A dolphin swimming near a wooden dock and a tree branch in the water.

Villas in Grassy Key

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Grassy Key villas

A living room with a view of the sea, a ceiling fan, a TV, and a dining area with outdoor seating.

1. Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.8 out of 10, Exceptional, (8 reviews)
"Great Location! The house was beautiful and clean We had a great time!"
United States
Andres
$506 nightly
The price is $567
Dec 3 - Dec 4
Total with taxes and fees
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
A resort with multiple white buildings, a golf course, and a clear view of the ocean and a pier in the background.

2. Villa del Sol - Sunset Views, Kayaks, 2/2.5

Villa del Sol - Sunset Views, Kayaks, 2/2.5
Duck Key
10.0 out of 10, Exceptional, (10 reviews)
"Really enjoy the time there"
United States
Han W.
$568 nightly
The price is $634
Nov 19 - Nov 20
Total with taxes and fees
Villa del Sol - Sunset Views, Kayaks, 2/2.5
Exterior Front

3. Seas the Keys Getaway with plunge pool/spa

Seas the Keys Getaway with plunge pool/spa
Marathon
9.6 out of 10, Exceptional, (15 reviews)
"Nice location "
United States
Gina W.
$445 nightly
The price is $496
Nov 17 - Nov 18
Total with taxes and fees
Seas the Keys Getaway with plunge pool/spa
A deck with outdoor seating, overlooking a marina and a body of water.

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

Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.4 out of 10, Exceptional, (23 reviews)
"Awesome place to stay"
United States
Takuma F.
$545 nightly
The price is $608
Nov 16 - Nov 17
Total with taxes and fees
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
A covered outdoor seating area with a table and chairs, overlooking a body of water and a beach.

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

Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA
Duck Key
10.0 out of 10, Exceptional, (3 reviews)
"The location was perfect, house was very clean, and the view was breathtaking. We will 100% return."
United States
Gina A.
$524 nightly
The price is $585
Nov 23 - Nov 24
Total with taxes and fees
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA
A waterfront hotel with a wooden dock leading to the entrance, featuring a sign that reads "Angler and Ale".

6. Duck Keys Escape! | 2BR Villa w/ Views, Spa & Pool

Duck Keys Escape! | 2BR Villa w/ Views, Spa & Pool
Duck Key
7.0 out of 10, Good, (2 reviews)
"good place, lots of room, only down fall i would say is the kitchen supplies. no baking sheets, one hand towel for the kitchen, no lids for the skillets. plenty of plates, cups and silverware. great location, key west is a little over an hour away. the resort itself and pool area is awesome. loved the overall experience and would return"
Canada
Reuben L.
$518 nightly
The price is $579
Nov 15 - Nov 16
Total with taxes and fees
Duck Keys Escape! | 2BR Villa w/ Views, Spa & Pool
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

Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
8.8 out of 10, Excellent, (9 reviews)
"Property was clean and comfortable with an excellent sunset view each evening."
United States
william d.
$524 nightly
The price is $585
Nov 16 - Nov 17
Total with taxes and fees
Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA
A covered outdoor area with a round table and chairs, a white railing, and a view of the ocean.

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

Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.6 out of 10, Exceptional, (64 reviews)
"Excellent place,"
United States
MONICA A.
$524 nightly
The price is $585
Nov 16 - Nov 17
Total with taxes and fees
Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA
A coastal resort with multiple bungalow-style buildings, a marina, and a large body of water.

9. Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA

Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA
Marathon
9.6 out of 10, Exceptional, (5 reviews)
"Hawks Cay is a really beautiful spot. Frank’s place is nice, clean and convenient to Marathon "
United States
Morgan W.
$965 nightly
The price is $1,077
Nov 11 - Nov 12
Total with taxes and fees
Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA
A covered outdoor deck with a table and chairs, overlooking a body of water and a grassy area.

10. Villa 5021 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5021 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
8.8 out of 10, Excellent, (6 reviews)
"The property was as described in the VRBO site. The view was very nice. I would stay here again, when the opportunity arises."
United States
Paul E.
$507 nightly
The price is $566
Nov 11 - Nov 12
Total with taxes and fees
Villa 5021 on Duck Key Boat Slip Available - 2BD 2.5BA
A covered balcony with white railings, a white wicker chair, and a small table.

11. Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available

Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available
Duck Key
10.0 out of 10, Exceptional, (5 reviews)
"House was fantastic. Back deck and pool area were so nice !!!"
United States
Ryan M.
$1,128 nightly
The price is $1,258
Nov 11 - Nov 12
Total with taxes and fees
Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available
A covered outdoor area with a table and two chairs, overlooking a body of water with a distant shoreline.

12. 2BR Villa in Duck Key | Dolphin Encounters + Pools

2BR Villa in Duck Key | Dolphin Encounters + Pools
Duck Key
10.0 out of 10, Exceptional, (1 review)
"The resort was beautiful. There were so many things to take in. Our villa was very nice. We’ll definitely come back to stay there."
United States
Pamela B.
$564 nightly
The price is $629
Nov 15 - Nov 16
Total with taxes and fees
2BR Villa in Duck Key | Dolphin Encounters + Pools
A covered outdoor area with a table and two chairs, overlooking a body of water with a distant shoreline.

13. 2BR Villa w/ Marina Views + Pools | No Hidden Fees

2BR Villa w/ Marina Views + Pools | No Hidden Fees
Duck Key
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay. We really enjoyed sitting on the balcony over the water!"
United States
Darcey C.
$579 nightly
The price is $646
Nov 15 - Nov 16
Total with taxes and fees
2BR Villa w/ Marina Views + Pools | No Hidden Fees
A covered outdoor area with a wooden deck, white railings, and a table with chairs.

14. Villa with Resort Amenities | Full Kitchen

Villa with Resort Amenities | Full Kitchen
Duck Key
10.0 out of 10, Exceptional, (1 review)
$640 nightly
The price is $715
Nov 15 - Nov 16
Total with taxes and fees
Villa with Resort Amenities | Full Kitchen
A covered outdoor area with wooden chairs and a view of a waterway.

15. Florida Keys | 2BR Stay – No Hidden Fees

Florida Keys | 2BR Stay – No Hidden Fees
Duck Key
$505 nightly
The price is $563
Nov 15 - Nov 16
Total with taxes and fees
Florida Keys | 2BR Stay – No Hidden Fees
A waterfront hotel with a wooden dock leading to the entrance, featuring a sign that reads "Angler and Ale".

16. Single-Level 2BR Villa w/ Full Kitchen & Porch

Single-Level 2BR Villa w/ Full Kitchen & Porch
Duck Key
$710 nightly
The price is $792
Dec 1 - Dec 2
Total with taxes and fees
Single-Level 2BR Villa w/ Full Kitchen & Porch
A resort with a central pool, surrounded by manicured lawns and palm trees, with a view of the ocean.

17. Beachfront Villa on a Private Florida Keys Beach

Beachfront Villa on a Private Florida Keys Beach
Marathon
$686 nightly
The price is $765
Dec 1 - Dec 2
Total with taxes and fees
Beachfront Villa on a Private Florida Keys Beach
A resort with a central pool, surrounded by manicured lawns and palm trees, with a view of the ocean.

18. Beachfront Villa w/ Ocean-View Balcony in the Keys

Beachfront Villa w/ Ocean-View Balcony in the Keys
Marathon
$711 nightly
The price is $793
Dec 1 - Dec 2
Total with taxes and fees
Beachfront Villa w/ Ocean-View Balcony in the Keys
A resort with a central pool, surrounded by manicured lawns and palm trees, with a view of the ocean.

19. Waterview Villa w/ Full Kitchen in the Keys

Waterview Villa w/ Full Kitchen in the Keys
Marathon
$594 nightly
The price is $664
Nov 12 - Nov 13
Total with taxes and fees
Waterview Villa w/ Full Kitchen in the Keys
A resort with a central pool, surrounded by manicured lawns and palm trees, with a view of the ocean.

20. Waterview Villa w/ Full Kitchen & Beach Access

Waterview Villa w/ Full Kitchen & Beach Access
Marathon
$606 nightly
The price is $678
Nov 12 - Nov 13
Total with taxes and fees
Waterview Villa w/ Full Kitchen & Beach Access
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Grassy Key Hotel Reviews

Captain Pips Marina & Hideaway

Captain Pips Marina & Hideaway

10/10 Excellent
"Awesome Relaxing Private !!"
Raymundo 2-night trip
Posted 4 hours ago
Captain Pips Marina & Hideaway

Find out more about Grassy Key

Grassy Key Villas information

Number of reviews
150
Accommodation
101 Villas
Lowest Price
$496
Highest Price
$1,258

Frequently asked questions

How much do villas in Grassy Key cost?
Prices for villas in Grassy Key range between $496 and $1,258 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 101 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 Center guarantee a good time for young and old.
Why book your villa in Grassy Key with Expedia?
With Expedia, it's easy to find your ideal villa in Grassy Key. Traveling with the family? Use our helpful filters to look for stays with perks like a pool. If you're on a budget, decide on how much you'd like to spend and the star rating of the property. We'll help you find the perfect place that suits your taste and style.
How can I find cheap villas in Grassy Key?
With Expedia's user-friendly filter tool, reserving cheap villas in Grassy Key is a breeze. To find options that'll make your wallet smile, tailor your search results by budget, amenities and star rating.

Explore a world of travel with Expedia