Grassy Key Vacation Home Rentals from CA $253: Search Top Private Vacation Homes for Rent

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

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Our top choices for Grassy Key vacation homes

A covered outdoor area with a ceiling fan, a view of the sea, and a distant building.

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

Duck Key

Grace L.

CA $709 total

includes taxes & fees

Sep 28 - Sep 29

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.

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

Duck Key

Kirk r.

CA $742 total

includes taxes & fees

Sep 28 - Sep 29

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

3. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Marathon

Arianna

CA $253 total

includes taxes & fees

Sep 27 - Sep 28

A marina with boats docked, a wooden dock, and a building with a covered area.

4. Waterfront Retreat

Duck Key

Joseph C.

CA $893 total

includes taxes & fees

Oct 24 - Oct 25

A swimming pool surrounded by palm trees and a thatched-roof structure.

5. SC3- Southern Comfort Three at 240 11th St. KCB. Private Pool, Dock & Tiki Bar.

Key Colony Beach

Richard B.

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.

6. Charming 3-bedroom house featuring a heated private pool.

Duck Key

lissa h.

CA $1,166 total

includes taxes & fees

Oct 4 - Oct 5

A modern kitchen with a large island, pendant lights, and a view to the outside.

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

Duck Key

Anonymous traveller

CA $1,487 total

includes taxes & fees

Sep 28 - Sep 29

A bedroom with a large bed, a balcony with a view, and a ceiling fan.

8. Villa 7079 on Duck Key - Boat Slip Available

Marathon

CA $1,373 total

includes taxes & fees

Sep 28 - Sep 29

A coastal residential area with houses featuring grey roofs and surrounded by lush greenery.

9. 4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request

Duck Key

gabe h.

CA $1,726 total

includes taxes & fees

Sep 28 - Sep 29

A two-story building with a pool, a boat dock, and a table set for dining.

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

Matecumbe

"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."

Mike H.

CA $1,408 total

includes taxes & fees

Oct 12 - Oct 13