Waterfront holiday rentals in Islamorada

4.92 out of 5 average rating, 390 reviews

The eco-friendly two-story River Queen vessel is anchored in a calm harbor, showcasing a modern design. The structure features large windows and a rooftop terrace, with a wind turbine on the left. The surrounding landscape includes lush greenery, complementing the serene water view.

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.

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.

4.98 out of 5 average rating, 233 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!! 28 day rental. Enjoy sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Houseboat in Islamorada Tavernier

4.9 out of 5 average rating, 261 reviews

Florida Keys Houseboat, unique waterfront stay-

Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers the perfect blend of comfort, adventure and true waterfront living. Wake up to breathtaking sunrises, sip your morning coffee as the marine life glide by, and fall asleep to the gentle sway of the water. Whether you’re celebrating something special or simply craving a one-of-a-kind getaway, this houseboat is the ideal home base for both keys adventures and peaceful retreats 💫

4.92 out of 5 average rating, 131 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.

4.95 out of 5 average rating, 175 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 Getaway - Kayaks - 2BR 2.5BA Villas

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, 192 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 home 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.

4.93 out of 5 average rating, 373 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.

4.93 out of 5 average rating, 222 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!!

4.95 out of 5 average rating, 135 reviews

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

Turtle lovers rejoyce! Enjoy this Two Bedroom/Two Bath Condo with the perfect blend of style, comfort and convenience. Featuring a spacious living room and a fully stocked Kitchen. The Master bedroom features a King size bed and ensuite master bathroom. The guest bedroom features a Queen bed with a unattached bathroom. Both bathrooms feature a walk-in shower. The balcony offers views of the nature preserve and peek-a-boo views of the Atlantic Ocean!

4.96 out of 5 average rating, 112 reviews

The living area features a spacious blue sectional sofa with decorative pillows and throws. A round coffee table sits at its center. Natural light fills the room, illuminating two framed beach-themed artworks on the wall, and the open kitchen and dining area are visible in the background.

Townhouse in Key Largo

Kawama K1 Beautiful Lagoon View free bikes & kayak

Escape to paradise at Kawama Yacht Club, a private community featuring 24-hour security and an array of exclusive amenities: Salt water lagoon, 2 heated pools, Kids playground, Tennis courts, Marina boat ramp, boat parking, Jetty & Fire pits. We also provide kayaks and bikes so you can fully immerse yourself in the beauty of the surrounding area. Don't miss out on the ultimate Florida Keys getaway, book your stay at Kawama Yacht Club now.

A vibrant sunset casts a warm glow over the outdoor area featuring a sheltered gazebo, surrounded by lush greenery and reflective water. Nearby, a modern living room is furnished with comfortable seating and a large screen, creating an inviting space for relaxation.

4.95 out of 5 average rating, 112 reviews

Coco Plum Waterfront Hideaway Home in Marathon

This Coco Plum home is the ultimate family getaway! With four bedrooms, two bathrooms, a modern living room with a 4K TV and surround sound, and an outdoor area that includes a fire pit, outdoor dining, and outdoor living space. The boat dock and breathtaking sunset views make this the perfect home for your fishing adventures. Beautiful Coco Plum beach is just a ten minute walk away. Make this home your next island adventure.

A shaded wooden gazebo features a thatched roof and offers an unobstructed view of tranquil waters. Comfortable seating is arranged on the deck, where sunlight casts shadows through the railing. The sparkling surface of the water reflects the sunlight, creating a serene coastal ambiance.

4.95 out of 5 average rating, 227 reviews

Top Floor - Oceanview condo with tennis courts, pickleball, hot tub, BBQ, marina & private beach. ★ "Exactly as described & very clean. Beautiful views & a nice peaceful escape." ➠ Resort size heated pool + Jacuzzi ➠ Balcony w/ ocean view ➠ Private beach access w/ sun lounger ➠ Fully equipped + stocked kitchen ➠ Double Master Suites ➠ 55” smart TVs w/ cable ➠ Car park (2 cars max) ➠ 250 Mbps WIFI

Popular amenities for Islamorada waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

Superhost

Apartment in Islamorada

5 out of 5 average rating, 6 reviews

Ocean View Duplex Penthouse | Pool | Vista Two

A bright living area features a light-colored sofa adorned with decorative pillows, complemented by a glass coffee table. Large windows invite natural light, revealing views of the lush landscape outside. A mounted television and coastal artwork complete the serene environment.

5 out of 5 average rating, 25 reviews

Oceanfront Bliss • Wall-to-Wall Water Views + Pool

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.

4.86 out of 5 average rating, 136 reviews

Beachside Unit 22 - Private Beach on Atlantic

5 out of 5 average rating, 6 reviews

Apartment in Marathon

Villa 4204 on Duck Key - Boat Slip available

5 out of 5 average rating, 7 reviews

Apartment in Marathon

New! Waterfront Views | Pool & Tiki Bar

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, 18 reviews

Panoramic Ocean Views, Ocean Pointe Condo

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, 54 reviews

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

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.

4.89 out of 5 average rating, 108 reviews

Ocean Pointe 2309 with Ocean Views

Waterfront house rentals

4.9 out of 5 average rating, 110 reviews

NEW! CASA PALMA - Golf Cart, 2 King-Size Beds, Pool, Kayaks

A two-story duplex is set amidst palm trees, featuring a blue exterior and multiple balconies. A vehicle is parked in the driveway, with a pathway leading towards the entrance, surrounded by landscaped areas that include gravel and greenery.

4.92 out of 5 average rating, 186 reviews

Blue House Marine in Key Largo

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.

4.94 out of 5 average rating, 111 reviews

Conch Cottage at Hawks Cay - Chic Tropical Retreat

Superhost

A spacious fishing pier extends into clear turquoise waters under a bright blue sky. The sandy beach surrounding the pier invites relaxation, while lush greenery can be seen in the distance. Minimal benches are positioned along the pier for enjoying the scenery.

Home in Islamorada

Marlin House @ Tarpon Point

A waterfront patio is shown with comfortable seating, overlooking a calm body of water. The sun sets in the distance, casting warm light over the scene. Tropical vegetation can be seen, adding to the serene atmosphere.

4.91 out of 5 average rating, 148 reviews

The Paradise 2

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.

4.96 out of 5 average rating, 124 reviews

Large Waterfront Home, w/Efficiency, Pool, Kayaks

A serene patio area showcases a private pool with illuminated edges, creating a calming ambiance. Outdoor furniture is arranged on a synthetic grass surface, framed by lush greenery and a tranquil water view, as the sky transitions to sunset hues in the background.

4.96 out of 5 average rating, 27 reviews

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

An aerial view showcases a canal front home with a pool and spacious deck, surrounded by palm trees. Two neighboring homes are visible along the water's edge, highlighting the serene and scenic environment.

4.9 out of 5 average rating, 103 reviews

Great key Largo home with water front and pool

Waterfront condo accommodation

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, 176 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.

4.95 out of 5 average rating, 128 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.

4.95 out of 5 average rating, 165 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

4.87 out of 5 average rating, 155 reviews

Condo in Key Largo

Waterfront Apt Key Largo #4, 10% Off 7+, 5% Off 4+

4.99 out of 5 average rating, 121 reviews

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

Enjoy sunsets & sunrise in your home away home.

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.

4.99 out of 5 average rating, 214 reviews

Ocean Views at Ocean Pointe

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, 102 reviews

Ocean views at “Sangria Sunrise” 10% off Charters

A well-lit living area showcases a comfortable sectional sofa and a wooden dining table with light-colored chairs. A decorative bowl of lemons sits at the center of the table, while large windows offer views of the surrounding landscape and allow natural light to fill the space.