Grassy Key Vacation Rentals

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Our top choices for Grassy Key vacation rentals

Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (223 reviews)
"This was an amazing experience and would stay in a houseboat again! It was so clean, quaint and cozy. The deck off the back was beautiful and we can’t wait to return!!"
United States
Stephanie
$284 nightly
The price is $320
May 31 - Jun 1
Total with taxes and fees
Aqua Lodge Rentals At Coconut Cay

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.0 out of 10, Wonderful, (2 reviews)
"La propiedad me encantó se las recomiendo 100/100%"
United States
Marta
$189 nightly
The price is $212
May 26 - May 27
Total with taxes and fees
Caloosa Cove Resort by CoolVacay

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,196 reviews)
"Good value for money. Would definitely stay again "
Canada
Raghavan
$108 nightly
The price is $119
Jun 17 - Jun 18
Total with taxes and fees
Knight's Key Suites

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (976 reviews)
"Came here for our honeymoon, we absolutely loved it! Clean, the bar and food truck was perfect."
United States
Izabella
$125 nightly
The price is $141
May 31 - Jun 1
Total with taxes and fees
Tropical Cottages

Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access

Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access
Matecumbe
10.0 out of 10, Exceptional, (10 reviews)
"Old Florida vibe with modern, clean condos. Perfect location to visit the Keys. "
United States
Beckie F.
$268 nightly
The price is $298
May 27 - May 28
Total with taxes and fees
Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,266 reviews)
"Great hotel in the keys with a great pool and bar area rooms were spectacular, kitchenette and dining room table were great, fantastic getaway"
United States
Randall
$220 nightly
The price is $248
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, (2 reviews)
"The condo was beautifully decorated and furnished as well as being exceptionally clean."
United States
Rose P.
$367 nightly
The price is $405
May 26 - May 27
Total with taxes and fees
Marina View Escape with Pool, Tiki Bar & Marina

Coastal Studio Getaway – Second Floor with Partial Water Views

Coastal Studio Getaway – Second Floor with Partial Water Views
Matecumbe
9.6 out of 10, Exceptional, (7 reviews)
"laid back and comfortable. "
United States
Joe M.
$209 nightly
The price is $233
May 26 - May 27
Total with taxes and fees
Coastal Studio Getaway – Second Floor with Partial Water Views

Tide & Seek: Oceanview Studio Escape in Islamorada

Tide & Seek: Oceanview Studio Escape in Islamorada
Matecumbe
$209 nightly
The price is $233
May 27 - May 28
Total with taxes and fees
Tide & Seek: Oceanview Studio Escape in Islamorada

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
$415 nightly
The price is $458
May 25 - May 26
Total with taxes and fees
Brand New Marina Suite with Pool + Free Breakfast

Luxury Marina View Suite with Pool & Tiki Bar

Luxury Marina View Suite with Pool & Tiki Bar
Marathon
$389 nightly
The price is $430
May 27 - May 28
Total with taxes and fees
Luxury Marina View Suite with Pool & Tiki Bar

Waterfront Suite with Pool + Daily Housekeeping

Waterfront Suite with Pool + Daily Housekeeping
Marathon
$439 nightly
The price is $486
May 25 - May 26
Total with taxes and fees
Waterfront Suite with Pool + Daily Housekeeping

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)
"Had a great time and host was helpful."
United States
Ramesh Y.
$345 nightly
The price is $383
May 27 - May 28
Total with taxes and fees
Sombrero Beach Tropical Getaway in the Heart of Marathon

Waterfront Luxury Condo with Pool + Tiki Bar

Waterfront Luxury Condo with Pool + Tiki Bar
Marathon
9.4 out of 10, Exceptional, (22 reviews)
"It was a wonderful stay, little trouble with the WiFi but other than that great stay"
United States
Joshua A.
$380 nightly
The price is $422
May 25 - May 26
Total with taxes and fees
Waterfront Luxury Condo with Pool + Tiki Bar

Flip-Flops & Sunshine: Islamorada Studio Escape

Flip-Flops & Sunshine: Islamorada Studio Escape
Matecumbe
10.0 out of 10, Exceptional, (6 reviews)
"Very nice clean place. Pool amazing with great views of ocean"
United States
Dawn S.
$209 nightly
The price is $233
May 26 - May 27
Total with taxes and fees
Flip-Flops & Sunshine: Islamorada Studio Escape

Stay Beachside: Ground Floor Studio with Gorgeous Ocean Views

Stay Beachside: Ground Floor Studio with Gorgeous Ocean Views
Matecumbe
9.4 out of 10, Exceptional, (13 reviews)
"We had a great stay, not only is the property and an amazing place but the staff was most accommodating and exceptional. "
United States
DAVID Y.
$209 nightly
The price is $233
May 26 - May 27
Total with taxes and fees
Stay Beachside: Ground Floor Studio with Gorgeous Ocean Views

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
$511 nightly
The price is $568
Jun 12 - Jun 13
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
$931 nightly
The price is $1,033
May 30 - May 31
Total with taxes and fees
SOMBRERO BEACH LARGE 4/3 HOME w/ HEATED POOL, 40 ft BOAT DOCK, BEACH NEARBY

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.
$572 nightly
The price is $635
May 25 - May 26
Total with taxes and fees
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Tiny Villa, Big Ocean Views| Breathtaking Sunsets
Duck Key
10.0 out of 10, Exceptional, (16 reviews)
"Nice place, clean, relaxing, and well maintained, with great communication from the host. It was a wonderful and relaxing getaway with our family. They offer a military discount, which we truly appreciated. We all enjoyed our stay. We will definitely be back for a longer stay."
United States
Mario S.
$487 nightly
The price is $514
May 25 - May 26
Total with taxes and fees
Tiny Villa, Big Ocean Views| Breathtaking Sunsets
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 $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.