Vacation rentals in Grassy Key

Beach House, Private Pool, Dock, Gulf View Sunsets

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.

NEW!The Hideaway~Pool~Pickleball~Putt-Putt~Kayaks!

NEW RENO! Welcome to The Keys Hideaway! 🌴🍍 The ✨ONLY✨ house in Marathon with its own private Pickleball Court and 4-Hole Putt-Putt Course!! Live your dream getaway in this Gorgeous 3BR Paradise in the heart of the Florida Keys. Sip a cold drink by your private pool🍹, play Pickleball🎾, enjoy Putt-Putt⛳, paddle out on a Kayak🌅, enjoy a bike ride🚲, or play Ping-Pong🏓, end the day with a family cookout🔥 At The Hideaway, you’ll have it all, adventure, relaxation, and unforgettable memories!✨

SAY'S BY THE SEA

Oceanfront 2BD/2BA and separate 1BD/1BA pool-side overlooking the Atlantic* Enter your paradise dream home with stunning views and privately nested away from the big city noise. You'll be staying in our large three bedrooms and three baths secluded retreat with a large terra overlooking the Atlantic Ocean. The home's rooftop deck on the third floor offers a panoramic and open observatory which is great for catching rays, watching sunrises, sunsets and shooting stars. RENTAL LICENSE #VACA-22-30

Luxury Boating Paradise+Pool+Sailing Kayaks

Captains Quarters, Your 4BR Waterfront Oasis on a deep-water ocean canal. This meticulously remodeled home provides a unique unforgettable Florida Keys experience for your entire family. 🏊‍♂️ Luxury heated pool & spillover spa ⛵ Private 75ft dock with sailing kayaks for ocean adventures 🕹️ Epic game room with Golden Tee, Pack Man, foosball table, Ping Pong & Infinity Game Table 🍳 Outdoor patio with BBQ grill & waterfront dining 💻 High-speed Wi-Fi for streaming & remote work 🛏️ Comfortable

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Tiny Home Aqua Lodges 2/1

This memorable place is anything but ordinary. Stay in our fully equipped aqua lodge with private surroundings. This lodge has 1 queen bed, 1 full bed, a sofa sleeper full size on the main floor, and 1 twin in the loft. It has a full kitchen, mini split ac, and full bathroom with hot water. This location has great sunset views and private BBQ waterfront area. All lodges have all bedding and dishes and cooking utensils. You will also have access to the Cabana Club located in Key Colony Beach.

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!

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock

Wake up to open-water views at your private oceanfront retreat in Marathon. Bring the boat, step into your private pool, Perfect for families and boating groups.Your private 60' dock offers direct water access, freshwater for rinsing gear and flushing engines, while parking accommodates up to 4 vehicles. • Direct oceanfront setting • Private swimming pool • Private 60' boat dock • Complimentary kayaks • Sleeps up to 10 • Parking for 4 vehicles • Wi-Fi + dedicated workspace

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

P58 - Gulf Front Luxury 4 bedroom 4 bath with priv

This beautiful Polynesian style home offers 4 bedrooms, 4 baths, beautifully landscaped grounds and a large, private, heat optional pool. Ideally located on the open water of the Gulf of Mexico the views are unlike any other. Located in Grassy Key, this allows guests to be away from the hustle and bustle of Marathon traffic. - Maximum Occupancy: 8 guest (includes adults and children of any age) (*children of any age, including infants, count toward occupancy)

Oceanfront w/ Dock, Kayaks, 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”.

Private Pool Tropical Oasis - Centrally Located

Centrally located in the Florida keys, this beautiful three-bedroom home is steps away from fishing, restaurants, boat rentals and water sports. The property features a private and lush backyard filled with your own private pool, loungers and outdoor games. In the evening, unwind with a refreshing drink under the outdoor lighting or in the heated pool. The villa includes a high chair, pack and play, bed rails, booster seat, baby gate and kids dishware.