Grassy Key Vacation Rentals

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Our top choices for Grassy Key vacation rentals

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (306 reviews)
"Fabulous place and location. Can not wait to go back"
United States
Dianne
$270 nightly
The price is $304
Jun 7 - Jun 8
Total with taxes and fees
Yacht Haven Marina

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (967 reviews)
"Great place nice people "
United States
Mark
$129 nightly
The price is $145
May 14 - May 15
Total with taxes and fees
Tropical Cottages

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,192 reviews)
"Ocean view from room balcony."
United States
Brian
$117 nightly
The price is $128
Jun 1 - Jun 2
Total with taxes and fees
Knight's Key Suites

Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (221 reviews)
"We had a wonderful vacation!"
United States
Yuanfen
$352 nightly
The price is $397
May 10 - May 11
Total with taxes and fees
Aqua Lodge Rentals At Coconut Cay

Brand New Marina Suite with Pool + Free Breakfast

Brand New Marina Suite with Pool + Free Breakfast
Marathon
10.0 out of 10, Exceptional, (1 review)
"Very clean and convenient to shops and restaurants "
United States
JOHN
$452 nightly
The price is $500
May 12 - May 13
Total with taxes and fees
Brand New Marina Suite with Pool + Free Breakfast

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,262 reviews)
"The staff was very nice, our room was spacious and comfortable, the area has lots to do"
United States
Carol
$221 nightly
The price is $249
May 31 - Jun 1
Total with taxes and fees
Skipjack Resort & Marina

Marina View Escape with Pool, Tiki Bar & Marina

Marina View Escape with Pool, Tiki Bar & Marina
Marathon
10.0 out of 10, Exceptional, (1 review)
"Great accommodations and best location in Marathon. Right at Skipjack Marina Resort where you can rent pontoon boats and the owner even let us know whenlive music was at the pool/tiki bar. Accommodations were extremely clean and beds were very comfortable. Saw wildlife right out the door in the water. Great spot and close to one of the very few beaches in the keys. We will be back! "
United States
victoria l.
$396 nightly
The price is $437
May 10 - May 11
Total with taxes and fees
Marina View Escape with Pool, Tiki Bar & Marina

Canal Front Luxury Condo with Pool + Breakfast

Canal Front Luxury Condo with Pool + Breakfast
Marathon
9.8 out of 10, Exceptional, (27 reviews)
"Super easy check in, great location in the Keys and very quiet in the room."
United States
Eric
$376 nightly
The price is $418
May 12 - May 13
Total with taxes and fees
Canal Front Luxury Condo with Pool + Breakfast

Luxury Marina View Suite with Pool & Tiki Bar

Luxury Marina View Suite with Pool & Tiki Bar
Marathon
$378 nightly
The price is $418
May 10 - May 11
Total with taxes and fees
Luxury Marina View Suite with Pool & Tiki Bar

Sombrero Beach Tropical Getaway in the Heart of Marathon

Sombrero Beach Tropical Getaway in the Heart of Marathon
Marathon
9.6 out of 10, Exceptional, (20 reviews)
"The location and nightly entertainment. "
United States
Robert H.
$322 nightly
The price is $358
May 13 - May 14
Total with taxes and fees
Sombrero Beach Tropical Getaway in the Heart of Marathon

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.6 out of 10, Exceptional, (51 reviews)
"It was a pleasant stay and the host was prompt when reaching out to him."
United States
Jill B.
$566 nightly
The price is $629
May 8 - May 9
Total with taxes and fees
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
10.0 out of 10, Exceptional, (6 reviews)
"Everything about the stay was nice. "
United States
Mario S.
$572 nightly
The price is $635
May 11 - May 12
Total with taxes and fees
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.4 out of 10, Exceptional, (21 reviews)
"Awesome place to stay"
United States
Takuma F.
$571 nightly
The price is $634
May 12 - May 13
Total with taxes and fees
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

Waterfront Suite with Pool + Daily Housekeeping

Waterfront Suite with Pool + Daily Housekeeping
Marathon
$438 nightly
The price is $485
May 8 - May 9
Total with taxes and fees
Waterfront Suite with Pool + Daily Housekeeping

Seas the Keys Getaway with plunge pool/spa

Seas the Keys Getaway with plunge pool/spa
Marathon
9.6 out of 10, Exceptional, (14 reviews)
"Great location, great accomodation, hot tub and patio in the back area was great for relaxing in the evenings."
United States
Justus
$441 nightly
The price is $490
May 21 - May 22
Total with taxes and fees
Seas the Keys Getaway with plunge pool/spa

SOMBRERO BEACH LARGE 4/3 HOME w/ HEATED POOL, 40 ft BOAT DOCK, BEACH NEARBY

SOMBRERO BEACH LARGE 4/3 HOME w/ HEATED POOL, 40 ft BOAT DOCK, BEACH NEARBY
Marathon
9.8 out of 10, Exceptional, (63 reviews)
"This was our second time staying in this house lots of room great location."
United States
Anonymous traveler
$906 nightly
The price is $1,008
May 30 - May 31
Total with taxes and fees
SOMBRERO BEACH LARGE 4/3 HOME w/ HEATED POOL, 40 ft BOAT DOCK, BEACH NEARBY

Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two

Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two
Matecumbe
10.0 out of 10, Exceptional, (1 review)
"Absolutely great location with a well stocked kitchen for making great meals in and plenty of space to relax after a fun day in the sun!"
United States
Lauren M.
$911 nightly
The price is $1,011
May 10 - May 11
Total with taxes and fees
Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two

Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA
Marathon
9.2 out of 10, Wonderful, (32 reviews)
"Wonderful experience, great views, clean rooms, great amount of space. Great price"
United States
Race
$572 nightly
The price is $635
May 11 - May 12
Total with taxes and fees
Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA
Duck Key
9.4 out of 10, Exceptional, (36 reviews)
"Perfect for our get away"
United States
Kelly H.
$572 nightly
The price is $635
May 11 - May 12
Total with taxes and fees
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

Charming 3-bedroom house featuring a heated private pool.

Charming 3-bedroom house featuring a heated private pool.
Duck Key
10.0 out of 10, Exceptional, (25 reviews)
"Left to go to key west decided to stay here on our drive back up because we enjoyed it so much!"
United States
Regan C.
$536 nightly
The price is $595
May 10 - May 11
Total with taxes and fees
Charming 3-bedroom house featuring a heated private pool.
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 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 $128 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.