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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Featured Villas in Grassy Key

KG Arrive any day, pool on beach, full Kitchen, W/D, Parking, Docks, balcony,
Exterior

KG Arrive any day, pool on beach, full Kitchen, W/D, Parking, Docks, balcony,

8.8 out of 10, Excellent, (36)
"The Property is centrally located in the keys between Key West and Islamorada and is convenient. Everything was clean and the beach was great to have. "
KG Arrive any day, pool on beach, full Kitchen, W/D, Parking, Docks, balcony,
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, (144)
"The place was as advertised and made for a great place to unwind and enjoy the beautiful Keys! The elevator was an awesome bonus that made moving our heavy luggage a breeze!"
iykyk WTF! ELEVATOR~TIKI BAR~BOAT SLIP on site! MOON DECK/POOL~GULF FRONT BABY!!
KA Beach, dock, Pool, Kitchen, Tennis, Hot Tub, tropical paradise
A heated pool

KA Beach, dock, Pool, Kitchen, Tennis, Hot Tub, tropical paradise

9.2 out of 10, Wonderful, (85)
"Had a great time "
KA Beach, dock, Pool, Kitchen, Tennis, Hot Tub, tropical paradise
DUPLEX IN DUCK KEY 3/2 W/90' Private Dock, Trailer Storage included
Exterior

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

10.0 out of 10, Exceptional, (203)
"Better than photos.Handy location to Key West or Islamorada.Would come back again."
DUPLEX IN DUCK KEY 3/2 W/90' Private Dock, Trailer Storage included
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, (159)
"Great place will come back for sure "
DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage
Charming 3-bedroom villa with WiFi, AC in welcoming Marathon
Exterior

Charming 3-bedroom villa with WiFi, AC in welcoming Marathon

Charming 3-bedroom villa with WiFi, AC in welcoming Marathon
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, (213)
"Property was great! Just what we needed. Clean, spacious and all the amenities needed. Very happy that it was so close to the pool area."
Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - Boat Slip Avail
Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA
Exterior

Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA

9.6 out of 10, Exceptional, (54)
"Very clean. "
The price is NZ$952
includes taxes & fees
30 Sept - 1 Oct
Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA
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, (171)
"Enjoy the stay in good location "
DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage INCL
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, (9)
"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, (71)
"Perfect place to relax "
Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!
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, (57)
"Great location, loved being in the end unit so you don’t have neighbors on both sides."
Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
Outdoor dining

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

9.2 out of 10, Wonderful, (18)
"The place was very clean and very comfortable. The location was great and we had a wonderful stay. The kitchen had all the utensils needed to cook a meal or two."
The price is NZ$921
includes taxes & fees
30 Sept - 1 Oct
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
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, (234)
"We loved the condo. It was perfect for just the two of us or maybe two couples or small Family. The bedrooms are extremely small but the two outdoor porches made up for it, especially the private pool! We had other family members staying g on condos nearby making a perfect place for a group to meet up!"
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
Stunning Waterfront Two-Story Villa in Duck Key!
Outdoor dining

Stunning Waterfront Two-Story Villa in Duck Key!

2.0 star property
9.6 out of 10, Exceptional, (4)
"Optimal for a week stay, close proximity to fishing charts, marinas and restaurants."
Stunning Waterfront Two-Story Villa in Duck Key!
Sombrero Beach Villa with Private Pool and Dock
Exterior

Sombrero Beach Villa with Private Pool and Dock

10.0 out of 10, Exceptional, (128)
"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
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!
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 NZ$1,005
includes taxes & fees
30 Sept - 1 Oct
Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun
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
Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA
Outdoor dining

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

9.0 out of 10, Wonderful, (8)
"Property was clean and comfortable with an excellent sunset view each evening."
The price is NZ$1,004
includes taxes & fees
29 Oct - 30 Oct
Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA
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

Tropical Cottages

Tropical Cottages

10/10 Excellent
"Great communication, easy check in, onsite parking, clean and very nice cottage! Super comfortable bed! "
Andrew 1-night trip
Posted 1 day ago
Tropical Cottages

Find out more about Grassy Key

Find out more about Grassy Key

Grassy Key Villas information

Number of reviews
1,476
Accommodation
85 Villas
Lowest Price
NZ$921
Highest Price
NZ$1,005

Frequently asked questions

How much do villas in Grassy Key cost?
Prices for villas in Grassy Key range between NZ$921 and NZ$1,005 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 85 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.

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