Grassy Key Holiday Rentals

    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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Grassy Key

Oceanfront Sandy Beach Vacation Rental Unit 1
Private beach
Oceanfront Sandy Beach Vacation Rental Unit 1
9.4 out of 10, Exceptional, (103)
"Me and the wife absolutely loved our stay "
Oceanfront Sandy Beach Vacation Rental Unit 1
4 Keys To Paradise | 5 Bed, 3.5 Bath
A heated pool
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
Skipjack Resort & Marina
Outdoor pool, pool loungers
Skipjack Resort & Marina
3.0 star property
8.6 out of 10, Excellent, (1129)
"Excellent front desk"
The price is HK$1,391
HK$1,845 total
includes taxes & fees
6 Nov - 7 Nov
Skipjack Resort & Marina
Aqua Lodge Rentals At Coconut Cay
Front of property
Aqua Lodge Rentals At Coconut Cay
3.5 star property
9.6 out of 10, Exceptional, (123)
"Clean, quiet. Balcony to the sea was a big plus. Everything was excellent."
The price is HK$1,237
HK$2,502 total
includes taxes & fees
18 Nov - 19 Nov
Aqua Lodge Rentals At Coconut Cay
Yacht Haven Marina
Living area
Yacht Haven Marina
3.5 star property
9.8 out of 10, Exceptional, (87)
"Loved location, the only downfall are the Roosters are noisy but it's no fault to the owners. Loved it"
The price is HK$1,470
HK$2,626 total
includes taxes & fees
12 Nov - 13 Nov
Yacht Haven Marina
Tropical Cottages
Exterior
Tropical Cottages
3.0 star property
8.4 out of 10, Very good, (743)
"Great place. Clean rooms and great staff. Thanks for the hospitality. Highly recommended "
The price is HK$738
HK$831 total
includes taxes & fees
10 Nov - 11 Nov
Tropical Cottages
Knight's Key Suites
Outdoor pool, pool loungers
Knight's Key Suites
3.0 star property
9.0 out of 10, Wonderful, (1060)
"It’s clean and updated. Walking distance to th 7 mile bridge. "
The price is HK$731
HK$989 total
includes taxes & fees
20 Nov - 21 Nov
Knight's Key Suites
Sunshine Key RV Resort & Marina
Sun deck
Sunshine Key RV Resort & Marina
2.0 star property
8.8 out of 10, Excellent, (140)
"A great place to relax and enjoy nature, fishing opportunities, and more"
The price is HK$2,769
HK$3,115 total
includes taxes & fees
6 Dec - 7 Dec
Sunshine Key RV Resort & Marina
Cabins at Bonefish Bay
Living area
Cabins at Bonefish Bay
3.0 star property
10.0 out of 10, Exceptional, (20)
"This place is amazing. The best cabin in all of Marathon. The cabins are beautiful, centrally located and close to the 7 mile bridge and several beaches. Highly recommended. The hosts were very friendly"
Cabins at Bonefish Bay
TA Beach, Pool, Marina, family friendly, Kitchen, Jacuzzi
On the beach, sun-loungers
TA Beach, Pool, Marina, family friendly, Kitchen, Jacuzzi
9.4 out of 10, Exceptional, (182)
"Had a great girls weekend. "
TA Beach, Pool, Marina, family friendly, Kitchen, Jacuzzi
Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer
Fridge, microwave, oven, stovetop
Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer
8.8 out of 10, Excellent, (44)
"Great stay. The location was perfect and the sunsets were gorgeous."
Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer
The BeachComer ~ Paradise in the Florida Keys!
Beach towels
The BeachComer ~ Paradise in the Florida Keys!
9.8 out of 10, Exceptional, (245)
"The house was really nice. The Comers have been so nice to work with. The house had everything we needed. I recommend the place highly. "
The BeachComer ~ Paradise in the Florida Keys!
Last Minute Discounts! Deep Water Canal w/ Pool, Walk to Ocean Front Tiki Bars!
Aerial view
Last Minute Discounts! Deep Water Canal w/ Pool, Walk to Ocean Front Tiki Bars!
10.0 out of 10, Exceptional, (145)
"Nice property. Would return."
Last Minute Discounts! Deep Water Canal w/ Pool, Walk to Ocean Front Tiki Bars!
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
On the beach
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
9.6 out of 10, Exceptional, (74)
"Key Colony Beach community is very welcoming, everyone is very nice. We loved going to the Cabana Club, Just relaxing by the pool and listening to the waves. Research"
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
Private beach, sun-loungers, beach towels
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
10.0 out of 10, Exceptional, (187)
"We absolutely loved this condo!! Everything about this property was perfect- the location, the gorgeous beach (a rare commodity in The Keys), the beautiful grounds, and the awesome pool. The central location was perfect for exploring the Keys in both directions. Michael was a phenomenal host. He called before we left for vacation with check-in instructions and many suggestions for a perfect stay. The condo itself was beautiful and extremely well-stocked. My husband and I always tend to...
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
Beautiful Coral Lagoon #12 - Waterfront - Boat Slips Available at the Marina
A heated pool
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
Dog-Friendly Gulf-Front Home w/ Private Pool/Dock, Fast WiFi, and Washer/Dryer
Interior
Dog-Friendly Gulf-Front Home w/ Private Pool/Dock, Fast WiFi, and Washer/Dryer
9.2 out of 10, Wonderful, (25)
"had a fun time"
Dog-Friendly Gulf-Front Home w/ Private Pool/Dock, Fast WiFi, and Washer/Dryer
TJ1 Beach, Pool, Kitchen, Sleep 6, HotTub, W&D, Dock, BBQ, WiFi, Parking, Tennis
On the beach, sun-loungers
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
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
A heated pool
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
Fully furnished studio, 50 yards from ocean, shared pool, fishing-jetty
Property grounds
Fully furnished studio, 50 yards from ocean, shared pool, fishing-jetty
9.8 out of 10, Exceptional, (56)
"It's a great location right on the water. The property was very clean and had everything I needed."
Fully furnished studio, 50 yards from ocean, shared pool, fishing-jetty
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
Sign in
Sign up, it's free

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

Rainbow Bend Resort
View from room
Rainbow Bend Resort
2.5 star property
8.2 out of 10, Very good, (518)
"Out of all of the properties we have visited, this has a beautiful location and I love that it was dog friendly. If I could suggest some things, I would suggest the property condos are spruced up a bit by paint and upgrading the furniture which would turn it into a 5 star for me. Also, the dining area was great and the service was phenomenal, however, coffee cups were tiny and the food was not good. If I were to suggest just putting in a continental breakfast with a waffle maker, that would be...
The price is HK$847
HK$1,614 total
includes taxes & fees
10 Nov - 11 Nov
Rainbow Bend Resort
Gulf View Waterfront Resort
Exterior
Gulf View Waterfront Resort
2.5 star property
8.6 out of 10, Excellent, (368)
"Very cute, older property.It was perfect for us! Located in the middle of key largo and key west which made it perfect for our adventures"
The price is HK$762
HK$858 total
includes taxes & fees
10 Nov - 11 Nov
Gulf View Waterfront Resort
Grassy Flats Resort & Beach Club
Exterior
Grassy Flats Resort & Beach Club
2.5 star property
9.4 out of 10, Exceptional, (199)
"Good size apartments a little tired and dated but had everything you needed. Heated pool and hot tub were a real bonus as the wind was fierce. Great on site restaurant "
The price is HK$1,252
HK$1,409 total
includes taxes & fees
19 Nov - 20 Nov
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.