Holiday Rentals in Grassy Key

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Our top choices for Grassy Key holiday rentals

Two Bedroom ADA Suite at Grassy Flats Conch House

Two Bedroom ADA Suite at Grassy Flats Conch House
Marathon
10.0 out of 10, Exceptional, (1 review)
"Incredibly gracious owner and staff"
United States
Michael R.
Two Bedroom ADA Suite at Grassy Flats Conch House

Three Bedroom Suite at Grassy Flats Conch House

Three Bedroom Suite at Grassy Flats Conch House
Marathon
Three Bedroom Suite at Grassy Flats Conch House

Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (208 reviews)
"Room was clean, staff was friendly, view from deck was amazing, took the free kayaks out and saw a Manatee, convenient location. Great experience!"
United States
Wendy
Aqua Lodge Rentals At Coconut Cay

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (271 reviews)
"Very clean and great staff. "
United States
Barbara
Yacht Haven Marina

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,227 reviews)
"Beautiful location clean rooms friendly staff "
United States
Tiffany
Skipjack Resort & Marina

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,173 reviews)
"Very a nice place clean nice location good price"
United States
Pawel
The price is €213
includes taxes & fees
11 Mar - 12 Mar
Knight's Key Suites

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (933 reviews)
"Very cozy and clean!"
United States
JUSTIN
The price is €236
includes taxes & fees
4 Mar - 5 Mar
Tropical Cottages

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, (47 reviews)
"Clean property! Great views! Great communication with owner! Perfect location- close to marathon and key west! "
United States
candi b.
The price is €684
includes taxes & fees
9 Mar - 10 Mar
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

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

Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One
Matecumbe
9.0 out of 10, Wonderful, (2 reviews)
"I was disappointed with noise of highway as our building was right across the highway. Beach was also not accessible contrarily to what was said on property description."
Canada
wilma e.
Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One

Marina, Pool & Boats with Beautiful Harbor Views

Marina, Pool & Boats with Beautiful Harbor Views
Marathon
Marina, Pool & Boats with Beautiful Harbor Views

Marina View Suite w/ Pool, Tiki Bar & Boats

Marina View Suite w/ Pool, Tiki Bar & Boats
Marathon
Marina View Suite w/ Pool, Tiki Bar & Boats

Luxury Waterfront Suite w/ Marina, Pool, Tiki Bar

Luxury Waterfront Suite w/ Marina, Pool, Tiki Bar
Marathon
The price is €647
includes taxes & fees
23 Feb - 24 Feb
Luxury Waterfront Suite w/ Marina, Pool, Tiki Bar

Villa del Sol - Sunset Views, Kayaks, 2/2.5 - Slip Available/Ramp/Free Pkg

Villa del Sol - Sunset Views, Kayaks, 2/2.5 - Slip Available/Ramp/Free Pkg
Duck Key
10.0 out of 10, Exceptional, (2 reviews)
"What a great place to stay in the Key. W had a great time, my wife and two boys who are 20 and 23 lived the Villa. The boys lived the kayaks and we took advantage of walking to our deep sea fishing charter just across the road as well as swimming with the the dolphins at Dolphin a discovery both on Duck Key. Very clean. Beautiful views, great amenitis in the home, just wonderful. Also great to be in the middle of the keys to explore the whole area."
United States
Matt B.
The price is €658
includes taxes & fees
10 Mar - 11 Mar
Villa del Sol - Sunset Views, Kayaks, 2/2.5 - Slip Available/Ramp/Free Pkg

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 €684
includes taxes & fees
2 Mar - 3 Mar
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 €685
includes taxes & fees
3 Mar - 4 Mar
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

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.
The price is €687
includes taxes & fees
19 Mar - 20 Mar
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

Ocean View Two Duplex Penthouses / Retreat amenities: tennis court, heated Pool | Vista Key

Ocean View Two Duplex Penthouses / Retreat amenities: tennis court, heated Pool | Vista Key
Matecumbe
Ocean View Two Duplex Penthouses / Retreat amenities: tennis court, heated Pool | Vista Key

Beach, Pool, Marina & Tiki Bar - Summer Getaway!

Beach, Pool, Marina & Tiki Bar - Summer Getaway!
Marathon
9.8 out of 10, Exceptional, (25 reviews)
"Everything was perfect and as described. Located near all the things we wanted to do especially the rental of pontoon boat right on site. Condo was clean and had all the things we needed for a beach day! We enjoyed the pool and bar! Kate was wonderful. Will definitely stay again!! "
United States
Shell B.
The price is €579
includes taxes & fees
18 Feb - 19 Feb
Beach, Pool, Marina & Tiki Bar - Summer Getaway!

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

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
8.6 out of 10, Excellent, (11 reviews)
"Unit was very clean and had everything we needed"
United States
Vanessa L.
The price is €696
includes taxes & fees
10 Mar - 11 Mar
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

Charming 2-bedroom house in Marathon with pool

Charming 2-bedroom house in Marathon with pool
Marathon
8.0 out of 10, Very good, (2 reviews)
"Great Home & Location & Enjoyable Stay! Thanks!"
United States
James J.
The price is €735
includes taxes & fees
18 Mar - 19 Mar
Charming 2-bedroom house in Marathon with pool
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 €213 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.