
Waterfront holiday 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.

Key Colony Beach Luxury Condo, New Modern Interior
Private studio condo at Key Colony Beach with a private balcony, heated pool and sandy beach. Unit #15 was recently renovated and offers one comfy King size bed and a fully equipped kitchen with essentials (stove, oven, toaster, microwave, blender, fridge, cooking utensils). Wifi, Amazon Echo and a TV. Enjoy a short walk to Sunset Park next door to experience a stunning Florida Keys sunset. Guests also have access to a private beach with lounge chairs, patio tabales, tiki huts, and BBQ grills.

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!!!

Ocean Shores Villa 3 with pool and boat slip
This centrally located boater's paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill downstairs. With only 4 units in the building the guests have half an acre of waterfront entertainment (boat slip, Kayaks, Bikes, Hammock and Pool). 32ft Dock Slip and Trailer Parking are included in the rental. Relaxing Balcony that looks down the Ocean Canal is the perfect place to have your morning coffee. Conveniently located near Sandbars, State parks and many attractions.

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!

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 Paradise Awaits You
Bring your boat to next vacation in tropical paradise surrounded by mangrove forest, coconut trees and the pristine turquoise Fl. Keys waters. Welcome to the most visited resort in the beautiful Florida Keys. Ocean Pointe is one of the most luxurious resorts in Tavernier, Florida Keys. The resort offers a private sandy beach, heated swimming pool, jacuzzi, tennis courts, oceanfront marina with boat ramp and dockage, boat & trailer storage, and more - all situated on 60 lush tropical acres.

Your Happy Place - Oceanfront
Experience the ultimate coastal getaway at Ocean Point in the Florida Keys. Nestled along the Atlantic Ocean, our 2 bed/2 bath condo offers unrivaled ocean views from the moment you step inside. Indulge in the array of amenities available at our property including a private beach, pier, marina, snorkeling, family pool and a full service restaurant. Our condo comfortably sleeps 6-7 guests. Equipped with full kitchen and washer/dryer, we provide all the conveniences for a seamless stay.

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.

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.

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 waterfront rentals in Islamorada
Waterfront apartment rentals

Ocean View Duplex Penthouse | Pool | Vista Two

Ocean Isles Seaside Oasis VACA-24-210

Beachside Unit 22 - Private Beach on Atlantic

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

Hidden Gem Islamorada | 1st Floor

Sea Side Dreams at Ocean Pointe - 07

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

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

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

Key Largo Waterfront: Tiki, Dock, Kayak & Pool

Escape to the Seaside!

Waterfront House with 37 ft Dock & Cabana Club

Angler’s Terrace Conde Nast Traveler’s Best Airbnb

Tiki Time 2

Waterview from three sides, Cabana Club, 30' Docks

Ocean Shores Villa 1 with Pool and Boat Slip
Waterfront apartment rentals

Villa 5087 on Duck Key BOAT SLIP available

Reel Large END Unit in Ocean Point Suites

Enjoy sunsets & sunrise in your home away home.

Tequila Sunrise

Sunrise Views in Key Largo | Boat Slip Access

Just a Few Friends - Ocean View and Bring your Boa

Tropical Getaway

Freshly Renovated Coastal Stay • 2 Kings • Marina
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £257 | £287 | £291 | £243 | £334 | £237 | £246 | £222 | £222 | £209 | £233 | £268 |
| 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 £67 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 & child-friendly amenities

Pet-friendly holiday rentals
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

Wifi availability
450 of Islamorada holiday 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
- Calusa Beach & Loggerhead Beach
- Coral Castle
- Sea Oats Beach
- Long Beach
- Schnebly Redland's Winery & Brewery
- Conch Key
- Everglades Alligator Farm
- Bahia Honda State Park
- Theater of the Sea
- Homestead-Miami Speedway
- Monkey Jungle
- Seven Mile Bridge
- Key Largo Kampground And Marina
- Calusa Campground
- Sunset Park
- Dolphin Research Center
- Robbies Marina Of Islamorada
- Florida Keys Aquarium Encounters
- The Turtle Hospital




