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Featured Villas in Grassy Key

DUPLEX IN DUCK KEY 3/2 W/90' Private Dock, Trailer Storage included

10.0 out of 10, Exceptional, (180)
" I was quite surprised with the property. The screened in back porch was a nice touch.As well as your own tiki bar by the pool The floor plan to the house is nice and open. Plenty of towels and even beach towels for the pool. I will stay there again if I get a chance."
DUPLEX IN DUCK KEY 3/2 W/90' Private Dock, Trailer Storage included

Villa 5027 on Duck Key BOAT SLIP available

9.6 out of 10, Exceptional, (46)
"Great location for our family.We love the Keys. Beautiful sunsets from balconies."
The price is AU$1,115
includes taxes & fees
3 Feb - 4 Feb
Villa 5027 on Duck Key BOAT SLIP available

Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!

9.6 out of 10, Exceptional, (49)
"Clean condo. Rooms are smaller than it appeared on the web site. beds very comfortable. Did not like that could not use resort ammenities. Plunge pool was useless. If it was a hot tub it would really add to the exerience!!"
Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!

DUPLEX IN DUCK KEY, 2 Bedroom /2 Bath w/40' Dock, Trailer Storage Incl.

10.0 out of 10, Exceptional, (156)
"Duck Key is amazing and this house has water and sunset views! Clean house, well appointed, and a great backyard area with a hot tub. "
DUPLEX IN DUCK KEY, 2 Bedroom /2 Bath w/40' Dock, Trailer Storage Incl.

DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage

10.0 out of 10, Exceptional, (141)
"Great outdoor area, enjoyed the heated pool, the tiki hut sitting area. The canal was a nice view. We all enjoyed the property very much."
DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage

Isla Marlin 28: Palm lined luxury villa w/dockage and sunset views

9.8 out of 10, Exceptional, (9)
"Lovely home. Great location for boating and convenient to dining and shopping. Pet friendly unit in a pet friendly community. "
Isla Marlin 28: Palm lined luxury villa w/dockage and sunset views

Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - Boat Slip Avail

10.0 out of 10, Exceptional, (197)
"Thank you we enjoyed our time at your peaceful, beautiful place"
Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - Boat Slip Avail

Sombrero Beach Villa with Private Pool and Dock

10.0 out of 10, Exceptional, (117)
"We really enjoyed our stay at this property. It’s perfect for a large family and the location was perfect. "
Sombrero Beach Villa with Private Pool and Dock

✦Unwind on your Oceanedge villa on Seapalm island✦

9.6 out of 10, Exceptional, (29)
"Beautiful home, pool, patios and view. House was truly equipped with everything you need for a stress free stay- right down to bathrobes in the master bathroom,every small appliance in the kitchen and wonderful coffee station. "
The price is AU$4,564
includes taxes & fees
8 Feb - 9 Feb
✦Unwind on your Oceanedge villa on Seapalm island✦

Relax by Sombrero Beach 21 mins away at our 2-bedroom Marathon Villa

9.6 out of 10, Exceptional, (67)
"Had a great time."
Relax by Sombrero Beach 21 mins away at our 2-bedroom Marathon Villa

Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC

8.8 out of 10, Excellent, (222)
"Wonderful well appointed villa save no ice cube trays in freezer. National support was rude and of no help."
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC

Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer

8.8 out of 10, Excellent, (45)
"Was what we were looking for. Not super fancy, but comfortable, and right next to the water, which is what we wanted. Central location for us to visit different keys during our stay. Wish they had bikes but they did have other things. Used the kitchen and washer/dryer!"
Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer

Brand New Single Family 5/5 -90ft dock, pool, paddle boards, bicycles plus more!

10.0 out of 10, Exceptional, (23)
"This property has everything you need to enjoy your stay in Marathon. It is close to restaurants and grocery stores, and you can walk to Sombrero beach daily. The heated/chilled pool welcomes you anytime, day or night. The bedrooms and ensuites provide fantastic privacy for everyone. The pool area is private and inviting, and set up for lounging and relaxation. Dennis, the property manager is super accommodating, responsive and helpful. We've been to several FLA VRBO's and this property is top...
Brand New Single Family 5/5 -90ft dock, pool, paddle boards, bicycles plus more!

203 Sombrero- 4 Bedroom/3 Bath Attached Villa w/ Private Boat Dock

8.8 out of 10, Excellent, (101)
"Enjoyed our time in Marathon. George was very responsive and helpful during our stay"
203 Sombrero- 4 Bedroom/3 Bath Attached Villa w/ Private Boat Dock

Bayside Home w/Shared Pool, Rooftop Terrace, Free WiFi, Gas Grill, and Views

9.0 out of 10, Wonderful, (89)
"Relaxing location to soak up some Florida sun. Property was clean and as described. Nice amenities, laundry, grill, access to pool and pier/doc."
Bayside Home w/Shared Pool, Rooftop Terrace, Free WiFi, Gas Grill, and Views

Villa 5087 on Duck Key BOAT SLIP available

9.4 out of 10, Exceptional, (14)
"We had a lovely weekend at Frank’s place for a birthday getaway. The unit was clean, comfortable and exactly as described. Frank is a wonderful host! Really helpful and friendly. We look forward to coming back! "
The price is AU$1,176
includes taxes & fees
4 Feb - 5 Feb
Villa 5087 on Duck Key BOAT SLIP available

Villa 5034 on Duck Key Boat Slip available

10.0 out of 10, Exceptional, (1)
"The Villa was perfect for our vacation. Beautiful sunsets every night. Frank was very responsive to our questions. Would stay again"
The price is AU$1,176
includes taxes & fees
3 Feb - 4 Feb
Villa 5034 on Duck Key Boat Slip available

Villa 5028 on Duck Key BOAT SLIP available

9.4 out of 10, Exceptional, (3)
"Great location on the water with beautiful sunset views. Plenty of room for our group. "
The price is AU$1,113
includes taxes & fees
13 Feb - 14 Feb
Villa 5028 on Duck Key BOAT SLIP available

New Listing: Waterfront Home w/ Private Heated Pool, Dock, Bikes, Kayak, Paddleboards... and so much more!!

9.8 out of 10, Exceptional, (6)
"This rental is absolutely beautiful and clean... better than advertised. Everything we needed was readily available. Ruth was always quick to respond with questions and advice. My family included an infant, 5 year old, teenager, adult kids, and us grand parents. We all had a blast and there was something for everyone. Marathon is a great location. Ruth, as advertised, is a great host. All the food that was provided when we arrived to the special chocolates, champagne and roses that was ordered...
New Listing: Waterfront Home w/ Private Heated Pool, Dock, Bikes, Kayak, Paddleboards... and so much more!!

Oceanfront Spanish Villa: 4 bed, loft, 8 guests

2.0 star property
10.0 out of 10, Exceptional, (1)
"Best house ever. Very friendly host and ready to please with any requests. The beds were top quality. The house is perfect for families, the kitchen is great to cook, they have games, fishing poles and is very clean. We have never seen such beautiful sunsets. Easy to get to from anywhere in the country. Marathon is a unique destination, great food, quaint and you don’t get tired of coming back every year. WE RECOMMEND THIS HOUSE."
Oceanfront Spanish Villa: 4 bed, loft, 8 guests
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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Other property types in Grassy Key

Oceanfront Sandy Beach Vacation Rental Unit 1

9.4 out of 10, Exceptional, (107)
"Very comfortable & great location! The apartment has beautiful views & has its own beach. We enjoyed our stay & would stay there again. "
Oceanfront Sandy Beach Vacation Rental Unit 1

Oceanfront Sandy Beach Vacation Rental Unit 2

9.6 out of 10, Exceptional, (127)
"This is our 2nd time here at this property. Already looking forward to many more!"
Oceanfront Sandy Beach Vacation Rental Unit 2

🌇 Ocean Sunset Views with Pool and Dock 🌇

9.2 out of 10, Wonderful, (35)
"It was peaceful "
🌇 Ocean Sunset Views with Pool and Dock 🌇
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.

Frequently asked questions

How much do villas in Grassy Key cost?
Villas in Grassy Key cost between AU$1,113 and AU$4,564 per night. These stays give you the privacy of your own space at a price that won’t stretch the budget. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Grassy Key?
Grassy Key has 67 villas to select from. Find your next perfect stay quickly and easily by clicking the “Villa” checkbox under the “Property type” tab in our filter tool.
What is there to do near my villa in Grassy Key?
There are loads of awesome things to do in Grassy Key. Check out attractions like Curry Hammock State Park, Coco Plum Beach and Florida Keys Aquarium Encounters. Crane Point Museum and Nature Centre, Captain Hooks Marina and Dive Centre and San Pablo Catholic Church are also visited by many.