Grassy Key Holiday Rentals

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Our top choices for Grassy Key holiday rentals

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (918 reviews)
"Decent stay, easy check in and contactless checkout. Very quiet and nice place! "
United States
Swastik
The price is NZ$308
includes taxes & fees
25 Jan - 26 Jan
Tropical Cottages

Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (207 reviews)
"A unique and interesting place to vacation. Relaxing yet close enough to things to do. I highly recommend the Aqua Loge rentals as a place to stay."
United States
Keith
Aqua Lodge Rentals At Coconut Cay

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (260 reviews)
"Great place. "
Canada
Elizabeth
Yacht Haven Marina

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,165 reviews)
"Nice shower and great location room was clean and comfortable"
United States
Bruce
The price is NZ$296
includes taxes & fees
25 Jan - 26 Jan
Knight's Key Suites

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,219 reviews)
"Beautiful location clean rooms friendly staff "
United States
Tiffany
Skipjack Resort & Marina

Tropical Oasis on Sombrero Beach in the Heart of Marathon FL

Tropical Oasis on Sombrero Beach in the Heart of Marathon FL
2.0 star property
Marathon
9.0 out of 10, Wonderful, (4 reviews)
"Unit was very clean and recently remodeled. The building was a little difficult to find in the dark at night, but I would definitely recommend staying here again."
United States
Nancy M.
Tropical Oasis on Sombrero Beach in the Heart of Marathon FL

Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA
Duck Key
10.0 out of 10, Exceptional, (1 review)
"The location was perfect, house was very clean, and the view was breathtaking. We will 100% return."
United States
Gina A.
The price is NZ$1,011
includes taxes & fees
26 Jan - 27 Jan
Villa 5008 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, (46 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$1,096
includes taxes & fees
25 Jan - 26 Jan
Villa 5053 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
9.2 out of 10, Wonderful, (20 reviews)
"Property was very nice, everything as expected based on listing. Very good place for families."
United States
Nicholas H.
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

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, (4 reviews)
"Everything about the stay was nice. "
United States
Mario S.
The price is NZ$1,078
includes taxes & fees
29 Jan - 30 Jan
Villa 5034 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, (32 reviews)
"A short weekend getaway was made perfect in this villa. The location is idyllic; especially the balcony overlooking the bay with a perfect sunset view. The home was well-appointed, simple yet all the necessities were covered. Communication with the property manager was excellent. Definitely will book again. "
United States
Natasha A.
The price is NZ$1,070
includes taxes & fees
27 Jan - 28 Jan
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

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, (30 reviews)
"Wonderful experience, great views, clean rooms, great amount of space. Great price"
United States
Race
The price is NZ$1,096
includes taxes & fees
25 Jan - 26 Jan
Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA

Waterfront Fun: Pool, Marina, Tiki Bar & Beach!

Waterfront Fun: Pool, Marina, Tiki Bar & Beach!
Marathon
9.6 out of 10, Exceptional, (18 reviews)
"It was a wonderful stay, little trouble with the WiFi but other than that great stay"
United States
Joshua A.
Waterfront Fun: Pool, Marina, Tiki Bar & Beach!

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

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
8.4 out of 10, Very good, (10 reviews)
"Unit was very clean and had everything we needed"
United States
Vanessa L.
The price is NZ$1,087
includes taxes & fees
29 Jan - 30 Jan
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Tiny Villa, Big Ocean Views| Breathtaking Sunsets
Duck Key
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful views. Very nice accommodations. Wonderfull location!"
United States
michael h.
The price is NZ$1,054
includes taxes & fees
27 Jan - 28 Jan
Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available

Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available
Duck Key
The price is NZ$1,854
includes taxes & fees
26 Jan - 27 Jan
Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available

Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun

Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun
Duck Key
10.0 out of 10, Exceptional, (13 reviews)
"We enjoyed our stay here! It was perfect for a family of 4!"
United States
Amy S.
The price is NZ$1,312
includes taxes & fees
27 Jan - 28 Jan
Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun

Blue Waters Stay - 2/2.5 Villa - OS Slip/Ramp/Pkg

Blue Waters Stay - 2/2.5 Villa - OS Slip/Ramp/Pkg
2.0 star property
Duck Key
The price is NZ$1,159
includes taxes & fees
4 Feb - 5 Feb
Blue Waters Stay - 2/2.5 Villa - OS Slip/Ramp/Pkg

Charming 3-bedroom house featuring a heated private pool.

Charming 3-bedroom house featuring a heated private pool.
Duck Key
10.0 out of 10, Exceptional, (4 reviews)
"Left to go to key west decided to stay here on our drive back up because we enjoyed it so much!"
United States
Regan C.
The price is NZ$1,104
includes taxes & fees
23 Jan - 24 Jan
Charming 3-bedroom house featuring a heated private pool.

Beach House - Kayak 2-2.5 Villa - OS Slip Ramp Pkg

Beach House - Kayak 2-2.5 Villa - OS Slip Ramp Pkg
Duck Key
9.8 out of 10, Exceptional, (28 reviews)
"Great location for day trips and very clean, well stocked apartment. "
United States
Phil V.
The price is NZ$1,174
includes taxes & fees
1 Feb - 2 Feb
Beach House - Kayak 2-2.5 Villa - OS Slip Ramp Pkg
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$308 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.