Holiday 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 Modern*3/2Duplex/37' Dock/Cabana/Kayaks/Bikes

Perfectly situated in KCB w/ 37.5' of dockage on a wide and pristine canal that leads easy access to both the Ocean & the Gulf, our newly listed 1/2 duplex is newly renovated w/ brand new AC, appliances, fixtures, furniture, mattresses, & decors. Featuring 3BR 2BA accommodating up to 8 ppl in a large & open living room & backyard, provided w/ multi-game table, bikes, kayaks, 6-burners grill, 2 mins walk to Sunset park, & Cabana Club access, it is the perfect Florida Keys getaway for your family.

Viamarhe House-Private beach, Kayak, yard games

If you are looking to enjoy the natural beauty and the captivating views of the Florida Keys, our charming Oceanfront house is the place for you. Enjoy the breathtaking views of the sunrise and the starry night show over the beautiful Atlantic ocean. You and your family can enjoy the exclusivity this property will give you, Viamarhe is its own little resort, 5 kayak and fishing rods, volleyball, chess and bowling ground, Domino, Billiards, Ping-Pong, and Football. the propane BBQ grill, fire pit

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!✨

Grassy Key Ocean Front Beach House

HEATED POOL $150 weekly. Experience relaxed island luxury with no neighbors within a block of the property, located on Grassy Key in the Middle Keys. Perched directly on the Atlantic with an unobstructed view, the property sits on private acreage and was designed to maximize the ocean panorama from every level. Whether you want to watch sunrise from the balcony, dine under the tiki hut, beside the oceanfront pool while listening to the surf, this is a place to reconnect with family and friends.

Beautiful Waterfront book now 2026 filling up fast

This property is like having your own private resort. We are on the Gulf of Mexico with a Million-dollar waterfront view & 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, marina. Kayaks/Paddleboards mostly available.

Paradise in the Keys

Welcome to Pura Vista otherwise known as Pure Views. Come enjoy a delightful stay at this beautiful direct waterfront property in the Florida Keys for your getaway. Breath taking views of the Atlantic Ocean and direct ocean access to the best boating activities in the warm turquoise waters of the Florida Keys. Well equipped with commodities to help your stay be the best. A great location to discover everything the Florida Keys has to offer. We look forward to hosting your stay! VACA – 22 - 376

Villa 5008 on Duck Key - Boat Slip Available

Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors and NO pets.

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!

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in the beautiful Florida Keys! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

Aquahouse Paradise easy access to the ocean

Take it easy at this canal front with quick acces to the ocean unique and tranquil getaway. Big Pine Key, know it for the key deers, one of the only 2 places in the entire world where you can interact with this endangered species. you can feed it during night they love bread and eggplants, here you can enjoy the florida weather conditions all year long. lot of activities. only 30 miles away from Key West. 2 miles from supermarket,pharmacy, hardware and auto parts.

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)