Search Holiday Rentals in Grassy Key

Save an average of 15% on thousands of properties with Expedia Rewards

Become a member for free and get more than just a booking discount. Members also earn points towards their next trip.

Search over 2.9 million properties and 550 airlines worldwide.

Find properties with these dates

This weekend
Next weekend

Top Holiday Rentals in Grassy Key

Casa De La Playa Oceanfront the Key to the Beach and 3 kayaks included
9.0 out of 10, Wonderful, (6)
"We had a great time on our family vacation at Casa De La Playa. We especially enjoyed the pool, pool toys, kayaks, back porch, and tropical landscaping. We also enjoyed using the beach toys and beach tent at area beaches."
Casa De La Playa Oceanfront the Key to the Beach and 3 kayaks included
Gorgeous Getaway with a Lush Yard, Private Pool, & Free WiFi
9.8 out of 10, Exceptional, (16)
"Property very comfy. Beds were awesome. Pool was great."
Gorgeous Getaway with a Lush Yard, Private Pool, & Free WiFi
Oceanfront Sandy Beach Vacation Rental Unit 1
9.6 out of 10, Exceptional, (98)
"Was absolutely breath taking. Was a beautiful place to stay and was so homey. Highly recommended and hope to stay there again"
Oceanfront Sandy Beach Vacation Rental Unit 1
Save an average of 15% on thousands of hotels when you're signed in
Southern Diversion Estate-see our reduced rates
10.0 out of 10, Exceptional, (81)
"Our family takes an annual trip together, there were 17 of us this time. The property had something for everyone, best aspects are the sunsets and the infinity pool. The property manager was one of the best we've ever had- very responsive."
Southern Diversion Estate-see our reduced rates
Skipjack Resort & Marina
3.0 star property
8.6 out of 10, Excellent, (1083)
"Overall a nice place to stay. Clean and King bed very comfortable. 1BR very spacious with sink, microwave and fridge. Tiki bar service was extremely slow due to new wait staff. I didn't have any hot water in the shower at first and it was late so rather than wait to have it fixed the next day or change rooms, I found the hot water temp controller adjustment in the living area closet and turned it up from 37C (body temp) to 43C so my wife could actually shower. Most would never figure this out....
The price is £217
per night
5 May - 6 May
Skipjack Resort & Marina
Tropical Cottages
3.0 star property
8.4 out of 10, Very good, (674)
"I do recommend "
The price is £134
per night
2 May - 3 May
Tropical Cottages
Aqua Lodge Rentals At Coconut Cay
3.5 star property
9.6 out of 10, Exceptional, (101)
"Very clean, comfortable and relaxing. "
The price is £325
per night
20 May - 21 May
Aqua Lodge Rentals At Coconut Cay
Yacht Haven Marina
3.5 star property
9.8 out of 10, Exceptional, (40)
"Enjoyed coffee in the mornings on the porch facing the water. Had a great time. "
The price is £251
per night
16 May - 17 May
Yacht Haven Marina
Knight's Key Suites
3.0 star property
9.0 out of 10, Wonderful, (1023)
"The room was very clean and you are across a restaurant so don’t need to drive anywhere unless you want to."
The price is £142
per night
8 May - 9 May
Knight's Key Suites
Cabins at Bonefish Bay
3.0 star property
10.0 out of 10, Exceptional, (8)
"Had a great time! Loved having so much room. The rest of the property was great and the entire staff was so friendly!! Close to restaurants, but also quietly nestled off the main highway. Just a real gem! Wish we could've stayed longer!! Will absolutely stay here again!"
Cabins at Bonefish Bay
Two-story waterfront condo with patio, balconies & boating
9.0 out of 10, Wonderful, (86)
"The property was as listed! The check in process was easy and everything we needed was conveniently provided. The only issues we ran into were that we couldn’t get the tv’s to work properly. Otherwise it was the perfect place!"
Two-story waterfront condo with patio, balconies & boating
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
8.8 out of 10, Excellent, (204)
"My wife and our friends wanted to come down and explore the Keys. So many other Vrbo options were so expensive but luckily we found this listing on Duck Key. It is basically in the middle of the Keys section off the highway and it provided such an easy way of exploring the various Keys without feeling like we were in the car the whole time. We loved unwinding in the personal pool on the patio after a nice day of exploring along with having some of the most beautiful sunrises and sunsets that we...
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
Lovely oceanfront home with dock, deck, patio, WiFi, W/D, & AC - great view
9.8 out of 10, Exceptional, (6)
"Excellent"
Lovely oceanfront home with dock, deck, patio, WiFi, W/D, & AC - great view
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
10.0 out of 10, Exceptional, (180)
"Beautiful property, well maintained and perfect location. It’s quiet and peaceful but close to some great restaurants and activities. All the stress just melted away! Thank you, Michael, for being a wonderful host!"
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
P98 - 2698 Sombrero Blvd
9.8 out of 10, Exceptional, (8)
"We LOVED this home! Everything was spotless, looked new - just as pictured. The kitchen had everything you could need to cook. Each room had a bathroom and a TV. We were vacationing with our two little kids and the pool was perfect for them and we spent every minute out there enjoying the beautiful outdoors space. This is our 4th time renting in Marathon and this house was by far our favorite."
P98 - 2698 Sombrero Blvd
Ocean front with private beach and pool
9.8 out of 10, Exceptional, (34)
"Great view Quiet and private setting Beach good for walking, not for swimming Nice pool Condo attractive, comfortable beds, kitchen well supplied, all appliances worked"
Ocean front with private beach and pool
Life in Paradise w/ Boat Slip at #1 Rated Resort in Marathon - Coral Lagoon
10.0 out of 10, Exceptional, (189)
"This was a great vacation for my daughter's 18 birthday with some friends and family. We saw manatees the first morning out back in the canal. There was always some type of animal in the very sheltered canal if you have a boat. We brought our pontoon boat and had a day of very bad weather. We never worried once because we could see the boat from the back porch (50 yards away) and the canal is very sheltered and nice. You have access to the ocean and the bay side as soon as you go around the...
Life in Paradise w/ Boat Slip at #1 Rated Resort in Marathon - Coral Lagoon
Great Water Front 2 Story Townhouse
8.6 out of 10, Excellent, (27)
"The price was great, the property was nice. It was like a neighborhood of beautiful row houses. I would definitely stay in this resort area again and maybe one more night."
Great Water Front 2 Story Townhouse
Bumpa's Big House - Bring the Grandkids!
9.6 out of 10, Exceptional, (4)
"The property was just as listed. We had a great time and would stay again. Great ocean view"
Bumpa's Big House - Bring the Grandkids!
COZY COTTAGE WITH PRIVATE DIPPING POOL OVERLOOKING BLUE WATER LAGOON
9.6 out of 10, Exceptional, (60)
"Cute little townhouse, clean and well stocked. We live on the west coast of Florida, my daughter and her family were staying at Hawks Cay for 5 days. We decided to drive over and see them. The location was awesome for us, this townhome is on Hawks Cay property, we brought bikes which made it super convenient getting to and from the hotel. The yard is adorable, our dog enjoyed dropping & retrieving his toys from the spa/pool. We will definitely be back!"
COZY COTTAGE WITH PRIVATE DIPPING POOL OVERLOOKING BLUE WATER LAGOON
Don't see what you're looking for?
See all available properties in Grassy Key
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.

Grassy Key Holiday Rental Travel Info

Other types of properties in Grassy Key you may be interested in

Rainbow Bend Resort
2.5 star property
8.2 out of 10, Very good, (467)
"Great private and clean the staff was super nice food was good and fast"
The price is £193
per night
5 May - 6 May
Rainbow Bend Resort
Gulf View Waterfront Resort
2.5 star property
8.6 out of 10, Excellent, (277)
"Greeting from the staff was unfriendly , but the property was easy to find and had a nice bar and restaurant next to the resort also another bar ( Bongo’s) just up the road. The room was very noisy from the main road that runs through the island and we were bitten to death by the no see ‘ums so take a good insect repellent "
The price is £136
per night
7 May - 8 May
Gulf View Waterfront Resort
Grassy Flats Resort & Beach Club
2.5 star property
9.4 out of 10, Exceptional, (154)
"I thought the food was great. Even had Foursquare rum, in the bar. Staff was very friendly and helpful, offered many recommendations for beaches and jet ski options. Swim with the Dolphins, is 5 min drive. Only thing i wasnt a fan of, was the tide would go out around 4pm, until 9pm. Leaving a not so great smell during that time. Obviously nothing they can do,but was mot great. Whwn tide was in,was very nice. The pier is nice at night toi."
The price is £323
per night
6 May - 7 May
Grassy Flats Resort & Beach Club
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.

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 £134 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. 

Recent reviews of Grassy Key properties
Expedia verified reviews