A dolphin swimming near a wooden dock and a tree branch in the water.

Holiday Homes in Grassy Key

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Grassy Key holiday homes

A resort with a pool, lounge chairs, and a view of the ocean.

1. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.2 out of 10, Wonderful, (147 reviews)
"It is an excellent place."
United States
Arianna
The price is €205
includes taxes & fees
29 Oct - 30 Oct
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
A covered outdoor area with a ceiling fan, a view of the sea, and a distant building.

2. 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)
"Great location. Pretty views of Bay. Comfortable rooms. Enjoyed our brief stay for July 4th."
United States
Jorge D.
The price is €468
includes taxes & fees
12 Oct - 13 Oct
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
A dining area with a round glass table, white chairs, and a chandelier. There is a sofa and a window with blinds in the background.

3. Waterfront Retreat

Waterfront Retreat
Duck Key
10.0 out of 10, Exceptional, (38 reviews)
"Really enjoyed our stay at Casa Wahoo! Very clean! Beautiful community."
United States
Joseph C.
Waterfront Retreat
A bedroom with a large bed, a balcony with a view, and a ceiling fan.

4. Villa 7079 on Duck Key - Boat Slip Available

Villa 7079 on Duck Key - Boat Slip Available
Marathon
Villa 7079 on Duck Key - Boat Slip Available
A living room with a sofa, two armchairs, a coffee table, and a ceiling fan. There is a large window with a view of the beach and a patio area with outdoor furniture.

5. 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.
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
A covered outdoor area with a table set for dining, overlooking a body of water and buildings.

6. 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
9.2 out of 10, Wonderful, (5 reviews)
"Place was perfect. Property manager was amazing and always answered questions within minutes. Definitely would stay again"
United States
lori p.
Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!
A spacious living area with a sliding glass door leading to a deck, a sofa, a coffee table, and a kitchen area with wooden cabinets and appliances.

7. 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, (45 reviews)
"We had a great stay!!"
United States
lissa h.
The price is €683
includes taxes & fees
13 Oct - 14 Oct
Charming 3-bedroom house featuring a heated private pool.
A covered outdoor dining area with a view of a turquoise pool and palm trees.

8. 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, (166 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.
Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!
A modern kitchen with a large island, pendant lights, and a view to the outside.

9. 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
10.0 out of 10, Exceptional, (1 review)
"Very relaxing, we were in the keys for my 65th it could not have been better.Thank you again!"
United States
Anonymous traveller
Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available
A coastal residential area with houses featuring grey roofs and surrounded by lush greenery.

10. 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
9.8 out of 10, Exceptional, (13 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.
4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request
A hammock, outdoor seating, and a view of the ocean.

11. Marathon Oceanfront 4BR, 3.5BA Private Pool 60’ Boat Dock

Marathon Oceanfront 4BR, 3.5BA Private Pool 60’ Boat Dock
Marathon Shores
10.0 out of 10, Exceptional, (2 reviews)
"This was our 3rd time staying at this property in Marathon. We always enjoyed our stay but this time the updates to the home were nice and the owners were very efficient at getting back with us on any questions we had!"
United States
Hannah M.
Marathon Oceanfront 4BR, 3.5BA Private Pool 60’ Boat Dock
A room with two beds, a ceiling fan, and framed pictures on the wall.

12. Easy Breezy Family Complex 5BR 3BTH 100ft Dock, Pool, & Beach!

Easy Breezy Family Complex 5BR 3BTH 100ft Dock, Pool, & Beach!
Marathon
The price is €1,457
includes taxes & fees
18 Oct - 19 Oct
Easy Breezy Family Complex 5BR 3BTH 100ft Dock, Pool, & Beach!
A balcony with a view of the sea, a dining area with chairs and a table, and a ceiling fan.

13. Beach Residence Private Overwater Dock Heated Pool Mahi Key

Beach Residence Private Overwater Dock Heated Pool Mahi Key
2.0 star property
Matecumbe
The price is €2,273
includes taxes & fees
14 Oct - 15 Oct
Beach Residence Private Overwater Dock Heated Pool Mahi Key
A two-story building with a pool, a boat dock, and a table set for dining.

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

Waterfront / Ocean Access Canal / Kamp Key / Homes
Matecumbe
8.8 out of 10, Excellent, (5 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.
Waterfront / Ocean Access Canal / Kamp Key / Homes
A balcony with a view of the ocean, furnished with a table and chairs, and palm trees.

15. 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, (4 reviews)
"Our stay here was very nice. Everything was clean and comfortable. The pool was enjoyable the one time we used it. Sitting on the deck gazing out to sea was exactly what I needed. Spotting a crocodile swim by was exciting!"
United States
Anonymous traveller
The price is €1,844
includes taxes & fees
13 Oct - 14 Oct
Private Beach / Private overwater dock / Heated Pool / Mahi 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

Captain Pips Marina & Hideaway

Captain Pips Marina & Hideaway

10/10 Excellent
"Anna, Katelyn and Penny at the front desk are ALWAYS helpful! This keeps us coming back! Beautiful facility on the Bayside. Big rooms, Great fishing, Great Kayaks in Lagoon.Great location! They are great on the little things too that matter. Greatest and Cheapest boat rentals !"
Joseph 1-night trip
Posted 9 hours ago
Captain Pips Marina & Hideaway

Find out more about Grassy Key

Grassy Key Holiday Homes information

Number of reviews
337
Accommodation
1264 Holiday Homes
Lowest Price
€205
Highest Price
€2,273

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