Grassy Key Vacation Rentals

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Vacation Rentals in Grassy Key

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
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
Oceanfront Sandy Beach Vacation Rental Unit 1
Private beach
Oceanfront Sandy Beach Vacation Rental Unit 1
9.4 out of 10, Exceptional, (100)
"First of all...the very first picture online is not the property. I'm not sure where it is but it is not this property. The property is right on the ocean and is a nice beach but does have lots of grass in the water. The bedroom picture, the picture with pelicans on the dock are also not this property. The owner is not very communicative. There was supposed to be an inspection while we were there and I left him a message about it. No answer from owner, no text or any kind of communication. The...
Oceanfront Sandy Beach Vacation Rental Unit 1
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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
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
Skipjack Resort & Marina
Outdoor pool, sun loungers
Skipjack Resort & Marina
3.0 star property
8.6 out of 10, Excellent, (1100)
"Good hotel ! Rooms are in great condition "
The price is $229
$294 total
includes taxes & fees
Jun 16 - Jun 17
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, (106)
" Very cool and very clean place. We saw a dolphin one morning off the back, a jelly fish and a huge manatee another day. A/C was great and place was furnished with all the essentials. Our only complaint was the shower, very poor water pressure and drained slowly as well. Other than that we enjoyed our stay for something different than a standard hotel. Would stay here again "
The price is $197
$369 total
includes taxes & fees
Jun 18 - Jun 19
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, (692)
"Property was great. Place was very nice and well kept. Great overall value for the area. I only have two complaints. First, the parking was extremely tight for my truck to get in and out of and there was a large lizard that had expired under the couch. Others than that I’d happily stay at this property again. "
The price is $129
$145 total
includes taxes & fees
Jun 20 - Jun 21
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, (52)
"House boat on the water"
The price is $169
$316 total
includes taxes & fees
Jun 28 - Jun 29
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, (1033)
"The view of the water and east access to the 7-mile bridge"
The price is $115
$151 total
includes taxes & fees
Jun 16 - Jun 17
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
Gulf views w/scenic elevated sundeck, heated shared pool, boat dock availability
Pool | Outdoor pool, a heated pool
Gulf views w/scenic elevated sundeck, heated shared pool, boat dock availability
9.0 out of 10, Wonderful, (87)
"We really enjoy staying at this property. House is clean, great location and neighborhood. Highly recommend this rental! Until next year, Joe!!"
Gulf views w/scenic elevated sundeck, heated shared pool, boat dock availability
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
On the beach
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
9.6 out of 10, Exceptional, (72)
"Very nice"
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
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
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!
Manatee Bay: Serene 2-Story Villa on Duck Key, Private Patio, DIP Pool & Mesmerizing Water Views!
Terrace/patio
Manatee Bay: Serene 2-Story Villa on Duck Key, Private Patio, DIP Pool & Mesmerizing Water Views!
9.8 out of 10, Exceptional, (16)
"The unit was clean and had everything we needed. The dip pool is anything but. The size of a a small hot tub without the bubbles and heat. Not really worth advertising. Additionally, there is a beautiful boardwalk out back but, you can’t get to it. It’s all boarded up and not accessible. We did really enjoy Duck Key as it’s centrally located in the Keys and the grounds are really nice and well maintained."
Manatee Bay: Serene 2-Story Villa on Duck Key, Private Patio, DIP Pool & Mesmerizing Water Views!
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
A heated pool
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
8.8 out of 10, Excellent, (210)
"The townhouse was very clean inside and outside, especially the pool. The boys had fun fishing right outside the canal that leads into the bay. There are some great mangrove snappers to catch and eat. Overall the place was small, but we made it work. The only negative thing I have to say is that I wish there was a squidgy to help remove some of the water in the patio area. Due to the kids splashing in the pool, the patio collected a lot of water."
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
Beach nearby, sun loungers, beach towels
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
10.0 out of 10, Exceptional, (181)
"We found your place on Vrbo and It was fantastic! The place we stayed was everything we needed. Relaxing , beautiful the view was beautiful and the beach is very nice and great chairs to relax, and take in the beauty! Micheal was amazing host and very helpful to help with ideas where to eat, get groceries, and just so Grateful he alllowed us to stay and enjoy 30 years. Loved just a short walk to sunset park to watch the beautiful view of sunset !!! If looking for a place to relax and enjoy a...
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
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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, (489)
"Free breackfast was the best."
The price is $139
$241 total
includes taxes & fees
Jun 16 - Jun 17
Rainbow Bend Resort
Gulf View Waterfront Resort
Exterior
Gulf View Waterfront Resort
2.5 star property
8.6 out of 10, Excellent, (301)
"Beautiful property and very friendly staff! "
The price is $152
$171 total
includes taxes & fees
Jun 17 - Jun 18
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, (169)
"Absolutely gorgeous, immaculate, clean and beautifully designed property with friendly, helpful staff. Rooms are well appointed, pool is lovely, beach and pier are fun. Restaurant on-site offers elevated dining. We’ll be back and recommend Grassy Flats to all our friends!"
The price is $285
$321 total
includes taxes & fees
Jul 8 - Jul 9
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 $115 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

Gulf View Waterfront Resort

Gulf View Waterfront Resort

5/5 Excellent
"Beautiful property and very friendly staff! "
A verified traveler stayed at Gulf View Waterfront Resort
Posted 1 day ago
Gulf View Waterfront Resort