Waterfront vacation rentals in Islamorada

4.91 out of 5 average rating, 380 reviews

The two-story eco-friendly River Queen vessel is anchored on tranquil waters. Its modern design is complemented by expansive windows, and a spacious rooftop deck is visible. The 10-foot dinghy is secured alongside, providing easy access to the shore.

Boat in Tavernier

Island Sanctuary Islamorada

Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored 1/8 mi offshore in a quite harbor close to shopping center, movie theater, hospital, bars & restaurants. A 10-foot dinghy with small outboard to come & go from shore "ONLY", nowhere else. I also offer Personal Training, deep tissue work & Life Coach sessions. I live on the vessel about a hundred yards from you so if there are any questions, etc. I will be there to assist you.

Houseboat in Islamorada Tavernier

4.89 out of 5 average rating, 251 reviews

Luxury remodeled Houseboat, oasis on the water

Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers a unique blend of comfort, adventure, and waterfront living. Wake up to breathtaking sunrises, sip your morning coffee with all the marine life, and fall asleep to the gentle movement of the boat. Whether your celebrating something special or simply want a one of a kind getaway-it's the perfect home base for Keys adventures or peaceful retreats. An amazing experience Free park

Superhost

An illuminated RV is showcased against a dusk sky, with blue lighting enhancing its modern design. Nearby, bright kayaks are propped against a picnic table, while a hammock sways slightly in the breeze, creating a relaxed outdoor space.

Camper/RV in Key Largo

4.96 out of 5 average rating, 246 reviews

NEW luxury RV, Marina, 6 beds&1.5 baths, 2 pools!

This hidden gem is anything but ordinary!!! Come enjoy a piece of paradise in Key Largo while you relax in this spacious NEW luxury RV. It has a BOAT RAMP, indoor/outdoor kitchen with a TV, outdoor speakers, 2 hammock chairs, outdoor sofa, outdoor dining, separate bedrooms including a bunk room that can sleep 5-6, 1.5 baths, 2 heated pools, 2 beaches, volleyball court, playground, & shuffleboard. There are so many outdoor activities to enjoy right at the Kampground, you'll never want to leave!

4.93 out of 5 average rating, 119 reviews

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

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.

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, 170 reviews

A serene waterfront view is framed by palm trees, with two green chaise lounges positioned for relaxation. The setting sun casts warm hues across the sky, reflecting on the water's surface. A Tiki structure adds charm, creating an inviting outdoor space.

Tiny homes in Key Largo

Oceanfront Lookout Point w/two Kayaks & Deck

Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.

A serene waterfront scene captures a vibrant sunset reflecting off calm waters. Multiple boats are docked along the marina, with silhouettes of masts against the colorful sky, creating a peaceful atmosphere ideal for relaxation.

4.99 out of 5 average rating, 209 reviews

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! Enjoy the sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! 28 day I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

4.96 out of 5 average rating, 160 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.

4.97 out of 5 average rating, 172 reviews

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 homes in Key Largo

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.

Vacation home in Key Largo

Two individuals wearing snorkeling gear are seen gliding through clear water above a coral reef, with a sea turtle swimming gracefully below. The underwater scene showcases vibrant coral formations and sandy sea floor, creating a serene marine environment.

4.88 out of 5 average rating, 269 reviews

6. Waterfront Key Largo Studio, Near Kayaks & Reef

Unwind in this Modern Key Largo waterfront studio, nestled on a canal with ocean access near Rodriguez Key, Mosquito Bank, and shipwrecks. Just minutes from John Pennekamp Park. Enjoy a full kitchen, ice-cold A/C, Smart TV, Wi-Fi, and assigned parking. Boaters can reserve our dock or use nearby Pilot House Marina. Snorkel reefs, kayak mangroves, or dine at local favorites like The Fish House, Sundowners, and Key Largo Fisheries. Comfort, adventure, and location in one perfect stay.

4.93 out of 5 average rating, 361 reviews

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

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.

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.

4.92 out of 5 average rating, 211 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!!

Popular amenities for Islamorada waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

5 out of 5 average rating, 15 reviews

An aerial view captures the layout of the Ocean Isles Fishing Village, showcasing multiple light blue condos with white roofs positioned along winding roads. The Atlantic Ocean glimmers in the background, surrounded by lush greenery and residential areas, illustrating the tranquil setting of the Florida Keys.

Apartment in Marathon

Oceanfront Getaway in Marathon!

Apartment in Key Colony Beach

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.

4.85 out of 5 average rating, 131 reviews

Beachside Unit 22 - Private Beach on Atlantic

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.

4.98 out of 5 average rating, 63 reviews

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

4.99 out of 5 average rating, 169 reviews

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

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

4.98 out of 5 average rating, 80 reviews

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

Hidden Gem Islamorada | 1st Floor

An aerial view captures a coastal area featuring a hotel building alongside a waterway. A sandy beach area with lounge chairs is visible near the water, while lush greenery surrounds the landscape. The scene showcases a calm and inviting atmosphere with clear blue skies.

5 out of 5 average rating, 15 reviews

Panoramic Ocean Views, Ocean Pointe Condo

A light-filled living area showcases a grey sofa adorned with decorative pillows. A round coffee table sits in the center, surrounded by a textured area rug. The space is complemented by a large pendant light and a wall featuring natural wood art, enhancing the relaxed ambiance.

4.92 out of 5 average rating, 99 reviews

Ocean Pointe 2309 with Ocean Views

A serene beachfront area is depicted, featuring rows of blue sun loungers arranged on soft white sand. Lush greenery and palm trees border the beach, while the tranquil turquoise waters stretch towards the horizon. A wooden pier extends into the water, enhancing the coastal view.

5 out of 5 average rating, 22 reviews

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis

Waterfront house rentals

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.

4.99 out of 5 average rating, 153 reviews

Sea Ray Cove w/ Pool, Beach, 80' Dock & Tiki hut

4.9 out of 5 average rating, 109 reviews

NEW! CASA PALMA – Golf Cart, 2 Kings, Pool, Kayaks

4.95 out of 5 average rating, 140 reviews

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

Aerial view of a waterfront community featuring multiple homes surrounded by lush greenery. Two circular pools are visible in the foreground, with docks extending into the water. A sailboat is seen on the horizon, showcasing the serene setting.

4.95 out of 5 average rating, 108 reviews

Large Waterfront Home, w/Efficiency, Pool, Kayaks

4.97 out of 5 average rating, 168 reviews

Key Largo Waterfront: Tiki, Dock, Kayak & Pool

4.91 out of 5 average rating, 113 reviews

Bay Sunsets Free Kayaks/Paddleboard Jacuzzi

4.97 out of 5 average rating, 116 reviews

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

Waterfront House with 37 ft Dock & Cabana Club

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.

5 out of 5 average rating, 120 reviews

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV

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.

4.87 out of 5 average rating, 165 reviews

Reel Large END Unit in Ocean Point Suites

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

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.

4.94 out of 5 average rating, 159 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

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

4.96 out of 5 average rating, 112 reviews

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

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

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.

4.97 out of 5 average rating, 101 reviews

Ocean views at “Sangria Sunrise” 10% off Charters

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.