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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Grassy Key vacation homes

Property grounds

1. 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)
"Very nice villa "
United States
Grace L.
The price is ￥26,575
￥77,738 total
includes taxes & fees
Sep 21 - Sep 22
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Living area

2. 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 ￥29,327
￥80,947 total
includes taxes & fees
Sep 21 - Sep 22
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Outdoor pool

3. 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, (144 reviews)
"It is an excellent place."
United States
Arianna
The price is ￥20,191
￥27,079 total
includes taxes & fees
Sep 20 - Sep 21
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
Outdoor dining

4. 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
9.2 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 ￥42,196
￥145,263 total
includes taxes & fees
Sep 20 - Sep 21
Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!
Outdoor dining

5. 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, (166 reviews)
"Kitchen was well-equipped. Views were spectacular and the peaceful setting was everything we needed and hoped for! Would definitely consider this place for a future stay. My kids' favorite feature was the nearby Cabana Club!"
United States
Ryan K.
The price is ￥59,337
￥161,966 total
includes taxes & fees
Oct 5 - Oct 6
Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!
Living area

6. 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, (42 reviews)
"We had a great stay!!"
United States
lissa h.
The price is ￥62,052
￥127,245 total
includes taxes & fees
Oct 4 - Oct 5
Charming 3-bedroom house featuring a heated private pool.
Interior

7. 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
10.0 out of 10, Exceptional, (1 review)
"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 ￥74,858
￥169,212 total
includes taxes & fees
Sep 28 - Sep 29
Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available
Exterior

8. 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.
The price is ￥91,900
￥182,133 total
includes taxes & fees
Sep 21 - Sep 22
4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request
Room

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

Easy Breezy Family Complex 5BR 3BTH 100ft Dock, Pool, & Beach!
Marathon
The price is ￥70,795
￥252,533 total
includes taxes & fees
Sep 29 - Sep 30
Easy Breezy Family Complex 5BR 3BTH 100ft Dock, Pool, & Beach!
Outdoor dining

10. Villa 7079 on Duck Key - Boat Slip Available

Villa 7079 on Duck Key - Boat Slip Available
Marathon
The price is ￥68,607
￥160,929 total
includes taxes & fees
Sep 24 - Sep 25
Villa 7079 on Duck Key - Boat Slip Available
Outdoor dining

11. Waterfront / Ocean Access Canal / Kamp Key / Homes

Waterfront / Ocean Access Canal / Kamp Key / Homes
Matecumbe
8.8 out of 10, Excellent, (5 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 ￥66,031
￥153,655 total
includes taxes & fees
Oct 12 - Oct 13
Waterfront / Ocean Access Canal / Kamp Key / Homes
Outdoor dining

12. 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, (3 reviews)
"This property and the entire community was amazing. This was a fantastic vacation. One of the best we have had in years!"
United States
Gmac W.
The price is ￥152,506
￥281,376 total
includes taxes & fees
Sep 28 - Sep 29
Private Beach / Private overwater dock / Heated Pool / Mahi Key
House

13. Beach Residence Private Overwater Dock Heated Pool Mahi Key

Beach Residence Private Overwater Dock Heated Pool Mahi Key
2.0 star property
Matecumbe
The price is ￥245,496
￥411,938 total
includes taxes & fees
Oct 14 - Oct 15
Beach Residence 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

Hawks Cay Resort

Hawks Cay Resort

8/10 Good
"The place are beautiful!!! The staff were very nice and welcoming!!! We booked the 3 bedroom premium villa which is upgraded and little bigger it was really cool we love it , the only thing was that we had an issue with the Wifi we complained the moment we found out they said we send someone no one come!!! We keeping asking and asking we went to the front desk we will send the IT guy in hour we were there for 5 days he never come!!!!! The Arcade room and fitness room Was open 8-5 nothing to do after 5pm very disappointed, the water park was closed the Dolphin was closed no Dolphin!!! Restaurant is little over priced!!!! The place is very beautiful !!!"
EYAL 4-night trip
Posted 3 hours ago
Hawks Cay Resort

Find out more about Grassy Key

Grassy Key Vacation Homes information

Number of reviews
293
Accommodation
1256 Vacation Homes
Lowest Price
￥27,079
Highest Price
￥411,938

Explore a world of travel with Expedia