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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Villas in Grassy Key and around

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

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

8.6 out of 10, Excellent, (53)
"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
Villa 5027 on Duck Key BOAT SLIP available
Outdoor dining

Villa 5027 on Duck Key BOAT SLIP available

9.6 out of 10, Exceptional, (54)
"Very clean. "
The price is €524
includes taxes & fees
4 Aug - 5 Aug
Villa 5027 on Duck Key BOAT SLIP available
Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - Boat Slip Avail
Exterior

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

10.0 out of 10, Exceptional, (212)
"Very nice place in a great location."
Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - Boat Slip Avail
iykyk WTF! ELEVATOR~TIKI BAR~BOAT SLIP on site! MOON DECK/POOL~GULF FRONT BABY!!
Terrace/patio

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

10.0 out of 10, Exceptional, (140)
"Nice place, can walk to restaurants.loved the top floor patio."
iykyk WTF! ELEVATOR~TIKI BAR~BOAT SLIP on site! MOON DECK/POOL~GULF FRONT BABY!!
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
Isla Marlin 28: Palm lined luxury villa w/dockage and sunset views
Property grounds

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
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 house was beautiful and the area was quite. Our stay was so relaxing. The boat slip on the property was so convenient. We will definitely be back. "
Refreshed & Elevated Indigo Reef Luxury Villa 15, 3BR, 2 1/2 BA with Boat Slip
Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!
Exterior

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

9.6 out of 10, Exceptional, (69)
"Perfect place to relax "
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
Crystal Waters - 2/2.5 Villa
Property grounds

Crystal Waters - 2/2.5 Villa

10.0 out of 10, Exceptional, (2)
"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
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
A heated pool

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
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, (156)
"We stayed for 4 nights, 2 adults and 2 kids. It was a pleasant stay. "
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✦
Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc
Outdoor pool, a heated pool

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
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 €649
includes taxes & fees
7 Aug - 8 Aug
Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun
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 €528
includes taxes & fees
26 Aug - 27 Aug
Villa 5028 on Duck Key BOAT SLIP available
5% Off Any Booking through Jan 31, 2026! Canal Front/Private Pool/Hot Tub/Dock!
Property grounds

5% Off Any Booking through Jan 31, 2026! Canal Front/Private Pool/Hot Tub/Dock!

10.0 out of 10, Exceptional, (94)
"We had a great two week stay. We especially enjoyed the private pool area encircled by Palm trees and foliage. "
5% Off Any Booking through Jan 31, 2026! Canal Front/Private Pool/Hot Tub/Dock!
Marlin House 52: Gated Luxury Villa w/ Dockage, Sunset Views and Pool
Property grounds

Marlin House 52: Gated Luxury Villa w/ Dockage, Sunset Views and Pool

10.0 out of 10, Exceptional, (51)
"Our family really enjoyed our stay at this property. It has amazing water views and the villa provided everything we needed for a great stay. Highly recommend, we would stay here again."
Marlin House 52: Gated Luxury Villa w/ Dockage, Sunset Views and Pool
Fabulous Canal Front Villa, Private Pool in KCB!
Outdoor dining

Fabulous Canal Front Villa, Private Pool in KCB!

10.0 out of 10, Exceptional, (24)
"We had a great stay at Blue Turtle Villa with our family. The home was clean and well cared for. Highly Recommended!"
Fabulous Canal Front Villa, Private Pool in KCB!
Villa 7075 on Duck Key BOAT SLIP available
Property grounds

Villa 7075 on Duck Key BOAT SLIP available

9.2 out of 10, Wonderful, (29)
"Great location, incredible view just as advertised. Definitely would stay there again."
The price is €535
includes taxes & fees
4 Aug - 5 Aug
Villa 7075 on Duck Key BOAT SLIP available
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

Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"It was a lovely property. Comfortable beds & clean."
Peter 2-night trip
Posted 2 days ago
Lime Tree Bay Resort

Frequently asked questions

How much do villas in Grassy Key cost?
Prices for villas in Grassy Key range between €524 and €649 per night. Whatever your budget, you'll find a place that fits your needs on Expedia. These prices were 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?
Pack your suitcase and pick from 82 villas in Grassy Key. For a family escape, a getaway with pals or anything in between, Expedia can help you find the perfect space in a few simple clicks.
Are there any family-friendly villas in Grassy Key?
Take the crew to Waterfront Luxury Villa - 14 - - 3 Bedroom Townhouse and make your getaway to Grassy Key a relaxing one. This family-friendly villa has a 3-star rating and amenities like a barbecue grill and an oven. Once you've checked in and unpacked your bags, there are tons of family-friendly attractions to see in and around Grassy Key. Coco Plum Beach and Crane Point Museum and Nature Centre guarantee a good time for young and old.