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Waterfront vacation rentals in Monroe County

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Monroe County

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A sparkling in-ground pool is visible in the foreground, surrounded by a spacious patio. Lounge chairs are positioned along the deck, offering views of the lagoon. Lush palm trees provide shade, while a clear sky enhances the tranquil atmosphere of the waterfront setting.

Home in Marathon

4.99 out of 5 average rating, 147 reviews

Sea Ray Cove; Pool, 75’ Dock and steps to Beach

2025 - New concrete dock, fenders & fish filet table. 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.

The living area features a spacious blue tufted sofa complemented by a sleek glass coffee table. A modern accent chair adds contrast, while large sliding glass doors provide ample natural light and stunning views of the surrounding skyline.

4.91 out of 5 average rating, 116 reviews

Make It Happen! Brand New with Amazing Water Views

Bluewater Realty Miami welcomes you to The Grand, located in Downtown Miami on Biscayne Bay. Our 2 bedroom Make It Happen! is the ultimate retreat, equipped with everything you could need. Enjoy views of Biscayne Bay and Margaret Pace Park that will leave you in awe. With South Miami Beach 3 miles away you can indulge in the sun of Miami Beach while still feeling the energy of downtown Miami, giving you the ultimate Miami experience. Your Airbnb Superhosts, Rachel and Mia Bluewater Realty Miami

A covered Tiki Hut is featured at the waterfront, furnished with comfortable seating arrangements. Views of the water and dock are visible beyond the structure, framed by lush greenery and palm trees. The space is designed for relaxation and enjoyment of the serene surroundings.

Home in Key Colony Beach

4.96 out of 5 average rating, 113 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

A motorboat is anchored on calm waters, featuring a spacious front deck. Two individuals are seated comfortably, enjoying the view. The boat's sleek design is complemented by a canopy overhead and small steps leading into the water, creating a relaxed atmosphere.

Boat in Key West

4.91 out of 5 average rating, 202 reviews

Stay on Roxie with FREE anytime cancellation!

Read our reviews and relax with last minute weather cancellation! 🌞 Shower, toilet and power to recharge phones, full cellular. Enjoy a peaceful night or two on the water! Free parking and one free round trip transport to/from Roxie per night stay! Roxie is anchored in ~3ft lagoon. We live on a boat a half-mile away if you need anything at all! Roxie has a Keurig, coffee pods, bread, peanut butter-jelly, and bottled waters. No cooking but you may bring to-go food, beer/booze/wine. 🛥️🌴🎣

Top guest favorite

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.

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 115 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!

Top guest favorite

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

4.95 out of 5 average rating, 154 reviews

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.

Top guest favorite

A private porch overlooks the tranquil harbor, featuring blue chairs beside a white railing. A boat is secured at the dock, with sailboats moored in the distance. Bright sunlight reflects off the water's surface, creating a serene atmosphere.

Vacation home in Key Largo

4.99 out of 5 average rating, 219 reviews

Waterfront, GROUND LEVEL, Awesome Sunsets!!!

This ground level unique location is close to everything. Walk to some of the most iconic restaurants and bars Key Largo has to offer for fresh seafood and awesome drinks! We Do Not allow fishing on our Property! Dockage Available for additional fee! Enjoy the amazing sunsets over the water from your private porch and dock. John Pennekamp Coral Reef State Park close by. Walk to dolphin research center!! 28 day rental I am a licensed charter boat captain and offer discounts for all guests

Top guest favorite

A sunset view is captured from a covered outdoor seating area, showcasing a tranquil waterway. Silhouettes of kayaks and a table are visible, while the setting sun creates a warm glow across the horizon. Natural textures are evident in the thatched roof above.

Tiny home in Key Largo

4.97 out of 5 average rating, 156 reviews

Oasis2 in Key Largo With a million dollar view

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.

A spacious living area features a comfortable futon adorned with a decorative pillow. Large windows provide views of the tranquil water, allowing natural light to brighten the space. The walls are designed in a soft, neutral tone, enhancing the overall welcoming feel.

Houseboat in Key West

4.95 out of 5 average rating, 131 reviews

Amazing houseboat with 2nd floor observation deck

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Garrison Bight Marina in Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

Top guest favorite

The image features a distant houseboat silhouetted against a vibrant sunset, reflecting shades of orange and purple on the water's surface. The view is taken from a skiff, with gentle ripples seen in the foreground, creating a serene atmosphere.

Boat in Islamorada

4.93 out of 5 average rating, 356 reviews

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Top guest favorite

A spacious wooden deck features two light blue lounge chairs and a white umbrella, offering a relaxing spot to enjoy ocean views. The gentle waves of the Atlantic can be seen in the background, while the shore is lined with natural sand and small rocks.

Condo in Key West

4.97 out of 5 average rating, 106 reviews

Hidden Beach unit 1 The Perfect Place to stay

This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

An aerial view of the waterfront area shows vibrant turquoise waters and lush greenery. The scene includes several residential buildings along the coastline and a nearby marina, with boats visible on the water and the horizon illustrating a scenic expanse.

Home in Marathon

4.92 out of 5 average rating, 206 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!!

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Luxury Stays

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Popular amenities for Monroe County waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

A modern kitchen is featured, equipped with stainless steel appliances and sleek cabinetry, offering ample counter space. Natural light fills the area from large windows, showcasing views of the city. A comfortable seating area is visible in the background, enhancing the spacious layout.

Apartment in Coconut Grove

4.94 out of 5 average rating, 227 reviews

Stunning Corner Water/City View Free Pkg/Pool

The expansive outdoor pool is framed by palm trees and surrounded by lounge chairs with blue umbrellas. The area is well-lit and features a shaded pavilion. The surrounding building showcases tropical landscaping, providing a relaxing atmosphere for guests.

Apartment in Key West

4.9 out of 5 average rating, 152 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

Top guest favorite

A corner two-story townhouse is shown, situated beside a tranquil saltwater lagoon. Lush greenery surrounds the property, and a staircase leads to a diving platform over the water. The reflection of the structure and trees can be seen on the still lagoon surface.

Apartment in Key Largo

4.99 out of 5 average rating, 159 reviews

Kawama Lagoon, 3D corner chickee 2bdr , 2 baths

A cozy living area features a light-colored sofa with decorative pillows, complemented by a coffee table and a patterned area rug. Expansive glass sliding doors provide natural light and views of palm trees outside, while a small dining table adds functionality to the space.

Apartment in Key Largo

4.89 out of 5 average rating, 299 reviews

Seaside Vista - Ocean Front 2/1 with dockage

An open living area features a white leather sofa, a coffee table with magazines, and two ottomans in teal. A mounted TV is positioned on a white console, while a dining area is visible in the background, showcasing a modern kitchen design.

Apartment in Miami

4.96 out of 5 average rating, 230 reviews

Condo in Brickell Business District

The modern living space features large windows offering sweeping views of Biscayne Bay. A comfortable seating area is provided with a stylish sofa and accent chairs, complemented by a dining table set for six. Natural light fills the room, highlighting the elegant decor.

Apartment in Miami

4.91 out of 5 average rating, 123 reviews

MVR - Steps from Miami-s Top Attractions

Top guest favorite

A light-filled living area features a blue sofa with decorative pillows and a wooden coffee table atop a woven area rug. Two accent chairs frame the seating arrangement, while natural decor elements, including tall grasses and wall art, enhance the welcoming ambiance.

Apartment in Tavernier

4.95 out of 5 average rating, 210 reviews

Boho FL Keys Condo

A modern studio is showcased, featuring a comfortable queen-sized bed and lounge area equipped with a Smart TV. Natural light floods the space from large windows. The kitchen is outfitted with stainless steel appliances, while the outdoor area includes tiki huts with thatched roofs, ideal for relaxation.

Apartment in Key Largo

4.92 out of 5 average rating, 299 reviews

Waterfront Studio 1| Kayaks | Pool |Bay View |Wifi

Waterfront house rentals

A modern living and dining area features a sleek white sectional sofa adorned with decorative pillows. A rustic wooden coffee table is centrally positioned. The dining table, surrounded by wooden chairs, complements the light-colored decor. A stylish light fixture hangs above, enhancing the open space.

Home in Key Largo

4.9 out of 5 average rating, 109 reviews

CASA PALMA Golf Cart, Kayaks, Pools, Beach,2 Kings

Palm trees are seen swaying gently in the breeze, framing the entrance to the cottage, which features a welcoming front porch with two wooden chairs. The interior showcases a modern dining area, complete with a chandelier and decorative plants. A plunge pool is visible in the outdoor space, surrounded by tropical greenery.

Home in Marathon

4.93 out of 5 average rating, 100 reviews

Conch Cottage at Hawks Cay - Chic Tropical Retreat

An aerial view showcases a coastal community with a spacious beach area, palm trees, and turquoise waters. The two-story unit features a large balcony above the entrance, with the surrounding buildings and lagoon clearly visible, highlighting the vibrant landscape of the area.

Home in Cudjoe Key

4.97 out of 5 average rating, 169 reviews

Cudjoe Key Home with a View

A serene view of a waterfront canal is captured from a covered porch. The calm water reflects the sky, with boats docked along the edges. Palm trees gently sway in the breeze, enhancing the coastal setting. Nearby structures suggest a vibrant community atmosphere.

Home in Cudjoe Key

4.81 out of 5 average rating, 280 reviews

Oct. Special 50% off! Oceanfront, 4 Bikes 2 Kayaks

Top guest favorite

A serene view of a canal populated by several pelicans floating on the water's surface. Palm trees line the shore, and colorful houses are visible in the background. A boat is docked nearby, enhancing the peaceful coastal scene.

Home in Key Colony Beach

4.98 out of 5 average rating, 113 reviews

Waterfront House with 37 ft Dock & Cabana Club

Top guest favorite

A private wooden dock extends over calm waters, featuring a boat with a blue canopy and a small table with colorful umbrellas nearby. Palm trees line the waterfront, and a series of pastel-colored homes are visible across the canal, creating a serene setting.

Home in Marathon

5 out of 5 average rating, 118 reviews

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV

A modern two-story home with a spacious outdoor area featuring a private pool. Comfortable lounge chairs surround the pool, and a staircase leads to the upper level. The structure is complemented by a rooftop terrace with a sail shade, enhancing the coastal atmosphere.

Home in Marathon

4.97 out of 5 average rating, 120 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

A view of a canal-side property featuring two Tiki huts with thatched roofs and a wooden deck. Multiple outdoor seating options are visible, framed by lush palm trees. The water reflects the clear blue sky, creating a serene atmosphere for relaxation.

Home in Key Colony Beach

4.89 out of 5 average rating, 141 reviews

Tiki Time

Waterfront condo rentals

A bright living space features a comfortable gray sofa and a recliner, complemented by a white coffee table adorned with decorative items. The dining area, with a white table and several chairs, extends into the modern kitchen equipped with stainless steel appliances and a breakfast bar with stools.

Condo in Tavernier

4.88 out of 5 average rating, 162 reviews

Reel Large END Unit in Ocean Point Suites

Condo in Tavernier

4.94 out of 5 average rating, 106 reviews

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

A modern studio apartment features an open layout with a well-equipped kitchen and seating for two at a sleek countertop. A cozy couch sits across from a queen bed, with a light rug underfoot. Natural light enters through a window framed by horizontal blinds.

Condo in Palmetto Bay

4.91 out of 5 average rating, 294 reviews

Bright Modern Studio Apartment

Top guest favorite

A private wrap-around balcony features two white lounge chairs overlooking the expansive blue ocean. City skyline and distant landmasses are visible under a bright sky with scattered clouds. The green carpet adds a touch of color to this outdoor space.

4.94 out of 5 average rating, 100 reviews

Front Facing Top Floor Penthouse with Ocean Views

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.

Condo in Tavernier

4.86 out of 5 average rating, 293 reviews

Condo in the Keys, Peaceful ocean view retreat!

A modern living area features a sectional sofa adorned with accent pillows, complemented by a sleek coffee table. Large windows showcase panoramic city views enhanced by the evening's soft glow. A flat-screen TV is mounted on the wall, while light-colored curtains frame the windows.

4.9 out of 5 average rating, 119 reviews

Stunning 2 bedroom+17 foot ceilings & heated pool

A wooden pier extends over calm waters, leading toward a thatched-roof gazebo. The scene is illuminated by a vibrant sunset, casting warm hues across the sky and reflecting on the water's surface. Lush greenery frames the sides, enhancing the serene atmosphere.

Condo in Tavernier

4.97 out of 5 average rating, 101 reviews

Ocean views at “Sangria Sunrise” 10% off Charters

A modern living area offers floor-to-ceiling windows with skyline views of Miami. White leather sofas are arranged around a glass coffee table, while a dining area with dark chairs is visible in the background. Bright natural light floods the space, accentuating the sleek design.

4.95 out of 5 average rating, 140 reviews

Upper Penthouse Corner Unit 2B/2B | Icon Brickell

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