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

Grassy Key Vacation Rentals

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Our top choices for Grassy Key vacation 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.
🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets

2. 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 $233
CA $303 total
includes taxes & fees
Nov 18 - Nov 19
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

3. 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 CA $268
CA $667 total
includes taxes & fees
Nov 18 - Nov 19
Tiny Villa, Big Ocean Views| Breathtaking Sunsets

4. 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 $351
CA $814 total
includes taxes & fees
Nov 17 - Nov 18
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

5. 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 $298
CA $704 total
includes taxes & fees
Nov 22 - Nov 23
Oceanfront Tiny Villa in the Heart of the FL Keys

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 CA $385
CA $1,339 total
includes taxes & fees
Nov 19 - Nov 20
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 CA $514
CA $1,074 total
includes taxes & fees
Nov 29 - Nov 30
Charming 3-bedroom house featuring a heated private pool.

8. 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 CA $427
CA $905 total
includes taxes & fees
Dec 1 - Dec 2
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

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 CA $606
CA $1,619 total
includes taxes & fees
Dec 11 - Dec 12
4 BR with 32 Ft Boat Slip, Sleeps 10

10. Blue Waters Stay - Kayaks - 2BR 2.5BA Coastal Villa

Blue Waters Stay - Kayaks - 2BR 2.5BA Coastal Villa
Duck Key
9.0 out of 10, Wonderful, (2 reviews)
"This was an excellent location, beautiful 2 level condo , in a quiet location with easy access to many of the adventures on the keys. I recommend this rental highly. The owner was responsive before and through our stay. A 10 out of 10! "
United States
Steven N.
The price is CA $549
CA $1,045 total
includes taxes & fees
Nov 22 - Nov 23
Blue Waters Stay - Kayaks - 2BR 2.5BA Coastal Villa

11. 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 CA $556
CA $1,053 total
includes taxes & fees
Dec 4 - Dec 5
Beach House - Waterfront Villa - Free Kayaks

12. Villa 7079 on Duck Key - Boat Slip Available

Villa 7079 on Duck Key - Boat Slip Available
Marathon
The price is CA $705
CA $1,470 total
includes taxes & fees
Nov 16 - Nov 17
Villa 7079 on Duck Key - Boat Slip Available

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 CA $897
CA $1,734 total
includes taxes & fees
Nov 15 - Nov 16
Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available

14. 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 CA $962
CA $1,812 total
includes taxes & fees
Nov 16 - Nov 17
4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request

15. 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.
The price is CA $551
CA $1,151 total
includes taxes & fees
Nov 15 - Nov 16
Coral Lagoon #13: Heated Pool, Views, easy Gulf & Atlantic Access via Vaca Cut

16. 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 CA $623
CA $948 total
includes taxes & fees
Nov 16 - Nov 17
Walk to Beach: Florida Keys Gem w/ Ocean Views

17. 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 CA $335
CA $642 total
includes taxes & fees
Nov 17 - Nov 18
Key Lime Cottage in Islamorada

18. Private Beach / Private overwater dock / Heated Pool / Mahi Key

Private Beach / Private overwater dock / Heated Pool / Mahi Key
Matecumbe
10.0 out of 10, Exceptional, (4 reviews)
"Our stay here was very nice. Everything was clean and comfortable. The pool was enjoyable the one time we used it. Sitting on the deck gazing out to sea was exactly what I needed. Spotting a crocodile swim by was exciting!"
United States
Anonymous traveller
The price is CA $2,021
CA $3,727 total
includes taxes & fees
Nov 20 - Nov 21
Private Beach / Private overwater dock / Heated Pool / Mahi Key
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

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Grassy Key Vacation Homes information

Number of reviews
481
Accommodation
1261 Vacation Homes
Lowest Price
CA $303
Highest Price
CA $3,727

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