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Waterfront vacation rentals in Islamorada

Find and book unique waterfront rentals on Airbnb

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Islamorada waterfront rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Waterfront apartment rentals

Guest favorite
A spacious living area features large glass doors that open to reveal ocean views. The comfortable seating arrangement includes a light-colored sofa and a wooden coffee table. Natural light floods the room, creating a bright and inviting atmosphere. A dining area is visible in the background.
Apartment in Islamorada
5 out of 5 average rating, 5 reviews

Ocean View Duplex Penthouse | Pool | Vista Two

Superhost
A shaded tiki hut with a thatched roof stands on the sandy shore, overlooking the calm, blue waters of the Atlantic Ocean. Two palm trees frame the structure, creating a serene beach environment, with gentle waves lapping at the rocks in the background.
Apartment in Key Colony Beach
4.84 out of 5 average rating, 122 reviews

Beachside Unit 22 - Private Beach on Atlantic

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, 156 reviews

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

Guest favorite
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, 296 reviews

Seaside Vista - Ocean Front 2/1 with dockage

Top guest favorite
Apartment in Tavernier
4.95 out of 5 average rating, 102 reviews

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

Guest favorite
A bright studio space features a plush queen-sized bed and a cozy seating area with a Roku-enabled TV. The modern kitchen includes bar seating. Balconies overlook water views and a communal pool area, while tiki huts provide shaded outdoor lounging. Kayaks and paddle boards are readily available.
Apartment in Key Largo
4.92 out of 5 average rating, 278 reviews

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Guest favorite
An open-concept living area features a spacious blue sectional sofa adorned with vibrant cushions. A round coffee table sits on the light wooden floor, while large windows offer views of the surrounding trees. Kitchen appliances and dining chairs can be seen in the background.
Apartment in Islamorada
4.97 out of 5 average rating, 73 reviews

Hidden Gem Islamorada | 1st Floor

Guest favorite
A waterfront view captures a serene canal lined with tropical greenery and residential boats. The white boat is positioned on the dock, with steps leading to an inviting home painted in a soft yellow. Clear blue skies enhance the tranquil atmosphere.
Apartment in Marathon
4.87 out of 5 average rating, 54 reviews

Little Venice in Marathon (in the Beautiful Keys)

Waterfront house rentals

Top guest favorite
A serene outdoor area features a heated pool surrounded by lush greenery and palm trees. Two chaise loungers sit on a small patch of grass, offering a perfect spot for relaxation. The ocean is visible beyond the white fence, enhancing the tranquil setting.
Home in Marathon
5 out of 5 average rating, 43 reviews

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

Guest favorite
A spacious outdoor area features a well-maintained dock alongside calm waters. Luce lounge chairs are arranged for comfort, with palm trees offering shade. The exterior of the duplex is visible, showcasing large windows and a patio area adjacent to the dock, enhancing the waterfront experience.
Home in Marathon
4.95 out of 5 average rating, 42 reviews

Florida Keys Oceanside Utopia

Guest favorite
A modern two-story home features a clean white exterior with navy blue accents. A set of black stairs leads to a covered balcony adorned with potted plants. Large windows allow natural light to enter, while a gravel driveway provides ample space in front.
Home in Marathon
5 out of 5 average rating, 42 reviews

Waterfront Escape -VACA-23-408

Top guest favorite
An aerial view shows the property in proximity to the Atlantic Ocean, surrounded by palm trees. A dock extends into the clear water, with the colorful buildings of the surrounding area visible. The scene captures a serene coastal landscape, enhancing the appeal of a beachfront getaway.
Home in Key Colony Beach
5 out of 5 average rating, 7 reviews

Keys to Ohana. Ocean views. Private Pool, Hot Tub

Guest favorite
An outdoor area features a private pool with an adjoining spa, surrounded by lounge chairs. Lush palm trees provide shade, while a spiral staircase leads to the upper level of the house. The setting offers a relaxing space for guests to enjoy.
Home in Marathon
4.92 out of 5 average rating, 12 reviews

Endless Summer

Top guest favorite
A serene pool area is framed by palm trees and lush greenery, offering views of the ocean. Comfortable lounge chairs are positioned around the pool, which features a spa. The scene includes bright umbrellas, enhancing a relaxing outdoor space under a clear blue sky.
Home in Marathon
4.98 out of 5 average rating, 52 reviews

Oceanfront with Pool near Sombrero Beach

Guest favorite
A spacious beachfront home is depicted, featuring a large outdoor area with neatly arranged tropical plants. A well-maintained pool is visible in the backyard, alongside a staircase leading to wraparound balconies that provide ample views of the surroundings.
Home in Marathon
4.9 out of 5 average rating, 68 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

Guest favorite
An aerial view of a spacious villa surrounded by lush greenery and palm trees. A tile roof highlights the second floor balcony which features comfortable seating. The property is situated near calm waters, enhancing its coastal appeal.
Home in Marathon
4.91 out of 5 average rating, 182 reviews

Beachfront Villa - Florida Keys

Waterfront condo rentals

Guest favorite
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, 160 reviews

Reel Large END Unit in Ocean Point Suites

Guest favorite
A light-filled living area features a comfortable chair and a spacious dining table. A TV is mounted on the wall, and large windows offer views of the ocean and surrounding greenery, while sheer blue curtains frame the scene.
Condo in Tavernier
4.9 out of 5 average rating, 124 reviews

500 Burton Drive Tavernier, Key Largo

Guest favorite
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.
Condo in Tavernier
4.94 out of 5 average rating, 109 reviews

Your Happy Place - Oceanfront

Guest favorite
An open-concept living area features a comfortable sofa and loveseat, designed for relaxation. A stylish dining table accommodates four. A wall-mounted TV and electric fireplace add modern touches, while large sliding glass doors offer natural light and views of the surrounding landscape.
Condo in Tavernier
4.94 out of 5 average rating, 153 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Guest favorite
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!

Guest favorite
A spacious living area features light blue walls and coastal decor. A comfortable sofa is positioned against the wall, accompanied by a patterned throw pillow. A coffee table is centrally placed, while a bar seating area with stools offers additional gathering space. Natural light fills the room.
Condo in Tavernier
4.93 out of 5 average rating, 104 reviews

Light, Bright & Nautical Condo at Ocean Pointe

Guest favorite
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

Guest favorite
A panoramic view captures the pristine turquoise waters extending to the horizon, adjacent to lush greenery and the resort's amenities. The interior showcases a bright, airy living space, featuring a well-equipped kitchen with modern appliances and a comfortable seating area with ocean views.
Condo in Tavernier
4.85 out of 5 average rating, 107 reviews

🏝 Oceanfront Paradise Awaits You

Quick stats about waterfront rentals in Islamorada

  • Total rentals

    460 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 before taxes and fees

  • Total number of reviews

    3.6K reviews

  • Family-friendly rentals

    330 properties are a good fit for families

  • Pet-friendly rentals

    270 properties allow pets

  • Rentals with a pool

    370 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada
  6. Waterfront rentals