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Waterfront vacation rentals in Islamorada

Find and book unique waterfront accommodations on Airbnb

Top-rated waterfront accommodations in Islamorada

Guests agree: these waterfront accommodations are highly rated for location, cleanliness, and more.

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Vacation home in Key Largo

4.84 out of 5 average rating, 252 reviews

Charming Waterside Cabana in Key Largo | Cabana 4

Enjoy water front living in Key Largo! Watch the boats go by with fresh catch served daily at the local restaurants. See manatees, nurse sharks and fish swim by the canal all day. Dock your boat at the Pilot House Marina just down the street. Our unit is Modern, Spacious and Spotless with Private Parking, Fast Wifi, Netflix, Cold AC, Plush Pillows and a Cozy bed. We are on a main canal to open ocean. Near Rodriguez Key, Mosquito Bank, Christ of the Abyss and many sunken shipwrecks for exploring.

Jul. 18 – 25

$300 CAD per night

Guest favourite

Condo in Tavernier

4.95 out of 5 average rating, 108 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Welcome to our remodeled costal 1BR 1 Bath condo nestled in the premier oceanfront complex in Tavernier, FL. Escape to paradise and enjoy the wonderful Ocean views from the private balcony while just a few steps away from the sunny private beach, marina, minutes away from restaurants, shops, and attractions. ✔ Comfortable Queen BR ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Balcony ✔ Smart TVs/WI FI ✔ Complex Amenities (Pool, Hot Tub, Marina, BBQ, Sports, Free Parking) Learn more below!

Aug. 30 – Sep. 6

$416 CAD per night

Guest favourite

Apartment in Key Largo

4.94 out of 5 average rating, 247 reviews

Waterfront Studio 1| Kayaks | Pool |Bay View |Wifi

Escape to Northern Key Largo for a relaxing vacation! Discover great restaurants, beautiful state parks, and marine life. This bright, modern studio boasts excellent views of Manatee Bay, free kayaks and paddle boards, and a full kitchen. With access to a swimming pool and docks, there’s always something to do. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

Oct. 28 – Nov. 4

$279 CAD per night

Guest favourite

Vacation home in Key Largo

4.99 out of 5 average rating, 145 reviews

Waterfront, GROUND LEVEL, Awesome Sunsets!!!

This ground level unique location is close to everything. Walk to some of the most iconic restaurants and bars Key Largo has to offer for fresh seafood and awesome drinks! We Do Not allow fishing on our Property! Dockage Available for additional fee! Enjoy the amazing sunsets over the water from your private porch and dock. John Pennekamp Coral Reef State Park close by. Walk to dolphin research center!! 28 day rental I am a licensed charter boat captain and offer discounts for all guests

Sep. 19 – 26

$326 CAD per night

Cottage in Islamorada

4.81 out of 5 average rating, 143 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. Each unit is private, and the neighborhood is tucked off the beaten path. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! A 5% lodging tax will be charged on arrival.

Sep. 3 – 10

$279 CAD per night

Guest favourite

Boat in Islamorada

4.92 out of 5 average rating, 327 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.

Oct. 24 – 31

$293 CAD per night

Guest favourite

Condo in Key Colony Beach

4.91 out of 5 average rating, 197 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Beautiful studio condo on the 1st floor only steps away from the private beach and heated pool. Condo features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Oct. 29 – Nov. 5

$535 CAD per night

Guest favourite

Condo in Tavernier

4.98 out of 5 average rating, 142 reviews

Ocean Views at Ocean Pointe

Conveniently located at MM 92.5, approximately 1 hour drive from Miami, you can enjoy a modern, newly redecorated Keys escape with amazing views of the sunrise right from your oceanside balcony. 2 bed/2 bath with full kitchen and washer/dryer. Pool, beach, pier, BBQ area, and private boat marina within this private community. Kayaks, paddle boards and bikes available for rent. No need to leave, but grocery stores, spas and ample restaurants are close by to fill any need.

May 31 – Jun. 7

$350 CAD per night

Guest favourite

Home in Marathon

4.99 out of 5 average rating, 106 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

2024 - New Weber grill This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Aug. 24 – 31

$681 CAD per night

Guest favourite

Guesthouse in Key Largo

4.91 out of 5 average rating, 191 reviews

Oceanside, 1 bedroom, Bungalow in Key Largo

Canal front bungalow with beautiful views of the ocean. Private water front and pergola with steamer chairs and hammock. BBQ your fresh catch while lounging on the back porch, relaxing in the tropical landscape. One bedroom with Queen bed. Queen size pull-out couch in the living-room. Full kitchen boasting high-end appliances. One Car Parking by unit. Centrally located between shopping centers and destination activities.

Oct. 5 – 12

$311 CAD per night

Home in Islamorada

4.98 out of 5 average rating, 140 reviews

Porter’s Corner

Very quiet place with almost no neighbors on a deep water canal with excellent fishing and bayside access. 30 feet of dock to park a boat or just enjoy sunsets over the lagoon and watch the resident family of manatees. Walking distance to a beach, convenience store and a fish market with fresh local seafood. The entire property is 100% solar powered. The house is a duplex and I live on one side.

Jun. 10 – 17

$709 CAD per night

Guest favourite

Guest suite in Tavernier

4.97 out of 5 average rating, 247 reviews

POOL ! Key Largo! Tavernier! Welcome to Paradise!

POOL! A perfect tropical getaway! Life is good today! Bright, airy, 500 plus sq ft., canal front studio, close to the bay. From the dock you can KAYAK to mangrove tunnels, fish, or just relax. Cold drink in your hand, life is good today! You are going to have an awesome vacation!! ( NOTE: THE POOL MAY BE SHARED ON OCCASION, WITH OUR FAMILY. A SIGNED LIABILITY RELEASE IS REQUIRED AT CHECK IN )

Sep. 29 – Oct. 6

$438 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Popular amenities for Islamorada waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Guest favourite

Apartment in Tavernier

4.83 out of 5 average rating, 255 reviews

Breathtaking Oceanfront Views at Tropical Daze

Apr. 3 – 10

$484 CAD per night

Guest favourite

Apartment in Key Largo

4.98 out of 5 average rating, 125 reviews

Key Largo Kawama Lagoon Free Cancel Deutsch Spain

Sep. 3 – 10

$485 CAD per night

Guest favourite

Apartment in Key Largo

4.89 out of 5 average rating, 205 reviews

Seaside Vista - Ocean Front 2/1 with dockage

Nov. 18 – 25

$453 CAD per night

Guest favourite

Apartment in Key Largo

5.0 out of 5 average rating, 21 reviews

Studio apartment in Calusa Resort & Campgrounds

Nov. 12 – 19

$269 CAD per night

Guest favourite

Apartment in Tavernier

5.0 out of 5 average rating, 12 reviews

Turtles Nest 2 Ocean Point condo

Jan. 10 – 17

$533 CAD per night

Guest favourite

Apartment in Marathon

5.0 out of 5 average rating, 8 reviews

Gated Oceanfront Heated Pool

Aug. 24 – 31

$394 CAD per night

Apartment in Tavernier

4.84 out of 5 average rating, 32 reviews

Serene Oceanfront Keys Condo

Jan. 17 – 24

$619 CAD per night

Guest favourite

Apartment in Tavernier

5.0 out of 5 average rating, 8 reviews

Modern-Coastal Suite with Vast Ocean views

Jul. 26 – Aug. 2

$580 CAD per night

Waterfront house rentals

Guest favourite

Home in Islamorada

4.91 out of 5 average rating, 107 reviews

SUPERHOST WATERFRONT PARADISE HOME- DOCK32 FT BOAT

Nov. 27 – Dec. 4

$707 CAD per night

Guest favourite

Home in Tavernier

4.87 out of 5 average rating, 208 reviews

Clean Houseboat w/ Great Wi-Fi,Luxury on the water

Oct. 29 – Nov. 5

$616 CAD per night

Guest favourite

Home in Marathon

4.97 out of 5 average rating, 117 reviews

Marathon one-level home on the Marina - with slip!

May 22 – 29

$882 CAD per night

Guest favourite

Home in Key Colony Beach

4.96 out of 5 average rating, 134 reviews

Beautiful open plan remodeled home in Key Colony

Oct. 23 – 30

$341 CAD per night

Guest favourite

Home in Key Largo

4.96 out of 5 average rating, 135 reviews

Key Largo Waterfront Home with Tiki & Boat Dock

Oct. 8 – 15

$440 CAD per night

Guest favourite

Home in Key Largo

4.88 out of 5 average rating, 163 reviews

Outdoor Paradise - Beach, Boats, Snorkeling & Sun!

Aug. 3 – 10

$322 CAD per night

Guest favourite

Home in Islamorada

4.94 out of 5 average rating, 17 reviews

3 Lux Ensuites Walk/Boat Island!

Mar. 22 – 29

$891 CAD per night

Guest favourite

Home in Key Largo

5.0 out of 5 average rating, 50 reviews

The Paradise 2

Mar. 20 – 27

$580 CAD per night

Waterfront condo rentals

Guest favourite

Condo in Key Colony Beach

4.91 out of 5 average rating, 112 reviews

Beachside Unit 39 Tiki Huts, Private Beach & Pool

Aug. 22 – 29

$367 CAD per night

Guest favourite

Condo in Tavernier

4.96 out of 5 average rating, 159 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

Sep. 29 – Oct. 6

$666 CAD per night

Guest favourite

Condo in Tavernier

4.93 out of 5 average rating, 133 reviews

It's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba

Jan. 24 – 31

$599 CAD per night

Guest favourite

Condo in Tavernier

4.91 out of 5 average rating, 110 reviews

500 Burton Drive Tavernier, Key Largo

Jan. 19 – 26

$480 CAD per night

Guest favourite

Condo in Key Largo

4.98 out of 5 average rating, 115 reviews

Oceanfront Condo w/Lake, Kayak, Paddleboard & Bike

Nov. 7 – 14

$778 CAD per night

Guest favourite

Condo in Tavernier

4.87 out of 5 average rating, 125 reviews

Reel Large END Unit in Ocean Point Suites

Nov. 7 – 14

$553 CAD per night

Guest favourite

Condo in Key Largo

4.97 out of 5 average rating, 146 reviews

KEYS BEACH RETREAT WITH CAPTIVATING WATERVIEW!

Nov. 13 – 20

$1,019 CAD per night

Condo in Tavernier

4.8 out of 5 average rating, 130 reviews

TROPICAL PARADISE Ocean Condo - Cabana Daydreamin'

Nov. 14 – 21

$380 CAD per night

Quick stats about waterfront rentals in Islamorada

Total rentals
290 properties
Rentals with a pool
200 properties have a pool
Pet-friendly rentals
100 properties allow pets
Family-friendly rentals
240 properties are a good fit for families
Total number of reviews
2.7K reviews
Nightly prices starting at
$82 CAD before taxes and fees

Destinations to explore