
Waterfront holiday rentals in Islamorada
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Top-rated waterfront accommodation in Islamorada
Guests agree: These waterfront accommodation options 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.

Florida Keys Houseboat, unique 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 💫

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!

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

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.

Blue Haven Key Largo | Ocean Pointe 1315
Tastefully decorated and newly renovated 2 Bedroom & 2 Bathroom Condo with a wonderful view of Florida Keys Nature. Relax and escape to this beautiful getaway in the heart of Tavernier, ideally located between Key Largo & Islamorada. The property itself has amenities galore: sparkling pool with hot tub and newly re opened POOL BAR, boat ramp and marina, tennis courts which convert into pickle ball courts, beach with pier, free parking and charcoal grills to cook your catch!

Ocean views at “Sangria Sunrise” 10% off Charters
Welcome to Sangria Sunrise at Ocean Pointe Suites in the beautiful Tavernier Key Florida. Relax and enjoy all of the options offered such as Jr. Olympic sized pool, beach, marina, kayak rentals, tennis courts, and so much more! We invite you to come stay at this cozy and updated one bedroom and one bathroom top floor condo with the most amazing ocean views. We offer a very comfortable queen sized bed and also a queen sleeper sofa that's equally as comfortable.

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!

Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath
Turtle lovers rejoyce! Enjoy this Two Bedroom/Two Bath Condo with the perfect blend of style, comfort and convenience. Featuring a spacious living room and a fully stocked Kitchen. The Master bedroom features a King size bed and ensuite master bathroom. The guest bedroom features a Queen bed with a unattached bathroom. Both bathrooms feature a walk-in shower. The balcony offers views of the nature preserve and peek-a-boo views of the Atlantic Ocean!

Luxury Top Floor Suite W/ Unobstructed Ocean View
Our spacious, 2 bedroom, well-appointed condo provides the perfect home away from home. Step onto your private balcony and soak in the mesmerizing views of the azure ocean and lush mangrove gardens. Escape to a tropical paradise and experience the ultimate keys retreat! Nestled in Tavernier, this property offers a perfect blend of comfort and breathtaking natural beauty. Indulge in the array of fantastic amenities available to our guests.

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 accommodation

Ocean View Duplex Penthouse | Pool | Vista Two

Beachside Unit 22 - Private Beach on Atlantic

Villa 4204 on Duck Key - Boat Slip available

Amazing Oceanview @Ocean Pointe

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Sea Side Dreams at Ocean Pointe - 07

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

Welcome to the Pelican Lodge !
Waterfront house rentals

NEW! CASA PALMA - Golf Cart, 2 King-Size Beds, Pool, Kayaks

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

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Key Largo Waterfront: Tiki, Dock, Kayak & Pool

Escape to the Seaside!

Waterfront House with 37 ft Dock & Cabana Club

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

Tiki Time 2
Waterfront condo accommodation

Reel Large END Unit in Ocean Point Suites

*NEW LUXURY*Sea Glass with Cabana Club Access

Seas the Day / 1BR Coastal Condo with 2 Balconies

Enjoy sunsets & sunrise in your home away home.

Ocean Views at Ocean Pointe

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

Just a Few Friends - Ocean View and Bring your Boa

Waterfront Apt Key Largo #1, 10% Off 7+, 5% Off 4+
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $490 AUD | $546 AUD | $555 AUD | $463 AUD | $635 AUD | $452 AUD | $469 AUD | $424 AUD | $424 AUD | $398 AUD | $443 AUD | $510 AUD |
| 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 holiday rentals
Explore 460 holiday rentals in Islamorada

Nightly prices starting at
Islamorada holiday rentals start at $127 AUD per night before taxes and fees

Verified guest reviews
Over 3,720 verified reviews to help you choose

Family-friendly holiday rentals
320 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 280 rentals that welcome pets

Holiday rentals with a pool
370 properties feature pools

Rentals with dedicated workspaces
320 properties have a dedicated workspace

Wi-Fi availability
450 of Islamorada holiday rentals include Wi-Fi 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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- Waterfront rentals Monroe County
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Biscayne National Park
- Calusa Beach & Loggerhead Beach
- Coral Castle
- Sea Oats Beach
- Schnebly Redland's Winery & Brewery
- Everglades Alligator Farm
- Long Beach
- Conch Key
- Bahia Honda State Park
- Theater of the Sea
- Monkey Jungle
- Homestead-Miami Speedway
- Key Largo Kampground And Marina
- Calusa Campground
- Sunset Park
- The Turtle Hospital
- Founder's Park
- Florida Keys Aquarium Encounters
- Dolphin Research Center
- Seven Mile Bridge




