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Beachfront holiday rentals in Islamorada

Find and book unique beachfront homes on Airbnb

Quick stats about beachfront rentals in Islamorada

  • Total holiday rentals

    Explore 220 holiday rentals in Islamorada

  • Nightly prices starting at

    Islamorada holiday rentals start at £67 per night before taxes and fees

  • Verified guest reviews

    Over 1,730 verified reviews to help you choose

  • Family-friendly holiday rentals

    100 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 150 rentals that welcome pets

  • Holiday rentals with a pool

    210 properties feature pools

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

  • Wifi availability

    210 of Islamorada holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Islamorada rentals

  • 4.6 Average rating

    Islamorada stays receive an average rating of 4.6 out of 5 from guests

Top-rated beachfront rentals in Islamorada

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

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Superhost
Home in Key Largo

NEW! Casa Azul - Golf Cart, 2 King, Pool, Kayaks

No Hidden Fees! Book with confidence. No added Airbnb, resort, guest, or management fee when booking any of my homes. Casa Azul - Where the Salt Life Meets Luxury Welcome to your Key Largo vacation rental. No animals permitted, including service animals, due to owner allergies. This villa includes a private golf cart, pools, one adult kayak, three kids' kayaks, pickleball, tennis courts, a swimming lagoon, and a beach area. Enjoy kayaking, fishing, and snorkeling. Hundreds of 5-star reviews!

4.89 out of 5 average rating, 119 reviews
Top guest favourite
Apartment in Tavernier

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.

4.97 out of 5 average rating, 234 reviews
Guest favourite
Apartment in Key Colony Beach

Amazing Ocean Front Views Key Colony Beach

Everything is brand new in this gorgeous condo with amazing oceanfront views. #40 has two queen beds, well equipped kitchen with full-size appliances and everything you need to cook & serve meals. Fast, reliable WiFi, large SmartTV. Super cold new A/C unit Enjoy stunning views of sunrise from your private balcony & sunsets next door at Sunset Park. Heated pool, beach BBQs & tiki huts for guest use We are centrally located to awesome Keys adventures just a few miles drive from the condo.

4.97 out of 5 average rating, 286 reviews
Top guest favourite
A serene beachfront area is presented with several white lounge chairs facing the tranquil blue waters. Rocky shoreline and greenery outline the space, creating a peaceful environment for relaxation.
Villa in Key Largo

Kawama Yacht Club and Molasses Reef Marine

Vacation in paradise. Beautiful sunsets. Swim at the salt water lagoon or at the beach plus two pools. Our villa is fully equipped, 3 bedrooms wish tv and 3 full baths First floor: garage, 1 bedroom, full bathroom, game room, pool table, bar, family room with TV, and terrace with barbecue and swing. Second floor 2 bedrooms and 2 full bathrooms, fully equipped kitchen and living a big TV, outside balcony with outdoor furniture . Tennis courts available. Optional 24' ft boat slip available.

4.93 out of 5 average rating, 126 reviews
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.
Apartment in Tavernier

🏝 Oceanfront Paradise Awaits You

Bring your boat to next vacation in tropical paradise surrounded by mangrove forest, coconut trees and the pristine turquoise waters. Welcome to the most visited resort in the beautiful Florida Keys. Ocean Pointe is one of the most luxurious resorts in Tavernier, Florida Keys. The resort offers a private sandy beach, heated swimming pool, jacuzzi, tennis courts, restaurant, bar, marina with boat ramp and dockage, boat & trailer storage, and more - all situated on 60 lush tropical acres.

4.85 out of 5 average rating, 126 reviews
Top guest favourite
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

My Little Oasis2 Waterfront Retreat, Key Largo

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.

4.97 out of 5 average rating, 236 reviews
Top guest favourite
Apartment in Key Largo

Tropical Getaway

This light, airy two bedroom condo is located in the community of Kawama. Overlooks a small lake, where people swim, kayak and paddleboard. The condo community features two pools, tennis courts, playground, fishing, beach and marina. A long jetty extends out in the ocean where you can watch the beautiful sunrises or sunsets in the afternoons. Centrally located in Key Largo near restaurants, shopping and attractions. Come down and enjoy the peaceful atmosphere of our tropical area.

4.9 out of 5 average rating, 197 reviews
Guest favourite
The image captures a view of the Atlantic Ocean framed by lush palm trees. A pathway meanders alongside the vibrant green lawn, leading toward the beach. The clear blue sky is visible above, enhancing the calm and serene coastal atmosphere.
Apartment in Key Colony Beach

Beachside Unit 33-Private Tropical Beach Plus Pool

Unit 33 Details: Second Floor, Walk-in shower, Two Queen Beds, Maximum Occupancy 4 Guests (0-2 years old count as a guest). No elevator on site and Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

4.88 out of 5 average rating, 168 reviews
Guest favourite
A shaded outdoor porch features four blue adirondack chairs arranged around a round table, overlooking tranquil water views. The surrounding area is adorned with lush greenery and distant views of a bridge, creating a serene space for relaxation.
Townhouse in Duck Key

Vibrant Beachfront Villa

Welcome to Beachfront Villa that has recently been renovated. The 2 bedroom 1.5 bath luxury villa is located in the popular area of Duck key alongside of Hawks Cay Resort. Duck Key marina is located across the street where you can dock your boat or charter a boat for the day. Enjoy stunning sunset views from the back porch. Kitchen includes all amenities including silverware ,plates , cups , and pots. Linens and towels provided. *** Pets welcome with host approval and pet fee. ****

4.81 out of 5 average rating, 238 reviews
Top guest favourite
A solar and wind powered houseboat is moored on calm waters, featuring bright yellow shutters and a roof deck. Wind turbines and an American flag adorn the top, contrasting with the soothing blue sky and fluffy clouds in the background.
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.

4.93 out of 5 average rating, 394 reviews
Top guest favourite
Apartment in Tavernier

Turtle Nest 1 Private beach,Pool, 2bed 2bath

Ocean Pointe Suite is located on the Atlantic. Featuring ocean views from living room, master bedroom and balconies. King bed in master bedroom, Queen bed in guest bedroom, pull out queen sofa, 2 bathrooms, Smart TV's with cable WIFI. Completely stocked kitchen with all appliances. Amenities include heated swimming pool, private beach, marina with boat launch & dockage for extra fee book through marine info in pictures. Tennis courts, gazebo, located on 60 tropical acres.

4.91 out of 5 average rating, 144 reviews
Superhost
Villa in Key Largo

Oceanfront Resort W/Indoor Pickleball - Speakeasy!

An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Key Largo's most upscale oceanfront community. The area has the distinction of being Key Largo's newest oceanfront gated destination, with some of the most unique amenities in all of the keys. It caters to those who simple desire the very best in luxury accommodations. Unique amenities include a Speakeasy Themed Rec. Area.

4.82 out of 5 average rating, 126 reviews

Popular amenities for beachfront rentals in Islamorada

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly beachfront home rentals

Guest favourite
The tranquil canal is illuminated by soft lights reflecting off the crystal-clear waters. Lush palm trees line the banks, and tiki huts with ambient lighting add to the serene atmosphere. The scene captures a peaceful nighttime setting with boats moored along the dock.
Cottage in Key Largo

2 bedroom & 25' Boat Dock Waterfront Atlantic Side

4.93 out of 5 average rating, 104 reviews
Guest favourite
An open concept living area features a dining table surrounded by wooden chairs. A large flat-screen TV is mounted on the wall opposite a decorative console table. The kitchen is equipped with modern appliances and a subtle blue accent wall enhances the space.
Townhouse in Key Largo

Relaxing Town home with great water views

4.89 out of 5 average rating, 143 reviews
Top guest favourite
The image captures a sparkling private pool overlooking the water, with a sandy beach and a wooden dock in the distance. A yellow kayak is positioned nearby, and several lounge chairs are arranged by the pool, inviting relaxation under the tropical sky.
Home in Marathon

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

4.92 out of 5 average rating, 49 reviews
Superhost
Two individuals are seated in blue chairs on a sandy waterfront, overlooking a serene bay during sunset. The sky is decorated with a blend of orange, pink, and purple hues, while boats are gently floating in the water, reflecting the vibrant colors.
Home in Key Largo

Deckhouse

4.78 out of 5 average rating, 86 reviews
Top guest favourite
A two-story home is showcased, featuring a spacious backyard with a swimming pool surrounded by lounge chairs and umbrellas. The exterior is illuminated under a twilight sky, while a stone walkway leads to the inviting entrance. Lush greenery adds a vibrant touch to the setting.
Home in Marathon

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

5.0 out of 5 average rating, 60 reviews
Guest favourite
An airy dining area features a white stone-topped table positioned beneath a stylish light fixture. Large glass doors allow natural light to flood the space, connecting indoor and outdoor seating areas. The wooden floor adds warmth to the contemporary design.
Home in Marathon

SeaEsta! Bring your boat & 1 block to the beach!

4.88 out of 5 average rating, 16 reviews
Guest favourite
A private backyard showcases a tranquil pool surrounded by a stone deck. Comfortable lounge chairs are positioned for relaxation, with a vibrant float placed in the water. The blue exterior of the house enhances the outdoor space under a partly cloudy sky.
Home in Marathon

New Private 4/3 Single Family - Kayaks & Bicycles+

4.94 out of 5 average rating, 94 reviews
Guest favourite
A two-story home is depicted, featuring a covered balcony with blue chairs and a ground-level terrace. A kayak is positioned nearby on gravel, alongside two adirondack chairs near natural landscaping. The surroundings are lush with greenery, enhancing the tranquil setting.
Home in Marathon

Boaters delight! 1 min to open water, Dock & Beach

4.92 out of 5 average rating, 24 reviews

Beachfront home rentals with a pool

Top guest favourite
An elegant living area is featured, showcasing a modern leather sectional sofa complemented by light-colored pillows. A ceiling fan hangs above, and large windows allow natural light to fill the space. A wooden rocking chair and a small coffee table complete the inviting atmosphere.
Apartment in Key Largo

Oceanfront Condo w/Lake, Kayak, Paddleboard & Bike

4.96 out of 5 average rating, 179 reviews
Guest favourite
A sandy beach area is captured, featuring several lounge chairs arranged under swaying palm trees. The turquoise waters of the Atlantic Ocean can be seen in the background, with a shaded gazebo and a wooden dock visible on the horizon.
Apartment in Tavernier

2BR - Key Largo Sunshine Getaway

4.88 out of 5 average rating, 181 reviews
Top guest favourite
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 van/Motorhome in Key Largo

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

4.96 out of 5 average rating, 308 reviews
Guest favourite
Home in Islamorada

The Villa by the Bay Pool/Boat Dock, Islamorada Fl

5.0 out of 5 average rating, 12 reviews
Top guest favourite
Townhouse in Islamorada

Closest Oceanfront Home - 3 Stories and Boat Dock

5.0 out of 5 average rating, 23 reviews
Top guest favourite
Aerial view of the resort-style community featuring a central heated pool surrounded by lush landscaping. Palm trees and outdoor seating areas are visible. The property borders a marina with docks for boats, highlighting the connection to the water.
Home in Islamorada

Exceptional vaca in Angler's Reef Islamorada

5.0 out of 5 average rating, 28 reviews
Guest favourite
A wide view of the sandy beach reveals several colorful umbrellas and lounge chairs arranged under palm trees, alongside Tiki huts offering shade. The clear blue ocean extends to the horizon under a partly cloudy sky, enhancing the peaceful beachfront setting.
Apartment in Tavernier

Islamorada Oceanfront 2 bdrm, 2 bath, View, Pool

4.89 out of 5 average rating, 19 reviews
Top guest favourite
A vibrant sunset casts an orange glow over the marina, with boats docked at several piers. Lush palm trees frame the scene, and a tiki hut with seating is visible in the foreground. Soft lights can be seen strung along the area, enhancing the serene waterfront atmosphere.
Apartment in Key Largo

Serenity at Moon Bay!

5.0 out of 5 average rating, 34 reviews

Private beachfront home rentals

Guest favourite
A dining area features a round wooden table set with yellow placemats and white napkins. Light blue walls complement the soft furnishings, while large windows provide a view of tropical foliage and the outdoors. Natural light fills the space, enhancing the inviting atmosphere.
Home in Marathon

Waterfront Villa & Sunset Views

4.85 out of 5 average rating, 113 reviews
Top guest favourite
A serene swimming pool, featuring a vibrant logo of the Fishing Village at its center, is set against a backdrop of clear blue skies and palm trees. Lounge chairs line the edges of the pool area, offering a tranquil space for relaxation.
Home in Marathon

Grouper Getaway @ Ocean Isles Fishing Village

4.99 out of 5 average rating, 76 reviews
Guest favourite
A living area is furnished with a comfortable sectional sofa and a glass coffee table, featuring a large flat-screen TV mounted on the wall. Natural light fills the space through sliding glass doors that open to a balcony overlooking greenery.
Townhouse in Key Largo

Corner townhouse w/saltwater lagoon views

4.89 out of 5 average rating, 38 reviews
Superhost
The sleeping area features a spacious bed centered beneath a vaulted wooden ceiling, with light-colored walls creating an airy atmosphere. Two bedside lamps are placed on either side of the bed, and a large arched window allows natural light to fill the room, framed by soft curtains.
Loft in Key Largo

Treetops Apt.Sleep1-4 Beach Steps Away

4.54 out of 5 average rating, 628 reviews
Guest favourite
The room features two spacious beds with light-colored bedding, complemented by decorative pillows. A ceiling fan is present above, while large windows with shutters allow natural light. Colorful artwork depicting flamingos adorns the walls beside bedside tables and lamps.
Flat in Key Colony Beach

2 Bdrm Oceanfront Complex Private Beach & Pool

4.93 out of 5 average rating, 41 reviews
Top guest favourite
Lounge chairs are positioned on the grass near the ocean, surrounded by palm trees. A soft gradient of colors in the sky, transitioning from pale pink to light blue, is visible above the tranquil waters. Rocky shoreline meets the beach, creating a peaceful environment.
Apartment in Key Colony Beach

Paradise found! Sea-Esta Condo beach and pool.

4.96 out of 5 average rating, 52 reviews
Top guest favourite
An expansive view of a private beach is captured, showcasing gentle ocean waves lapping at the shore. Lounge chairs are arranged on a green lawn, offering relaxation options while a solitary figure strolls along the sandy beach. Palm trees frame the scene under a partly cloudy sky.
Apartment in Key Colony Beach

Private Beach in Marathons Key Colony Beach

5.0 out of 5 average rating, 29 reviews
Superhost
A spacious living area features a gray sectional sofa adorned with blue accent pillows. Light wood tables complement the hardwood floor. A large painting of a coastal scene is displayed on the wall, and natural light filters in through shuttered windows.
Holiday home in Marathon

Cabana Club Condo: Key Colony Beach, FL

4.93 out of 5 average rating, 55 reviews

When is the best time to visit Islamorada?

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