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Check prices for these dates

Next weekend
18 July - 20 July
In two weeks
25 July - 27 July
In one month
8 Aug - 10 Aug
In two months
5 Sept - 7 Sept

Featured Villas in Grassy Key

Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer
Fridge, microwave, oven, stovetop

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

8.6 out of 10, Excellent, (51)
"This was a great place to stay away from the business but close enough to Marathon to go to dinner or activities. The condo was cozy and had a great sunset view. Will definitely look at this place again if we return to the Keys."
Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer
Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - Boat Slip Avail
Beach nearby

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

10.0 out of 10, Exceptional, (210)
"Had a great stay at Coral Lagoon, the place was immaculate and the property manager was very responsive to any request we had. Look forward to a return visit."
Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - Boat Slip Avail
DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage INCL
A heated pool

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

9.8 out of 10, Exceptional, (168)
"Enjoy the stay in good location "
DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage INCL
New Florida Keys Vacation Rentals- Beach House on Sombrero Beach Dock Pool 6 bed
Outdoor dining

New Florida Keys Vacation Rentals- Beach House on Sombrero Beach Dock Pool 6 bed

2.0 star property
10.0 out of 10, Exceptional, (3)
"The house and dock space was extremely accommodating for the amount of people we had staying in the house. "
New Florida Keys Vacation Rentals- Beach House on Sombrero Beach Dock Pool 6 bed
WTF? ELEVATOR~TIKI BAR~BOAT SLIP on site! MOON DECK/POOL~GULF FRONT BABY!!
Terrace/patio

WTF? ELEVATOR~TIKI BAR~BOAT SLIP on site! MOON DECK/POOL~GULF FRONT BABY!!

10.0 out of 10, Exceptional, (137)
"Nice place, can walk to restaurants.loved the top floor patio."
WTF? ELEVATOR~TIKI BAR~BOAT SLIP on site! MOON DECK/POOL~GULF FRONT BABY!!
Refreshed & Elevated Indigo Reef Luxury Villa 15, 3BR, 2 1/2 BA with Boat Slip
Marina

Refreshed & Elevated Indigo Reef Luxury Villa 15, 3BR, 2 1/2 BA with Boat Slip

10.0 out of 10, Exceptional, (8)
"The grounds of the property were beautiful and well maintained, the Villa was super clean, newly updated and decorated beautifully, the property manager was very responsive and attentive."
Refreshed & Elevated Indigo Reef Luxury Villa 15, 3BR, 2 1/2 BA with Boat Slip
Isla Marlin 28: Palm lined luxury villa w/dockage and sunset views
Pool

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

9.8 out of 10, Exceptional, (10)
"From the location to the views to the villa itself, everything was just so special and beautiful! This was our third time to Marathon but first time staying here and we are already working on our next trip! Thank you for the sweetest memories! "
Isla Marlin 28: Palm lined luxury villa w/dockage and sunset views
Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!
Beach

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

9.6 out of 10, Exceptional, (67)
"We had a great visit here! We were attending a conference at Hawks Cay and the VRBO was super convenient. Very clean, plenty of space for our group of 3, and the patio out back was great for relaxing. "
Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!
PLUNGE POOL VILLA ON BLUE WATER LAGOON DUCK Key/MARATHON, FL
A heated pool

PLUNGE POOL VILLA ON BLUE WATER LAGOON DUCK Key/MARATHON, FL

9.6 out of 10, Exceptional, (73)
"We enjoyed our stay!"
PLUNGE POOL VILLA ON BLUE WATER LAGOON DUCK Key/MARATHON, FL
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
Property grounds

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

8.6 out of 10, Excellent, (233)
"The property has potential but needs A lot of maintenance and upgrades. Also wasn’t very clean. In addition since they do not participate of hawks cay resort program you can’t enjoy the area. I stayed in this area and other owners are part of the program so you can enjoy the amenities around "
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
Sombrero Beach Villa with Private Pool and Dock
Interior

Sombrero Beach Villa with Private Pool and Dock

10.0 out of 10, Exceptional, (127)
"We loved our stay here. We stayed with our adult children and our 1 1/2 year old grandson and it was a great. We would stay here again. "
Sombrero Beach Villa with Private Pool and Dock
Villa 5027 on Duck Key BOAT SLIP available
TV

Villa 5027 on Duck Key BOAT SLIP available

9.6 out of 10, Exceptional, (52)
"Very clean. "
The price is AU$902
includes taxes & fees
14 July - 15 July
Villa 5027 on Duck Key BOAT SLIP available
Crystal Waters - 2/2.5 Villa
Smart TV

Crystal Waters - 2/2.5 Villa

10.0 out of 10, Exceptional, (1)
"We had a wonderful expérience in Duck Key.Thank you Ana for your kind hospitality!See you next time !"
Crystal Waters - 2/2.5 Villa
DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage
Outdoor dining

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

9.8 out of 10, Exceptional, (153)
"Enjoyed our stay here and hoping to be back next year! Host was super responsive with any questions. "
DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage
✦Unwind on your Oceanedge villa on Seapalm island✦
Outdoor pool, a heated pool

✦Unwind on your Oceanedge villa on Seapalm island✦

9.8 out of 10, Exceptional, (32)
"Great house. Nice amenities- peaceful and secluded. However no beach access from house. Nearest beach is Sombrero beach which is very nice."
✦Unwind on your Oceanedge villa on Seapalm island✦
Florida Keys | 2BR Stay – No Hidden Fees
A heated pool

Florida Keys | 2BR Stay – No Hidden Fees

9.0 out of 10, Wonderful, (2)
"It is a nice place"
Florida Keys | 2BR Stay – No Hidden Fees
Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc
Sun-loungers, beach towels

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

10.0 out of 10, Exceptional, (44)
"Property was amazing. House was extreamly well stocked which made flying a breeze. Beds were super comfortable and clean. Would definitely stay again."
Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc
Villa 5028 on Duck Key BOAT SLIP available
Outdoor dining

Villa 5028 on Duck Key BOAT SLIP available

9.6 out of 10, Exceptional, (7)
"Great location on the water with beautiful sunset views. Plenty of room for our group. "
The price is AU$924
includes taxes & fees
3 Aug - 4 Aug
Villa 5028 on Duck Key BOAT SLIP available
Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun
Exterior

Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun

10.0 out of 10, Exceptional, (13)
"We enjoyed our stay."
The price is AU$1,044
includes taxes & fees
15 July - 16 July
Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun
JUNE 1-8 AVAILABLE @ SPECIAL RATE! Canal Front/Private Pool/Hot Tub/Dock Beach!
Outdoor pool, a heated pool

JUNE 1-8 AVAILABLE @ SPECIAL RATE! Canal Front/Private Pool/Hot Tub/Dock Beach!

10.0 out of 10, Exceptional, (93)
"Had a great stay couldn’t ask for anything more. "
JUNE 1-8 AVAILABLE @ SPECIAL RATE! Canal Front/Private Pool/Hot Tub/Dock Beach!
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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Frequently asked questions

How much do villas in Grassy Key cost?
Villas in Grassy Key cost between AU$902 and AU$1,044 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 87 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.