
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.

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.

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!!!

Key Largo's Premier Family Friendly Resort!
Mariners Club Key Largo! The vacation destination of the keys. A gated oceanfront resort and marina on the Atlantic. Key Largo is AKA the Diving Capital of the World. Our private 3 story home can be 2 separate units. Combined total is 3 bedroom 3.5 bath. The resort has 2 pools one that is the Keys largest beach entry style pool, 2 hot tubs one that is a grotto style, fishing pier, fitness center, game room, tennis, pickle and basketball courts. It's a beautiful well maintained peaceful place.

Baycation Houseboat * Florida Keys 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 💫

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.

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.

Beach House Getaway - Free Kayaks 2/2.5
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.

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!!

Waterfront Duck Key Villa - Sleeps 8 (7058)
BEST VIEW IN DUCK KEY!!!! Waterfront Villa at the heart of the Florida Keys - Duck Key Florida. Beautiful location with easy access to both the Atlantic Ocean and the Gulf of Mexico. Come check us out and see for yourself what the exclusive Duck Key area has to offer. DOCK INCLUDED-35 Foot. Conveniently behind the village! The Village at Hawks Cay Villas by KeysCaribbean are not affiliated with the Hawks Cay Resort; our guests do not have access to hotel amenities.

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!
Popular amenities for Islamorada waterfront rentals
Waterfront apartment rentals

Beachside Unit 22 - Private Beach on Atlantic

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

Waterfront Escape | Pool, Tiki, Breakfast & Marina

Panoramic Ocean Views, Ocean Pointe Condo

Elevated Retreat | Sunset Access + Boat Basin

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

Ocean Pointe 2309 with Ocean Views

Welcome to the Pelican Lodge !
Waterfront house rentals

Hawks Cay Island Retreat - Duck Key - Pool & Patio

Heated&Cooled PrivatePool/CabanaClub/Bikes/PaddleB

The Paradise 2

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

4BR 3B, Heated Pool & Spa, 60' Dock

Waterfront Key Largo Home - Tropical Paradise

Sombrero Sunset-Marathon 7BR 6BA Waterfront Pool

Luxury Boating Paradise+Pool+Sailing Kayaks
Waterfront condo rentals

Villa 5087 on Duck Key BOAT SLIP available

Reel Large END Unit in Ocean Point Suites

Your Happy Place - Oceanfront

Keys Breeze Ocean View Condo & Pool - Key Colony

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

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

Ocean Views at Ocean Pointe

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 | $538 CAD | $569 CAD | $623 CAD | $457 CAD | $628 CAD | $446 CAD | $463 CAD | $418 CAD | $418 CAD | $393 CAD | $438 CAD | $504 CAD |
| 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 500 vacation rentals in Islamorada

Nightly prices starting at
Islamorada vacation rentals start at $126 CAD per night before taxes and fees

Verified guest reviews
Over 3,820 verified reviews to help you choose

Family-friendly vacation rentals
310 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 280 rentals that welcome pets

Vacation rentals with a pool
410 properties feature pools

Rentals with dedicated workspaces
330 properties have a dedicated workspace

Wifi availability
500 of Islamorada vacation rentals include wifi access

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

4.7 Average rating
Islamorada stays receive an average rating of 4.7 out of 5 from guests
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Biscayne National Park
- Schnebly Redland's Winery & Brewery
- Coral Castle
- Homestead-Miami Speedway
- Calusa Campground
- Robbies Marina Of Islamorada
- Everglades Alligator Farm
- Seven Mile Bridge
- Theater of the Sea
- Bahia Honda State Park
- Ernest F. Coe Visitor Center
- Monkey Jungle
- The Turtle Hospital
- Florida Keys Aquarium Encounters
- Conch Key
- Key Largo Kampground And Marina
- Dolphin Research Center
- Founder's Park
- Harry Harris Beach and Park
- History Of Diving Museum





