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

Villas in Grassy Key

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Grassy Key villas

A covered outdoor area with a round table and chairs, a white railing, and a view of the ocean.

1. 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, (62 reviews)
"Excellent place,"
United States
MONICA A.
$423 nightly
The price is $472
Sep 29 - Sep 30
Total with taxes and fees
Villa 5027 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)
"Awesome place to stay"
United States
Takuma F.
$444 nightly
The price is $496
Sep 29 - Sep 30
Total with taxes and fees
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

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.
$433 nightly
The price is $484
Sep 29 - Sep 30
Total with taxes and fees
Seas the Keys Getaway with plunge pool/spa
A covered outdoor seating area with a table and chairs, overlooking a body of water and a beach.

4. 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.
$444 nightly
The price is $496
Sep 29 - Sep 30
Total with taxes and fees
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA
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
$423 nightly
The price is $472
Sep 29 - Sep 30
Total with taxes and fees
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
A covered outdoor patio with a table and chairs, a ceiling fan, and a view of trees and a white building.

6. 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.
$423 nightly
The price is $472
Sep 29 - Sep 30
Total with taxes and fees
Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA
A covered outdoor deck with a table and chairs, overlooking a body of water and a grassy area.

7. 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.
$423 nightly
The price is $472
Sep 29 - Sep 30
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.

8. 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.
$888 nightly
The price is $992
Sep 29 - Sep 30
Total with taxes and fees
Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available
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.
$846 nightly
The price is $945
Sep 29 - Sep 30
Total with taxes and fees
Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA
A clear swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

10. Waterview Villa w/ Full Kitchen in the Keys

Waterview Villa w/ Full Kitchen in the Keys
Marathon
$549 nightly
The price is $613
Sep 30 - Oct 1
Total with taxes and fees
Waterview Villa w/ Full Kitchen in the Keys
A beachfront hotel with multiple balconies, a dock, and palm trees.

11. Waterview Villa w/ Full Kitchen & Beach Access

Waterview Villa w/ Full Kitchen & Beach Access
Marathon
$558 nightly
The price is $623
Sep 30 - Oct 1
Total with taxes and fees
Waterview Villa w/ Full Kitchen & Beach Access
A wooden deck with blue chairs, a white railing, and a view of the water.

12. Waterfront Villa w/ Uninterrupted Ocean Views

Waterfront Villa w/ Uninterrupted Ocean Views
Marathon
$569 nightly
The price is $635
Sep 30 - Oct 1
Total with taxes and fees
Waterfront Villa w/ Uninterrupted Ocean Views
A beach view with palm trees and a pool area.

13. Beachfront Villa on a Private Florida Keys Beach

Beachfront Villa on a Private Florida Keys Beach
Marathon
$590 nightly
The price is $659
Sep 30 - Oct 1
Total with taxes and fees
Beachfront Villa on a Private Florida Keys Beach
A coastal resort with multiple white buildings, a sandy beach, and a calm water body.

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

Beachfront Villa w/ Ocean-View Balcony in the Keys
Marathon
$582 nightly
The price is $650
Sep 30 - Oct 1
Total with taxes and fees
Beachfront Villa w/ Ocean-View Balcony in the Keys
A balcony with a view of the beach and ocean, equipped with ceiling fans, outdoor furniture, and a railing.

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

Beachfront Estate - Two Villas / Heated Pools / Docks / Dolphin & Mahi Key
Matecumbe
$3,622 nightly
The price is $4,055
Oct 13 - Oct 14
Total with taxes and fees
Beachfront Estate - Two Villas / Heated Pools / Docks / Dolphin & Mahi Key
A resort with a pool, palm trees, and a view of the ocean.

16. 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.
$2,369 nightly
The price is $2,646
Oct 1 - Oct 2
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

Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

10/10 Excellent
"Every thing was excellent"
DARIEL 2-night trip
Posted 11 hours ago
Isla Bella Beach Resort & Spa

Find out more about Grassy Key

Grassy Key Villas information

Number of reviews
74
Accommodation
107 Villas
Lowest Price
$472
Highest Price
$4,055

Frequently asked questions

How much do villas in Grassy Key cost?
Prices for villas in Grassy Key range between $472 and $4,055 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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