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

Grassy Key Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Grassy Key vacation homes

A pool area with lounge chairs and a view of the ocean.

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 $699
CA $1,745 total
includes taxes & fees
Nov 9 - Nov 10
🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets
A resort with a swimming pool, lounge chairs, and a view of the ocean.

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 $260
CA $332 total
includes taxes & fees
Nov 19 - Nov 20
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
A covered outdoor area with a ceiling fan, a view of the sea, and a distant building.

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 CA $278
CA $752 total
includes taxes & fees
Oct 31 - Nov 1
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
A round table set for two with a view of the ocean and palm trees.

4. 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 $270
CA $696 total
includes taxes & fees
Nov 18 - Nov 19
Tiny Villa, Big Ocean Views| Breathtaking Sunsets
A spacious living area with a sliding glass door leading to a deck, a sofa, a coffee table, and a kitchen area with wooden cabinets and appliances.

5. 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)
"We had a great stay!!"
United States
lissa h.
The price is CA $378
CA $944 total
includes taxes & fees
Oct 31 - Nov 1
Charming 3-bedroom house featuring a heated private pool.
A living room with a sofa, two armchairs, a coffee table, and a ceiling fan. There is a large window with a view of the beach and a patio area with outdoor furniture.

6. 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 $304
CA $785 total
includes taxes & fees
Oct 31 - Nov 1
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
A multi-story house with a balcony, surrounded by lush greenery and a clear turquoise water body.

7. 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 $441
CA $937 total
includes taxes & fees
Nov 8 - Nov 9
Blue Waters Stay - Kayaks - 2BR 2.5BA Coastal Villa
A covered outdoor area with a table set for dining, overlooking a body of water and buildings.

8. 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 $447
CA $1,554 total
includes taxes & fees
Nov 7 - Nov 8
Canal Front, 3 BR, Cabana Club, Sleeps 8
A spacious living area with a large island, a dining table, and a kitchen area with white cabinetry and a tiled floor.

9. 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 CA $280
CA $1,019 total
includes taxes & fees
Nov 6 - Nov 7
Key Colony Beach Paradise
A covered outdoor dining area with a view of a turquoise pool and palm trees.

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 CA $634
CA $1,790 total
includes taxes & fees
Nov 12 - Nov 13
4 BR with 32 Ft Boat Slip, Sleeps 10
A covered outdoor area with a table and chairs, overlooking a body of water with boats and a dock.

11. Villa 7079 on Duck Key - Boat Slip Available

Villa 7079 on Duck Key - Boat Slip Available
Marathon
The price is CA $729
CA $1,529 total
includes taxes & fees
Nov 2 - Nov 3
Villa 7079 on Duck Key - Boat Slip Available
Living area

12. 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, (28 reviews)
"The house and property was very nice. Quiet street and community. "
United States
Troy B.
The price is CA $413
CA $1,044 total
includes taxes & fees
Nov 22 - Nov 23
Key Colony Home with Dock and Cabana Club Access- Pets Welcomed
A two-story house with a balcony, a covered patio, and a well-maintained garden with palm trees and shrubs.

13. 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 $823
CA $1,708 total
includes taxes & fees
Oct 31 - Nov 1
4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request
A modern kitchen with a large island, pendant lights, and a view to the outside.

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 CA $928
CA $1,841 total
includes taxes & fees
Nov 1 - Nov 2
Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available
A swimming pool with lounge chairs, palm trees, and a view of the ocean.

15. Oceanview Villa w/ Private Rooftop & Pool

Oceanview Villa w/ Private Rooftop & Pool
Marathon
8.0 out of 10, Very good, (1 review)
"Looks like you are renting a property with share pool with one other home. Not true. There are several homes only 2 on water front. We were on the main pain over looking not so attractive neighborhoodDryer did not dry and dish washer did not clean. Great space just not the way lace you think you are renting. "
United States
roberta r.
The price is CA $602
CA $1,528 total
includes taxes & fees
Nov 3 - Nov 4
Oceanview Villa w/ Private Rooftop & Pool
A covered outdoor seating area with blue cushions and a table, overlooking a body of water and greenery.

16. Easy Breezy Family Complex 5BR 3BTH 100ft Dock, Pool, & Beach!

Easy Breezy Family Complex 5BR 3BTH 100ft Dock, Pool, & Beach!
Marathon
10.0 out of 10, Exceptional, (1 review)
The price is CA $891
CA $2,496 total
includes taxes & fees
Nov 15 - Nov 16
Easy Breezy Family Complex 5BR 3BTH 100ft Dock, Pool, & Beach!
A balcony with a view of the ocean, furnished with a table and chairs, and palm trees.

17. 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 $2,301
CA $4,060 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

Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"Everyone very helpful. Property clean and beautiful."
Crystal 1-night trip
Posted 1 hour ago
Lime Tree Bay Resort

Find out more about Grassy Key

Grassy Key Vacation Homes information

Number of reviews
328
Accommodation
1261 Vacation Homes
Lowest Price
CA $332
Highest Price
CA $4,060

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