
Waterfront vacation rentals in Islamorada
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Islamorada
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

4. Cozy Waterfront Apartment in Key Largo!
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.

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.

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!

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.

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!

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.

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!!!

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.

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.

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.

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.

SaltSpray Bungalow Oceanside, 1 bedroom
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.
Popular amenities for Islamorada waterfront rentals
Waterfront apartment rentals

Ocean Isles Seaside Oasis

Beachside Unit 22 - Private Beach on Atlantic

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

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

Panoramic Ocean Views, Ocean Pointe Condo

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

Ocean Pointe 2309 with Ocean Views

Boho FL Keys Condo
Waterfront house rentals

Discount Available! Pool 100' Dock, Fun Amenities!

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

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

The Roseate House at Grassy Key Lic. #VACA-25-222

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Luxury Boating Paradise+Pool+Sailing Kayaks

Captain’s Quarters Ahoy Mateys! Florida, Keys

Angler’s Terrace Conde Nast Traveler’s Best Airbnb
Waterfront condo rentals

Luxury Top Floor Suite W/ Unobstructed Ocean View

Villa 5087 on Duck Key BOAT SLIP available

Your Happy Place - Oceanfront

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

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

Enjoy sunsets & sunrise in your home away home.

Condo in the Keys, Peaceful ocean view retreat!

Modern and Coastal Ocean Pointe 2307
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$72,640 GYD | G$81,013 GYD | G$82,269 GYD | G$68,663 GYD | G$94,202 GYD | G$66,988 GYD | G$69,500 GYD | G$62,801 GYD | G$62,801 GYD | G$64,476 GYD | G$60,708 GYD | G$73,268 GYD |
| Avg. temp | 20°C | 22°C | 23°C | 25°C | 27°C | 28°C | 29°C | 29°C | 28°C | 27°C | 24°C | 22°C |
Quick stats about waterfront rentals in Islamorada

Total vacation rentals
Explore 450 vacation rentals in Islamorada

Nightly prices starting at
Islamorada vacation rentals start at G$14,654 GYD per night before taxes and fees

Verified guest reviews
Over 3,610 verified reviews to help you choose

Family-friendly vacation rentals
320 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 270 rentals that welcome pets

Vacation rentals with a pool
370 properties feature pools

Rentals with dedicated workspaces
310 properties have a dedicated workspace

Wi-Fi availability
450 of Islamorada vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Islamorada rentals

4.8 Average rating
Islamorada stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- St Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Havana Vacation rentals
- Fort Lauderdale Vacation rentals
- Four Corners Vacation rentals
- Tampa Vacation rentals
- Kissimmee Vacation rentals
- Rentals with a fire pit Islamorada
- Rentals with a hot tub Islamorada
- Condo rentals Islamorada
- Resort rentals Islamorada
- Family-friendly rentals Islamorada
- Pet-friendly rentals Islamorada
- Apartment rentals Islamorada
- Townhouse rentals Islamorada
- Beach condo rentals Islamorada
- Rentals with a kayak Islamorada
- Rentals with a patio Islamorada
- Beach house rentals Islamorada
- Rentals with outdoor seating Islamorada
- Rentals with breakfast Islamorada
- Luxury rentals Islamorada
- Rentals with a fireplace Islamorada
- Beachfront rentals Islamorada
- House rentals Islamorada
- Villa rentals Islamorada
- Hotel rooms Islamorada
- Fitness-friendly rentals Islamorada
- Rentals with pools Islamorada
- Rentals with a washer and dryer Islamorada
- Rentals with an EV charger Islamorada
- Rentals with beach access Islamorada
- Waterfront rentals Monroe County
- Waterfront rentals Florida
- Waterfront rentals United States
- Everglades National Park
- Sombrero Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Biscayne National Park
- Coral Castle
- Cocoa Plum Beach
- Calusa Beach & Loggerhead Beach
- Cannon Beach
- Sea Oats Beach
- Far Beach
- Conch Key
- Everglades Alligator Farm
- Theater of the Sea
- Monkey Jungle
- Long Key State Park
- Long Beach
- Horseshoe Beach
- Schnebly Redland's Winery & Brewery
- EAA Air Museum
- Bahia Honda State Park
- Windley Key Fossil Reef Geological State Park
- Keys' Meads
- Sandspur Beach




