Grassy Key Vacation 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
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks

Vacation Rentals in Grassy Key

🌇 Ocean Sunset Views with Pool and Dock 🌇

9.2 out of 10, Wonderful, (35)
"It was peaceful "
🌇 Ocean Sunset Views with Pool and Dock 🌇

Oceanfront Spanish Villa: 4 bed, loft, 8 guests

2.0 star property
10.0 out of 10, Exceptional, (1)
"Best house ever. Very friendly host and ready to please with any requests. The beds were top quality. The house is perfect for families, the kitchen is great to cook, they have games, fishing poles and is very clean. We have never seen such beautiful sunsets. Easy to get to from anywhere in the country. Marathon is a unique destination, great food, quaint and you don’t get tired of coming back every year. WE RECOMMEND THIS HOUSE."
Oceanfront Spanish Villa: 4 bed, loft, 8 guests

Oceanfront Sandy Beach Vacation Rental Unit 2

9.6 out of 10, Exceptional, (128)
"Thank you so much for sharing your beautiful apartment and view with us!!! Once we got there, could not get the box unlocked to grab the keys for almost 30! Minutes! Had to walk away and come back, got the key and WOW, what a view!!! The view is unbelievable! The apartment is just as advertised!! We had an awesome week and loved waking up on the beach!! The only other thing is the property to the south is a rental also!! They had so many coming and going for our whole week, and ALWAYS had there...
Oceanfront Sandy Beach Vacation Rental Unit 2

Beachfront Explorer!

Beachfront Explorer!

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1156)
"We had a great trip. The staff were great, food was good although a limited menu and no inside dining for dinner. The pool was great but several busy days not enough pool chairs. The rooms are not the ones depicted on the website but sufficient and clean. Would definately stay again. "
The price is ¥64,037
¥77,415 total
includes taxes & fees
Mar 2 - Mar 3
Skipjack Resort & Marina

Yacht Haven Marina

3.5 star property
9.8 out of 10, Exceptional, (113)
"Great experiance"
The price is ¥49,110
¥73,908 total
includes taxes & fees
Feb 24 - Feb 25
Yacht Haven Marina

Tropical Cottages

3.0 star property
8.4 out of 10, Very Good, (781)
"The tropical cottages was a spectacular place to stay. Online check in did not work well and the lady i dealt with when i arrived spoke zero English, although she did get me checked in and showed me to my cottage. The scenery outside the cottage was beautiful, and the cottage itself was inviting and comfortable. I would stay again in a heartbeat. "
The price is ¥31,197
¥35,097 total
includes taxes & fees
Mar 2 - Mar 3
Tropical Cottages

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (137)
"We thoroughly enjoyed our stay at the Aqua Lodge at Coconut Cay! The unit was very clean and included a nice size living room area along with a full refrigerator and stovetop. The sleeping space and bathroom were a little tight, but it was fine and expected in this type of rental. We enjoyed sitting on the deck off the back, and the pool and beach area were very enjoyable! It was very close to Sombrero Beach. The staff was very helpful with providing recommendations of places to visit. There was...
The price is ¥43,139
¥72,044 total
includes taxes & fees
Feb 27 - Feb 28
Aqua Lodge Rentals At Coconut Cay

Cabins at Bonefish Bay

3.0 star property
10.0 out of 10, Exceptional, (29)
"Property is well-maintained "
Cabins at Bonefish Bay

Aqua Lodges at 47th Street Gulfside

3.0 star property
8.4 out of 10, Very Good, (20)
"Had a wonderful time. So much to do in the area. We enjoyed the Cabana Club beach only a short drive away and included in the fee. We were there for the coldest week of the year. The maintenance gentleman, Scott and his assistant were kind enough to bring a hard to find space heater that kept us toasty warm as well a giving spot on recommendations for great places to eat. Some construction in the area but tolerable. Hope to return someday. "
The price is ¥28,077
¥50,245 total
includes taxes & fees
Mar 24 - Mar 25
Aqua Lodges at 47th Street Gulfside

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1090)
"The property was in a great location for us to take a day trip to Key West "
The price is ¥28,078
¥34,798 total
includes taxes & fees
Mar 12 - Mar 13
Knight's Key Suites

Sunshine Key RV Resort & Marina

2.0 star property
8.8 out of 10, Excellent, (143)
"We enjoyed the stay so much. Great pool area and very friendly staff!!"
Sunshine Key RV Resort & Marina

Beautiful Waterfront Home Perfect for Fishing.

9.4 out of 10, Exceptional, (100)
"Sleeps a lot of people, open floor plan, very nice and clean. I was very happy with our stay. "
Beautiful Waterfront Home Perfect for Fishing.

Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!

9.8 out of 10, Exceptional, (51)
"Convenient property. It had everything we needed. No issues at all. Would stay there again."
Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!

Fishing and Family Fun paradise Oceanfront 60'ft dock 3 bed 2bath private pool

10.0 out of 10, Exceptional, (22)
"This property was in a great location. The neighborhood was quiet and convenient to everything. The view was fabulous and we spent many hours on the covered patio. The home & beds were very comfortable and the owner was quick to respond to questions. We'll be back next year."
Fishing and Family Fun paradise Oceanfront 60'ft dock 3 bed 2bath private pool

CheCheboat

5.2 out of 10, (13)
"Nightmare, we were rented a houseboat that did not exist and explains that to your customer service was like talking to a brick wall. This is our last VRBO ever"
The price is ¥37,318
¥55,604 total
includes taxes & fees
Mar 1 - Mar 2
CheCheboat

Indigo Reef Resort Villas & Marina by KeysCaribbean

3.5 star property
9.2 out of 10, Wonderful, (49)
"The unit we stayed in was very clean, beds comfy. The unit itself is showing some wear and tear but that did NOT affect the cleanliness. The view of the ocean was why i chose to stay here and was not disappointed. The patios of each unit are fairly close and do not lend alot of privacy--not genetally a problem, unless the neighbors decide to get affectionate (if you know what I mean 😀) The pool was clean and offered plenty of seating. I would definitely stay here again."
Indigo Reef Resort Villas & Marina by KeysCaribbean

PERFECT OCEAN FRONT/PRIVATE ELEVATOR/DOCK/HEAT POOL. MARATHON LIC PLR2017-00465

9.4 out of 10, Exceptional, (44)
"Beautiful condo, nicely decorated. Elevator to use, has a roof top table and chairs to relax and get all the sun you need. Has a smaller pool but nice "
PERFECT OCEAN FRONT/PRIVATE ELEVATOR/DOCK/HEAT POOL. MARATHON LIC PLR2017-00465

Keys Waterfront Half-Duplex, Ocean side 37' Dock,

10.0 out of 10, Exceptional, (95)
"The rental was perfect for us. A couple in our 60's. We are laid back. The bed was very comfortable. We used the screen porch extensively as well as the patio. The view of the stars at night was amazing. Laz was very responsive. We had one minor issue and let Laz know and it was corrected within hours. We did not have a boat but it would have been a great place to have a boat. We will be back!"
Keys Waterfront Half-Duplex, Ocean side 37' Dock,

WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

9.6 out of 10, Exceptional, (76)
"Great and clean place to stay. Chris was the perfect host. "
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
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, (571)
"We were given very little information when we checked in. We were not told that a restaurant was available for dinner so we were too late to make a reservation that night. They advertise on the beach, but the beach is sand only, no water access. Just rocks like the coast of Maine. There is a definite lack of help in the restaurant in the morning. One guy running around trying to do everything. He was very pleasant. The whole resort needs a little TLC. If you want anything you must go to the...
The price is ¥31,197
¥41,814 total
includes taxes & fees
Feb 24 - Feb 25
Rainbow Bend Resort

Grassy Flats Resort & Beach Club

2.5 star property
9.4 out of 10, Exceptional, (236)
"Grassy Flats resort is a beautiful, private, secluded property. We felt so relaxed here. There is not much of a “beach” area but seeing the high and low tide reveal the “grassy flats” was so cool. There are beach chairs/lounge chairs everywhere (by pools and along ocean front) so you can post up wherever you want. The pool was awesome and shady. The restaurant The Rhum House was gorgeous and the food was excellent. The room was so beautifully decorated, and the balcony was wonderful. I would...
The price is ¥61,387
¥69,060 total
includes taxes & fees
Feb 24 - Feb 25
Grassy Flats Resort & Beach Club

Gulf View Waterfront Resort

2.5 star property
8.6 out of 10, Excellent, (418)
"Maria is very nice."
The price is ¥42,855
¥48,211 total
includes taxes & fees
Mar 2 - Mar 3
Gulf View Waterfront 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.