Grassy Key Vacation Rentals

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Vacation Rentals in Grassy Key

Oceanfront Sandy Beach Vacation Rental Unit 1
Private beach
Oceanfront Sandy Beach Vacation Rental Unit 1
9.6 out of 10, Exceptional, (99)
"location is great. close enough to marathon for easy access to activities and restaurants, but far enough away to avoid heavy traffic and crowds. clean property. excellent communication with owner when needed. nice private beach on which to sit and relax or read or just bird watch. have already booked same property for christmas this year."
Oceanfront Sandy Beach Vacation Rental Unit 1
4 Keys To Paradise | 5 Bed, 3.5 Bath
A heated pool
4 Keys To Paradise | 5 Bed, 3.5 Bath
9.6 out of 10, Exceptional, (23)
"Fantastic location, beautiful view . Like a dream."
4 Keys To Paradise | 5 Bed, 3.5 Bath
Authentic And Charming Little Cottage 60 Ft From The Ocean
Pool
Authentic And Charming Little Cottage 60 Ft From The Ocean
9.8 out of 10, Exceptional, (169)
"Cottage was very clean and comfortable. Host was amazing and very accommodating! Private beach was a plus and relaxing. Love that this was adult only and non smoking property, which includes a gas grill. The location was central and great for day trips in both upper and lower keys. Would definitely book here on my next trip! We are not condo people so this was perfect! Quaint historic Florida style!"
Authentic And Charming Little Cottage 60 Ft From The Ocean
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Southern Diversion Estate-see our reduced rates
Property grounds
Southern Diversion Estate-see our reduced rates
10.0 out of 10, Exceptional, (82)
"We were celebrating my wife’s 40th birthday. There were 17 people in our group. Adults and children. Something for everyone to do. We enjoyed relaxing at the property by the pools, fishing from the dock, kayaking and paddle boarding. We went scuba diving with better than most scuba, deep sea fishing on the tail walker. We hired chef Heather for several dinners. It was an amazing trip."
Southern Diversion Estate-see our reduced rates
Gorgeous Getaway with a Lush Yard, Private Pool, & Free WiFi
A heated pool
Gorgeous Getaway with a Lush Yard, Private Pool, & Free WiFi
9.8 out of 10, Exceptional, (17)
"We had a wonder time. The house was spotless in a very nice quite location loved the iguana greeting us at the door over all very pleasant and will be booking again for next year if not sooner"
Gorgeous Getaway with a Lush Yard, Private Pool, & Free WiFi
Casa De La Playa Oceanfront the Key to the Beach and 3 kayaks included
On the beach
Casa De La Playa Oceanfront the Key to the Beach and 3 kayaks included
9.2 out of 10, Wonderful, (9)
"Great spot for families or larger groups. We celebrated my birthday with friends and family. Fantastic view, lots of amenities. Quiet but close enough to restaurants, bars, shopping, boating/fishing outings."
Casa De La Playa Oceanfront the Key to the Beach and 3 kayaks included
Skipjack Resort & Marina
Outdoor pool, sun loungers
Skipjack Resort & Marina
3.0 star property
8.6 out of 10, Excellent, (1098)
"Good hotel ! Rooms are in great condition "
The price is $229
$294 total
includes taxes & fees
Jun 3 - Jun 4
Skipjack Resort & Marina
Aqua Lodge Rentals At Coconut Cay
Front of property
Aqua Lodge Rentals At Coconut Cay
3.5 star property
9.6 out of 10, Exceptional, (104)
"Right on the water. Very neat place. "
The price is $145
$304 total
includes taxes & fees
Jun 4 - Jun 5
Aqua Lodge Rentals At Coconut Cay
Tropical Cottages
Superior Bungalow, Ensuite (Cottage 04) | Exterior
Tropical Cottages
3.0 star property
8.4 out of 10, Very Good, (690)
"Nice place with nice view. Accommodation are very clean . "
The price is $124
$140 total
includes taxes & fees
Jun 6 - Jun 7
Tropical Cottages
Yacht Haven Marina
Standard Bungalow | Living area | 42-inch Smart TV with digital channels, Netflix, Hulu
Yacht Haven Marina
3.5 star property
9.8 out of 10, Exceptional, (51)
"Everything was so clean, enjoyed the atmosphere of the Marina. The only issue was flooding on the only road to access the property, caused by a "freak" rainstorm. This was by no means the fault of property management. Publix, Winn Dixie and Walgreens are all in walking distance. "
The price is $180
$327 total
includes taxes & fees
Jun 20 - Jun 21
Yacht Haven Marina
Knight's Key Suites
Outdoor pool, sun loungers
Knight's Key Suites
3.0 star property
9.0 out of 10, Wonderful, (1031)
"The view of the water and east access to the 7-mile bridge"
The price is $119
$155 total
includes taxes & fees
Jun 3 - Jun 4
Knight's Key Suites
Sunshine Key RV Resort & Marina
Sundeck
Sunshine Key RV Resort & Marina
2.0 star property
8.8 out of 10, Excellent, (130)
"Nice place, very clean and quiet. The chair and sofa bed was peeling and the kitchen ledge is uneven so we almost fell."
Sunshine Key RV Resort & Marina
Cabins at Bonefish Bay
Exclusive Cabin | Living area | Flat-screen TV
Cabins at Bonefish Bay
3.0 star property
10.0 out of 10, Exceptional, (10)
"Cabin was very clean and nice. "
Cabins at Bonefish Bay
Life in Paradise w/ Boat Slip at #1 Rated Resort in Marathon - Coral Lagoon
Beach nearby
Life in Paradise w/ Boat Slip at #1 Rated Resort in Marathon - Coral Lagoon
10.0 out of 10, Exceptional, (191)
"We just wanted a short vacation getaway. It was great. We rented a boat and spent our time in the water. Great time with friends."
Life in Paradise w/ Boat Slip at #1 Rated Resort in Marathon - Coral Lagoon
Vibrant, waterfront retreat with WiFi, balcony & dock access
Beach
Vibrant, waterfront retreat with WiFi, balcony & dock access
8.6 out of 10, Excellent, (4)
"We saw manatees in the inlet, swam the pool morning and evening, and drove just a few minutes to Sombrero beach. We liked the attached Greek restaurant and boaters bar down the dock a bit."
Vibrant, waterfront retreat with WiFi, balcony & dock access
Beautiful Coral Lagoon #12 - Waterfront - Boat Slip & Heated Pool
A heated pool
Beautiful Coral Lagoon #12 - Waterfront - Boat Slip & Heated Pool
10.0 out of 10, Exceptional, (123)
"We were participating in the Underwater and shore cleanup. The property was better than online pics, extremely clean and everything was in perfect working order. Owners and property managers were easy to contact and prompt to respond"
Beautiful Coral Lagoon #12 - Waterfront - Boat Slip & Heated Pool
No Name Cottage- Close to everything you need in Marathon
Exterior
No Name Cottage- Close to everything you need in Marathon
10.0 out of 10, Exceptional, (14)
"The house was beautiful and everything we needed was right there. If I could have changed anything about the house, it would be to add a dresser in each bedroom. I'm not a live out of a suitcase kind of girl. So having a place to put my clothes that don't hang up would be nice. But, it had very large closets in each bedroom. Thank you for everything. God Bless! Teresa G."
No Name Cottage- Close to everything you need in Marathon
Lovely oceanfront home with dock, deck, patio, WiFi, W/D, & AC - great view
Property grounds
Lovely oceanfront home with dock, deck, patio, WiFi, W/D, & AC - great view
9.8 out of 10, Exceptional, (7)
"Everything was clean, questions were answered in a timely manner."
Lovely oceanfront home with dock, deck, patio, WiFi, W/D, & AC - great view
COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property
Terrace/patio
COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property
10.0 out of 10, Exceptional, (27)
"This house is roomy, clean, and located perfectly in Marathon for anywhere in the Keys you may want to travel to. The hot tub, pool, and grill were well used by us all, and communication with the host was immediate and friendly. We will stay there again on next trip to the Florida Keys."
COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property
Bumpa's Big House - Bring the Grandkids!
A heated pool
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!
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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 Vacation Rental Travel Info

Popular accommodation
Grassy Key private vacation homes
International airports
Miami, FL (MIA-Miami Intl.) and Key West, FL (EYW-Key West Intl.)

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

Rainbow Bend Resort
Signature Suite, 2 Bedrooms, Oceanfront | View from room
Rainbow Bend Resort
2.5 star property
8.2 out of 10, Very Good, (484)
"I realize I am a hard sell. The suite we were in was nice and well taken care of. Need to upgrade bath towels though. We were in the signature suite and when you were on the balcony all you could see was the lot next to Rainbow that was full of garbage. A 10-minute sweep could take care of that. Also, lots of "stuff" in the parking area that should be removed, i.e. boxes with things in them and an old boat. We enjoyed their breakfast. All-in-all it was a pleasant stay and we would go back...
The price is $139
$226 total
includes taxes & fees
Jun 3 - Jun 4
Rainbow Bend Resort
Gulf View Waterfront Resort
Exterior
Gulf View Waterfront Resort
2.5 star property
8.6 out of 10, Excellent, (292)
"The property was very nice. Great sunset. And the room was clean and comfortable. Checking in as late arrival was real easy. I wish we had more time to enjoy the all the property had to offer. Thank you guys!!! "
The price is $149
$168 total
includes taxes & fees
Jun 6 - Jun 7
Gulf View Waterfront Resort
Grassy Flats Resort & Beach Club
Exterior
Grassy Flats Resort & Beach Club
2.5 star property
9.4 out of 10, Exceptional, (166)
"We stayed at this hotel several times. It is very nice, It’s nice that they have a separate area for adults. They also have 3 in house places to eat, a tiki bar for lunch, a roof top for breakfast and bar in the evening and a restaurant for dinner (didn’t go to this one though). They include free paddle boards and kayaks. The rooms could have better A/C, they added another portable fan and seem to be having issues with A/C, hopefully will be resolved soon. Also they don’t have room service...
The price is $336
$378 total
includes taxes & fees
Jun 16 - Jun 17
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Grassy Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Grassy Key vacation 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 low season months. For more hustle and bustle, you may prefer to visit Grassy Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $119 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Grassy Key rentals

At Expedia, we put the best Grassy Key vacation 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 vacation.

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

Faro Blanco Resort & Yacht Club

Faro Blanco Resort & Yacht Club

5/5 Excellent
"Highly recommend. They are doing remodeling right now. I was worried about this but honestly it worked to our favor. Fewer guests, front door parking, extra attentive staff. Our room was recently remodeled and perfect for our family of four. Great location in marathon!"
A verified traveler stayed at Faro Blanco Resort & Yacht Club
Posted 18 hours ago
Faro Blanco Resort & Yacht Club