Vacation rentals with a pool in Duck Key

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Top-rated rentals with a pool in Duck Key

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Guest favourite

Townhouse in Duck Key

4.97 out of 5 average rating, 59 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.

Aug. 24 – 31

$528 CAD per night

Guest favourite

Villa in Duck Key

4.98 out of 5 average rating, 57 reviews

Waterfront Island Escape with Private Plunge Pool

Come and relax in your own private plunge pool that overlooks a turquoise canal on the beautiful Duck Key. The outdoor living space is quiet and serene, making it a perfect place to unwind. Families and honeymooners alike can enjoy this island oasis. Centrally located at Mile Marker 61, Duck Key is just a short drive to Key West. Explore everything the Florida Keys have to offer or stay locally to enjoy world-renowned restaurants, fishing, snorkeling, and diving. The opportunities are endless.

Aug. 29 – Sep. 5

$601 CAD per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 17 reviews

Grouper Getaway @ Ocean Isles Fishing Village

Escape to paradise at the Grouper Getaway located at Ocean Isles Fishing Village in Marathon Key, FL. This beautifully Brand New fully furnished 1 bed/2 bath studio townhouse, offers a central location and an array of luxurious amenities for a truly unforgettable vacation. Steps away from the the Atlantic ocean, enjoy the largest pool in Marathon with clear views of the VACA Cut boat traffic and the Sombrero Light House. Enjoy fishing, paddle boarding, kayaking, tiki huts, beach, and grills.

May 8 – 15

$274 CAD per night

Guest favourite

Guest suite in Marathon

4.98 out of 5 average rating, 185 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

Oct. 12 – 19

$348 CAD per night

Guest favourite

Home in Marathon

4.95 out of 5 average rating, 41 reviews

Florida Keys Cottage with Pool - Hawks Cay Resort

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.

Aug. 21 – 28

$697 CAD per night

Guest favourite

Condo in Key Colony Beach

4.91 out of 5 average rating, 197 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Beautiful studio condo on the 1st floor only steps away from the private beach and heated pool. Condo features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Oct. 29 – Nov. 5

$539 CAD per night

Superhost

Villa in Marathon

4.89 out of 5 average rating, 145 reviews

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!

Apr. 3 – 10

$697 CAD per night

Guest favourite

Townhouse in Marathon

4.97 out of 5 average rating, 116 reviews

Boater’s Paradise 3br/2.5ba waterfront with slip!

Spectacular PET FRIENDLY 3 bed/2.5 bath 1350sf villa in beautiful Coral Lagoon, complete with a 40 foot wet slip and all the amenities! Spread out and enjoy the spacious, clean interior with free high speed wifi. Step outside to your boat and enjoy all the Gulf and Atlantic have to offer - both easily accessible in minutes. Relax with a drink at the pool after a long day of fun in the sun. NEW in 2021! Mattresses, bedding, towels, appliances, paint, grill, dinnerware.

Nov. 30 – Dec. 7

$885 CAD per night

Guest favourite

Home in Marathon

4.99 out of 5 average rating, 106 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

2024 - New Weber grill This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Aug. 24 – 31

$687 CAD per night

Guest favourite

Home in Marathon

4.97 out of 5 average rating, 33 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

You don't come to the islands to stay in a town! Relax in our tropical paradise beach home away from the traffic and noise of US Hwy #1. The perfect location has now been turned into the perfect oasis. Special features include a gourmet kitchen, private pool surrounded by lush landscaping, private 300' pier/dock with a fish cleaning station. Our guests enjoy luxury bedding with quality linens, fluffy towels and bathrobes. Wireless internet service and cable tv.

Dec. 14 – 21

$961 CAD per night

Guest favourite

Condo in Key Colony Beach

4.91 out of 5 average rating, 112 reviews

Beachside Unit 39 Tiki Huts, Private Beach & Pool

Unit 39 Details: Second Floor Unit, Tub with Shower, Two Queen Beds, 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. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

Aug. 22 – 29

$370 CAD per night

Guest favourite

Home in Duck Key

5.0 out of 5 average rating, 31 reviews

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.

Nov. 20 – 27

$905 CAD per night