Waterfront holiday rentals in Islamorada

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Popular amenities for waterfront rentals in Islamorada

Waterfront apartment rentals

Superhost
Flat in Islamorada
5 out of 5 average rating, 3 reviews

Ocean View Duplex Penthouse | Pool | Vista Two

AnneRating, 5 stars3 months ago
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.
Superhost
Flat in Key Colony Beach
4.84 out of 5 average rating, 115 reviews

Beachside Unit 22 - Private Beach on Atlantic

JamesRating, 5 stars3 weeks ago
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.
Top guest favourite
Flat in Tavernier
4.98 out of 5 average rating, 42 reviews

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

TomRating, 5 stars1 week ago
Awesome stay. Very responsive host!
Top guest favourite
Flat in Key Largo
4.99 out of 5 average rating, 151 reviews

Kawama Lagoon, 3D corner chickee 2bdr , 2 baths

DonnaRating, 5 stars3 weeks ago
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.
Guest favourite
Flat in Key Largo
4.88 out of 5 average rating, 282 reviews

Seaside Vista - Ocean Front 2/1 with dockage

JeremyRating, 5 stars5 days ago
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!
Guest favourite
Flat in Tavernier
4.95 out of 5 average rating, 95 reviews

Turtles Nest 2 Ocean Point condo

AndreaRating, 5 stars2 weeks ago
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.
Superhost
Flat in Tavernier
4.9 out of 5 average rating, 77 reviews

Ocean Pointe 2309 with Ocean Views

GraceRating, 5 stars1 week ago
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!
Superhost
Flat in Marathon
4.86 out of 5 average rating, 51 reviews

Little Venice in Marathon (in the Beautiful Keys)

AlisonRating, 5 stars1 month ago
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

Top guest favourite
Home in Marathon
4.99 out of 5 average rating, 137 reviews

Cancellation Deal: 08/02 thru 08/09

KevinRating, 5 stars1 week ago
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
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 26 reviews

Million Dollar View

JohnRating, 5 stars1 month ago
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.
Guest favourite
Home in Key Largo
4.79 out of 5 average rating, 146 reviews

Escape to the Seaside!

CarlyRating, 5 stars2 months ago
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.
Guest favourite
Home in Marathon
4.92 out of 5 average rating, 12 reviews

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

HansRating, 5 stars3 weeks ago
Loved every minute of our time here. Communication was excellent before during and after our stay and the house was superb. Highly recommended
Guest favourite
Home in Key Largo
4.91 out of 5 average rating, 101 reviews

New Oceanside Casa Azul! Voted #1! Golf Cart-Beach

AshlynRating, 5 stars2 months ago
Martha was super helpful and responsive. The place was very nice, clean, and had incredible amenities. Kids loved it!
Top guest favourite
Home in Key Colony Beach
4.98 out of 5 average rating, 106 reviews

Waterfront House with 37 ft Dock & Cabana Club

CaseyRating, 5 stars6 days ago
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.
Guest favourite
Home in Marathon
4.97 out of 5 average rating, 149 reviews

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

BillieRating, 5 stars1 month ago
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.
Top guest favourite
Home in Marathon
5 out of 5 average rating, 114 reviews

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV

LaurenRating, 5 stars2 months ago
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

Superhost
Apartment in Tavernier
4.88 out of 5 average rating, 154 reviews

Reel Large END Unit in Ocean Point Suites

PatrickRating, 5 stars1 week ago
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
Top guest favourite
Apartment in Duck Key
5 out of 5 average rating, 38 reviews

Oceanfront and Sunrise Views!

StephenRating, 5 stars3 weeks ago
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!
Superhost
Apartment in Key Largo
4.93 out of 5 average rating, 72 reviews

Mariner's Club 522 - Don't worry Beach Happy!

BillRating, 5 stars1 week ago
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!
Guest favourite
Apartment in Key Largo
4.87 out of 5 average rating, 131 reviews

Waterfront Spacious Condo Key Largo #4, 10% Off 7+

ChristopherRating, 5 stars2 days ago
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.
Guest favourite
Apartment in Key Largo
4.94 out of 5 average rating, 50 reviews

Million dollar view in Key Largo!

DarrylRating, 5 stars2 months ago
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.
Top guest favourite
Apartment in Tavernier
4.98 out of 5 average rating, 196 reviews

Ocean Views at Ocean Pointe

PattyRating, 5 stars1 month ago
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!
Guest favourite
Apartment in Tavernier
4.98 out of 5 average rating, 111 reviews

Modern and Coastal Ocean Pointe 2307

JimRating, 5 stars3 weeks ago
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
Top guest favourite
Apartment in Marathon
4.96 out of 5 average rating, 103 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

AlexRating, 5 stars3 weeks ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada
  6. Waterfront rentals