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. 🌊 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 AU$1,743
includes taxes & fees
7 Nov - 8 Nov
🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets

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)
"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 AU$649
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 AU$797
includes taxes & fees
3 Nov - 4 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 AU$709
includes taxes & fees
8 Nov - 9 Nov
Oceanfront Tiny Villa in the Heart of the FL Keys

5. 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 AU$771
includes taxes & fees
5 Nov - 6 Nov
Waterfront Retreat

6. 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 AU$973
includes taxes & fees
21 Nov - 22 Nov
Beach House - Waterfront Villa - Free Kayaks

7. 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 AU$877
includes taxes & fees
3 Nov - 4 Nov
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

8. 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 AU$1,282
includes taxes & fees
21 Nov - 22 Nov
Charming 3-bedroom house featuring a heated private pool.

9. 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 AU$1,575
includes taxes & fees
15 Nov - 16 Nov
Canal Front, 3 BR, Cabana Club, Sleeps 8

10. 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, (166 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 AU$1,723
includes taxes & fees
3 Nov - 4 Nov
4 BR with 32 Ft Boat Slip, Sleeps 10

11. Villa 7079 on Duck Key - Boat Slip Available

Villa 7079 on Duck Key - Boat Slip Available
Marathon
The price is AU$1,492
includes taxes & fees
3 Nov - 4 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 AU$1,898
includes taxes & fees
1 Dec - 2 Dec
4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request

13. 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 AU$1,728
includes taxes & fees
3 Nov - 4 Nov
Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available

14. Key Colony Beach Paradise

Key Colony Beach Paradise
Key Colony Beach
8.8 out of 10, Excellent, (64 reviews)
"Beautiful home. Was close to everything we needed. Key Colony inn is a must. Great happy hour meals. Best in the area. Will def keep this place in mind for next year."
United States
Ann S.
The price is AU$990
includes taxes & fees
5 Nov - 6 Nov
Key Colony Beach Paradise

15. 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 AU$1,057
includes taxes & fees
22 Nov - 23 Nov
Key Colony Home with Dock and Cabana Club Access- Pets Welcomed

16. 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 AU$324
includes taxes & fees
2 Dec - 3 Dec
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
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
381
Accommodation
1264 Holiday Homes
Lowest Price
AU$324
Highest Price
AU$1,898

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