Grassy Key Holiday Rentals

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Holiday Rentals in Grassy Key

MILLION DOLLAR VIEW very private 4 bedroom resort with pool, pier, kayaks, spa

Marathon
10.0 out of 10, Exceptional, (30)
"Was everything we hoped it would be and more!"
United States
Michael R.
MILLION DOLLAR VIEW very private 4 bedroom resort with pool, pier, kayaks, spa

Beach House🌴Waterfront, Private Pool, Boat Dock on Gulf with Amazing Sunsets!☀️

Marathon
10.0 out of 10, Exceptional, (123)
"Wonderful home! Planning on staying again."
United States
Susan S.
Beach House🌴Waterfront, Private Pool, Boat Dock on Gulf with Amazing Sunsets!☀️

Beachfront Explorer!

Marathon
10.0 out of 10, Exceptional, (1)
"Great stay for 3 fisherman. Very nice RV park with pool. Rv close to Shower and Bath house. Very comfortable. "
United States
Dan M.
Beachfront Explorer!

Waterfront Marathon Keys Escape • Pool, Dock & Comfort for 10 Guests

Marathon
Waterfront Marathon Keys Escape • Pool, Dock & Comfort for 10 Guests

Wide Horizon oceanfront. 4 bedroom, 4 ½ bath, kayaks, pool + observation deck.

Marathon
10.0 out of 10, Exceptional, (32)
"Beautiful, spacious property - had a relaxing time"
United States
Brenda S.
Wide Horizon oceanfront. 4 bedroom, 4 ½ bath, kayaks, pool + observation deck.

P58 - Gulf Front Luxury 4 bedroom 4 bath with private pool and deep water dockage?

Marathon
9.6 out of 10, Exceptional, (55)
"We had an amazing time at this beautiful home!! We had a party of eight - my husband & me, our 3 teens (ages 17 & 18), & 3 additional teens (ages 18 & 19). There was plenty of space - all of the beds were very comfortable, the kitchen was adequately stocked to meet all of our needs, & the bathrooms were wonderful. We loved the location and spent most of our week in Marathon or Big Pine, but did take off to Key West twice. It was a fantastic vacation and we cried actual tears when it was time to...
United States
Lisa G.
P58 - Gulf Front Luxury 4 bedroom 4 bath with private pool and deep water dockage?

Gorgeous, updated, waterfront, pet friendly, home w/ pool, dock & kayaks

Marathon
9.6 out of 10, Exceptional, (77)
"Amazing view and pier. Great pool and outdoor area and inside is very updated and open. Guest services were very responsive."
United States
Anthony A.
Gorgeous, updated, waterfront, pet friendly, home w/ pool, dock & kayaks

Yacht Haven Marina

3.5 star property
Marathon
9.8 out of 10, Exceptional, (231)
"Nice Lodge nice area close to grocery store & shops, will love to stay there again."
United States
Xiomeidy
Yacht Haven Marina

Skipjack Resort & Marina

3.0 star property
Marathon
8.6 out of 10, Excellent, (1213)
"Stayed just one night but have a great experience. The staff nice and helpful. Room was clean and comfy and spacious. "
United States
Esther
Skipjack Resort & Marina

Tropical Cottages

3.0 star property
Marathon
8.6 out of 10, Excellent, (907)
"Beautiful place, conveniently located "
United States
Clifton
The price is NZ$185
includes taxes & fees
8 Dec - 9 Dec
Tropical Cottages

Knight's Key Suites

3.0 star property
Marathon
9.0 out of 10, Wonderful, (1155)
"Room were clean and staff was very helpful "
United States
Leonard
The price is NZ$210
includes taxes & fees
8 Dec - 9 Dec
Knight's Key Suites

Aqua Lodge Rentals At Coconut Cay

3.5 star property
Marathon
9.6 out of 10, Exceptional, (196)
"Clean room, spacious, nice and quiet. "
United States
Douglas
Aqua Lodge Rentals At Coconut Cay

Cabins at Bonefish Bay

3.0 star property
Marathon
9.6 out of 10, Exceptional, (81)
"The staff were very nice. The place was clean. We stayed in aqua 2, the view wasn’t great but by no means bad. Just be prepared for the noseeums, they could ruin your trip!"
United States
Shanna
Cabins at Bonefish Bay

The Hammocks at Marathon

2.5 star property
Marathon
9.0 out of 10, Wonderful, (113)
"It was my first time staying there but it won’t be my last."
United States
Dennis
The Hammocks at Marathon

Waterfront home with dock, pool table & private pool - walk to Sombrero Beach

Marathon
8.8 out of 10, Excellent, (33)
"We loved the pool area. The home was very well appointed. Great location, near the beach and shopping."
United States
Tania K.
Waterfront home with dock, pool table & private pool - walk to Sombrero Beach

TF Pool Beach Kitchen Sleep 6, Hot Tub W&D Marina WiFi Parking

Marathon
9.4 out of 10, Exceptional, (121)
"Quiet and friendly "
United States
Damon J.
TF Pool Beach Kitchen Sleep 6, Hot Tub W&D Marina WiFi Parking

Marlin Bay Resort & Marina

4.0 star property
Marathon
Marlin Bay Resort & Marina

Piece of Paradise located at Hawks Cay in Duck Key

Duck Key
9.8 out of 10, Exceptional, (8)
"Amazing place. "
United States
Pilar G.
Piece of Paradise located at Hawks Cay in Duck Key

Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool

Marathon
9.4 out of 10, Exceptional, (75)
"My brother my son and three other friends stayed the first five days. Fish bonded had a great time everyone thought the accommodations were great. Second five days my son the rest of my family joined us eight adults for children. Accommodated all of us very well. Pool was great location was very good."
United States
Mike S.
Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool

Vacation with attitude!

Marathon
10.0 out of 10, Exceptional, (8)
"This is a nice house and location. I have been coming to the Keys for 20 years, multiple times a year, and this is one of my favorites. "
United States
Nick N.
Vacation with attitude!
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, 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$185 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.