Holiday houses 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.

Location · Value · Laundry

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!✨

Location · Family · Decor

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

Location · Family · Kitchen

Discounts all Fall! Private Pool, SUPs, Kayak!

Paradise Awaits You!! With a Beautiful Private Pool, 40’ Dock, Kayaks, SUPs, & Bikes; Welcome to Paradise is the Perfect Place to Stay & Play in the Sun & on the Water! Our home w Breezy Palms is centrally located w Beaches, Boating, Fishing, Diving, Swimming, Dining & Refreshing Cocktails just minutes away! We are owners, Luis & Aysie. We put all our love of the Keys into our home, & we just know you will love it too. Message us or book instantly & start planning your trip to Paradise!

Location · Value · Parking

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.

Location · Value · Cleanliness

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!

Value · Family · Biking

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.

Location · Value · Air conditioning

Perfect escape to the ocean

Enjoy the sounds of nature when you stay in this unique place. What awaits you is fun filled days living and exploring out on the fabulous florida keys waters in your own private floating paradise that is completely solar powered and all the amenities run 24/7! This fabulous floating home was build in 2025 and very nice, update and comfortable, it is 100% solar powered and eco friendly All the amenities run off batteries and solar power so you'll be able to enjoy cold ac, fridge, tv , 24/7

Location · Family · View

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!

Location · Value · Pets

Beautiful Large Waterfront Private Property

This property is like having your own private resort. Beautiful water veiws & sunsets. 4BR + bonus room w/queen bed & futon. 2 full bathrooms 4 TVs. Pool, Private Dock. Watch the Dolphins daily. We a located next to the World-Famous Dolphin Research Center. House has wrapped around deck plenty of seating inside/out. Large private yard with plenty of room for all your needs. Walking distance to restaurant SS Wreck at end of driveway , marina. Kayaks/Paddleboard mostly available.

Location · Value · Pool

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)

Location · Family · Sleep quality

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”.

Value · Location · Indoor spaces