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Beach house holiday rentals in Islamorada

Find and book unique beach houses on Airbnb

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Popular amenities for Islamorada beach house rentals

Beachfront house rentals

Top Guest favourite
Home in Marathon
4.89 out of 5 average rating, 37 reviews

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

LydiaRating, 5 stars10 months ago
We booked this home last minute and now have our go-to vacation spot in Marathon! Alida is a friendly host with great communication. The home is very clean. Beds are very comfortable. Kitchen is well stocked with pots, pans, etc. The kayaks and paddle board made our vacation even more special! The steet is very quiet and peaceful. The setting in the back yard is very private, as is the long dock. We had a 23' rental boat for our stay. The view is amazing and the sunsets are a special treat each evening. I very much appreciated the ample, comfortable seating everywhere - inside and outside of the home. Thank you Alida. We made great family memories here!
Top Guest favourite
Home in Key Colony Beach
4.98 out of 5 average rating, 124 reviews

Paradise found!Key Colony Beach,Cabana Club.

ColinRating, 5 stars2 weeks ago
We had a great week at Kari's place. We were blown away by the view from the terrace. The apartment was well appointed and had everything we needed. The use of the nearby Cabana club was a real bonus. Colony Key is about an hour from Key West, so it was well located for all sorts of activities. Would love to return one day. Thanks Kari. Colin & Lynne Moore. Buckinghamshire, UK
Top Guest favourite
Home in Marathon
4.97 out of 5 average rating, 39 reviews

Grouper Getaway @ Ocean Isles Fishing Village

JessicaRating, 5 stars6 days ago
One of the best airbnbs we have stayed in. They had everything including paddle board, kayak, bikes, bogg bag, yeti cooler, fishing gear, bait cooler full of bait, fishing poles, life jackets, and even sunscreen. Also anything you could imagine for a kid (pack and play, stroller, toys). Will definitely be returning.
Guest favourite
Home in Cudjoe Key
4.93 out of 5 average rating, 178 reviews

106 Newly Renovated House with Oceanview and Pool

JoanRating, 5 stars1 month ago
As always, Michael’s place was spotless, perfectly stocked and just as pictured. We come back here annually to fish at Sugarloaf Marina and are always satisfied. Michaels house is in the perfect location, with the best sunsets, an amazing dock and pool, and the house is always stocked and we're able to relax for another day of tarpon fishing.
Guest favourite
Home in Marathon
4.89 out of 5 average rating, 66 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

RobinRating, 5 stars3 weeks ago
This home is even more than the pictures show! It is an extraordinary home for people who love the sun, shade, beach, and the beautiful home just makes it a luxurious vacation. I could not find one aspect I didn’t love.❤️
Guest favourite
Home in Upper Sugarloaf Key
4.94 out of 5 average rating, 95 reviews

Lighthouse - Beach Houses Key West

AlexisRating, 5 stars3 weeks ago
We loved our stay at The Lighthouse! The place was clean, host was responsive, pool area was great, and the ocean was beautiful. While we were in heavy seaweed time, we enjoyed coffee on the deck every morning with beautiful sunrises and water scenes. The pool and BBQ area was amazing!! We grilled almost every night there and had all we needed. We enjoyed having bikes to ride the island! 10/10 stay and we will definitely be back!
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 179 reviews

Beachfront Villa - Florida Keys

MorganRating, 5 stars1 month ago
We had a great stay at Loretta’s place. The location offered a good jumping off point to explore the keys. The beach nearby along with canal access and kayaks was a huge plus. The garden area was nice though the mosquitos were intense. The place accommodated our group of 7 ppl well and everything was clean and well furnished. Overall, the place worked great for our group and we’d stay again!
Guest favourite
Home in Key Largo
4.91 out of 5 average rating, 102 reviews

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

JuanRating, 5 stars2 weeks ago
Excellent place fun for the kids, the pool was amazing,the house has everything you need, the gulf cart was a plus. Highly recommended!

Beach house rentals with a pool

Guest favourite
Home in Marathon
5 out of 5 average rating, 15 reviews

Waterfront 2-bedroom Home w/Pool and Spa

ChrisRating, 5 stars6 months ago
Great place! Exactly like the pictures. AMAZING heated pool! Very clean. Ruth was an excellent host! She had fresh flowers, toiletries and even snacks and breakfast items to get us started! Most Airbnb’s you have to provide your own TP, paper towels, trash bags and soap but not here! Ruth had the place very well stocked. We will definitely be returning! Thanks for a memorable Thanksgiving week Ruth!!
Top Guest favourite
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!
Top Guest favourite
Home in Marathon
5 out of 5 average rating, 16 reviews

Waterfront home w/pool, dock & close to beach

ElaineRating, 5 stars1 month ago
Our family (of six adults) had the most wonderful two weeks in Ruth’s beautiful home, and we loved every single minute of it, apart from our departure as we all wanted to stay! The house is absolutely beautiful, spotlessly clean and very well equipped. The refrigerator/kitchen was thoughtfully stocked with a very generous supply of breakfast items and other snacks, and there were fresh flowers in place. We were lucky enough to have manatees visiting us a few times, which was an incredible experience. The location is amazing, and after travelling the length and breadth of the Keys, it is definitely the best place to be. Ruth was the best ever host - very hospitable & responsive, and we cannot thank you enough! We really can’t wait to come back! Thank you so much!
Superhost
Home in Key Colony Beach
4.82 out of 5 average rating, 158 reviews

Waterview from three sides, Cabana Club, 30' Docks

NoraRating, 5 stars3 weeks ago
A Perfect Getaway! Our stay at this fabulous Airbnb was nothing short of amazing! The house was beautiful, clean, and offered breathtaking panoramic views of the open water. Waking up to the sunrise over the water was absolutely unforgettable. Brad, our host, was fantastic—super responsible, quick to respond, and incredibly easy to communicate with. He made the entire experience smooth and enjoyable from start to finish. The location was ideal for anyone who loves peace, nature, and especially fishing. We had plenty of opportunities to fish right from the property, which was a huge bonus. Highly recommend this place to anyone looking for a relaxing waterfront escape. We can't wait to come back!.

Private beach house rentals

Top Guest favourite
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!
Home in Marathon
4.91 out of 5 average rating, 22 reviews

Walk to Sombrero Beach, 50’Dock, SPA, Kayaks,Bikes

StacieRating, 5 stars3 months ago
the home known as Islandville was amazing, and both Monica and Roly were superb hosts. From the initial booking to final checkout, they were super responsive and super helpful. The home was perfect for our group of 5 and had every amenity you could possibly need. We used the kayaks, paddleboards, bikes, and hot tub daily and the dock was awesome for a 3 day boat rental. We were greeted by a sweet gift of Key lime pie, local chips and salsa, and champagne. On top of that I had inquired about the dock light and they had a handyman there that week to repair and install a new one! I can't say enough about our time in Marathon. The only issue was that our time went by way too fast! If you have any questions about whether you should book this home for an amazing Keys vacation... I'll make it easy and answer yes for you. Michael and Stacie Whidbey Island, Washington
Superhost
Home in Key Colony Beach
4.82 out of 5 average rating, 158 reviews

Waterview from three sides, Cabana Club, 30' Docks

NoraRating, 5 stars3 weeks ago
A Perfect Getaway! Our stay at this fabulous Airbnb was nothing short of amazing! The house was beautiful, clean, and offered breathtaking panoramic views of the open water. Waking up to the sunrise over the water was absolutely unforgettable. Brad, our host, was fantastic—super responsible, quick to respond, and incredibly easy to communicate with. He made the entire experience smooth and enjoyable from start to finish. The location was ideal for anyone who loves peace, nature, and especially fishing. We had plenty of opportunities to fish right from the property, which was a huge bonus. Highly recommend this place to anyone looking for a relaxing waterfront escape. We can't wait to come back!.
Guest favourite
Home in Marathon
5 out of 5 average rating, 15 reviews

Waterfront 2-bedroom Home w/Pool and Spa

ChrisRating, 5 stars6 months ago
Great place! Exactly like the pictures. AMAZING heated pool! Very clean. Ruth was an excellent host! She had fresh flowers, toiletries and even snacks and breakfast items to get us started! Most Airbnb’s you have to provide your own TP, paper towels, trash bags and soap but not here! Ruth had the place very well stocked. We will definitely be returning! Thanks for a memorable Thanksgiving week Ruth!!
Top Guest favourite
Home in Marathon
5 out of 5 average rating, 16 reviews

Waterfront home w/pool, dock & close to beach

ElaineRating, 5 stars1 month ago
Our family (of six adults) had the most wonderful two weeks in Ruth’s beautiful home, and we loved every single minute of it, apart from our departure as we all wanted to stay! The house is absolutely beautiful, spotlessly clean and very well equipped. The refrigerator/kitchen was thoughtfully stocked with a very generous supply of breakfast items and other snacks, and there were fresh flowers in place. We were lucky enough to have manatees visiting us a few times, which was an incredible experience. The location is amazing, and after travelling the length and breadth of the Keys, it is definitely the best place to be. Ruth was the best ever host - very hospitable & responsive, and we cannot thank you enough! We really can’t wait to come back! Thank you so much!

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