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

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
We absolutely loved our stay here!!! Norma worked to accommodate us even with our tight schedules and helped make our stay unforgettable! The rooms were spectacular, the lagoon was amazing and the view from the point was breathtaking! We will definitely make this our go-to place in Key Largo!

Turtles Nest 2 Ocean Point condo
Amazing condo! The view from the balcony is beautiful for sunrises and sunsets! My family had a great time at the pool and restaurant on the property. We will definitely be coming back! 😊

Waterfront Studio 2| Couples Oasis | Kayaks | Pool
Our stay at this dockside Airbnb was absolutely perfect for the two of us. The home was spotlessly clean and had every amenity we could have possibly needed. Everything was exactly as described—if not better—and the attention to detail made it clear that the guest experience was a top priority here. The location, tucked into a peaceful boating community, made for a truly relaxing atmosphere. We loved being right on the water, and while we didn’t have time to use the kayaks they offered, it was such a thoughtful touch to have them available. Communication with the host was flawless. They were incredibly responsive, friendly, and accommodating throughout the entire process. It really made the whole experience feel seamless and welcoming. We would absolutely stay here again without hesitation. Highly recommend this place for anyone looking for a clean, comfortable, and guest-focused getaway on the water!

Little Venice in Marathon (in the Beautiful Keys)
This is our 2nd time staying here. Great location and super clean. We love it here and look forward to booking again for next year! It is a nice and familiar place for us.

Boho FL Keys Condo
We really enjoyed our stay. The location is great and the view is amazing. It is very clean and very well maintained. Would definitely stay again.

Studio apartment in Calusa Resort & Campgrounds
So must say 10/10 we stay in a lot of places and this one we will deff come back to over and over again it was perfect and I must say the price is a steal honestly when we first booked we were nervous because of the price was cheap and I must say dosent reflect at all it is a amazing studio super clean super comfy can’t wait to come back highly recommend
Waterfront house rentals

Cancellation Deal: 08/02 thru 08/09
Had a wonderful stay, would recommend to anyone looking for a convenient, beautiful spot in Marathon. Eddie was an excellent host!

Endless Summer
We very much enjoyed our stay, the house was as expected based on previous reviews & pictures. The location was perfect for us to access from Key Largo to Key West easily. The pool was nice & the kids had fun snorkeling off the back dock & looking for all kinds of wildlife both on land & in the water with their flashlights after dark. We found the sunsets at the house to be better than what we experienced in Key West. If you need beach chairs and/or beach umbrella, we recommend you rent those.

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.

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!

Anglers Terrace, Condé Nast Traveler's Best Airbnb
The house was beautiful!We thoroughly enjoyed all the outdoor spaces.With 4 bedrooms and an 8 month old, the house offered many spaces for everyone to be comfortable. The beds were comfortable and we were all well rested. The rooftop area for grilling and chilling was amazing. The outdoor seating area off the main level was where we celebrated Father’s Day dinner. Morning snuggles were spent in the seating area off the den.The pool area was where we laughed and swam and had many a cocktail. We loved our week as a family there and had no reason to leave except for a few dinners out.Andy was very responsive, dropped off bagels one morning and a great resource for recommendations. Highly recommend Anglers Terrace as we loved our week there!

Tropical Waterfront, Boat Dock, Sunset View, Kayak
Great place to stay if you have a boat it’s a short run to get out to the ocean and you’re right at the end of the canal so you’re right there on the bay. Tons of good restaurants around even though they were quite expensive but then again you’re in the keys.

Private Pool! Luxury Paradise Pointe, Pet Friendly
Amazing Stay in the Florida Keys! We had an absolutely incredible time at this home in the Florida Keys! Everything about our stay was perfect. The house was clean, comfortable, and had everything we needed for a relaxing getaway. The highlight was definitely the pool — it was beautiful, well-maintained, and the perfect spot to unwind after a day of exploring. The outdoor space was peaceful and made it feel like our own private paradise. Loved the tv out by the pool! We couldn’t have asked for a better place to stay. The location was great, the home was even better than expected, and we left feeling completely refreshed. Highly recommend and would definitely stay here again!

Islamorada Waterfront House on Canal w Boat dock
Lisa is the best! Very accommodating and super responsive The house is very private and very very quiet! Lots to do in Islamorada We had a great stay and will be booking again for sure ⭐️⭐️⭐️⭐️⭐️
Waterfront condo rentals

Newly Renovated Piece ofParadise
We had such a wonderful stay at Todd’s Airbnb in beautiful Key Largo! The place was modern, spotless, and thoughtfully decorated—it felt like a true home away from home. The kitchen was well stocked with everything we needed, which made cooking a breeze. There were so many fun things to do on the property, from grilling out on the BBQs to relaxing in the hammocks, and playing foosball or ping pong. The pool was awesome, and the marina was absolutely stunning—especially at sunset. Todd was an incredible host, full of helpful information and spot-on recommendations that made our trip even better. We’d highly recommend his place to anyone looking for a fun, comfortable, and well-located home base in Key Largo. Can’t wait to come back!

Reel Large END Unit in Ocean Point Suites
Something for the whole family to do right at location. Pool was great.

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!

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!

Tequila Sunrise
Kathryn's condo was great! Perfect for 2 couples, a small girls weekend or small family. It's on the end of a row which makes it extra quiet. The little extras in the bathroom and kitchen was really nice (toothpaste-that I forgot...coffee and creamer really get you started, pool floats too!) The overall location was perfect. There's a bar/restaurant on property which was nice and a concession/bar at the pool. The best restaurant was in Islamorada called Square Grouper and Key Lime Pie Factory is a MUST do! I highly recommend Kathryn's place!

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
Host was extremely helpful and communicative. Check in was a breeze and all the amenities needed for a pleasurable stay. Bonus outdoor bait freezer!

Ocean Potion 1B/2B 3Balconies Ocean View
The place was very comfortable, very well appointed and centrally located to all kinds of great things to do! The one issue we reported was addressed right away! Would definitely go back!

Modern and Coastal 3212 is Across from Pool
This is the perfect place to stay to explore the areas of Key Largo and Islamorada. The unit is very clean and nicely decorated. We had no issues and would stay there again. Highly recommend!
Quick stats about waterfront rentals in Islamorada
Total rentals
480 properties
Nightly prices starting at
R1,248 ZAR 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
- Theater of the Sea
- Everglades Alligator Farm
- Long Beach
- Cocoa Plum Beach
- EAA Air Museum
- Far Beach
- Sea Oats Beach
- Horseshoe Beach
- Monkey Jungle
- Windley Key Fossil Reef Geological State Park
- Keys' Meads
- Long Key State Park