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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Grassy Key vacation homes

Outdoor dining

Private Beach / Private overwater dock / Heated Pool / Mahi Key

Private Beach / Private overwater dock / Heated Pool / Mahi Key
Matecumbe
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 12,424
AED 17,318 total
includes taxes & fees
14 Mar - 15 Mar
Private Beach / Private overwater dock / Heated Pool / Mahi Key
Property grounds

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.6 out of 10, Exceptional, (47 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 2,951 total
includes taxes & fees
9 Mar - 10 Mar
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Outdoor pool

SPECIAL-2 Bed 2 Bath Villa with Cabana Club and Boat Slip 279 nt. Feb 23-Mar 2

SPECIAL-2 Bed 2 Bath Villa with Cabana Club and Boat Slip 279 nt. Feb 23-Mar 2
Marathon
9.8 out of 10, Exceptional, (142 reviews)
"Great location and very neat place!"
United States
FERNANDO S.
The price is AED 1,025
AED 2,329 total
includes taxes & fees
23 Feb - 24 Feb
SPECIAL-2 Bed 2 Bath Villa with Cabana Club and Boat Slip 279 nt. Feb 23-Mar 2
TV

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
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 1,576
AED 3,029 total
includes taxes & fees
2 Mar - 3 Mar
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Outdoor dining

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA
Duck Key
9.4 out of 10, Exceptional, (32 reviews)
"A short weekend getaway was made perfect in this villa. The location is idyllic; especially the balcony overlooking the bay with a perfect sunset view. The home was well-appointed, simple yet all the necessities were covered. Communication with the property manager was excellent. Definitely will book again. "
United States
Natasha A.
The price is AED 1,539
AED 2,984 total
includes taxes & fees
3 Mar - 4 Mar
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA
Outdoor dining

Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Tiny Villa, Big Ocean Views| Breathtaking Sunsets
Duck Key
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful views. Very nice accommodations. Wonderfull location!"
United States
michael h.
The price is AED 1,535
AED 2,763 total
includes taxes & fees
25 Feb - 26 Feb
Tiny Villa, Big Ocean Views| Breathtaking Sunsets
Exterior

Charming 3-bedroom house featuring a heated private pool.

Charming 3-bedroom house featuring a heated private pool.
Duck Key
10.0 out of 10, Exceptional, (7 reviews)
"We were the first guests to this villa, Fantastic villa great service from the host and swift response to messages. Amazing location, very clean and tidy, great furniture. Amazing private pool deck. My only negative would be the aircon is very very noisy in the master bedroom. To sum up. Amazing "
United Kingdom
John W.
The price is AED 1,837
AED 3,474 total
includes taxes & fees
7 Mar - 8 Mar
Charming 3-bedroom house featuring a heated private pool.
Outdoor dining

Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!

Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!
Marathon
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 2,461
AED 5,306 total
includes taxes & fees
4 Mar - 5 Mar
Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!
Exterior

4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request

4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request
Duck Key
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 3,486
AED 6,165 total
includes taxes & fees
23 Feb - 24 Feb
4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request
Interior

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

Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available
Duck Key
The price is AED 3,118
AED 5,671 total
includes taxes & fees
16 Feb - 17 Feb
Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available
Outdoor dining

Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!

Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!
Marathon
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 1,910
AED 4,605 total
includes taxes & fees
22 Feb - 23 Feb
Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!
Exterior

Heated Pool, Views, Vaca Cut , Gulf & Atlantic Access. Availability Nov + Dec

Heated Pool, Views, Vaca Cut , Gulf & Atlantic Access. Availability Nov + Dec
Coral Lagoon
10.0 out of 10, Exceptional, (272 reviews)
"Excellent stay for a family."
United States
Sandra P.
The price is AED 1,818
AED 3,453 total
includes taxes & fees
10 Mar - 11 Mar
Heated Pool, Views, Vaca Cut , Gulf & Atlantic Access. Availability Nov + Dec
Terrace/patio

Charming 2-bedroom house in Marathon with pool

Charming 2-bedroom house in Marathon with pool
Marathon
8.0 out of 10, Very Good, (2 reviews)
"Great Home & Location & Enjoyable Stay! Thanks!"
United States
James J.
The price is AED 1,557
AED 3,330 total
includes taxes & fees
13 Mar - 14 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

Kingsail Resort

Kingsail Resort

10/10 Excellent
"Staff was very pleasant (even apologetic for the cooler than usual temperature!). Rooms were a bit dated but the overall quality of our stay was very good."
Don 2-night trip
Posted 2 days ago
Kingsail Resort