A dolphin swimming near a wooden dock and a tree branch in the water.

Holiday Homes in Grassy Key

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Our top choices for Grassy Key holiday homes

1. 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 NZ$413
includes taxes & fees
13 Dec - 14 Dec
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

2. Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Tiny Villa, Big Ocean Views| Breathtaking Sunsets
Duck Key
10.0 out of 10, Exceptional, (24 reviews)
"Perfect rental, can’t say enough about it. The host was fantastic. Would definitely stay here again."
United States
Tammy C.
The price is NZ$842
includes taxes & fees
18 Nov - 19 Nov
Tiny Villa, Big Ocean Views| Breathtaking Sunsets

3. 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 NZ$1,028
includes taxes & fees
17 Nov - 18 Nov
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

4. 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 NZ$887
includes taxes & fees
22 Nov - 23 Nov
Oceanfront Tiny Villa in the Heart of the FL Keys

5. 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 NZ$1,132
includes taxes & fees
1 Dec - 2 Dec
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

6. 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)
"We had a great stay at this Duck Key townhouse! It was the perfect place for our family trip. The area was beautiful, peaceful, and incredibly relaxing, which was exactly what we were looking for. We really enjoyed our time together and loved being in the Keys. The townhouse was a great home base for everything we wanted to do, while still giving us a quiet place to come back to and unwind. We made some great family memories here and would definitely stay again!"
United States
shawn m.
The price is NZ$1,670
includes taxes & fees
29 Nov - 30 Nov
Canal Front, 3 BR, Cabana Club, Sleeps 8

7. 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, (51 reviews)
"It was perfect for our girl trip!"
United States
Brandy
The price is NZ$1,350
includes taxes & fees
29 Nov - 30 Nov
Charming 3-bedroom house featuring a heated private pool.

8. Beach House - Waterfront Villa - Free Kayaks

Beach House - Waterfront Villa - Free Kayaks
Duck Key
9.8 out of 10, Exceptional, (33 reviews)
"We had a lovely stay and our communications with the host we timely, and very helpful."
Canada
Russell
The price is NZ$1,323
includes taxes & fees
4 Dec - 5 Dec
Beach House - Waterfront Villa - Free Kayaks

9. 4 BR with 32 Ft Boat Slip, Sleeps 10

4 BR with 32 Ft Boat Slip, Sleeps 10
Marathon
10.0 out of 10, Exceptional, (167 reviews)
"Very nice house, nicely decorated and clean. The children really enjoyed being on the canal, fishing, paddle boarding and kayaking. Plenty of room for our boat on the nice dock. We checked out the pool that was a drive down to Key Colony Beach area but did miss having our own pool at the house for our convenience. Our host was always available and helpful with any questions."
United States
Debra B.
The price is NZ$2,021
includes taxes & fees
11 Dec - 12 Dec
4 BR with 32 Ft Boat Slip, Sleeps 10

10. Key Colony Home with Dock and Cabana Club Access- Pets Welcomed

Key Colony Home with Dock and Cabana Club Access- Pets Welcomed
Key colony beach
9.8 out of 10, Exceptional, (29 reviews)
"The house and property was very nice. Quiet street and community. "
United States
Troy B.
The price is NZ$1,256
includes taxes & fees
22 Nov - 23 Nov
Key Colony Home with Dock and Cabana Club Access- Pets Welcomed

11. Villa 7079 on Duck Key - Boat Slip Available

Villa 7079 on Duck Key - Boat Slip Available
Marathon
The price is NZ$1,835
includes taxes & fees
16 Nov - 17 Nov
Villa 7079 on Duck Key - Boat Slip Available

12. 4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request

4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request
Duck Key
9.8 out of 10, Exceptional, (13 reviews)
"10/10 would absolutely stay here again. Frank is an excellent host and the property was beautiful."
United States
Evan M.
The price is NZ$2,255
includes taxes & fees
16 Nov - 17 Nov
4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request

13. Coral Lagoon #13: Heated Pool, Views, easy Gulf & Atlantic Access via Vaca Cut

Coral Lagoon #13: Heated Pool, Views, easy Gulf & Atlantic Access via Vaca Cut
Coral Lagoon
10.0 out of 10, Exceptional, (296 reviews)
"Was a lovely short vacation in the Keys"
United States
John W.
Coral Lagoon #13: Heated Pool, Views, easy Gulf & Atlantic Access via Vaca Cut

14. Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available

Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available
Duck Key
9.0 out of 10, Wonderful, (2 reviews)
"Very relaxing, we were in the keys for my 65th it could not have been better.Thank you again!"
United States
Anonymous traveller
The price is NZ$2,158
includes taxes & fees
16 Nov - 17 Nov
Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available

15. Walk to Beach: Florida Keys Gem w/ Ocean Views

Walk to Beach: Florida Keys Gem w/ Ocean Views
Layton
9.2 out of 10, Wonderful, (5 reviews)
"The location is pretty good and stay is better than what shown in image "
United States
Shanikumar G.
The price is NZ$1,203
includes taxes & fees
16 Nov - 17 Nov
Walk to Beach: Florida Keys Gem w/ Ocean Views

16. Key Lime Cottage in Islamorada

Key Lime Cottage in Islamorada
Matecumbe
10.0 out of 10, Exceptional, (49 reviews)
"Cute little cottage perfect for a weekend getaway. Enjoyed pool area, convenient location on our road trip down the Keys!"
United States
Karen L.
The price is NZ$780
includes taxes & fees
16 Nov - 17 Nov
Key Lime Cottage in Islamorada
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

Grassy Key Holiday Homes information

Number of reviews
475
Accommodation
1257 Holiday Homes
Lowest Price
NZ$413
Highest Price
NZ$2,255

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