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, (307 reviews)
"We love the accommodations and ability to cook with a full kitchen."
United States
Cheryl
The price is CA $179
CA $393 total
includes taxes & fees
Jun 2 - Jun 3
Yacht Haven Marina

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
The price is CA $126
CA $171 total
includes taxes & fees
Jun 1 - Jun 2
Knight's Key Suites

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (970 reviews)
"Came here for our honeymoon, we absolutely loved it! Clean, the bar and food truck was perfect."
United States
Izabella
The price is CA $176
CA $198 total
includes taxes & fees
May 26 - May 27
Tropical Cottages

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
The price is CA $272
CA $529 total
includes taxes & fees
May 18 - May 19
Aqua Lodge Rentals At Coconut Cay

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
The price is CA $248
CA $334 total
includes taxes & fees
Jun 2 - Jun 3
Skipjack Resort & Marina

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
The price is CA $322
CA $673 total
includes taxes & fees
May 12 - May 13
Brand New Marina Suite with Pool + Free Breakfast

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
The price is CA $191
CA $560 total
includes taxes & fees
May 12 - May 13
Canal Front Luxury Condo with Pool + Breakfast

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.
The price is CA $256
CA $589 total
includes taxes & fees
May 11 - May 12
Marina View Escape with Pool, Tiki Bar & Marina

Sombrero Beach Tropical Getaway in the Heart of Marathon

Sombrero Beach Tropical Getaway in the Heart of Marathon
Marathon
9.8 out of 10, Exceptional, (21 reviews)
"The location and nightly entertainment. "
United States
Robert H.
The price is CA $182
CA $492 total
includes taxes & fees
May 13 - May 14
Sombrero Beach Tropical Getaway in the Heart of Marathon

Luxury Marina View Suite with Pool & Tiki Bar

Luxury Marina View Suite with Pool & Tiki Bar
Marathon
The price is CA $295
CA $639 total
includes taxes & fees
May 11 - May 12
Luxury Marina View Suite with Pool & Tiki Bar

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.
The price is CA $382
CA $874 total
includes taxes & fees
May 12 - May 13
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

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, (52 reviews)
"It was a pleasant stay and the host was prompt when reaching out to him."
United States
Jill B.
The price is CA $382
CA $874 total
includes taxes & fees
May 11 - May 12
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.
The price is CA $382
CA $874 total
includes taxes & fees
May 11 - May 12
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA

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.
The price is CA $246
CA $746 total
includes taxes & fees
May 11 - May 12
Charming 3-bedroom house featuring a heated private pool.

Waterfront Suite with Pool + Daily Housekeeping

Waterfront Suite with Pool + Daily Housekeeping
Marathon
The price is CA $328
CA $680 total
includes taxes & fees
May 13 - May 14
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
The price is CA $251
CA $692 total
includes taxes & fees
May 18 - May 19
Seas the Keys Getaway with plunge pool/spa

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
The price is CA $382
CA $874 total
includes taxes & fees
May 11 - May 12
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.
The price is CA $382
CA $874 total
includes taxes & fees
May 11 - May 12
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.0 out of 10, Wonderful, (14 reviews)
"Everything was perfect. Great place to stay"
United States
Kirk r.
The price is CA $436
CA $944 total
includes taxes & fees
May 11 - May 12
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

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 traveller
The price is CA $408
CA $1,413 total
includes taxes & fees
May 30 - May 31
SOMBRERO BEACH LARGE 4/3 HOME w/ HEATED POOL, 40 ft BOAT DOCK, BEACH NEARBY
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Grassy Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.