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Holiday Rentals in Grassy Key

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Our top choices for Grassy Key holiday rentals

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (333 reviews)
"We love the accommodations and ability to cook with a full kitchen."
United States
Cheryl
The price is €236
includes taxes & fees
9 Jul - 10 Jul
Yacht Haven Marina

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 €256
includes taxes & fees
21 Jul - 22 Jul
Aqua Lodge Rentals At Coconut Cay

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (983 reviews)
"It was a very enjoyable stay, highly recommend."
United States
Andrea
The price is €119
includes taxes & fees
6 Jul - 7 Jul
Tropical Cottages

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,208 reviews)
"Great view of the 7 mile bridge, great restaurant close by"
United States
Eric
The price is €105
includes taxes & fees
5 Jul - 6 Jul
Knight's Key Suites

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 €296
includes taxes & fees
6 Jul - 7 Jul
Caloosa Cove Resort by CoolVacay

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,276 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 €213
includes taxes & fees
2 Aug - 3 Aug
Skipjack Resort & Marina

Waterfront Suite with Pool, Tiki Bar & Marina

Waterfront Suite with Pool, Tiki Bar & Marina
Marathon
The price is €377
includes taxes & fees
8 Jul - 9 Jul
Waterfront Suite with Pool, Tiki Bar & Marina

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 €228
includes taxes & fees
8 Jul - 9 Jul
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Canal Front Retreat with Pool + Free Breakfast

Canal Front Retreat with Pool + Free Breakfast
Marathon
9.8 out of 10, Exceptional, (27 reviews)
"Super easy check in, great location in the Keys and very quiet in the room."
United States
Eric
Canal Front Retreat with Pool + Free Breakfast

Waterfront Escape with Pool, Tiki, Breakfast & Marina

Waterfront Escape with Pool, Tiki, Breakfast & Marina
Marathon
10.0 out of 10, Exceptional, (1 review)
"This is a clean, stylish condo in a location close to everything we needed, including grocery stores, restaurants, and fun things to do. It's convenient, but also feels tucked back into a private area. We enjoyed having a waterfront view. It was also nice to have access to the Skipjack resort amenities including the poolside bar and a laundry room. The included breakfast at the resort is basic, but convenient, and the staff of the resort were very welcoming and helpful. Our favorite thing about...
United States
Julie P.
Waterfront Escape with Pool, Tiki, Breakfast & Marina

Flip-Flops & Sunshine: Islamorada Studio Escape

Flip-Flops & Sunshine: Islamorada Studio Escape
Matecumbe
10.0 out of 10, Exceptional, (6 reviews)
"Very nice clean place. Pool amazing with great views of ocean"
United States
Dawn S.
The price is €331
includes taxes & fees
6 Jul - 7 Jul
Flip-Flops & Sunshine: Islamorada Studio Escape

Tropical Oasis on Sombrero Beach in the Heart of Marathon FL

Tropical Oasis on Sombrero Beach in the Heart of Marathon FL
Marathon
9.8 out of 10, Exceptional, (11 reviews)
"Great little place. Very clean. Hot continental breakfast every day. 10/10 would go back again. Thank you! "
United States
Mandi P.
The price is €353
includes taxes & fees
3 Jul - 4 Jul
Tropical Oasis on Sombrero Beach in the Heart of Marathon FL

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 €569
includes taxes & fees
2 Aug - 3 Aug
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

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 €331
includes taxes & fees
14 Jul - 15 Jul
Coastal Studio Getaway – Second Floor with Partial Water Views

Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.8 out of 10, Exceptional, (7 reviews)
"Everything about the stay was nice. "
United States
Mario S.
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA

Tide & Seek: Oceanview Studio Escape in Islamorada

Tide & Seek: Oceanview Studio Escape in Islamorada
Matecumbe
The price is €331
includes taxes & fees
14 Jul - 15 Jul
Tide & Seek: Oceanview Studio Escape in Islamorada

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.
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 €613
includes taxes & fees
14 Jul - 15 Jul
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

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 €569
includes taxes & fees
1 Aug - 2 Aug
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Waterfront / Ocean Access Canal / Kamp Key / Homes

Waterfront / Ocean Access Canal / Kamp Key / Homes
Matecumbe
10.0 out of 10, Exceptional, (2 reviews)
"Excellent house. Very clean. We had a little trouble with the check in code and we were immediately contacted and the code was changed and we were in within minutes. The maintenance guy stopped by to make sure we got in and everything was good. EXCELLENT Customer Service!!!!!House was very well stocked with pots and pans and misc things needed for a week stay! Right on a nice little canal with plenty of room for our boat."
United States
Mike H.
The price is €1,023
includes taxes & fees
9 Jul - 10 Jul
Waterfront / Ocean Access Canal / Kamp Key / Homes
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 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, apart-hotels, 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 favorite 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 depends 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 €105 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 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. 

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