Beachfront vacation rentals in Islamorada

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Top-rated beachfront rentals in Islamorada

Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A spacious houseboat is illuminated at night, surrounded by gently swaying palm trees adorned with soft yellow lighting. The deck features a modern outdoor seating area, complemented by vibrant red umbrellas. Nearby boats are moored in the marina, contributing to the serene waterfront atmosphere.

Houseboat in Tavernier

4.89 out of 5 average rating, 237 reviews

Florida Keys Luxury Houseboat on the water WiFi

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

Top guest favorite

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, 105 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.

Top guest favorite

A zero gravity electric recliner is positioned near a large glass door that opens to a balcony with an ocean view. Colorful artwork featuring tropical fish adorns the wall above, while natural light brightens the spacious room.

Condo in Tavernier

4.96 out of 5 average rating, 192 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

***IMPORTANT*** The pictures you see here are of OUR unit. What you see is what YOU GET. No surprise when you arrive at Ocean Pointe. NO bait and switch. We own in the Prominent Building #3 just steps from the Pool & Jacuzzi. Wireless Internet Netflix & Cable TV, XBOX ONE. ***Most of our guests (99%) claim this is the cleanest Airbnb they have ever stayed in.*** You will get a TRUE UNIMPEDED OCEAN VIEW in our unit. Read our reviews, our past guests tell it all. ⭐ 5 STAR ⭐ Get what you pay for.

Guest favorite

An aerial view of the beachfront complex showcases a vibrant landscape with lush palms surrounding the property. The well-maintained grounds feature lounge areas and tiki huts adjacent to the sandy beach. The ocean's gentle waves are visible along the shoreline, reflecting the clear blue sky.

Condo in Key Colony Beach

4.91 out of 5 average rating, 180 reviews

Exquisite Oceanfront Paradise - Key Colony Beach

Exquisite renovation just completed (Nov 2024). Unobstructed ocean views from our beachfront condo in Key Colony Beach. Ground floor and just a few steps away from our private beach and heated pool. Location just does not get any better. Stunning, clean white interior - kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests can enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Top guest favorite

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 home in Key Largo

4.97 out of 5 average rating, 145 reviews

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.

Guest favorite

A charming cabin is nestled among lush greenery, featuring a cozy porch with comfortable seating. The pathway is lined with vibrant tropical plants and palms, creating a serene and inviting entrance. Sunlight filters through the canopy, illuminating the peaceful surroundings.

Guesthouse in Key Largo

4.87 out of 5 average rating, 443 reviews

Romantic Cabin/Guesthouse, beach Sunsets, fishing.

Private Romantic Bayside Cabin/Guesthouse, peaceful settings, lovely sunsets, beach, fishing pier, lush gardens surrounded by nature and wildlife, birds, iguanas, manatees, dolphin’s, eagles, the beach is just a short walk away from the Guesthouse enjoying a cocktail, fishing, boats cruising by, kayaking, snorkeling or an amazing sunset. *This Guesthouse is on bayside not Bayfront ! Same property but private from the residence! "No pets, Airbnb-granted pets Exemption cus allergies reasons"

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, 139 reviews

Beach House - Kayaks & 2/2.5 Villa

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.

Guest favorite

A spacious living area features a light and airy design with coastal decor. Large windows offer views of the ocean, while a modern flat-screen television is mounted on the wall. A marble countertop provides a stylish separation from the kitchen area, and natural light enhances the overall ambiance.

Condo in Tavernier

4.96 out of 5 average rating, 139 reviews

Ocean View Corner Penthouse Ocean Pointe 5416

Coastal decor greets you in this serene Penthouse unit with all around views of the Atlantic ocean. This end unit is located in fabulous Ocean Pointe Suites, complete with small beach, pier, marina, large pool, jacuzzi, tennis and pickle ball court and even basket ball hoop. This unit is smack dab in the middle between Key Largo and Islamorada in the Florida Keys. Very close to amazing waterfront dining, snorkeling, diving, fishing, paddle boarding and kayaking. Must stay to believe!

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, 349 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 charming seaside tiny house features a thatched roof and a deck lined with seating. The entrance is accessed by wooden steps leading from the water's edge. Natural elements, such as stone and plants, complement the home’s inviting design.

Tiny home in Key Largo

4.96 out of 5 average rating, 133 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, And most importantly a super comfortable queen size bed, There is also a community pool for your enjoyment The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

Guest favorite

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.

Condo in Tavernier

4.94 out of 5 average rating, 127 reviews

BEAUTIFULLY DESIGNED OCEANFRONT CONDO

Enjoy a Tavernier adventure on a private 60-acre oceanfront sanctuary. The condo was recently renovated & is beautifully designed with comfortable, beach chic decor. It offers an abundance of natural light surrounded by windows overlooking lush landscaping and the Atlantic Ocean. Ocean Pointe Suites offers a private sandy beach, a junior Olympic sized pool, a 14-person spa, a boardwalk, a pickleball court, deep-water marina, gazebo, 2 tennis courts & more!

Guest favorite

A window reveals a lush garden filled with tropical plants and flowers. The words 'Keys Life' are displayed on a wooden sign above the window, enhancing the connection to the surrounding nature.

Cottage in Key Largo

4.9 out of 5 average rating, 350 reviews

Cottage By The Sea

Cottage By The Sea....Your home away from home in the Florida Keys!!! Our 2 bedroom Guest House is located on the Oceanside of Key Largo in a quaint and quiet neighborhood, with a huge yard surrounded by exotic flowers and trees. Be sure to meet Frank out 120 pound Sulcata tortoise.Minutes from either Oceanside or Bayside boat ramps. It is walking distance to a famous local's Tiki Bar and Restaurant as well as Jet ski and Kayak rentals