Holiday rentals with a pool in Duck Key

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.

Family · Value · TV

Charming 2BR cottage in prime keys location w/pool

Your slice of Islamorada awaits at Key Lime Cottage! Step inside this 2-bedroom retreat and you’ll instantly feel at home. Tucked in a quiet neighborhood yet right in the heart of the Florida Keys, it’s the perfect blend of relaxation and convenience. Enjoy a full kitchen, access to a beautiful pool shared with just six homes, outdoor seating with a grill and fire pit and paddle boards. Whether you’re here to unwind, explore, or fish, everything you need for a perfect Keys getaway is right here.

Location · Value · Barbecue

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!

Value · Location · Nearby

Villa with Pool - Hawks Cay - Duck Key

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.

Value · Location · Quiet

Beautiful View! 3BR 3 BA, Cabana Club Membership!

Sun Kissed Tails in Hawks Cay on Duck Key is a 3 bedroom 3 bath townhome with a fully stocked kitchen in the Hawks Cay resort on Duck Key, MM61. This property does not have a boat slip, but you can possibly rent one based on availability. Enjoy the local beaches a short drive away (Coco Plum Beach and Sombrero Beach) and ENJOY THE POOL AND BEACH AT THE OCEAN FRONT CABANA CLUB, just a 15 drive to Key Colony Beach. The Cabana Club has a pool, Tiki Bar and restaurant, ocean front sandy beach!

Location · Family · Nearby

My Little Oasis2 Waterfront Retreat, Key Largo

Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

Family · Value · Beach

Villa 7205 on Duck Key- Boat Slip Available

We offer a newly renovated Sanctuary Villa located on the island of Duck Key. This 3 bedroom 3 bath villa sleeps 8 people comfortably. Features: You’re own Private pool/Splash tub is set at 81 degrees. Boat slip is additional $100/per night(ask for availability) Downstairs bedroom w/ King bed and full bath on first floor 2 bedrooms upstairs and 2 full bathrooms Park 2 cars in our private car port, additional free parking available onsite. EV charger available for extra charge$

Location · Family · Comfort

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!

Location · Value · Heating

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.

Family · Location · Cleanliness

4BR 3B, Heated Pool & Spa, 60' Dock

Enjoy breathtaking views of the Gulf and Ocean from the screened in patio of this beautiful 4 BEDROOM/3 BATH canal front home. Bring your boat to the 60' dock on a 200' wide canal just 10' away from the Ocean. Relax by the pool/spa area after a day of fishing. A pool heater is offered as an option for your convenience. Please inquire about water heater fee and operating instructions before booking. (VR Lic # PLR2020-00104)

Family · Location · Nearby

Villa in Paradise. Plunge pool. Middle of the Keys

Baja Breeze 🏝, a freshly updated, family-friendly, resort-style villa in the ♥ of the Keys. ♥ Please save Baja Breeze by clicking on the heart in the top right hand corner, this will help you find it again and share with others! 🛶 Waterfront canal view 🌴 Gated Resort Area 👙 Private spa pool 📍 Halfway between Key Largo and Key West ☀️ Outdoor dining/lounge area 🍳 Fully stocked Kitchen 📶 300Mbps+ Wifi

Location · Family · Walkability

Florida Keys Sanctuary

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 and loungers. 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 and kids dishware.

Location · Family · Cleanliness