Holiday rentals in Duck Key

4.98 out of 5 average rating, 93 reviews

Waterfront Retreat

BOAT SLIP - We have an exclusive relationship for Casa Wahoo with a local marina. If you are bringing a boat down to enjoy the beautiful Florida Keys, we want to help! We are able to secure local prices for our listing. Although the price changes daily, a wet slip will average around $75 per day. Please ask directly for more details, if you are wanting to bring your boat. Casa Wahoo is a (2) Bedroom (2 and half) Bath townhouse located on Duck Key, within the Hawk's Cay Resort that comfortably sleeps (6). This light-filled waterfront property hosts a plunge pool and outdoor enclosed and private patio space that you will likely find to be the main gathering spot for your family and friends during your stay. Duck Key is located at mile marker 61, along the overseas highway. You can travel to Key West for the day, which is about an hour and a half drive.

4.8 out of 5 average rating, 137 reviews

Villa 5103 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.

5 out of 5 average rating, 73 reviews

Duck Key *Delight* private plunge pool

This beautiful townhouse was remodeled in late 2021 with a modern tropical inspired scheme. High speed internet-1,000 mbps, and 4K Smart TV's provide great entertainment. The patio's lush landscape with torches create a cozy setting at night and during the day the water sounds over the plunge pool allow for relaxation and fun. Take a break, lounge, have a morning cup of coffee and observe nature wake up. Explore close by fun tropical activities and great restaurants. Delve into Conch life!

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 109 reviews

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!

4.94 out of 5 average rating, 90 reviews

Conch Cottage at Hawks Cay - Chic Tropical Retreat

Welcome to our tropical Conch Cottage, a lovely place to create memories on your idyllic Florida Keys vacation in paradise. Our stylish waterfront villa sits alongside a clear turquoise canal on picturesque Duck Key, inside the Hawk's Cay resort, and just 10 minutes from busy Marathon. Get involved in on-site activities like snorkeling, scuba diving, fishing, boating and dolphin encounters—or simply lay out on the coral stone patio, soak up the sun, and slide into your private plunge pool.

4.95 out of 5 average rating, 140 reviews

Villa in Duck Key

Beach House - Kayaks & 2/2.5 Villa

Welcome to Beach House Getaway, a charming villa tucked away on the serene island of Duck Key and perfectly situated in the heart of the Florida Keys. Nestled between Key Largo and Key West, Duck Key serves as a peaceful yet convenient base for your island getaway. Its central location means you’re just a short drive from some of the most iconic destinations in the Keys, including the natural wonders of Bahia Honda State Park, the famous waters around Islamorada, and the lively Key West.

4.8 out of 5 average rating, 270 reviews

Boat in Marathon

Paradise awaits on this cozy houseboat!

Our vision is for you to kick back, relax, and find your home away from home! Wether you want to celebrate with your loved one or retreat by yourself this floating home offers comfortable space for 2 adults. Located near the 7 mile bridge in Marathon Florida on the Atlantic Ocean nestled in a quiet, reserved mangrove area. This spot is fantastic because you have unparalleled access to out of this world sunset/sunrise views. Kayak through the mangrove and explore the surrounding areas.

4.95 out of 5 average rating, 116 reviews

Home in Key Colony Beach

Waterfront Home 37.5-ft dock, Cabana Club Included

Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

4.84 out of 5 average rating, 176 reviews

Vibrant Beachfront Villa

Welcome to Beachfront Villa that has recently been renovated. The 2 bedroom 1.5 bath luxury villa is located in the popular area of Duck key alongside of Hawks Cay Resort. Duck Key marina is located across the street where you can dock your boat or charter a boat for the day. Enjoy stunning sunset views from the back porch. Kitchen includes all amenities including silverware ,plates , cups , and pots. Linens and towels provided. *** Pets welcome with host approval and pet fee. ****

4.83 out of 5 average rating, 148 reviews

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.

4.92 out of 5 average rating, 193 reviews

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!!

4.91 out of 5 average rating, 320 reviews

Villa in Marathon

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!

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Popular amenities for Duck Key holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Duck Key

5 out of 5 average rating, 12 reviews

Luxury 5Bdrm/6bath New in 2024

CatherineRating, 5 stars2 weeks ago

Timothy’s house was spacious, comfortable, and clean. The pool was a great way to beat the Florida Keys heat and the sunset views from the 3rd floor were awesome! Boaters will love the boat ramp next door. The fish cleaning table and outdoor freezer were a huge plus.

4.86 out of 5 average rating, 7 reviews

Hotel room in Marathon

Breathtaking Waterfront Hotel w/ / Outdoor Pools

KevinRating, 5 stars3 months ago

This place has it all , great property, food and location. Wish we had a few more nights

5 out of 5 average rating, 4 reviews

The Roseate House at Grassy Key

MollyRating, 5 stars2 weeks ago

I don’t even know where to begin. From start to finish, our stay was absolute perfection. The views could not be beat. There are kayaks to venture out into the gulf and the mangroves, a pool that’s COOLED (you know how hot pools can get during the summer. It was so refreshing) and a garden oasis full of some of the most beautiful foliage I’ve ever seen. I’m from Charleston, SC. I’m used to waterfront living, but this was just something more magical than I could’ve ever predicted. I’m already planning my trip back for next year. Heidi left a great list of recs for restaurants and activities to do, but the property was so incredible, I only left to eat really. If you’re looking for a relaxing place to stay, with on site water days this is the place for you. The house is nice, but also has that old school beach vibe which is my absolute favorite. I just can’t say enough good things. Thank you so much, Heidi, for sharing your stunning home with us.

4.73 out of 5 average rating, 22 reviews

Private room in Marathon

Viamarhe Cabin-Private beach, Kayak, yard games

StephanieRating, 5 stars3 weeks ago

We stayed for a week and loved our stay, the location was perfect for getting to all the places we wanted to see, the amenities we’re great for being able to make food at the B&B, we enjoyed the view and sitting in the hammock. Beautiful place. If you go walking the ocean recommend staying away from the resort on the left-hand side of the property due to they’re being sinking sand over there.

4.89 out of 5 average rating, 9 reviews

Water View Keys Retreat: Waterfront Villa Duck Key

LuisRating, 5 stars2 months ago

Great location if you are staying in The Keys.

5 out of 5 average rating, 21 reviews

Villa in Marathon

Seas the Keys Getaway with plunge pool/spa

JenniferRating, 5 starstoday

The location was ideal for driving to various local attractions. We also walked over to Hawks Cay and had a lovely visit with the dolphins, which was an awesome experience! The house was perfect for our stay and the plunge pool was a great amenity that we took full advantage of!We had a great vacation!

Townhouse in Marathon

4.78 out of 5 average rating, 54 reviews

Beachy Townhome Perfect For A Relaxing Getaway!

DoranRating, 5 stars1 week ago

Very cute spot. Worked well for our family of 5. Close to Marathon restaurants, grocery stores etc. My kids loved fishing in the canals.