Grassy Key Vacation Rentals from ￥22,508: Search Short-Term Rentals

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Vacation Rentals in Grassy Key

"Wow! We enjoyed this beautiful home and had everything we could possibly need. The house has more than you need and it is clean and the beds are very comfortable. All the furniture was comfortable and the outdoors are amazing. I can’t describe just how special this home feels. I would highly recommend."

"Best house ever. Very friendly host and ready to please with any requests. The beds were top quality. The house is perfect for families, the kitchen is great to cook, they have games, fishing poles and is very clean. We have never seen such beautiful sunsets. Easy to get to from anywhere in the country. Marathon is a unique destination, great food, quaint and you don’t get tired of coming back every year. WE RECOMMEND THIS HOUSE."

"Most an amazing place, with an amazing view. Frank was great to work with if had any questions or needs. We have been coming down to Marathon for 10 years and had one place we rented be sold, this was our first year at this location. So private, pool was amazing, kitchen had everything you need, all bedrooms had own bathroom, screen porch had unreal views. We will definitely be back next year and hopefully many years in the future. A little piece of heaven on earth."

"This is the first vacation for our three blended families. The house was just as the pictures indicated. We were able to kayak from the beach. The house was well stocked and cool when we arrived.we had a wonderful week. It is a great place to stay."

"Great property, loved the pool,screened porch, pier for fishing and just great views, Host was great. We locked ourselves out once and he sent somebody to resolve the issue in less than 10 minutes.Place is kind of "Old School"but it was right for us. Gives of a good classic Keys Vibe,"

"Overall a great property but needs a few updates. Would still recommend and return."

"We had a wonderful stay. The staff at the pool bar were amazing!!! Poli Kala!!!!"

￥56,251 total

includes taxes & fees

Mar 30 - Mar 31

42-inch Smart TV with digital channels, Netflix, Hulu

"Very friendly helpful and professional staff"

￥54,400 total

includes taxes & fees

Apr 7 - Apr 8

"This was an excellent choice. We arrived at 10 pm and the directions sent before checking in were perfect. Had absolutely no trouble and the grounds were very well taken care of. Super cute cottages and very comfortable."

￥26,886 total

includes taxes & fees

Mar 30 - Mar 31

Deluxe Cabin, Lagoon View | Private kitchen | Toaster

"Right next to the ocean at boat docking.. can feel the ocean breeze.. "

￥47,603 total

includes taxes & fees

Apr 26 - Apr 27

"Loved, loved our stay, so peaceful out on the back porch having our morning coffee. So clean and stocked with all the things you need. Perfect for two people or a couple and two small kids. The free bikes were great. We will definely be back again. Thank you "

￥57,411 total

includes taxes & fees

Apr 1 - Apr 2

"Great Location"

￥28,570 total

includes taxes & fees

Apr 7 - Apr 8

Family Cabin | Living area | Flat-screen TV

"The cabins were immaculately clean and very family friendly. The pool was still pretty cold but kept clean. The facility has bikes, kayaks, grills, pickleball and a dock to launch from. The property was very clean and quiet at night. Perfect little getaway!"

Deluxe Villa | Private kitchen | Full-size fridge, microwave, oven, stovetop

"Dated but very charming, clean, safe, quiet and private location. Parking is nice and easy! Pool is decent, although it would be nice if it stayed open a little later. The staff was very nice and accommodating (office hours are a bit limited). My only complaint is the water pressure is not great in the showers, but the water was nice and hot! Overall, it’s a great place to stay and would definitely stay there again. "

"We enjoyed the stay so much. Great pool area and very friendly staff!!"

"Everything in the listing was completely accurate. Halfway point in the Keys. The home was very clean. Air Conditioning was spot on. We used the pool/hottub a lot. Surprised how much we used the hot tub as almost every day it was clear and hot. Although it didn’t bother us, the home is located in the direct path of a variety of planes jets and helicopters landing at Airport nearby. Noise was quite loud and may scare some dogs. Our Morkie had no issues. Definitely would rent property...

"The location was easy to find. Very clean. Having the elevator was great for a family member that has difficulty with stairs. Would stay here again."

"My family (10 of us all together) stayed at this beautiful property and could not have been more pleased! It was spacious enough for all of us and close to all the things we wanted to do! Beth was super responsive anytime we reached out to her! The only thing I would note is that the house is in the DIRECT landing path for the airport down the road. It was a little startling when some of the jets were flying in. This is nothing against the house itself, just something to be aware of.We hope to...

"Highly recommend staying at this condo. "

"Beautiful outdoor patio, amazing pool, and a very well air conditioned house. We had a great week here, only thing we wished was different was the jacuzzi connected to the pool was the same temperature as the pool, other than that, fantastic host and property. "

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

Signature Suite, 2 Bedrooms, Oceanfront | View from room

"Check in was seamless and efficient. Great customer service. "

￥50,813 total

includes taxes & fees

Mar 30 - Mar 31

"Amazing place to stay, we stayed on the 2nd floor the third floor was a bit noisy. Beautiful view of the water, staff were helpful and nice. We really enjoyed our stay. "

￥40,412 total

includes taxes & fees

Mar 30 - Mar 31

"If you’re looking for a stress-free zone, this is it! Also, plenty of nearby services, restaurants, etc. "

￥44,397 total

includes taxes & fees

Mar 31 - Apr 1

Find out more about Grassy Key

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Recent reviews of Grassy Key properties

5/5 Excellent

"The staff was friendly and helpful, the room was clean and well kept as was the office. The mini 'fridge didn't get very cold even turned up full , but the drinks we stored there got to drinkable coolness. The only negative really wasn't a big deal, but it appeared that at some point someone had tried to pry thier way past the door's deadbolt as the door frame was damaged and unpainted on the outside edge of the frame. But, that's a minore quibble. Overall, our experience was great."

A verified traveler stayed at Coconut Cay Resort & Marina

Posted 14 hours ago

Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton

5/5 Excellent

"Beautiful property, great staff, very clean!! Restaurant was overpriced & not good service at all!! Only other complaint was you have to pay to park your car which is absolutely ridiculous as there is no reason to have your guests pay to use a parking lot that is pretty much empty, no security watching your vehicle either. You are a guest at their hotel and paying good money to already stay there and then you pay to park to just stupid - no reason for it but greed!"

A verified traveler stayed at Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton

Posted 4 days ago

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Grassy Key Vacation Rentals

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Vacation Rentals in Grassy Key

Waterfront Beauty 8-guests, Dock, Kayaks and more

Waterfront Beauty 8-guests, Dock, Kayaks and more

Oceanfront Spanish Villa: 4 bed, loft, 8 guests

Oceanfront Spanish Villa: 4 bed, loft, 8 guests

🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets

🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets

Casa De La Playa Oceanfront the Key to the Beach and 2 kayaks included

Casa De La Playa Oceanfront the Key to the Beach and 2 kayaks included

🌇 Ocean Sunset Views with Pool and Dock 🌇

🌇 Ocean Sunset Views with Pool and Dock 🌇

Breeze On Inn: A Waterfront Retreat with 2 Bedrooms 2 bathrooms and Dockage

Breeze On Inn: A Waterfront Retreat with 2 Bedrooms 2 bathrooms and Dockage

Skipjack Resort & Marina

Skipjack Resort & Marina

Yacht Haven Marina

Yacht Haven Marina

Tropical Cottages

Tropical Cottages

Aqua Lodges at 47th Street Gulfside

Aqua Lodges at 47th Street Gulfside

Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay

Knight's Key Suites

Knight's Key Suites

Cabins at Bonefish Bay

Cabins at Bonefish Bay

The Reef at Marathon, Florida Keys

The Reef at Marathon, Florida Keys

Sunshine Key RV Resort & Marina

Sunshine Key RV Resort & Marina

COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property

COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property

PERFECT OCEAN FRONT/PRIVATE ELEVATOR/DOCK/HEAT POOL. MARATHON LIC PLR2017-00465

PERFECT OCEAN FRONT/PRIVATE ELEVATOR/DOCK/HEAT POOL. MARATHON LIC PLR2017-00465

2499 Rental Rate ANY WEEK March-Aug 2025 fees and taxes add, except holidays

2499 Rental Rate ANY WEEK March-Aug 2025 fees and taxes add, except holidays

Coral Lagoon #13: Pool, Water Views, Both Gulf & Atlantic Access via Vaca Cut

Coral Lagoon #13: Pool, Water Views, Both Gulf & Atlantic Access via Vaca Cut

Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!

Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!

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

Rainbow Bend Resort

Rainbow Bend Resort

Gulf View Waterfront Resort

Gulf View Waterfront Resort

Grassy Flats Resort & Beach Club

Grassy Flats Resort & Beach Club

Find out more about Grassy Key

Find out more about Grassy Key

Recent reviews of Grassy Key properties

Recent reviews of Grassy Key properties

Coconut Cay Resort & Marina

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Expedia's Latest Trends