Search Holiday Rentals in Grassy Key

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Grassy Key holiday rentals

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (326 reviews)
"We love the accommodations and ability to cook with a full kitchen."
United States
Cheryl
The price is £232
includes taxes & fees
22 Jun - 23 Jun
Yacht Haven Marina

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,271 reviews)
The price is £171
includes taxes & fees
6 Jul - 7 Jul
Skipjack Resort & 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 £269
includes taxes & fees
28 Jun - 29 Jun
Aqua Lodge Rentals At Coconut Cay

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,204 reviews)
"Great view of the 7 mile bridge, great restaurant close by"
United States
Eric
The price is £97
includes taxes & fees
15 Jul - 16 Jul
Knight's Key Suites

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.6 out of 10, Exceptional, (5 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 £164
includes taxes & fees
23 Jun - 24 Jun
Caloosa Cove Resort by CoolVacay

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 £110
includes taxes & fees
7 Jul - 8 Jul
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 £173
includes taxes & fees
29 Jun - 30 Jun
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Boot Key Harbor Retreat with Pool & Breakfast

Boot Key Harbor Retreat with Pool & Breakfast
Marathon
10.0 out of 10, Exceptional, (2 reviews)
"The condo was beautifully decorated and furnished as well as being exceptionally clean."
United States
Rose P.
Boot Key Harbor Retreat with Pool & 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 £312
includes taxes & fees
19 Jul - 20 Jul
Sombrero Beach Tropical Getaway in the Heart of Marathon

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 £192
includes taxes & fees
25 Jun - 26 Jun
Flip-Flops & Sunshine: Islamorada Studio Escape

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 £349
includes taxes & fees
23 Jun - 24 Jun
Marina View Getaway with Pool & Free Breakfast

Tropical Oasis on Sombrero Beach in the Heart of Marathon FL

Tropical Oasis on Sombrero Beach in the Heart of Marathon FL
Marathon
9.6 out of 10, Exceptional, (9 reviews)
"Great"
United States
John M.
The price is £294
includes taxes & fees
29 Jun - 30 Jun
Tropical Oasis on Sombrero Beach in the Heart of Marathon FL

Waterfront Suite with Pool, Tiki Bar & Marina

Waterfront Suite with Pool, Tiki Bar & Marina
Marathon
The price is £312
includes taxes & fees
23 Jun - 24 Jun
Waterfront Suite with Pool, Tiki Bar & Marina

Island Time Starts Here: Cozy Ground Floor Suite in Islamorada

Island Time Starts Here: Cozy Ground Floor Suite in Islamorada
Matecumbe
8.0 out of 10, Very good, (2 reviews)
"We had a wonderful stay. Beautiful view. Enjoyed the pool. Staff was very friendly and helpful. Everything was VERY CLEAN!!! Thank you very much!"
United States
Lu D.
The price is £266
includes taxes & fees
25 Jun - 26 Jun
Island Time Starts Here: Cozy Ground Floor Suite in Islamorada

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 £192
includes taxes & fees
22 Jun - 23 Jun
Coastal Studio Getaway – Second Floor with Partial Water Views

Tide & Seek: Oceanview Studio Escape in Islamorada

Tide & Seek: Oceanview Studio Escape in Islamorada
Matecumbe
The price is £192
includes taxes & fees
22 Jun - 23 Jun
Tide & Seek: Oceanview Studio Escape in Islamorada

Resort Suite with Marina Views, Pool & Free Breakfast

Resort Suite with Marina Views, Pool & Free Breakfast
Marathon
The price is £329
includes taxes & fees
22 Jun - 23 Jun
Resort Suite with Marina Views, Pool & Free Breakfast

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)
"No staff but the unit was beautiful and clean. "
United States
Ferdinando
The price is £443
includes taxes & fees
23 Jun - 24 Jun
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA

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 £460
includes taxes & fees
21 Jun - 22 Jun
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

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
The price is £341
includes taxes & fees
21 Jun - 22 Jun
Canal Front Retreat with Pool + Free Breakfast
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.
Save an average of 15% on thousands of hotels when you're signed in

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 £97 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. 

Explore a world of travel with Expedia