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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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
$457 nightly
The price is $507
Oct 20 - Oct 21
Total with taxes and fees
Villa 5034 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.
$485 nightly
The price is $538
Oct 26 - Oct 27
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.
$505 nightly
The price is $560
Oct 23 - Oct 24
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 covered outdoor patio with a table and chairs, a ceiling fan, and a view of trees and a white building.

5. 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 20 - Oct 21
Total with taxes and fees
Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA
A covered balcony with white railings, a white wicker chair, and a small table.

6. 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 20 - Oct 21
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.

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.
$446 nightly
The price is $495
Oct 20 - Oct 21
Total with taxes and fees
Villa 5021 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.
$457 nightly
The price is $507
Oct 20 - Oct 21
Total with taxes and fees
Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA
An aerial view of a resort with a circular water feature, surrounded by palm trees and a dock with boats.

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

Beachfront Villa w/ Ocean-View Balcony in the Keys
Marathon
$642 nightly
The price is $713
Oct 29 - Oct 30
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.

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

Beachfront Estate - Two Villas / Heated Pools / Docks / Dolphin & Mahi Key
Matecumbe
$4,425 nightly
The price is $4,935
Nov 8 - Nov 9
Total with taxes and fees
Beachfront Estate - Two Villas / Heated Pools / Docks / Dolphin & Mahi Key
A porch with a white railing, blue chairs, and a bed with blue and white bedding.

11. Waterview Villa w/ Full Kitchen in the Keys

Waterview Villa w/ Full Kitchen in the Keys
Marathon
$547 nightly
The price is $610
Nov 1 - Nov 2
Total with taxes and fees
Waterview Villa w/ Full Kitchen in the Keys
A white colonial-style building with a central entrance, flanked by two palm trees and a manicured hedge.

12. Waterfront Villa w/ Uninterrupted Ocean Views

Waterfront Villa w/ Uninterrupted Ocean Views
Marathon
$592 nightly
The price is $661
Nov 1 - Nov 2
Total with taxes and fees
Waterfront Villa w/ Uninterrupted Ocean Views
A coastal resort with multiple white buildings, a sandy beach, and a calm water body.

13. Waterview Villa w/ Full Kitchen & Beach Access

Waterview Villa w/ Full Kitchen & Beach Access
Marathon
$558 nightly
The price is $623
Nov 1 - Nov 2
Total with taxes and fees
Waterview Villa w/ Full Kitchen & Beach Access
A white colonial-style building with a central entrance, flanked by two palm trees and a manicured hedge.

14. Beachfront Villa on a Private Florida Keys Beach

Beachfront Villa on a Private Florida Keys Beach
Marathon
$689 nightly
The price is $765
Oct 29 - Oct 30
Total with taxes and fees
Beachfront Villa on a Private Florida Keys Beach
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.
$2,895 nightly
The price is $3,220
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

Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

10/10 Excellent
"Amazing resort. Room was above expectations, everything was so clean, staff so friendly. Great accommodations & dining options. We will be back!"
Anthony 2-night trip
Posted 1 hour ago
Isla Bella Beach Resort & Spa

Find out more about Grassy Key

Grassy Key Villas information

Number of reviews
123
Accommodation
107 Villas
Lowest Price
$495
Highest Price
$4,935

Frequently asked questions

How much do villas in Grassy Key cost?
Prices for villas in Grassy Key range between $495 and $4,935 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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