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Our top choices for Grassy Key vacation homes

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, (52 reviews)
"It was a pleasant stay and the host was prompt when reaching out to him."
United States
Jill B.
The price is AED 1,025
AED 2,332 total
includes taxes & fees
25 May - 26 May
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Tiny Villa, Big Ocean Views| Breathtaking Sunsets
Duck Key
10.0 out of 10, Exceptional, (16 reviews)
"Nice place, clean, relaxing, and well maintained, with great communication from the host. It was a wonderful and relaxing getaway with our family. They offer a military discount, which we truly appreciated. We all enjoyed our stay. We will definitely be back for a longer stay."
United States
Mario S.
Tiny Villa, Big Ocean Views| Breathtaking Sunsets

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, (36 reviews)
"The ease of check in and checkout. "
United States
teressa v.
The price is AED 1,025
AED 2,332 total
includes taxes & fees
25 May - 26 May
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

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

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.0 out of 10, Wonderful, (14 reviews)
"Everything was perfect. Great place to stay"
United States
Kirk r.
The price is AED 1,172
AED 2,534 total
includes taxes & fees
26 May - 27 May
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

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
8.8 out of 10, Excellent, (3 reviews)
"Place was perfect. Property manager was amazing and always answered questions within minutes. Definitely would stay again"
United States
lori p.
The price is AED 1,267
AED 3,794 total
includes taxes & fees
25 May - 26 May
Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!

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, (25 reviews)
"Left to go to key west decided to stay here on our drive back up because we enjoyed it so much!"
United States
Regan C.
The price is AED 1,466
AED 3,001 total
includes taxes & fees
10 Jun - 11 Jun
Charming 3-bedroom house featuring a heated private pool.

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 2,163
AED 4,487 total
includes taxes & fees
25 May - 26 May
Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available

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, (163 reviews)
"Everything was as advertised. Meredith was so helpful and on it. Very well maintained and clean. "
United States
John J.
The price is AED 1,899
AED 4,578 total
includes taxes & fees
4 Jun - 5 Jun
Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!

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)
"House was awesome, great shape, comfortable beds, clean. Great location, it was central to all the keys. Would definitely stay again "
United States
gabe h.
The price is AED 3,302
AED 5,845 total
includes taxes & fees
26 May - 27 May
4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request

Waterfront villa Family Friendly 2 bedroom

Waterfront villa Family Friendly 2 bedroom
Duck Key
8.6 out of 10, Excellent, (14 reviews)
"We were very pleased with our stay. "
United States
Jeffrey S
The price is AED 1,304
AED 2,543 total
includes taxes & fees
22 May - 23 May
Waterfront villa Family Friendly 2 bedroom

SOMBRERO BEACH LARGE 4/3 HOME w/ HEATED POOL, 40 ft BOAT DOCK, BEACH NEARBY

SOMBRERO BEACH LARGE 4/3 HOME w/ HEATED POOL, 40 ft BOAT DOCK, BEACH NEARBY
Marathon
9.8 out of 10, Exceptional, (63 reviews)
"This was our second time staying in this house lots of room great location."
United States
Anonymous traveler
SOMBRERO BEACH LARGE 4/3 HOME w/ HEATED POOL, 40 ft BOAT DOCK, BEACH NEARBY

Luxurious 3-bedroom home with Pool and Dock in Key Colony Beach

Luxurious 3-bedroom home with Pool and Dock in Key Colony Beach
Coury
10.0 out of 10, Exceptional, (6 reviews)
"Great location, great water access, very clean and well kept!"
United States
trevor l.
The price is AED 2,204
AED 6,885 total
includes taxes & fees
12 Jun - 13 Jun
Luxurious 3-bedroom home with Pool and Dock in Key Colony Beach
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