Family-friendly holiday rentals in Duck Key

The modern kitchen features stainless steel appliances, including a refrigerator and oven. White cabinetry and a light countertop provide a bright atmosphere. A dining area is visible nearby, with seating for multiple guests. Large windows allow for natural light and views of the outdoor scenery.

4.82 out of 5 average rating, 173 reviews

Villa 5020 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.

The charming cottage displays a pastel-colored exterior with a triangular roof and white trim. A small front porch is set above the entrance, flanked by two sets of French doors. Lush greenery and a white picket fence enhance the welcoming entryway.

4.96 out of 5 average rating, 182 reviews

3Bd 3Ba Cottage/Village at Hawks Cay/Ocean Views

Our Cottage is located between Islamorada and Marathon Key on Duck Key at the Village of Hawks Cay; one of the most desirable locations in the Florida Keys. This is at Mile Marker 61. With ocean views, high end finishes, comfy beds and plenty to do in the surrounding areas, the Cottage offers something for everyone. The outdoor green space overlooking the water is gorgeous. Sunsets are amazing right off the screened in lanai. We hope to host you as our guest in the beautiful Florida Keys.

Guest suite in Key Colony Beach

A wooden dock extends over calm waters, flanked by posts leading to a serene view of the sky at sunset. Lush palm trees are visible in the background, enhancing the tranquil atmosphere of the canal.

4.99 out of 5 average rating, 119 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!

4.96 out of 5 average rating, 161 reviews

A spacious outdoor porch features a round dining table surrounded by four chairs. A kayak is positioned nearby, and lush greenery and water views are visible in the background, enhancing the inviting outdoor space.

Villa in Duck Key

Beach House - Kayak 2/2.5 Villa - OS Slip/Ramp/Pkg

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.

Condo in Key Colony Beach

A bright and airy studio room features two queen-sized beds with crisp white bedding and anchor-themed decorative pillows. Light blue accents are present throughout, complemented by coastal artwork on the walls. Large windows allow natural light to fill the space, enhancing its serene atmosphere.

4.91 out of 5 average rating, 328 reviews

Coastal Key Colony Beach Condo, Oceanfront Complex

Lovely coastal Keys studio condo in Key Colony Beach oceanfront complex with heated pool and private beach. Unit #17 has new beds with memory foam mattress toppers and renovated kitchen with granite countertops stocked with everything needed to cook a complete meal (dishes, cookware, appliances and of course blender, etc). Relax on the back balcony and enjoy sunsets from Sunset Park right next door. Private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

A spacious patio is visible, featuring a round wooden table surrounded by four chairs. The view includes calm waters framed by palm trees and lush greenery, under a sky dotted with fluffy white clouds.

4.82 out of 5 average rating, 157 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.

4.9 out of 5 average rating, 433 reviews

Three modern Aqua Lodges are positioned on water, featuring white exteriors and blue roofs. Each lodge has a furnished deck with chairs, providing relaxed seating options. A smooth, concrete path runs alongside the lodges, leading to a marina setting with sailboats in the background.

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!

4.97 out of 5 average rating, 126 reviews

A serene pool area is surrounded by lush tropical landscaping and palm trees. Lounge chairs are positioned around the pool, along with blue umbrellas providing shade. The clear water sparkles under the bright sun, creating an inviting space for relaxation.

Cottage in Islamorada

2br/1ba w heated pool, 1 mile to robbies marina

Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

4.86 out of 5 average rating, 109 reviews

A welcoming entrance features a door labeled '8A' and is flanked by two red chairs with blue and white striped cushions. A small table rests between them, surrounded by potted plants. A window offers a glimpse of natural light within the unit.

Apartment in Marathon

Cozy Keys Efficiency 8a

Efficiency has a queen size bed, a 3-seat sofa and a small dining table with 2 chairs. Private bathroom. AC will keep you cool. Kitchen is fully equipped with 4 burner stove, microwave, medium size refrigerator with freezer. Enjoy the breezes on your patio, each unit has a gas BBQ grill and a picnic bench outside. Enjoy a swim in our shared pool. Optional boat slip can be rented for $25/night Efficiency has a 2 person maximum occupancy - no exceptions.

Condo in Key Colony Beach

The image captures a view of the Atlantic Ocean framed by lush palm trees. A pathway meanders alongside the vibrant green lawn, leading toward the beach. The clear blue sky is visible above, enhancing the calm and serene coastal atmosphere.

4.87 out of 5 average rating, 143 reviews

Beachside Unit 33-Private Tropical Beach Plus Pool

Unit 33 Details: Second Floor, Walk-in 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.”

The living area features contemporary furnishings and large windows, allowing for bright natural light and views of the waterways. A dining table is positioned beside the seating area. The spacious lanai showcases an outdoor dining setup with a view of the dock and water.

4.95 out of 5 average rating, 129 reviews

Paradise in Key Colony Beach + Cabana Club

Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

4.89 out of 5 average rating, 112 reviews

An outdoor lounge area features a private spa pool surrounded by tropical plants and seating. Soft lighting creates a welcoming atmosphere, while the vibrant sunset sky adds a colorful backdrop. Sliding doors connect the space to the interior of the villa.

Villa in Marathon

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

Popular amenities for Duck Key family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 119 reviews

Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath

A private beach area is revealed, featuring rows of blue lounge chairs set on soft, sandy ground. Lush greenery borders the beach, while a wooden pier extends into the calm, turquoise water. A thatched gazebo provides shade, and scattered palm trees complete the coastal scene.

4.94 out of 5 average rating, 113 reviews

Your Happy Place - Oceanfront

4.95 out of 5 average rating, 140 reviews

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

Campervan/RV in Key Largo

A person stands on a paddle board in calm waters, holding a paddle. A dog wearing a life jacket sits comfortably on the board. The background shows a serene body of water with subtle ripples, enhancing the peaceful outdoor setting.

4.95 out of 5 average rating, 256 reviews

New Tinyhouse RV, Kayak, Beach, Fish, Marina, Pool

A private beach area is visible, featuring soft white sand and arranged lounge chairs facing the calm ocean. Lush greenery lines the shore, with a small tree providing shade. In the background, a wooden pier extends into the water under a partly cloudy sky.

4.9 out of 5 average rating, 302 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

A serene sunset is visible over the Atlantic Ocean, with warm orange and yellow hues blending into the sky. A sailboat is seen on the horizon, adding a touch of tranquility to the scenic view.

4.85 out of 5 average rating, 298 reviews

Condo in the Keys, Peaceful ocean view retreat!

A dining area features a round table surrounded by four wicker chairs. A large window offers views of the lush greenery outside, while a comfortable armchair with a tropical print is positioned nearby. Art depicting palm trees adorns the wall, complementing the coastal decor.

4.98 out of 5 average rating, 116 reviews

Modern and Coastal Ocean Pointe 2307

A spacious living room features a light color palette with a large flat-screen television mounted on the wall. Comfortable seating is arranged around a coffee table, and large windows provide a view of the ocean and natural light. Coastal decor enhances the atmosphere.

4.91 out of 5 average rating, 138 reviews

Luxurious Suite+Open Ocean Views+Pool & Cabana Bar

Family- and pet-friendly home rentals

A spacious outdoor area is surrounded by tropical landscaping, featuring a BBQ grill and a hot tub. Comfortable lounge chairs are available under umbrellas, with a gravel walkway leading to various seating arrangements. Sunlight filters through the palm fronds, creating a relaxing atmosphere.

4.95 out of 5 average rating, 39 reviews

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys

4.85 out of 5 average rating, 474 reviews

A charming cabin is nestled among lush greenery, featuring a cozy porch with comfortable seating. The pathway is lined with vibrant tropical plants and palms, creating a serene and inviting entrance. Sunlight filters through the canopy, illuminating the peaceful surroundings.

Guesthouse in Key Largo

Romantic cozy peaceful Guesthouse beach Sunsets.

4.97 out of 5 average rating, 201 reviews

The living area features a comfortable light blue sofa and a glass-top coffee table, complemented by tropical-themed decor. A ceiling fan circulates air above, while a kitchen bar with high chairs is visible in the background. Natural light enters through multiple windows, enhancing the welcoming atmosphere.

Home in Islamorada

Flakey's

4.85 out of 5 average rating, 117 reviews

An aerial view showcases a waterfront villa surrounded by vibrant blue waters. Lush greenery lines the shoreline, while neighboring properties reflect a tropical aesthetic. A wooden dock extends into the canal, providing access to boats and scenic views of the surrounding area.

Townhouse in Marathon

Waterfront Duck Key Villa - Sleeps 8 (7058)

A scenic pool area is visible, featuring a hot tub adjacent to the water's edge. Palm trees sway gently in the breeze, providing a tropical atmosphere. The blue sky reflects on the tranquil water, enhancing the serene setting.

4.74 out of 5 average rating, 31 reviews

Sunset Views, Pool and Dock

A paved outdoor patio features two lounge chairs and a small round table, surrounded by tropical plants and palms. The tranquil canal is visible in the background, offering a serene waterfront view.

4.95 out of 5 average rating, 132 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

4.96 out of 5 average rating, 150 reviews

A shaded outdoor dining area features a wooden table surrounded by chairs, with a view of the private canal lined with palm trees. Nearby boats are docked along the lush green banks, creating a serene waterfront setting.

Townhouse in Marathon

Boater’s Paradise 3br/2.5ba at Coral Lagoon

A shaded tiki hut is situated on a stone patio beside a tranquil canal. The space is furnished with a table and chairs, surrounded by palm trees. Brightly colored kayaks are neatly arranged on a nearby dock, adding to the outdoor ambiance.

4.9 out of 5 average rating, 104 reviews

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

Family-friendly home rentals with a pool

4.9 out of 5 average rating, 10 reviews

P14 - Charming 2 Bedroom, 2 bath waterfront duplex

4.81 out of 5 average rating, 21 reviews

Condo in Marathon

1st Floor Condo w Boat Slip, Pool, Adjustable Bed

A tranquil pool is surrounded by lush palm trees, offering a serene atmosphere. The water reflects sunlight, while seating options are provided by the poolside. The design features a curved edge and a spa section, creating an inviting outdoor retreat.

5 out of 5 average rating, 11 reviews

The Roseate House at Grassy Key Lic. #VACA-25-222

A peaceful canal scene is presented with clear blue skies and palm trees lining the water's edge. The calm water reflects the greenery and nearby structures, creating a serene atmosphere. A patterned walkway runs alongside the canal, adding to the tranquil setting.

5 out of 5 average rating, 14 reviews

Chiquita Waterfront Canal Home

5 out of 5 average rating, 6 reviews

The exterior of a modern waterfront home showcases a private pool surrounded by a grassy area. Comfortable lounge chairs line the poolside, and a hammock is positioned nearby. A dock extends into the water, accommodating a boat, while the house features multiple balconies.

Home in Key Largo

Luxury Waterfront Home

An open living space is featured, highlighted by a round dining table surrounded by comfortable seating. A large television is mounted on the wall, while light-colored walls enhance the bright atmosphere. A serene coastal artwork depicting a pier adds a calming touch to the decor.

5 out of 5 average rating, 29 reviews

Bohemian Beach Bungalow

The exterior of the newly renovated home is showcased, featuring a large covered porch supported by white columns. Palm trees line the surroundings, and warm lighting illuminates the entrance, creating an inviting atmosphere against the twilight sky.

4.95 out of 5 average rating, 156 reviews

Marathon one-level home on the Marina - with slip!

An aerial view of a private splash pool surrounded by a sun deck. Several lounge chairs are arranged around the pool, framed by vibrant tropical landscaping. The sandy beach and tranquil waters of the Atlantic Ocean are visible in the background.