Holiday Rentals in Grassy Key

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Grassy Key

Oceanfront Sandy Beach Vacation Rental Unit 1

9.4 out of 10, Exceptional, (104)
"Such a wonderful location and property. Great for exploring the keys. Very comfortable and nicely decorated. Lovely folded towels at the start of our stay was a beautiful touch. Very quiet and plenty of lovely restaurants and attractions nearby. We would love to stay again! Thank you Wluld"
Oceanfront Sandy Beach Vacation Rental Unit 1

4 Keys To Paradise | 5 Bed, 3.5 Bath

9.6 out of 10, Exceptional, (25)
"The house was large and very clean. We had three families staying with 10 total people and we never felt cramped. Wouldn't hesitate to stay here again."
4 Keys To Paradise | 5 Bed, 3.5 Bath

Beachfront 8-bedroom villa just a short walk to Coco Plum Beach

9.8 out of 10, Exceptional, (85)
"Can’t wait to return. Thanks for providing the perfect venue to reconnect as a family."
Beachfront 8-bedroom villa just a short walk to Coco Plum Beach

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1133)
"Large rooms, clean, quiet."
The price is €168
includes taxes & fees
5 Dec - 6 Dec
Skipjack Resort & Marina

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (124)
"Clean, quiet. Balcony to the sea was a big plus. Everything was excellent."
The price is €297
includes taxes & fees
2 Dec - 3 Dec
Aqua Lodge Rentals At Coconut Cay

Yacht Haven Marina

3.5 star property
9.8 out of 10, Exceptional, (92)
"We needed to escape the crazy busy before the holidays, this was exactly what we needed. Manatee every morning while i drank my coffee on the deck. Just very relaxing."
Yacht Haven Marina

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1064)
"I liked full kitchen. Balcony door dos not close, but it’s not a big deal. Location is central to Fla Keys. "
The price is €114
includes taxes & fees
2 Dec - 3 Dec
Knight's Key Suites

Tropical Cottages

3.0 star property
8.4 out of 10, Very good, (745)
"Great place. Clean rooms and great staff. Thanks for the hospitality. Highly recommended "
The price is €91
includes taxes & fees
4 Dec - 5 Dec
Tropical Cottages

Cabins at Bonefish Bay

3.0 star property
10.0 out of 10, Exceptional, (22)
"Nice place to stay. "
Cabins at Bonefish Bay

TA Beach, Pool, Marina, family friendly, Kitchen, Jacuzzi

9.4 out of 10, Exceptional, (184)
"Beautiful beach view. Turquoise blue water. Close to a lot of fun things to see, like the Dolphin Research Center and the Sea Turtle Hospital. "
TA Beach, Pool, Marina, family friendly, Kitchen, Jacuzzi

PF Pool Beach Kitchen Sleep 6, Hot Tub W&D Marina WiFi Parking

9.6 out of 10, Exceptional, (38)
"The property is right on a beach, although the beach is not great. Small and it was muddy and weedy when we were there, but it might have been due to the waves. The bungalow was clean and spacious. The only draw back is that the bathrooms are located upstairs and you have to climb circular stairs."
PF Pool Beach Kitchen Sleep 6, Hot Tub W&D Marina WiFi Parking

TJ1 Beach, Pool, Kitchen, Sleep 6, HotTub, W&D, Dock, BBQ, WiFi, Parking, Tennis

9.6 out of 10, Exceptional, (17)
"We enjoyed our stay at the keys. The pool was amazing! My favorite spot was sitting under the coconut tree gazing out over the ocean and watching the sunset."
TJ1 Beach, Pool, Kitchen, Sleep 6, HotTub, W&D, Dock, BBQ, WiFi, Parking, Tennis

Beautiful Coral Lagoon #12 - Waterfront - Boat Slips Available at the Marina

10.0 out of 10, Exceptional, (126)
"We enjoyed our stay at Coral Lagoon #12. The property was everything advertised. The townhome had comfortable beds, plenty of seating, and a nice kitchen with all the right pots and pans. We were able to keep the boat we rented right in front of the condo at no extra charge. There were good places to eat near by and it was a short drive to Key West. All in all a good trip."
Beautiful Coral Lagoon #12 - Waterfront - Boat Slips Available at the Marina

Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - Boat Slip Avail

10.0 out of 10, Exceptional, (195)
"Loved the property and the Marina folks were excellent. Owners were very responsive, not so much for their managers though. Called them three times, left two VMs and no one ever called us back. The place is wonderful though..."
Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - Boat Slip Avail

Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC

8.8 out of 10, Excellent, (220)
"This was a fantastic property for two couples looking for a long weekend getaway. The location was fantastic - easy drive to Marathon, walking distance to Hawks Cay’s public restaurant and marina, private access to the canal. The private pool was big enough for four adults to cool off from the Florida sun and humidity. A great stay!"
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC

OPEN WATERFRONT [not canal] HOUSE [not duplex] Snorkel right from your backyard

9.0 out of 10, Wonderful, (17)
"We had a wonderful stay! Juan was a great hist. He kept in contact with us a week before the stay and gave us updates on the property. The house was comfortable and perfect for our needs. I have stayed in several vacation homes and I will stay this is the MOST well stocked home ive ever stayed in. Juan thought of everything. Even down to a beach umbrella and pool noodles. My only complaint (which is not the fault of the host) is the floating dock was damaged prior to our arrival and had to be...
OPEN WATERFRONT [not canal] HOUSE [not duplex] Snorkel right from your backyard

Relax by Sombrero Beach 21 mins away at our 2-bedroom Marathon Villa

9.6 out of 10, Exceptional, (66)
"Clean, comfortable, well-equipped kitchen. Perfect for our 2nd girls getaway at this property. We will be back! Thank you, Debbie. "
Relax by Sombrero Beach 21 mins away at our 2-bedroom Marathon Villa

KA Beach, dock, Pool, Kitchen, Tennis, Hot Tub, tropical paradise

9.4 out of 10, Exceptional, (73)
"It was nice having the beach and pool to go to. Lots of seaweed though. Good location and food close by"
KA Beach, dock, Pool, Kitchen, Tennis, Hot Tub, tropical paradise

Vibrant, waterfront retreat with WiFi, balcony & dock access

8.4 out of 10, Very good, (11)
"Great place "
Vibrant, waterfront retreat with WiFi, balcony & dock access

Canal-front condo with amazing views & convenient location

8.6 out of 10, Excellent, (39)
"Everything we needed"
Canal-front condo with amazing views & convenient location
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.
Don't see what you're looking for?
See all available properties in Grassy Key
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Grassy Key you may be interested in

Rainbow Bend Resort

2.5 star property
8.2 out of 10, Very good, (531)
"The Hieaway Cafe on premise is the reason to stay here. It was cute and fabulous "
The price is €174
includes taxes & fees
8 Dec - 9 Dec
Rainbow Bend Resort

Gulf View Waterfront Resort

2.5 star property
8.6 out of 10, Excellent, (373)
"We enjoyed our stay! We had 2 bedrooms and a large living area . We were given an upgrade without asking! There was plenty of room to enjoy. The location was lovely and we enjoyed the heated pool on cool nights . "
The price is €107
includes taxes & fees
5 Dec - 6 Dec
Gulf View Waterfront Resort

Grassy Flats Resort & Beach Club

2.5 star property
9.4 out of 10, Exceptional, (205)
"The room was very nice and the view was incredible. Restaurant and bars were great. The pool area for adults was very nice. "
The price is €191
includes taxes & fees
8 Dec - 9 Dec
Grassy Flats Resort & Beach Club
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.