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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Grassy Key villas

A covered outdoor patio with a table and chairs, a ceiling fan, and a view of trees and a white building.

1. 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.
$446 nightly
The price is $495
Oct 19 - Oct 20
Total with taxes and fees
Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA
A deck with outdoor seating, overlooking a marina and a body of water.

2. 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)
$467 nightly
The price is $519
Oct 19 - Oct 20
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.

3. 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, (2 reviews)
"The location was perfect, house was very clean, and the view was breathtaking. We will 100% return."
United States
Gina A.
$500 nightly
The price is $555
Oct 18 - Oct 19
Total with taxes and fees
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA
A coastal resort with multiple bungalow-style buildings, a marina, and a large body of water.

4. 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.
$747 nightly
The price is $829
Oct 26 - Oct 27
Total with taxes and fees
Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA
A living room with a view of the sea, a ceiling fan, a TV, and a dining area with outdoor seating.

5. 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
$457 nightly
The price is $507
Oct 19 - Oct 20
Total with taxes and fees
Villa 5034 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.

6. 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.
$457 nightly
The price is $507
Oct 19 - Oct 20
Total with taxes and fees
Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA
A covered balcony with white railings, a white wicker chair, and a small table.

7. 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.
$883 nightly
The price is $980
Oct 19 - Oct 20
Total with taxes and fees
Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available
A covered outdoor deck with a table and chairs, overlooking a body of water and a grassy area.

8. 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.
$446 nightly
The price is $495
Oct 19 - Oct 20
Total with taxes and fees
Villa 5021 on Duck Key Boat Slip Available - 2BD 2.5BA
A resort with multiple white buildings, a sandy beach, and palm trees.

9. Waterview Villa w/ Full Kitchen in the Keys

Waterview Villa w/ Full Kitchen in the Keys
Marathon
$570 nightly
The price is $635
Oct 19 - Oct 20
Total with taxes and fees
Waterview Villa w/ Full Kitchen in the Keys
A balcony with a view of the beach and ocean, equipped with ceiling fans, outdoor furniture, and a railing.

10. Beachfront Estate - Two Villas / Heated Pools / Docks / Dolphin & Mahi Key

Beachfront Estate - Two Villas / Heated Pools / Docks / Dolphin & Mahi Key
Matecumbe
$4,369 nightly
The price is $4,872
Nov 8 - Nov 9
Total with taxes and fees
Beachfront Estate - Two Villas / Heated Pools / Docks / Dolphin & Mahi Key
An aerial view of a resort with a circular water feature, surrounded by palm trees and a dock with boats.

11. Waterfront Villa w/ Uninterrupted Ocean Views

Waterfront Villa w/ Uninterrupted Ocean Views
Marathon
$574 nightly
The price is $640
Oct 19 - Oct 20
Total with taxes and fees
Waterfront Villa w/ Uninterrupted Ocean Views
A covered outdoor area with a wooden deck, blue chairs, and a view of a beach with palm trees.

12. Waterview Villa w/ Full Kitchen & Beach Access

Waterview Villa w/ Full Kitchen & Beach Access
Marathon
$581 nightly
The price is $648
Oct 19 - Oct 20
Total with taxes and fees
Waterview Villa w/ Full Kitchen & Beach Access
A beachfront hotel with multiple balconies, a sandy walkway, and palm trees.

13. Beachfront Villa on a Private Florida Keys Beach

Beachfront Villa on a Private Florida Keys Beach
Marathon
$671 nightly
The price is $745
Oct 19 - Oct 20
Total with taxes and fees
Beachfront Villa on a Private Florida Keys Beach
A pool area with palm trees, lounge chairs, and umbrellas.

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

Beachfront Villa w/ Ocean-View Balcony in the Keys
Marathon
$647 nightly
The price is $718
Oct 29 - Oct 30
Total with taxes and fees
Beachfront Villa w/ Ocean-View Balcony in the Keys
A resort with a pool, palm trees, and a view of the ocean.

15. PRIVATE BEACH / Heated Pool / Private Dock / Dolphin Key

PRIVATE BEACH / Heated Pool / Private Dock / Dolphin Key
Matecumbe
10.0 out of 10, Exceptional, (1 review)
"Very nice house. Easy to communicate with host. Views just as pictured, great. Dock in front of house is too shallow for a boat but host can provide boat slip very within walking distance 30’ boat max."
United States
Jason B.
$2,701 nightly
The price is $3,008
Nov 8 - Nov 9
Total with taxes and fees
PRIVATE BEACH / Heated Pool / Private Dock / Dolphin Key
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

Hawks Cay Resort

Hawks Cay Resort

8/10 Good
"We love staying at Hawks Cay we have been going for years. The Property amenities are amazing. However, the Villa we stayed at (7039) was in horrible condition. Roaches in kitchen and bathroom, Shades on windows were broken in rooms. The jacuzzi outside was dirty and we were not able to use. We were extremely disappointed to have found it in that condition. I reported to the front office when we checked out. I didn't bother saying anything while there because I am pretty sure they didn't have another one available."
Ivonne 3-night trip
Posted 1 hour ago
Hawks Cay Resort

Find out more about Grassy Key

Grassy Key Villas information

Number of reviews
123
Accommodation
107 Villas
Lowest Price
$495
Highest Price
$4,872

Frequently asked questions

How much do villas in Grassy Key cost?
Prices for villas in Grassy Key range between $495 and $4,872 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 107 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.

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