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

Search Vacation Homes in Grassy Key

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

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.
🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets
A covered outdoor area with a ceiling fan, a view of the sea, and a distant building.

2. 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 AED 1,098
AED 2,408 total
includes taxes & fees
29 Nov - 30 Nov
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.

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)
"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 AED 713
AED 1,768 total
includes taxes & fees
18 Nov - 19 Nov
Tiny Villa, Big Ocean Views| Breathtaking Sunsets
An outdoor dining area with tables and chairs, overlooking a body of water.

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.
Oceanfront Tiny Villa in the Heart of the FL Keys
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, (48 reviews)
"We had a great stay!!"
United States
lissa h.
The price is AED 992
AED 2,448 total
includes taxes & fees
30 Oct - 31 Oct
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 AED 799
AED 2,038 total
includes taxes & fees
30 Oct - 31 Oct
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
A covered outdoor area with a table and chairs, overlooking a body of water with boats and a dock.

7. Villa 7079 on Duck Key - Boat Slip Available

Villa 7079 on Duck Key - Boat Slip Available
Marathon
Villa 7079 on Duck Key - Boat Slip Available
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.
Canal Front, 3 BR, Cabana Club, Sleeps 8
A resort with a swimming pool, lounge chairs, and a view of the ocean.

9. 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 AED 684
AED 873 total
includes taxes & fees
18 Nov - 19 Nov
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
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 AED 1,405
AED 3,919 total
includes taxes & fees
2 Nov - 3 Nov
4 BR with 32 Ft Boat Slip, Sleeps 10
A modern kitchen with a large island, pendant lights, and a view to the outside.

11. 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 traveler
The price is AED 2,439
AED 4,837 total
includes taxes & fees
1 Nov - 2 Nov
Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available
A coastal residential area with houses featuring grey roofs and surrounded by lush greenery.

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)
"House was awesome, great shape, comfortable beds, clean. Great location, it was central to all the keys. Would definitely stay again "
United States
gabe h.
4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request
A swimming pool with lounge chairs, palm trees, and a view of the ocean.

13. 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.
Oceanview Villa w/ Private Rooftop & Pool
A balcony with a view of the ocean, furnished with a table and chairs, and palm trees.

14. 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 traveler
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Grassy Key Hotel Reviews

Yacht Haven Marina

Yacht Haven Marina

10/10 Excellent
"Much better than i expected, The property is just as it appears in the photos. Very clean and comfortable. Check-in was great as i arrived after hours. The aqua lodges could actually sleep 6 to 7 people, but that would be pushing it for only 1 bathroom. Manatees actually swim right up to back deck daily. Very peaceful location with beach access less than1 mile away. Grocery stores and restaurants only 2 blocks away. This was my first time staying on the property and will be the place i return to for years to come."
Anonymous traveler 6-night trip
Posted 8 hours ago
Yacht Haven Marina

Explore a world of travel with Expedia