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

Holiday 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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Grassy Key holiday homes

Waterfront / Ocean Access Canal / Kamp Key / Homes

Waterfront / Ocean Access Canal / Kamp Key / Homes
Matecumbe
10.0 out of 10, Exceptional, (2 reviews)
"Excellent house. Very clean. We had a little trouble with the check in code and we were immediately contacted and the code was changed and we were in within minutes. The maintenance guy stopped by to make sure we got in and everything was good. EXCELLENT Customer Service!!!!!House was very well stocked with pots and pans and misc things needed for a week stay! Right on a nice little canal with plenty of room for our boat."
United States
Mike H.
The price is NZ$2,081
includes taxes & fees
9 July - 10 July
Waterfront / Ocean Access Canal / Kamp Key / Homes

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, (53 reviews)
"Very nice villa "
United States
Grace L.
The price is NZ$1,137
includes taxes & fees
1 Aug - 2 Aug
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA
Duck Key
9.4 out of 10, Exceptional, (36 reviews)
"Great location great views! "
United States
Stephen M.
The price is NZ$1,214
includes taxes & fees
14 July - 15 July
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

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, (30 reviews)
"Left to go to key west decided to stay here on our drive back up because we enjoyed it so much!"
United States
Regan C.
The price is NZ$1,215
includes taxes & fees
8 July - 9 July
Charming 3-bedroom house featuring a heated private pool.

Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!

Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!
Marathon
9.0 out of 10, Wonderful, (4 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 NZ$2,039
includes taxes & fees
12 July - 13 July
Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!

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, (15 reviews)
"Everything was perfect. Great place to stay"
United States
Kirk r.
The price is NZ$1,236
includes taxes & fees
5 July - 6 July
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!

Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!
Marathon
10.0 out of 10, Exceptional, (163 reviews)
"We traveled for a wedding with a fairly large group of family members. The property was beautiful, clean and well kept. I can’t say enough about Meredith - she responded quickly to any questions and even helped us out when our flights were cancelled due to the snowstorm in NY! Will definitely be going back again. Highly recommend."
United States
Eileen H.
The price is NZ$2,875
includes taxes & fees
26 July - 27 July
Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!

Waterfront villa Family Friendly 2 bedroom

Waterfront villa Family Friendly 2 bedroom
Duck Key
8.6 out of 10, Excellent, (14 reviews)
"We were very pleased with our stay. "
United States
Jeffrey S
The price is NZ$1,218
includes taxes & fees
21 July - 22 July
Waterfront villa Family Friendly 2 bedroom

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
9.6 out of 10, Exceptional, (9 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.
The price is NZ$2,575
includes taxes & fees
1 Aug - 2 Aug
4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request

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
The price is NZ$2,266
includes taxes & fees
14 July - 15 July
Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available

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, (140 reviews)
"This was the perfect place, right on the ocean and a full kitchen so you can cook your own meals. The room was very clean, I loved that they had a laundry basket and laundry detergent in the room for you, came in handy seeing as we stayed for 7 days. Amazing place to watch the sunset from a hammock and we got lucky enough to see some nurse sharks at the docks right outside of our hotel."
United States
Andrew Jackson
The price is NZ$458
includes taxes & fees
8 July - 9 July
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Grassy Key Hotel Reviews

Find out more about Grassy Key

Grassy Key Holiday Homes information

Number of reviews
451
Accommodation
1272 Holiday Homes
Lowest Price
NZ$458
Highest Price
NZ$2,875

Explore a world of travel with Expedia