Grassy Key Vacation Rentals

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Our top choices for Grassy Key vacation rentals

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.8 out of 10, Exceptional, (6 reviews)
"Easy check in if you come After business hours. Kayaks and sport equipment available. Has a small beach which is unique to the Keys. Pool pretty much vacant at all times. Great views. Highly recommend."
United States
Dana
The price is CA $445
CA $549 total
includes taxes & fees
Jul 6 - Jul 7
Caloosa Cove Resort by CoolVacay

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,206 reviews)
"Great view of the 7 mile bridge, great restaurant close by"
United States
Eric
The price is CA $132
CA $179 total
includes taxes & fees
Jul 15 - Jul 16
Knight's Key Suites

Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (225 reviews)
"Cleanness relaxing location, nice views, good air conditioning"
United States
Hakan
The price is CA $191
CA $436 total
includes taxes & fees
Jul 6 - Jul 7
Aqua Lodge Rentals At Coconut Cay

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (328 reviews)
"We love the accommodations and ability to cook with a full kitchen."
United States
Cheryl
The price is CA $185
CA $407 total
includes taxes & fees
Jul 20 - Jul 21
Yacht Haven Marina

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,274 reviews)
"I love the staff, really helping me when we need The place is excellent location, the bungalow was in pristine condition, and the area outside was wonderful"
United States
Ysabel
The price is CA $235
CA $321 total
includes taxes & fees
Jun 28 - Jun 29
Skipjack Resort & Marina

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (981 reviews)
"It was a very enjoyable stay, highly recommend."
United States
Andrea
The price is CA $183
CA $206 total
includes taxes & fees
Jun 29 - Jun 30
Tropical Cottages

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.2 out of 10, Wonderful, (140 reviews)
"This was the perfect place, right on the ocean and a full kitchen so you can cook your own meals. The room was very clean, I loved that they had a laundry basket and laundry detergent in the room for you, came in handy seeing as we stayed for 7 days. Amazing place to watch the sunset from a hammock and we got lucky enough to see some nurse sharks at the docks right outside of our hotel."
United States
Andrew Jackson
The price is CA $254
CA $326 total
includes taxes & fees
Jun 28 - Jun 29
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access

Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access
Matecumbe
10.0 out of 10, Exceptional, (10 reviews)
"Old Florida vibe with modern, clean condos. Perfect location to visit the Keys. "
United States
Beckie F.
Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access

Coastal Studio Getaway – Second Floor with Partial Water Views

Coastal Studio Getaway – Second Floor with Partial Water Views
Matecumbe
9.6 out of 10, Exceptional, (7 reviews)
"laid back and comfortable. "
United States
Joe M.
The price is CA $270
CA $397 total
includes taxes & fees
Jun 29 - Jun 30
Coastal Studio Getaway – Second Floor with Partial Water Views

Florida Keys Getaway w/ Stunning Ocean Views

Florida Keys Getaway w/ Stunning Ocean Views
4.0 star property
Long Key
The price is CA $765
CA $1,491 total
includes taxes & fees
Jun 28 - Jun 29
Florida Keys Getaway w/ Stunning Ocean Views

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.6 out of 10, Exceptional, (53 reviews)
"Very nice villa "
United States
Grace L.
The price is CA $402
CA $914 total
includes taxes & fees
Jun 28 - Jun 29
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Florida Keys Getaway w/ Stunning Ocean Views

Florida Keys Getaway w/ Stunning Ocean Views
Layton
8.8 out of 10, Excellent, (18 reviews)
"Beautiful location"
United States
Aaron M.
The price is CA $685
CA $1,501 total
includes taxes & fees
Jun 28 - Jun 29
Florida Keys Getaway w/ Stunning Ocean Views

Marina View Getaway with Pool & Free Breakfast

Marina View Getaway with Pool & Free Breakfast
Marathon
10.0 out of 10, Exceptional, (1 review)
"Very clean and convenient to shops and restaurants "
United States
JOHN
The price is CA $304
CA $661 total
includes taxes & fees
Jun 29 - Jun 30
Marina View Getaway with Pool & Free Breakfast

Sombrero Beach Tropical Getaway in the Heart of Marathon

Sombrero Beach Tropical Getaway in the Heart of Marathon
Marathon
9.8 out of 10, Exceptional, (22 reviews)
"Loved this place, fun atmosphere! Can’t wait to come back.. "
United States
jeff l.
The price is CA $257
CA $596 total
includes taxes & fees
Jul 13 - Jul 14
Sombrero Beach Tropical Getaway in the Heart of Marathon

Second Floor Den Suite – Sunny Islamorada Escape, Pool, Beach, Marina, Sleeps 6

Second Floor Den Suite – Sunny Islamorada Escape, Pool, Beach, Marina, Sleeps 6
Matecumbe
The price is CA $466
CA $644 total
includes taxes & fees
Jul 6 - Jul 7
Second Floor Den Suite – Sunny Islamorada Escape, Pool, Beach, Marina, Sleeps 6

Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.4 out of 10, Exceptional, (23 reviews)
"Awesome place to stay"
United States
Takuma F.
The price is CA $417
CA $934 total
includes taxes & fees
Jun 29 - Jun 30
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA
Marathon
9.2 out of 10, Wonderful, (32 reviews)
"Great stay. I love being on the boardwalk. "
United States
Rachael C.
The price is CA $348
CA $842 total
includes taxes & fees
Jun 25 - Jun 26
Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA
Duck Key
9.4 out of 10, Exceptional, (36 reviews)
"Great location great views! "
United States
Stephen M.
The price is CA $367
CA $865 total
includes taxes & fees
Jun 25 - Jun 26
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.0 out of 10, Wonderful, (15 reviews)
"Everything was perfect. Great place to stay"
United States
Kirk r.
The price is CA $375
CA $876 total
includes taxes & fees
Jun 25 - Jun 26
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!

Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!
Marathon
10.0 out of 10, Exceptional, (163 reviews)
"We traveled for a wedding with a fairly large group of family members. The property was beautiful, clean and well kept. I can’t say enough about Meredith - she responded quickly to any questions and even helped us out when our flights were cancelled due to the snowstorm in NY! Will definitely be going back again. Highly recommend."
United States
Eileen H.
The price is CA $733
CA $1,775 total
includes taxes & fees
Jun 28 - Jun 29
Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!
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

Everything you need to know about Grassy Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Grassy Key vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Grassy Key vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Grassy Key vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Grassy Key vacation rentals we have selected for you start as low as CA $179 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Grassy Key rentals

At Expedia, we put the best Grassy Key vacation 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 vacation.

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. 

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