Grassy Key Vacation Rentals

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Vacation Rentals in Grassy Key

Pool
Authentic And Charming Little Cottage 60 Ft From The Ocean
9.8 out of 10, Exceptional, (168)
"Perfect stay, very peaceful !"
Authentic And Charming Little Cottage 60 Ft From The Ocean
A heated pool
Gorgeous Getaway with a Lush Yard, Private Pool, & Free WiFi
9.8 out of 10, Exceptional, (17)
"We had a wonder time. The house was spotless in a very nice quite location loved the iguana greeting us at the door over all very pleasant and will be booking again for next year if not sooner"
Gorgeous Getaway with a Lush Yard, Private Pool, & Free WiFi
Private beach
Oceanfront Sandy Beach Vacation Rental Unit 1
9.6 out of 10, Exceptional, (98)
"Was absolutely breath taking. Was a beautiful place to stay and was so homey. Highly recommended and hope to stay there again"
Oceanfront Sandy Beach Vacation Rental Unit 1
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A heated pool
4 Keys To Paradise | 5 Bed, 3.5 Bath
9.6 out of 10, Exceptional, (23)
"Fantastic location, beautiful view . Like a dream."
4 Keys To Paradise | 5 Bed, 3.5 Bath
Property grounds
Southern Diversion Estate-see our reduced rates
10.0 out of 10, Exceptional, (81)
"Our family takes an annual trip together, there were 17 of us this time. The property had something for everyone, best aspects are the sunsets and the infinity pool. The property manager was one of the best we've ever had- very responsive."
Southern Diversion Estate-see our reduced rates
On the beach
Casa De La Playa Oceanfront the Key to the Beach and 3 kayaks included
9.0 out of 10, Wonderful, (7)
"The house was beautiful and very accurately described. The beach was a disappointment. It was pretty impossible to even get anywhere with a kayak. I imagine it had to do with the timing (tides, etc). The bugs were brutal and I think the beach area breeds them. In our past vacations in the keys we have also been in neighborhoods where we could walk and take the babies for walks as well. That wasn't possible here so for us personally the location didn't meet our needs. The management was very...
Casa De La Playa Oceanfront the Key to the Beach and 3 kayaks included
Outdoor pool, sun loungers
Skipjack Resort & Marina
3.0 star property
8.6 out of 10, Excellent, (1092)
"Remodeled and very nice. Just wish our balcony overlooked the water and nit a torn up parking lot. Room was great and staff was very friendly. Breakfast was very good "
The price is CA $312
CA $400 total
includes taxes & fees
May 28 - May 29
Skipjack Resort & Marina
Front of property
Aqua Lodge Rentals At Coconut Cay
3.5 star property
9.6 out of 10, Exceptional, (103)
"highly recommended, very clean ,pace full and nice place "
The price is CA $221
CA $444 total
includes taxes & fees
May 27 - May 28
Aqua Lodge Rentals At Coconut Cay
Superior Bungalow, Ensuite (Cottage 04) | Exterior
Tropical Cottages
3.0 star property
8.4 out of 10, Very good, (684)
"Weather was prefect. There’s a lot of bugs and cottage 9 does NOT have a stove. Most street noise but nothing to loud "
The price is CA $162
CA $183 total
includes taxes & fees
Jun 11 - Jun 12
Tropical Cottages
Outdoor pool, sun loungers
Knight's Key Suites
3.0 star property
9.0 out of 10, Wonderful, (1028)
"Wonderful location, next to 7 miles bridge and a look out see restaurant. "
The price is CA $161
CA $210 total
includes taxes & fees
May 23 - May 24
Knight's Key Suites
Standard Bungalow | Living area
Yacht Haven Marina
3.5 star property
9.8 out of 10, Exceptional, (47)
"The house boat was beautiful, clean and the patio over looking the lagoon was very relaxing. There are manatees that visit too. :) The neighbors are very friendly, as is the staff. The kayaks and bicycles are included in the rental, which is fantastic. The location s very close to groceries and local parks. We took an airplane scenic ride which was the highlight of the trip. The small airport is only 3 miles away. We will come back to Yacth Haven !"
The price is CA $197
CA $392 total
includes taxes & fees
Jun 2 - Jun 3
Yacht Haven Marina
Sundeck
Sunshine Key RV Resort & Marina
2.0 star property
8.8 out of 10, Excellent, (130)
"Nice place, very clean and quiet. The chair and sofa bed was peeling and the kitchen ledge is uneven so we almost fell."
Sunshine Key RV Resort & Marina
Exclusive Cabin | Living area
Cabins at Bonefish Bay
3.0 star property
10.0 out of 10, Exceptional, (9)
"Our group arrived not knowing what to expect after a long days travel, as soon as we pulled into the office to get our keys we were amazed at quaint cabin that awaited us. It was super easy to get the keys after hours. The cabin itself was perfect!!!! Plenty of room for a group of 5. The towels provided were perfect for the relaxing pool area. Every thing we would need for cooking was already in the cabin. The rooms were clean and bright with natural wood. The area was quiet and very well...
Cabins at Bonefish Bay
A heated pool
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
8.8 out of 10, Excellent, (205)
"My wife and our friends wanted to come down and explore the Keys. So many other Vrbo options were so expensive but luckily we found this listing on Duck Key. It is basically in the middle of the Keys section off the highway and it provided such an easy way of exploring the various Keys without feeling like we were in the car the whole time. We loved unwinding in the personal pool on the patio after a nice day of exploring along with having some of the most beautiful sunrises and sunsets that we...
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
Beach nearby
Life in Paradise w/ Boat Slip at #1 Rated Resort in Marathon - Coral Lagoon
10.0 out of 10, Exceptional, (190)
"This was a great vacation for my daughter's 18 birthday with some friends and family. We saw manatees the first morning out back in the canal. There was always some type of animal in the very sheltered canal if you have a boat. We brought our pontoon boat and had a day of very bad weather. We never worried once because we could see the boat from the back porch (50 yards away) and the canal is very sheltered and nice. You have access to the ocean and the bay side as soon as you go around the...
Life in Paradise w/ Boat Slip at #1 Rated Resort in Marathon - Coral Lagoon
Terrace/patio
COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property
10.0 out of 10, Exceptional, (27)
"This house is roomy, clean, and located perfectly in Marathon for anywhere in the Keys you may want to travel to. The hot tub, pool, and grill were well used by us all, and communication with the host was immediate and friendly. We will stay there again on next trip to the Florida Keys."
COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property
Property grounds
Lovely oceanfront home with dock, deck, patio, WiFi, W/D, & AC - great view
9.8 out of 10, Exceptional, (6)
"Excellent"
Lovely oceanfront home with dock, deck, patio, WiFi, W/D, & AC - great view
Beach towels
Keys Vacation Price Drop! Book Now! New lower rates for Sep 5 - Nov 4, 2023
9.8 out of 10, Exceptional, (233)
"Great stay! As advertised!"
Keys Vacation Price Drop! Book Now! New lower rates for Sep 5 - Nov 4, 2023
TV
Private 2/2 half duplex | 2 Bed, 2 Bath
9.4 out of 10, Exceptional, (8)
"Nice home"
Private 2/2 half duplex | 2 Bed, 2 Bath
Exterior
No Name Cottage- Close to everything you need in Marathon
10.0 out of 10, Exceptional, (14)
"The house was beautiful and everything we needed was right there. If I could have changed anything about the house, it would be to add a dresser in each bedroom. I'm not a live out of a suitcase kind of girl. So having a place to put my clothes that don't hang up would be nice. But, it had very large closets in each bedroom. Thank you for everything. God Bless! Teresa G."
No Name Cottage- Close to everything you need in Marathon
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See all available properties in Grassy 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.

Grassy Key Vacation Rental Travel Info

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

Signature Suite, 2 Bedrooms, Oceanfront | View from room
Rainbow Bend Resort
2.5 star property
8.2 out of 10, Very good, (479)
"Breakfast was good "
The price is CA $190
CA $268 total
includes taxes & fees
May 27 - May 28
Rainbow Bend Resort
Exterior
Gulf View Waterfront Resort
2.5 star property
8.6 out of 10, Excellent, (288)
"This place is a hidden gem"
The price is CA $203
CA $228 total
includes taxes & fees
May 28 - May 29
Gulf View Waterfront Resort
Exterior
Grassy Flats Resort & Beach Club
2.5 star property
9.4 out of 10, Exceptional, (162)
"IF you are looking for hotel with the beach...look for the other resorts. The resort is very well kept but the beach is smelly and you can't enjoy your balcony or swimming pool because of horrible smell. Sorry...but people should now."
The price is CA $417
CA $470 total
includes taxes & fees
May 29 - May 30
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Grassy Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Recent reviews of Grassy Key properties
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