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Waterfront vacation rentals in Islamorada

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Vacation rentals for every style

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Popular amenities for Islamorada waterfront rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Waterfront apartment rentals

Superhost
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, 4 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, 120 reviews

Beachside Unit 22 - Private Beach on Atlantic

Top guest favorite
A tranquil beach scene features several blue lounge chairs arranged in neat rows on the sandy shore. A wooden pier extends into the water, accompanied by a thatched-roof gazebo. Lush greenery and a peaceful sky with scattered clouds complete the coastal vista.
Apartment in Tavernier
4.98 out of 5 average rating, 48 reviews

Ocean View 2br/2ba w/pool, bar and dockage 28ft

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, 152 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
4.88 out of 5 average rating, 290 reviews

Seaside Vista - Ocean Front 2/1 with dockage

Superhost
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, 274 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
4.99 out of 5 average rating, 71 reviews

Hidden Gem Islamorada | 1st Floor

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, 200 reviews

Boho FL Keys Condo

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Waterfront house rentals

Top guest favorite
A vibrant sunset paints the sky in shades of orange and pink, reflecting off the tranquil canal water. Palm trees frame the scene, while nearby boats are anchored along the dock. The peaceful ambiance captures the essence of coastal living in Key Colony Beach.
Home in Key Colony Beach
4.98 out of 5 average rating, 126 reviews

Paradise found!Key Colony Beach,Cabana Club.

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, 6 reviews

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

Guest favorite
A collage highlights an inviting outdoor space featuring a heated pool, hot tub, and two putting greens on lush lawn. The open living area showcases comfortable seating, light-colored furnishings, and ocean-themed decor. Exterior views reveal spacious patios and well-maintained landscaping under a colorful sunset.
Home in Marathon
4.95 out of 5 average rating, 137 reviews

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

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
4.91 out of 5 average rating, 11 reviews

Endless Summer

Top guest favorite
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.
Home in Key Colony Beach
4.95 out of 5 average rating, 121 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

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, 67 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

Superhost
A serene beach area is highlighted by sandy shores and gentle waves. Palm trees sway in the breeze, while lounge chairs are arranged neatly in the foreground. A wooden dock extends into the water, framed by lush greenery in the background.
Home in Key Largo
4.79 out of 5 average rating, 149 reviews

Escape to the Seaside!

Guest favorite
A modern living area features a spacious white sectional sofa adorned with blue and green decorative pillows. A wooden dining table with white chairs is positioned nearby. Above, a stylish fan circulates air while artwork in calming hues decorates the walls, complementing the light wood flooring.
Home in Key Largo
4.91 out of 5 average rating, 104 reviews

Casa Azul New Oceanside Voted #1! Golf Cart-Beach

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Waterfront condo rentals

Superhost
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, 158 reviews

Reel Large END Unit in Ocean Point Suites

Superhost
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
4.89 out of 5 average rating, 123 reviews

500 Burton Drive Tavernier, Key Largo

Top guest favorite
A private dock extends over calm waters, lined with white posts and illuminated by a golden sunset. A thatched-roof structure is visible at the end of the dock, surrounded by gentle waves reflecting the muted sky.
Condo in Key Largo
4.99 out of 5 average rating, 114 reviews

Enjoy sunsets & sunrise in your home away home.

Superhost
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, 290 reviews

Condo in the Keys, Peaceful ocean view retreat!

Top guest favorite
A clear view of the ocean is captured from the balcony, showcasing the shimmering water beneath a bright blue sky. Lush greenery lines the foreground, while a dock extends into the sea. The scene conveys a serene coastal atmosphere.
Condo in Tavernier
4.99 out of 5 average rating, 200 reviews

Ocean Views at Ocean Pointe

Top guest favorite
A light-filled living area is visible, featuring a comfortable seating arrangement and a mounted television. A dining table occupies the foreground, adorned with a bowl of oranges. The walls are painted in soft blue, providing a relaxed atmosphere, with a ceiling fan overhead.
Condo in Marathon
4.96 out of 5 average rating, 105 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

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, 100 reviews

Ocean views at “Sangria Sunrise” 10% off Charters

Superhost
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, 101 reviews

🏝 Oceanfront Paradise Awaits You

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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