Waterfront vacation rentals in Islamorada

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Popular amenities for Islamorada waterfront rentals

Waterfront apartment rentals

Superhost
A shaded tiki hut with a thatched roof stands on the sandy shore, overlooking the calm, blue waters of the Atlantic Ocean. Two palm trees frame the structure, creating a serene beach environment, with gentle waves lapping at the rocks in the background.
Apartment in Key Colony Beach
4.84 out of 5 average rating, 116 reviews

Beachside Unit 22 - Private Beach on Atlantic

JamesRating, 5 stars4 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 favorite
A tranquil beach scene features several blue lounge chairs arranged in neat rows on the sandy shore. A wooden pier extends into the water, accompanied by a thatched-roof gazebo. Lush greenery and a peaceful sky with scattered clouds complete the coastal vista.
Apartment in Tavernier
4.98 out of 5 average rating, 42 reviews

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

TomRating, 5 stars2 weeks ago
Awesome stay. Very responsive host!
Top guest favorite
A corner two-story townhouse is shown, situated beside a tranquil saltwater lagoon. Lush greenery surrounds the property, and a staircase leads to a diving platform over the water. The reflection of the structure and trees can be seen on the still lagoon surface.
Apartment in Key Largo
4.99 out of 5 average rating, 152 reviews

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

SherryRating, 5 stars2 days ago
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!
Guest favorite
Apartment in Tavernier
4.95 out of 5 average rating, 96 reviews

Turtles Nest 2 Ocean Point condo

LaneyRating, 5 stars1 day ago
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! 😊
Superhost
A bright studio space features a plush queen-sized bed and a cozy seating area with a Roku-enabled TV. The modern kitchen includes bar seating. Balconies overlook water views and a communal pool area, while tiki huts provide shaded outdoor lounging. Kayaks and paddle boards are readily available.
Apartment in Key Largo
4.93 out of 5 average rating, 269 reviews

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

CharlesRating, 5 stars1 week ago
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!
Superhost
A waterfront view captures a serene canal lined with tropical greenery and residential boats. The white boat is positioned on the dock, with steps leading to an inviting home painted in a soft yellow. Clear blue skies enhance the tranquil atmosphere.
Apartment in Marathon
4.87 out of 5 average rating, 52 reviews

Little Venice in Marathon (in the Beautiful Keys)

KellieRating, 5 stars2 weeks ago
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.
Guest favorite
A light-filled living area features a blue sofa with decorative pillows and a wooden coffee table atop a woven area rug. Two accent chairs frame the seating arrangement, while natural decor elements, including tall grasses and wall art, enhance the welcoming ambiance.
Apartment in Tavernier
4.95 out of 5 average rating, 197 reviews

Boho FL Keys Condo

MarkRating, 5 stars3 weeks ago
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.
Guest favorite
A covered outdoor area features a dining table surrounded by white chairs. A sectional sofa is positioned against the wall, offering seating. Light blue walls complement the spacious tile flooring, which reflects natural light. A BBQ grill and other furniture are visible at the far end.
Apartment in Key Largo
4.83 out of 5 average rating, 60 reviews

Studio apartment in Calusa Resort & Campgrounds

JuanRating, 5 stars4 weeks ago
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

Top guest favorite
A sparkling in-ground pool is visible in the foreground, surrounded by a spacious patio. Lounge chairs are positioned along the deck, offering views of the lagoon. Lush palm trees provide shade, while a clear sky enhances the tranquil atmosphere of the waterfront setting.
Home in Marathon
4.99 out of 5 average rating, 138 reviews

Cancellation Deal: 08/02 thru 08/09

ShelleyRating, 5 stars1 week ago
Had a wonderful stay, would recommend to anyone looking for a convenient, beautiful spot in Marathon. Eddie was an excellent host!
Guest favorite
An outdoor area features a private pool with an adjoining spa, surrounded by lounge chairs. Lush palm trees provide shade, while a spiral staircase leads to the upper level of the house. The setting offers a relaxing space for guests to enjoy.
Home in Marathon
4.91 out of 5 average rating, 11 reviews

Endless Summer

LisaRating, 5 stars1 month ago
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.
Guest favorite
A serene beach area is highlighted by sandy shores and gentle waves. Palm trees sway in the breeze, while lounge chairs are arranged neatly in the foreground. A wooden dock extends into the water, framed by lush greenery in the background.
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.
Top guest favorite
A private wooden dock extends over calm waters, featuring a boat with a blue canopy and a small table with colorful umbrellas nearby. Palm trees line the waterfront, and a series of pastel-colored homes are visible across the canal, creating a serene setting.
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!
Guest favorite
A serene waterfront scene showcases a calm body of water bordered by lush palm trees. Two white lounge chairs are positioned on a stone patio, with a boat dock visible extending towards the water. A sailboat can be seen in the distance, enhancing the tranquil atmosphere.
Home in Marathon
4.97 out of 5 average rating, 115 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

SusanneRating, 5 stars2 days ago
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!
Top guest favorite
An aerial view reveals a long wooden dock lined with boats, surrounded by lush mangroves along the canal. Kayaks are stored on the dock, while the vibrant green foliage frames the serene waterway, enhancing the natural beauty of the waterfront setting.
Home in Key Largo
4.96 out of 5 average rating, 89 reviews

Tropical Waterfront, Boat Dock, Sunset View, Kayak

Richard & FranRating, 5 stars1 month ago
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.
Guest favorite
A private pool is bordered by lush palm trees and a thatched Tiki Hut. Lounge chairs are arranged around the pool area, and colorful outdoor decor adds a cheerful touch. Clear blue skies and sunshine illuminate the space, creating an inviting outdoor retreat.
Home in Key Colony Beach
4.95 out of 5 average rating, 20 reviews

Private Pool! Luxury Paradise Pointe, Pet Friendly

KimberlyRating, 5 stars1 month ago
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!
Superhost
A waterfront home is nestled along a serene canal, showcasing a white exterior and surrounded by lush greenery. A screened-in porch offers views of the calm water, while boats are docked nearby. The sky is clear, reflecting vibrant blue hues on the water's surface.
Home in Tavernier
4.91 out of 5 average rating, 23 reviews

Islamorada Waterfront House on Canal w Boat dock

AR AngieRating, 5 stars1 week ago
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

Top guest favorite
A well-lit heated pool area is surrounded by lounge chairs and palm trees, creating a relaxed atmosphere. Soft blue lights illuminate the pool in the evening, while the ocean is visible in the background, adding to the inviting ambiance.
Condo in Key Largo
5 out of 5 average rating, 20 reviews

Newly Renovated Piece ofParadise

WolfgangRating, 5 stars2 weeks ago
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!
Superhost
A bright living space features a comfortable gray sofa and a recliner, complemented by a white coffee table adorned with decorative items. The dining area, with a white table and several chairs, extends into the modern kitchen equipped with stainless steel appliances and a breakfast bar with stools.
Condo in Tavernier
4.88 out of 5 average rating, 155 reviews

Reel Large END Unit in Ocean Point Suites

JenniferRating, 5 stars1 week ago
Something for the whole family to do right at location. Pool was great.
Top guest favorite
A modern living area features a gray sofa and a blue accent chair, complemented by a coffee table with decorative items. Large windows provide views of the outdoor patio and water. A flat-screen TV is mounted on a white entertainment unit, enhancing the open atmosphere.
Condo in Duck Key
5 out of 5 average rating, 38 reviews

Oceanfront and Sunrise Views!

StephenRating, 5 stars1 month 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!
Top guest favorite
A clear view of the ocean is captured from the balcony, showcasing the shimmering water beneath a bright blue sky. Lush greenery lines the foreground, while a dock extends into the sea. The scene conveys a serene coastal atmosphere.
Condo 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!
Top guest favorite
A light-filled living room reveals ocean views through sliding glass doors. A spacious white couch and armchair offer comfort, while a wooden coffee table rests on a patterned rug. Decorative elements include natural wall art and a bright indoor plant, enhancing the coastal ambiance.
Condo in Tavernier
5 out of 5 average rating, 55 reviews

Tequila Sunrise

MicheleRating, 5 stars1 day ago
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!
Top guest favorite
A light-filled living area is visible, featuring a comfortable seating arrangement and a mounted television. A dining table occupies the foreground, adorned with a bowl of oranges. The walls are painted in soft blue, providing a relaxed atmosphere, with a ceiling fan overhead.
Condo in Marathon
4.96 out of 5 average rating, 104 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

PaulRating, 5 stars2 weeks ago
Host was extremely helpful and communicative. Check in was a breeze and all the amenities needed for a pleasurable stay. Bonus outdoor bait freezer!
Top guest favorite
The view captures a stunning sunset over the marina, with vibrant orange and pink hues reflecting on the water. Palm trees line the waterfront, enhancing the tropical atmosphere. The image is framed by a balcony railing, establishing a sense of tranquility and connection to the outdoors.
Condo in Marathon
5 out of 5 average rating, 14 reviews

Ocean Potion 1B/2B 3Balconies Ocean View

SueRating, 5 stars1 month ago
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!
Guest favorite
Condo in Tavernier
4.94 out of 5 average rating, 111 reviews

Modern and Coastal 3212 is Across from Pool

Amanda Rating, 5 stars4 weeks ago
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

Destinations to explore

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