Grassy Key Holiday Rentals

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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, (297 reviews)
"great place great views"
United States
Matthew
The price is NZ$494
includes taxes & fees
13 May - 14 May
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, (220 reviews)
"Convenient location, clean and well maintained property. Fun experience being on a houseboat. "
United States
Brooke
The price is NZ$596
includes taxes & fees
6 May - 7 May
Aqua Lodge Rentals At Coconut Cay

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (956 reviews)
"Had a great time here. Towels were clean everyday, coffee was available at the bar at our convenience, check in was simple as well as the door lock, happy with our decision to stay here, This is our 2nd time here and we will be back again. "
United States
jennifer
The price is NZ$265
includes taxes & fees
3 May - 4 May
Tropical Cottages

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,185 reviews)
"Great accommodations, very clean and comfortable. The view of the 7 Mile Bridge was a great surprise. Location was perfect! "
United States
Cheryl
The price is NZ$265
includes taxes & fees
26 Apr - 27 Apr
Knight's Key Suites

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,252 reviews)
"The pool was ok. It was crowded for most of our stay. "
United States
Teresa
The price is NZ$417
includes taxes & fees
3 May - 4 May
Skipjack Resort & Marina

Brand New Marina View Suite – Pool and Tiki Bar

Brand New Marina View Suite – Pool and Tiki Bar
Marathon
10.0 out of 10, Exceptional, (1 review)
"Very clean and convenient to shops and restaurants "
United States
JOHN
The price is NZ$724
includes taxes & fees
16 Apr - 17 Apr
Brand New Marina View Suite – Pool and Tiki Bar

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, (51 reviews)
"Clean property! Great views! Great communication with owner! Perfect location- close to marathon and key west! "
United States
candi b.
The price is NZ$976
includes taxes & fees
16 Apr - 17 Apr
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Marina View Luxury Suite – Pool and Tiki Bar

Marina View Luxury Suite – Pool and Tiki Bar
Marathon
The price is NZ$767
includes taxes & fees
18 Apr - 19 Apr
Marina View Luxury Suite – Pool and Tiki Bar

Villa 5086 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5086 on Duck Key Boat Slip Available - 2BD 1.5BA
Duck Key
8.6 out of 10, Excellent, (27 reviews)
"Great location! We enjoyed our time there."
United States
Erin T.
The price is NZ$955
includes taxes & fees
16 Apr - 17 Apr
Villa 5086 on Duck Key Boat Slip Available - 2BD 1.5BA

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

Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
10.0 out of 10, Exceptional, (6 reviews)
"Everything about the stay was nice. "
United States
Mario S.
The price is NZ$976
includes taxes & fees
16 Apr - 17 Apr
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA

Marina View Escape – Pool, Tiki Bar and Boats

Marina View Escape – Pool, Tiki Bar and Boats
Marathon
The price is NZ$768
includes taxes & fees
16 Apr - 17 Apr
Marina View Escape – Pool, Tiki Bar and Boats

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, (35 reviews)
"Perfect for our get away"
United States
Kelly H.
The price is NZ$983
includes taxes & fees
22 Apr - 23 Apr
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

Sombrero Beach Tropical Getaway in the Heart of Marathon

Sombrero Beach Tropical Getaway in the Heart of Marathon
Marathon
9.6 out of 10, Exceptional, (17 reviews)
"We loved our stay! The condo was clean and super comfortable. The property was perfect. So nice to have a bar a restaurant right there. We would definitely stay again. "
United States
Jamie F.
The price is NZ$694
includes taxes & fees
6 May - 7 May
Sombrero Beach Tropical Getaway in the Heart of Marathon

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

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
8.8 out of 10, Excellent, (13 reviews)
"Unit was very clean and had everything we needed"
United States
Vanessa L.
The price is NZ$1,005
includes taxes & fees
22 Apr - 23 Apr
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

Waterfront Marina Suite – Pool, Tiki Bar and Views

Waterfront Marina Suite – Pool, Tiki Bar and Views
Marathon
The price is NZ$817
includes taxes & fees
20 Apr - 21 Apr
Waterfront Marina Suite – Pool, Tiki Bar and Views

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)
"Wonderful experience, great views, clean rooms, great amount of space. Great price"
United States
Race
The price is NZ$1,005
includes taxes & fees
21 Apr - 22 Apr
Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA

Waterfront Condo – Pool, Tiki Bar and Marina

Waterfront Condo – Pool, Tiki Bar and Marina
Marathon
9.8 out of 10, Exceptional, (26 reviews)
"Super easy check in, great location in the Keys and very quiet in the room."
United States
Eric
The price is NZ$749
includes taxes & fees
16 Apr - 17 Apr
Waterfront Condo – Pool, Tiki Bar and Marina

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, (162 reviews)
"Everything was as advertised. Meredith was so helpful and on it. Very well maintained and clean. "
United States
John J.
The price is NZ$1,880
includes taxes & fees
29 Apr - 30 Apr
Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!

Florida Keys Getaway w/ Stunning Ocean Views

Florida Keys Getaway w/ Stunning Ocean Views
4.0 star property
Long Key
The price is NZ$1,772
includes taxes & fees
14 May - 15 May
Florida Keys Getaway w/ Stunning Ocean Views

Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two

Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two
Matecumbe
10.0 out of 10, Exceptional, (1 review)
"Absolutely great location with a well stocked kitchen for making great meals in and plenty of space to relax after a fun day in the sun!"
United States
Lauren M.
The price is NZ$1,858
includes taxes & fees
10 May - 11 May
Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two
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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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 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 NZ$265 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.