Grassy Key Holiday Rentals

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Holiday Rentals in Grassy Key

Our top choices for Grassy Key holiday rentals

🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets

9.2 out of 10, Wonderful, (45)
"The property supported our needs to a “T”! We travel to the Keys annually and need a place that is on the water, has a dock, a pool, is clean, and has the necessary amenities. This place had all of that and had lots of wildlife in and out of the water. We will stay here again if available on our next visit to the Keys."
🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets

Yacht Haven Marina

3.5 star property
9.8 out of 10, Exceptional, (197)
"We loved our weekend stay here. "
Yacht Haven Marina

Cabins at Bonefish Bay

3.0 star property
9.8 out of 10, Exceptional, (62)
"We stayed in one of the aqua lodges, which is basically a houseboat on the water. It was well equipped and worked nicely for us."
Cabins at Bonefish Bay

Tropical Cottages

3.0 star property
8.6 out of 10, Excellent, (856)
"Wish check in was sooner but made out well, very quiet, personal parking, food truck near by and was all around a good stay"
The price is AU$138
includes taxes & fees
10 Sept - 11 Sept
Tropical Cottages

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1199)
"Great stay"
Skipjack Resort & Marina

Private Island ~Oceanfront-Fishing-Diving~ FL Keys

10.0 out of 10, Exceptional, (20)
"We had a great relaxing and quiet vacation with great views and daily visits by dolphins, turtles and resident iguanas. Great place to get away from it all."
Private Island ~Oceanfront-Fishing-Diving~ FL Keys

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1143)
"Nice roomy accommodations and helpful staff I would stay here again "
The price is AU$152
includes taxes & fees
8 Sept - 9 Sept
Knight's Key Suites

The Hammocks at Marathon

2.5 star property
9.0 out of 10, Wonderful, (98)
"Very nice and clean nice pool area nice tity bar an restant easy to get in and out good gym area"
The Hammocks at Marathon

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (179)
"Very very nice place"
Aqua Lodge Rentals At Coconut Cay

Aqua Lodges at 47th Street Gulfside

3.0 star property
8.6 out of 10, Excellent, (50)
"10/10 property and boat was clean. It was perfect for my family with 2 littles. "
Aqua Lodges at 47th Street Gulfside

Piece of Paradise located at Hawks Cay in Duck Key

9.4 out of 10, Exceptional, (3)
"Amazing place. "
Piece of Paradise located at Hawks Cay in Duck Key

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

10.0 out of 10, Exceptional, (33)
"We had a wonderful time watching marine life from the sea wall. Manatees cruised by daily!Part of the outdoor area is covered so if you need to get out of the sun it is perfect.The host communication was above and beyond too."
Fishing and Family Fun paradise Oceanfront 60'ft dock 3 bed 2bath private pool

Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool

9.4 out of 10, Exceptional, (72)
"Property was great for our group. 2 miles to grocery stores. Pool was great! Used the bikes and had a great time here. "
Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool

Waterfront home with dock, pool table & private pool - walk to Sombrero Beach

8.8 out of 10, Excellent, (29)
"So enjoyed our stay here with a couple friends. Place has everything you need, is immaculate, fantastic view, and so close to either the beach in one direction and grocery stores in the other. Also located in a very nice residential neighborhood. Plan on returning! Thanks for the lovely stay!! "
Waterfront home with dock, pool table & private pool - walk to Sombrero Beach

One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!

10.0 out of 10, Exceptional, (202)
"The property was very clean and tidy. We thoroughly enjoyed our stay. The neighborhood was very quiet yet conveniently located near restaurants and other attractions. Highly recommend."
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!

Water Front Condo in Duck Key. FREE WIFI! Overlooking the Gulf of Mexico.

9.6 out of 10, Exceptional, (57)
"Lovely location; lovely setting."
Water Front Condo in Duck Key. FREE WIFI! Overlooking the Gulf of Mexico.

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

9.2 out of 10, Wonderful, (84)
"Had a great time "
KA Beach, dock, Pool, Kitchen, Tennis, Hot Tub, tropical paradise

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

9.6 out of 10, Exceptional, (31)
"Nice property . Well kept. Good management "
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Bumpa's Big House - Bring the Grandkids!

10.0 out of 10, Exceptional, (27)
"House was perfect! Pool, hot tub, putting green, 3 full size fridges, HUGE laundry room!! SO much more!"
Bumpa's Big House - Bring the Grandkids!

Waterfront 2BR w/ Dock, Hot Tub & Easy Ocean Access – Boaters Welcome!

10.0 out of 10, Exceptional, (5)
"Wonderful place to stay for a vacation in the Marathon area of the Keys! Canal front location with lovely sunrises! Owner and property manager very responsive. Check in was simple. Nice kitchen to make some meals and comfy beds to get a good night’s sleep! "
Waterfront 2BR w/ Dock, Hot Tub & Easy Ocean Access – Boaters Welcome!
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.
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Top Grassy Key Hotel Reviews

Find out more about Grassy Key

Find out more about Grassy Key

Everything you need to know about Grassy Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Grassy Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Grassy Key holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Grassy Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Grassy Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Grassy Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Grassy Key holiday rentals we have selected for you start as low as AU$138 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Grassy Key rentals

At Expedia, we put the best Grassy Key holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Grassy Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Grassy Key holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Grassy Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.