Find out more about Grassy Key

Everything you need to know about Grassy Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Grassy Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Grassy Key vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Grassy Key vacation rentals we have selected for you start as low as CA $125 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 vacation 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 vacation.

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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