Grassy Key Vacation Rentals from $108: Search Short-Term Rentals

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Our top choices for Grassy Key vacation rentals

A pool area with lounge chairs and a view of the ocean.

1. 🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets

Marathon

Becky F.

$1,112 nightly

Nov 7 - Nov 8

Total with taxes and fees

An outdoor seating area with wicker furniture and cushions, a thatched-roof structure, and lush greenery.

2. Tropical Cottages

Marathon

Aaron

$99 nightly

Oct 22 - Oct 23

Total with taxes and fees

A nighttime pool area with a clear view of the pool, surrounding palm trees, and a building with a sign.

3. Skipjack Resort & Marina

Marathon

Justin

$173 nightly

Oct 22 - Oct 23

Total with taxes and fees

A spacious living area with a gray sectional sofa, wooden beams, and a ceiling fan.

4. Aqua Lodge Rentals At Coconut Cay

Marathon

Susan

$227 nightly

Oct 26 - Oct 27

Total with taxes and fees

A hotel room with two beds, each with a wooden headboard, white bedding, and a bedside table with a lamp.

5. Knight's Key Suites

Marathon

Brandy

$98 nightly

Oct 27 - Oct 28

Total with taxes and fees

A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

6. Yacht Haven Marina

Marathon

Lauren

$244 nightly

Oct 26 - Oct 27

Total with taxes and fees

A covered outdoor patio with a table and chairs, a ceiling fan, and a view of trees and a white building.

7. Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA

Duck Key

william d.

$446 nightly

Oct 26 - Oct 27

Total with taxes and fees

8. Seas the Keys Getaway with plunge pool/spa

Marathon

Gina W.

$432 nightly

Oct 22 - Oct 23

Total with taxes and fees

A covered outdoor area with a ceiling fan, a view of the sea, and a distant building.

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

Duck Key

Jorge D.

$446 nightly

Oct 22 - Oct 23

Total with taxes and fees

10. Aqua Lodges at 47th Street Gulfside

Marathon

Lauren

$244 nightly

Oct 22 - Oct 23

Total with taxes and fees

A resort with a pool, lounge chairs, and a view of the ocean.

11. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Marathon

Arianna

$204 nightly

Oct 28 - Oct 29

Total with taxes and fees

A dining area with a round glass table, white chairs, and a chandelier. There is a sofa and a window with blinds in the background.

12. Waterfront Retreat

Duck Key

"We had an amazing stay and couldn't have asked for a better place to spend the week in the Keys! The home was exactly as described—clean, comfortable, and in a beautiful location. We especially loved relaxing outside and taking in the gorgeous views. It truly felt like a home away from home.The host was wonderful, responsive, and made everything easy from check-in to check-out. We made so many great memories here and would absolutely stay again. Highly recommend this property to anyone looking...

Katie B.

$465 nightly

Oct 24 - Oct 25

Total with taxes and fees

A spacious living room with a gray sofa, a wooden coffee table, and a TV on a wooden cabinet.

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

Duck Key

Takuma F.

$478 nightly

Oct 28 - Oct 29

Total with taxes and fees

A covered outdoor seating area with a table and chairs, overlooking a body of water and a beach.

14. Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA

Duck Key

Gina A.

$500 nightly

Oct 23 - Oct 24

Total with taxes and fees

A spacious living area with a sliding glass door leading to a deck, a sofa, a coffee table, and a kitchen area with wooden cabinets and appliances.

15. Charming 3-bedroom house featuring a heated private pool.

Duck Key

lissa h.

$586 nightly

Oct 23 - Oct 24

Total with taxes and fees

A poolside area with sun loungers and umbrellas, palm trees, and a clear blue sky.

16. Resort Condo with Marina Views, Pool, Tiki, Breakfast

Marathon

Heather K.

$341 nightly

Oct 24 - Oct 25

Total with taxes and fees

A round table set for two with a view of the ocean and palm trees.

17. Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Duck Key

Stephanie

$466 nightly

Oct 22 - Oct 23

Total with taxes and fees

A living room with a sofa, two armchairs, a coffee table, and a ceiling fan. There is a large window with a view of the beach and a patio area with outdoor furniture.

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

Duck Key

Kirk r.

$467 nightly

Oct 22 - Oct 23

Total with taxes and fees

A coastal resort with multiple buildings, a marina, and clear blue waters.

19. Villa 4204 on Duck Key Boat Slip Available - 3BD 2BA

Marathon

Kelsey S.

$662 nightly

Oct 22 - Oct 23

Total with taxes and fees

A poolside area with lounge chairs and umbrellas, a pool, and palm trees.

20. Marina View Escape with Pool, Tiki & Breakfast

Marathon

Jennifer W.

$344 nightly

Oct 25 - Oct 26

Total with taxes and fees

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Top Grassy Key Hotel Reviews

Rainbow Bend Resort

10/10 Excellent

"Room size excellent.Kitchen large with everything I needed.Bedroom large with plenty of drawer space.Complimentary breakfast large and great quality.Treated with dignity and respect by staff."

Coconut Cay Resort & Marina

10/10 Excellent

"We stayed here for one night during our visit to Marathon in the Florida Keys. The location was nice enough and convenient for exploring the area. Our room was situated at the front of the property, so there was quite a lot of road and car park noise, although this was somewhat expected given the location. It did feel as though the front window was open, despite being closed, as it did very little to block out the outside noise. On the positive side, the room was incredibly spacious, with a lovely large TV and a super comfortable bed. The shower was great, and the amenities provided were good. Ice and drinks were also available from reception, which was handy. The reception staff were exceptionally friendly and welcoming. The air conditioning worked overtime but didn’t seem to cool the room particularly well and was rather noisy itself. However, this was more of a minor observation than a complaint. The only real disappointment was the cleanliness of the floor. After showering, the floor became slightly wet, and walking around barefoot left the bottoms of my feet noticeably dirty, which was a shame. Overall, a perfectly reasonable place to stay for a night in Marathon. A few minor improvements would make a difference, but we had a comfortable stay, and the friendly staff were certainly a highlight."

Captain Pips Marina & Hideaway

10/10 Excellent

"Just the right compromise between price, location, amenities, room. The "full" kitchen was great but could have used more lighting. A good amount of space in the suite. We checked out the free bikes to ride the Old 7 Mile Bridge to Pigeon Key for snorkeling. The bikes were dated but acceptable (esp. for free). Although we could have spent more (or less) money, Pip's was a good choice."

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 $108 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.

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Check prices for these dates

Our top choices for Grassy Key vacation rentals

1. 🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets

2. Tropical Cottages

3. Skipjack Resort & Marina

4. Aqua Lodge Rentals At Coconut Cay

5. Knight's Key Suites

6. Yacht Haven Marina

7. Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA

8. Seas the Keys Getaway with plunge pool/spa

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

10. Aqua Lodges at 47th Street Gulfside

11. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

12. Waterfront Retreat

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

14. Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA

15. Charming 3-bedroom house featuring a heated private pool.

16. Resort Condo with Marina Views, Pool, Tiki, Breakfast

17. Tiny Villa, Big Ocean Views| Breathtaking Sunsets

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

19. Villa 4204 on Duck Key Boat Slip Available - 3BD 2BA

20. Marina View Escape with Pool, Tiki & Breakfast

Find vacation rentals that suit your style

Top Grassy Key Hotel Reviews

Rainbow Bend Resort

Find out more about Grassy Key

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