
Waterfront vacation rentals in Islamorada
Find and book unique waterfront rentals on Airbnb
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 ﺩ.ﺇ 294 per night before taxes and fees

Verified guest reviews
Over 4,190 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 290 rentals that welcome pets

Vacation rentals with a pool
410 properties feature pools

Rentals with dedicated workspaces
320 properties have a dedicated workspace

Wi-Fi availability
500 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!
Top-rated waterfront rentals in Islamorada
Guests agree: these waterfront rentals 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.
RiverViewWalkability

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 💫
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Tiny Home on Waterfront | Bay Views | Deck | Pool
Down by the waters of Manatee Bay, you’ll find this idyllic tiny home for 6. With a full kitchen, three comfy beds,and access to a community pool, this is a prime location to enjoy the best of Key Largo. Sit on the deck and dip your toes in the water or explore the bay using the available kayaks and paddle boards. 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!
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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.
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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.
BeachViewLong stay

Beach House Getaway - Free 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.
BeachRiverBathroom

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.
ViewBeachGetting around

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.
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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!!
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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.
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Kawama N2 Relaxing Lagoon View free bikes & kayaks
Relax and enjoy our family friendly 3 bedroom/3 bathroom Villa Lago in Key Largo! Salt water swimming lagoon, Pools, the Ocean, fishing pier, Marina, Tennis, Bikes, fire pit and playground. Enjoy resort like amenities in the comfort of a home. This beautifully decorated villa sleeps 8 and is conveniently located in a very central location in Key Largo. Close to some great restaurants, diving, fishing, boat tours, State Park. Kawama is fun for all ages.
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4BR 3B, Heated Pool & Spa, 60' Dock
Enjoy breathtaking views of the Gulf and Ocean from the screened in patio of this beautiful 4 BEDROOM/3 BATH canal front home. Bring your boat to the 60' dock on a 200' wide canal just 10' away from the Ocean. Relax by the pool/spa area after a day of fishing. A pool heater is offered as an option for your convenience. Please inquire about water heater fee and operating instructions before booking. (VR Lic # PLR2020-00104)
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Popular amenities for Islamorada waterfront rentals
Waterfront apartment rentals

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
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5. Key Largo Waterfront Studio | Kayak & Reef
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Ocean View 2br/2ba w/pool, bar, gym + dockage 28ft
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Beachside Unit 22 - Private Beach on Atlantic
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Elevated Retreat | Sunset Access + Boat Basin
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Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
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Breezy Bonefish | Free Breakfast + Pool + Tiki Bar
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Oceanfront Bliss • Wall-to-Wall Water Views + Pool
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Waterfront house rentals

Angler’s Eden
ViewBeachHospitality

Coco Plum Waterfront Hideaway Home in Marathon
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Off The Charts-Waterfront Tiki Bar & Private Dock
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Las Olas
PoolFamilyNearby

Heart of Islamorada ~ Private Boat Dockage
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Marlin House @ Tarpon Point
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Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
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Beach House, Private Pool, Dock, Gulf View Sunsets
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Waterfront condo rentals

BEAUTIFULLY DESIGNED OCEANFRONT CONDO
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Turtle Nest 1 Private beach,Pool, 2bed 2bath
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Tiki Time! Ocean Pointe Top Floor King 1 Br/1Ba
BeachViewGetting around

Reel Large END Unit in Ocean Point Suites
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Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach
ViewBeachLong stay

Oceanfront Sunrise Condo Private Beach Heated Pool
ViewBeachAir conditioning

🏝 Oceanfront Paradise Awaits You
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Your Happy Place - Oceanfront
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When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,418 | ﺩ.ﺇ 1,498 | ﺩ.ﺇ 1,642 | ﺩ.ﺇ 1,410 | ﺩ.ﺇ 1,285 | ﺩ.ﺇ 1,238 | ﺩ.ﺇ 1,219 | ﺩ.ﺇ 1,102 | ﺩ.ﺇ 1,102 | ﺩ.ﺇ 1,036 | ﺩ.ﺇ 1,153 | ﺩ.ﺇ 1,326 |
| 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 |
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Biscayne National Park
- Calusa Campground
- Schnebly Redland's Winery & Brewery
- Homestead-Miami Speedway
- Coral Castle
- Bahia Honda State Park
- Robbies Marina Of Islamorada
- Seven Mile Bridge
- Everglades Alligator Farm
- Theater of the Sea
- Ernest F. Coe Visitor Center
- Key Largo Kampground And Marina
- Florida Keys Aquarium Encounters
- Monkey Jungle
- Dolphin Research Center
- Harry Harris Beach and Park
- Founder's Park
- History Of Diving Museum
- Homestead Bayfront Park
- Conch Key





