
Waterfront holiday rentals in Islamorada
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Top-rated waterfront rentals in Islamorada
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Popular amenities for waterfront rentals in Islamorada
Waterfront apartment rentals

Ocean View Duplex Penthouse | Pool | Vista Two
Beautiful, very clean property with a fantastic location. Excellent proximity to snorkeling, restaurants and other local attractions. Short stroll to excellent walking path that takes you along route 1 with amazing morning views of the beautiful water. Great views all around, in fact. Plenty of soft, plush towels and similarly luxurious bed linens. We had a wonderful family vacation staying at this property.

Beachside Unit 22 - Private Beach on Atlantic
Very nice condo in key colony beach, affordable, great stay for a family. Clean rooms, nice pool, nice private beach area, will bring family down again.

Ocean View 2br/2ba w/pool, bar and dockage 28ft
Awesome stay. Very responsive host!

Kawama Lagoon, 3D corner chickee 2bdr , 2 baths
Norma was the most responsive host I’ve ever encountered. Her replies were prompt and she provided outstanding recommendations for local restaurants and entertainment. She checked in with us frequently. Her rental is adorably nautical, clean and well-maintained. I loved her style! She made sure we had everything we needed.

Seaside Vista - Ocean Front 2/1 with dockage
We had to make a very last-minute booking for a two-night stay and were thrilled to find this boat- and pet-friendly spot with space to park our boat trailer. Justin was incredibly quick to respond and made the whole process seamless. The accommodations were clean, comfortable, and exactly what we needed. There was more than enough room for our 24-foot boat, which stayed well-protected from wind and waves. A freshwater hose was conveniently available to rinse the boat off after a day on the water, and the on-site fish cleaning station was a great bonus. The property is just three doors down from Snappers Bar & Grill, where we enjoyed live music, great food, and drinks. We even had the pleasure of meeting the property owners during our stay—truly some of the nicest people you could hope to meet. Overall, a great stay. We’ll definitely be back!

Turtles Nest 2 Ocean Point condo
Had a fantastic stay! The home is very nicely decorated, the beds were super comfortable, everything was nice and clean. Of you intend to hop around to the different parts of the keys this is a good location in between everything. Very peaceful, safe, and easy to find and access.

Ocean Pointe 2309 with Ocean Views
Jacqueline was a fantastic host! My group had the best time staying the Florida Keys for my sister’s birthday, and Ocean Point is the perfect spot for swimming, exploring, and having a blast! Thank you so much Jacqueline!

Little Venice in Marathon (in the Beautiful Keys)
We (two couples) enjoyed a great week here. Being on the canal was nice, outside sitting spots were great. The house had plenty of cooking supplies needed. Was a tad bit smaller than I expexted, but worked out just fine. Remember to bring your shampoo, body wash etc as it's not provided. Comfortable and bright, was quiet even with boats going by. Would definitely stay here again!
Waterfront house rentals

Cancellation Deal: 08/02 thru 08/09
The house was very clean and inviting upon arrival. Nice location short drive to great restaurants and local grocery stores also less than 5min walk to the beach. Mr Eddie responded in a timely manner when we had questions. All in all we had a great time and very much enjoyed our stay! Thanks Mr Eddie

Million Dollar View
This home was everything we expected and more. Stunning location with absolute privacy. The extra long dock was amazing, the pool was fantastic, and the grounds were meticulous. It’s literally your own private resort. Roman, the host, was very quick with communication. He and his wife actually met us when we checked in to see if we had any questions and provided us with an arrival gift. If you have looked at the listing and are thinking of renting it, do it. You will not be disappointed at all. Excellent value all around.

Escape to the Seaside!
Perfect spot for a long weekend beach getaway! This was our first time visiting the Florida Keys, and we loved being right on the water with a small beach area to ourselves. The space was ideal for our group of friends, and the location was great—close to local bars and restaurants, some within walking distance or just a short drive away.

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront
Loved every minute of our time here. Communication was excellent before during and after our stay and the house was superb. Highly recommended

New Oceanside Casa Azul! Voted #1! Golf Cart-Beach
Martha was super helpful and responsive. The place was very nice, clean, and had incredible amenities. Kids loved it!

Waterfront House with 37 ft Dock & Cabana Club
Enjoyed the stay! If you’re looking for a low key place to stay this is it. Great location for day adventures in the keys.

Marathon one-level home on the Marina - with slip!
It was a very nice. The front porch sunrises were amazing. My family enjoyed the accommodations. The pool was fantastic and not crowded. The resort was quiet except for an occassional boat and landscapers.

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV
We had a wonderful time staying at Tim’s place! He was an excellent host who was always available if I had a question. The house is in a beautiful location. We enjoyed sitting on and fishing off the dock. The house had everything we needed for a fantastic stay and a very enjoyable vacation. I can’t say enough good things about our experience at the home. We were able to meet Tim and he was a lovely host. Thank you for a great vacation! We hope to come back in the future!
Waterfront apartment rentals

Reel Large END Unit in Ocean Point Suites
very kind and flexible hosts. Let us check out an hour after checkout time and we're also very communicative, friendly and service oriented. definitely recommend

Oceanfront and Sunrise Views!
We had an amazing stay in this wonderful Condominium! The host was absolutely fabulous - super responsive, friendly, and made sure we had everything we needed. The apartment itself was clean, comfortable, and perfectly located. The whole experience was top-notch, and we highly recommend this place to anyone looking for a great stay. Thanks again to the host for making it so special!

Mariner's Club 522 - Don't worry Beach Happy!
Location of unit is beautiful! Amenities were also wonderful and resort like. Host provided a prompt response regarding some questions about the unit and addressed any concerns presented. Thank you for a relaxing stay!

Waterfront Spacious Condo Key Largo #4, 10% Off 7+
Great stay at Javiers’s place. Beautiful views and great quiet neighborhood location. Bar and Restaurant a 2 minute walk away and everything else you could need a 5 minute drive.

Million dollar view in Key Largo!
The condo was very nice. Lots of room, clean and easy to access. We loved the balcony, and spent a lot of time there. We enjoyed the kayaks a couple of different times as well. Our first time to The Keys and we enjoyed this spot.

Ocean Views at Ocean Pointe
We had a fantastic stay at this condo in Tavernier! The location was ideal—close to everything we wanted to see and do in the Keys. The unit was clean, comfortable, and well-stocked, with a beautiful view of the ocean that made every morning feel like a dream. The host was extremely responsive and made everything easy from check-in to check-out. Highly recommend this place—we’d love to come back!

Modern and Coastal Ocean Pointe 2307
Clean, comfortable, nicely decorated, and in a nice complex. Love the pickleball courts. Condo is conveniently located for exploring the Keys with plenty of services nearby. Host’s managers are friendly and responsive. Strongly recommended

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
Absolutely perfect for a honeymoon getaway, quiet perfect amount of space for us, the set up was great with 2 bathrooms and a huge walkin closet, the couches were super comfy, the TV was big enough to see from across the room, we enjoyed everything about it. Got to meet some of the neighbors and they were all very welcoming and enjoyed talking to them. Scott had some great local recommendations and we enjoyed everything.
Quick stats about waterfront rentals in Islamorada
Total rentals
480 properties
Nightly prices starting at
₹6,074 before taxes and fees
Total number of reviews
3K reviews
Family-friendly rentals
340 properties are a good fit for families
Pet-friendly rentals
280 properties allow pets
Rentals with a pool
340 properties have a pool
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Bahia Honda State Park
- Coral Castle
- Cannon Beach
- Biscayne National Park
- Conch Key
- Calusa Beach & Loggerhead Beach
- Everglades Alligator Farm
- Theater of the Sea
- EAA Air Museum
- Long Beach
- Cocoa Plum Beach
- Far Beach
- Sea Oats Beach
- Monkey Jungle
- Horseshoe Beach
- Windley Key Fossil Reef Geological State Park
- Keys' Meads
- Long Key State Park