Vacation rentals in Grassy Key

Key Colony Beach Luxury Condo, New Modern Interior

Private studio condo at Key Colony Beach with a private balcony, heated pool and sandy beach. Unit #15 was recently renovated and offers one comfy King size bed and a fully equipped kitchen with essentials (stove, oven, toaster, microwave, blender, fridge, cooking utensils). Wifi, Amazon Echo and a TV. Enjoy a short walk to Sunset Park next door to experience a stunning Florida Keys sunset. Guests also have access to a private beach with lounge chairs, patio tabales, tiki huts, and BBQ grills.

Beach House, Private Pool & Dock, Gulf Sunset view

You don’t come to the islands to stay in a town—you come to slow down. Welcome to our tropical keys beach home, tucked away from the traffic and noise of US Hwy #1. Sway with the palms on the wraparound deck, soak in wide-open panoramic bay views, and catch fiery sunsets right off your dock. Fire up the BBQ, brew a Keurig, float in the private pool, or cast a line from the 300’ private pier/dock. Easy going island living with ocean / gulf breezes, comfy beds, quality linens, Wi-Fi, and cable TV.

Casa de Lolo

Located in beautiful Key Colony Beach, an exclusive community near Marathon, about 2 hours from Miami or Key West. This 2 bed / 2 bath half duplex is the ultimate tropical escape with a tiki hut and balcony that invite you to relax and outdoor dine with your very own grill. The space comfortably sleeps up to 4 plus your pup. Cabana club inc Sleeping arrangements: --Primary bedroom with a plush king bed and ensuite bathroom --Guest room with two twin beds (can convert into a king for a couple)

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

7 DAY MINIMUM BOOKINGS / MAX 4 PERSONS NAUTI HIDEAWAY - This Nauti Stays Vacation Rental property is a 2-bedroom, 2-bath 2nd level 925 sq ft. condo located in Coco Plum, Marathon. Set in a well-protected, deep canal on the Atlantic, comes with a deep slip (length up to 40 ft) next to pool allowing access to the Atlantic Ocean and Florida Bay. ONSITE boat ramp & trailer (36 ft max) parking! Enjoy a heated or chilled pool after a boat day! Dock has water, power hook ups & fish cleaning station.

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

*NEW LUXURY*Sea Glass with Cabana Club Access

Sea Glass, a stunning beachfront condo that embodies the perfect blend of luxury, comfort, and coastal charm. This brand new, 2-bedroom, 2-bathroom retreat boasts. Expansive pool and beach views from the balcony, perfect for sunrise coffee or sunset cocktails. Prime location, just steps from the ocean's edge and all its amenities Sea Glass is the ultimate beachfront escape, offering a unique combination of style, comfort, and convenience. Make this incredible condo your home away from home.

Ultra Quiet & Peaceful Getaway Marathon Treehouse

Welcome to THE FLORIDA KEYS TREEHOUSE IN MARATHON! A refuge among the trees, The Treehouse is a private and secluded getaway for family & friends, featuring two bedrooms, a super cozy living space, as well as a large deck. Surround yourself with shady trees and enjoy the ocean breeze as you soak in the beautiful Florida Keys. ✰ 3 mins to the nearest Public Boat Ramp ✰ 6 mins to Curry Hammock State Park ✰ 10 mins from Markets & Popular Restaurants Looking forward to hosting you!

The Ocean Beckons! 2/2 Village at Hawks Cay 5047

The Village at Hawks Cay Villa 5047 on Sunset Village Drive is located on Duck Key. Let this astonishing villa be your home away from home for your Next Florida Keys vacation. Captivating decor with the Florida Key in mind will keep you both comfortable and relaxed for your much needed vacation. Sip on your favorite cocktails from the patio overlooking the water or enjoy the water directly from your Villa or walk the waters edge with nature on Duck Key as your own back yard.

Beachside Unit 37 - Come Relax on the Atlantic!

Unit 37 Details: Second Floor, Walk-in shower, Two Queen Beds, Twin Sofa Sleeper, Maximum Occupancy 4 Guests, No elevator on site and Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.” Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean.

Viamarhe Cabin-Private beach, Kayak, yard games

If you are looking to enjoy the natural beauty, and romantic stay in a rear cabin with complete bath and kitchen independent of the main house but with a patio that shares the amenities of games and entertainment of a mini resort our Oceanfront small apartment is the place for you. You and your couple can enjoy the exclusivity this property will give you, like the 5 kayak and fishing rods, volleyball, chess, bowling, carbon and propane BBQ grill, and a fire pit.

Oceanfront w/ Dock, Hot Tub & Secluded

Buchanan Keys Cottage Take a step back into “Old Keys” living. Once Upon A Tide; there was a sense of tranquility & peacefulness found throughout the Keys, like the one you will uncover when choosing to stay at this private, serene, 1/1 oceanfront cottage. Located on Grassy Key, this beautiful home is just 10 minutes from the City of Marathon. Far enough to be away from the hustle & bustle, but close enough to make a grocery/store run a “Keys breeze”.

Cozy Keys Efficiency 8a

Efficiency has a queen size bed, a 3-seat sofa and a small dining table with 2 chairs. Private bathroom. AC will keep you cool. Kitchen is fully equipped with 4 burner stove, microwave, medium size refrigerator with freezer. Enjoy the breezes on your patio, each unit has a gas BBQ grill and a picnic bench outside. Enjoy a swim in our shared pool. Optional boat slip can be rented for $25/night Efficiency has a 2 person maximum occupancy - no exceptions.