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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Grassy Key vacation homes

Outdoor dining

Vacation Home in Matecumbe

Private Beach / Private overwater dock / Heated Pool / Mahi Key
10.0 out of 10, Exceptional, (1 review)
"This property and the entire community was amazing. This was a fantastic vacation. One of the best we have had in years!"
United States
Gmac W.
The price is AED 13,338
AED 18,493 total
includes taxes & fees
14 Mar - 15 Mar
Private Beach / Private overwater dock / Heated Pool / Mahi Key
Outdoor pool

Vacation Home in Marathon

SPECIAL-2 Bed 2 Bath Villa including Cabana Club membership which
9.8 out of 10, Exceptional, (144 reviews)
"Great location and very neat place!"
United States
FERNANDO S.
The price is AED 1,025
AED 2,259 total
includes taxes & fees
1 Mar - 2 Mar
SPECIAL-2 Bed 2 Bath Villa including Cabana Club membership which
Property grounds

Vacation Home in Duck Key

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
9.6 out of 10, Exceptional, (48 reviews)
"Clean property! Great views! Great communication with owner! Perfect location- close to marathon and key west! "
United States
candi b.
The price is AED 1,539
AED 2,962 total
includes taxes & fees
9 Mar - 10 Mar
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Outdoor dining

Vacation Home in Duck Key

Tiny Villa, Big Ocean Views| Breathtaking Sunsets
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful views. Very nice accommodations. Wonderfull location!"
United States
michael h.
The price is AED 1,153
AED 2,266 total
includes taxes & fees
9 Mar - 10 Mar
Tiny Villa, Big Ocean Views| Breathtaking Sunsets
TV

Vacation Home in Duck Key

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
8.6 out of 10, Excellent, (11 reviews)
"Unit was very clean and had everything we needed"
United States
Vanessa L.
The price is AED 1,539
AED 2,992 total
includes taxes & fees
3 Mar - 4 Mar
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Outdoor dining

Vacation Home in Duck Key

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA
9.4 out of 10, Exceptional, (32 reviews)
"Perfect for our get away"
United States
Kelly H.
The price is AED 1,539
AED 2,966 total
includes taxes & fees
3 Mar - 4 Mar
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA
Outdoor dining

Vacation Home in Marathon

Oceanfront Tiny Villa in the Heart of the FL Keys
10.0 out of 10, Exceptional, (13 reviews)
"Would stay here again! Fast and responsive host. Beautiful views!"
United States
Carson F.
Oceanfront Tiny Villa in the Heart of the FL Keys
Outdoor dining

Vacation Home in Marathon

Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!
10.0 out of 10, Exceptional, (161 reviews)
"Awesome place on the canal. Great view, clean, and just about everything we needed was there. Other than needing a water hose down by the dock for washing the boat at the end of the day. Overall, couldn’t be happier with this place. Definitely would stay here again. "
United States
JD F.
The price is AED 2,454
AED 5,297 total
includes taxes & fees
4 Mar - 5 Mar
Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!
Exterior

Vacation Home in Duck Key

Charming 3-bedroom house featuring a heated private pool.
10.0 out of 10, Exceptional, (9 reviews)
"This villa exceeded our expectations. All the bedrooms have king size beds and there is a 3/4 bath on the first floor which was unexpected and perfect as all the couples had there own bathroom. Melissa was very fast to respond to some issues (smoke alarm in one of the bedrooms needed batteries) and maintenance was there within the hour. The pool was heated and very private. I would highly recommend this place to stay. "
United States
Melissa B.
The price is AED 2,134
AED 3,819 total
includes taxes & fees
27 Mar - 28 Mar
Charming 3-bedroom house featuring a heated private pool.
Exterior

Vacation Home in Duck Key

Blue Waters Stay - 2/2.5 Villa - OS Slip/Ramp/Pkg
Blue Waters Stay - 2/2.5 Villa - OS Slip/Ramp/Pkg
Pool

Vacation Home in Duck Key

Piece of Paradise located at Hawks Cay in Duck Key
9.8 out of 10, Exceptional, (16 reviews)
"Amazing place. "
United States
Pilar G.
The price is AED 2,545
AED 3,461 total
includes taxes & fees
1 Mar - 2 Mar
Piece of Paradise located at Hawks Cay in Duck Key
Exterior

Vacation Home in Duck Key

4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request
9.6 out of 10, Exceptional, (8 reviews)
"The villa is in a great location, and has a very private and secluded feeling to it when inside and around the pool. We had a great time, the villa met and exceeded or expectations, there were 6 of us staying there and the age ranges were from 27 to 64, we rented a charter boat out of marathon so the villa location was perfect.Thank you very much for such a great place to stay, we will try and stay here again if we come back down."
United States
Kevin J.
The price is AED 3,669
AED 6,397 total
includes taxes & fees
12 Mar - 13 Mar
4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request
Outdoor dining

Vacation Home in Marathon

Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!
6.0 out of 10, (1 review)
"Easy booking process and host was gracious and welcoming, available through duration of our stay.Unit: location was good, unit was clean when we arrived, easy to access with front door code, reasonably stocked bathrooms with necessities. Layout is exactly what we expected and gave our family of four plenty of space to spread out, probably more space than we needed but we had larger party at time of booking and several backed out semi-last minute. Living room furniture was tired and worn, patio...
United States
Stephanie B.
The price is AED 2,171
AED 4,935 total
includes taxes & fees
22 Mar - 23 Mar
Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!
Interior

Vacation Home in Duck Key

Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available
Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available
Exterior

Vacation Home in Coral Lagoon

Heated Pool, Views, Vaca Cut , Gulf & Atlantic Access. Availability Nov + Dec
10.0 out of 10, Exceptional, (272 reviews)
"Excellent stay for a family."
United States
Sandra P.
The price is AED 1,818
AED 3,468 total
includes taxes & fees
10 Mar - 11 Mar
Heated Pool, Views, Vaca Cut , Gulf & Atlantic Access. Availability Nov + Dec
Terrace/patio

Vacation Home in Marathon

Charming 2-bedroom house in Marathon with pool
8.0 out of 10, Very Good, (2 reviews)
"Great Home & Location & Enjoyable Stay! Thanks!"
United States
James J.
The price is AED 1,414
AED 3,161 total
includes taxes & fees
24 Mar - 25 Mar
Charming 2-bedroom house in Marathon with pool
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

10/10 Excellent
"The view from our water view king studio were spectacular! The room was extra large with everything we needed and more. The staff were wonderful. We would definitely come back. The only minor negative thing we experienced was Thursday night dance party at the outdoor bar near our room. The music had our room thumping when we were trying to get sleep. "
William 4-night trip
Posted 2 days ago
Hawks Cay Resort