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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Grassy Key vacation homes

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1. 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, (36 reviews)
"We had a great stay!!"
United States
lissa h.
The price is ￥28,397
￥86,098 total
includes taxes & fees
Aug 13 - Aug 14
Charming 3-bedroom house featuring a heated private pool.
Outdoor dining

2. Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Tiny Villa, Big Ocean Views| Breathtaking Sunsets
Duck Key
9.8 out of 10, Exceptional, (20 reviews)
"This was without a doubt one of the nicest places we have ever stayed! Our hostess was PHENOMENAL and went above and beyond to be sure we were comfortable and had everything we needed for our stay. Literally the best vacation we’ve had!!!’ I suggest this place to everyone!"
United States
Stephanie
Tiny Villa, Big Ocean Views| Breathtaking Sunsets
Property grounds

3. 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, (55 reviews)
"Very nice villa "
United States
Grace L.
The price is ￥32,822
￥86,165 total
includes taxes & fees
Aug 11 - Aug 12
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Outdoor dining

4. 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, (165 reviews)
"Kitchen was well-equipped. Views were spectacular and the peaceful setting was everything we needed and hoped for! Would definitely consider this place for a future stay. My kids' favorite feature was the nearby Cabana Club!"
United States
Ryan K.
The price is ￥67,048
￥178,250 total
includes taxes & fees
Aug 18 - Aug 19
Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!
Property grounds

5. 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 ￥56,005
￥110,177 total
includes taxes & fees
Aug 11 - Aug 12
Waterfront villa Family Friendly 2 bedroom
TV

6. 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, (16 reviews)
"Everything was perfect. Great place to stay"
United States
Kirk r.
The price is ￥44,812
￥101,232 total
includes taxes & fees
Sep 9 - Sep 10
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Outdoor dining

7. 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
9.0 out of 10, Wonderful, (4 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 ￥47,328
￥153,855 total
includes taxes & fees
Aug 17 - Aug 18
Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!
Interior

8. 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 ￥98,766
￥200,226 total
includes taxes & fees
Aug 11 - Aug 12
Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available
Exterior

9. 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, (10 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 ￥107,758
￥211,446 total
includes taxes & fees
Aug 11 - Aug 12
4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request
Outdoor pool, pool umbrellas, sun loungers

10. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.0 out of 10, Wonderful, (141 reviews)
"This was the perfect place, right on the ocean and a full kitchen so you can cook your own meals. The room was very clean, I loved that they had a laundry basket and laundry detergent in the room for you, came in handy seeing as we stayed for 7 days. Amazing place to watch the sunset from a hammock and we got lucky enough to see some nurse sharks at the docks right outside of our hotel."
United States
Andrew Jackson
The price is ￥24,003
￥31,441 total
includes taxes & fees
Sep 7 - Sep 8
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
Outdoor dining

11. Waterfront / Ocean Access Canal / Kamp Key / Homes

Waterfront / Ocean Access Canal / Kamp Key / Homes
Matecumbe
10.0 out of 10, Exceptional, (2 reviews)
"Excellent house. Very clean. We had a little trouble with the check in code and we were immediately contacted and the code was changed and we were in within minutes. The maintenance guy stopped by to make sure we got in and everything was good. EXCELLENT Customer Service!!!!!House was very well stocked with pots and pans and misc things needed for a week stay! Right on a nice little canal with plenty of room for our boat."
United States
Mike H.
The price is ￥65,328
￥144,902 total
includes taxes & fees
Sep 8 - Sep 9
Waterfront / Ocean Access Canal / Kamp Key / Homes
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

Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

10/10 Excellent
"I did not have my itinerary from Expedia and raised an issue about the bill with the front desk. The representative explained how the discount normally applied. I believed it to be different. I found the itinerary and the representative was absolutely correct. The representative still provided me an additional credit which they did not have to do as the issue was my error. Very nice gesture by them. We have stayed at the hotel before and enjoyed our stay as always. The food we ordered at the Tiki Bar was delivered hot and was very good on each occasion we ordered. Staff was great both inside the hotel and at the pool and Tiki Bar. Great location, great service and great time. We can't wait to go back."
David 4-night trip
Posted less than an hour ago
Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

Find out more about Grassy Key

Grassy Key Vacation Homes information

Number of reviews
Accommodation
1256 Vacation Homes
Lowest Price
￥31,441
Highest Price
￥31,441

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