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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

Guest favourite
Home in Marathon
4.94 out of 5 average rating, 35 reviews

Florida Keys Oceanside Utopia

CaroleRating, 5 stars1 month ago
Shane and Kelly were fabulous! My husband and I enjoyed a week away and loved exploring Marathon. Fishing from the back deck was so much fun. We caught some mangrove snapper that we made for dinner which was exquisite! I also caught a Jack Cravalle and my hubby caught a shark. Definitely fun times! Explored beaches, hiked and went to Key West for a day. Weather did not disappoint. Highly recommend this great vacation home!
Guest favourite
Home in Marathon
5 out of 5 average rating, 9 reviews

Sandbox

CretiaRating, 5 stars1 week ago
⭐️⭐️⭐️⭐️⭐️ Absolute Paradise in the Heart of the Keys! Our stay at this vacation house in Marathon was nothing short of incredible. From the moment we arrived, we felt like we had found our own private slice of paradise. The house was spotless, beautifully decorated, and had all the comforts of home—plus the added bonus of breathtaking ocean views and island vibes. The location couldn’t have been better. Tucked away in a peaceful part of Marathon, we were just minutes from everything—the beach, boat rentals, amazing restaurants, and the iconic Seven Mile Bridge. The property itself was incredibly well-equipped: a fully stocked kitchen, super comfortable beds, high-speed WiFi. What really made this place stand out was the outdoor space. The private dock was perfect for fishing and sunset cocktails, and the pool made it hard to ever want to leave. We even spotted dolphins just off the dock one morning—unreal! The hosts were friendly, responsive, and went out of their way to make sure we
Superhost
Home in Marathon
5 out of 5 average rating, 3 reviews

KCB Tropical Escape

JosephRating, 5 stars2 months ago
This was better than I expected. A very spacious 2 bedroom with large kitchen, family room. The screened in porch was huge, and a great place to have meals and watch TV and the sunrise. The fully equipped kitchen was awesome for those like us that love to cook. It was a great home away from home. This place was so comfortable and was the best we ever rented.
Top guest favourite
Home in Marathon
5 out of 5 average rating, 41 reviews

Discount Available! 100' Dock, Lots of Amenities!

DanaRating, 5 stars3 weeks ago
We came down for a weeks vacation brought two boats, plenty of space on the docks. Communication with Meredith was great. Great location.
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
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!
Superhost
Home in Key Largo
4.86 out of 5 average rating, 100 reviews

Cary’s Oceanside

KrissieRating, 5 stars5 months ago
We had a great time at Cary’s Oceanside! Beautiful location, beautiful and comfortable accommodations! Maria was very helpful and responsive with our questions. We really enjoyed the pool and outdoor area.
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 34 reviews

Viamarhe House-Private beach, Kayak, yard games

AmandaRating, 5 stars2 weeks ago
Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.

Beach house rentals with a pool

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

Waterfront Escape -VACA-23-408

NatalieRating, 5 stars2 weeks ago
we were a family of 6 staying and had more then enough room. the house was perfect and had everything you needed. we enjoyed fishing off the deck and watching the manatees everyday day swimming by. the backyard was absolutely perfect to hang out and relax. Carmen is a great host and communicates fast. would absolutely stay here again.
Top guest favourite
Home in Marathon
5 out of 5 average rating, 12 reviews

Waterfront Oasis w/Private Pool-Dockage-Beach

DaveRating, 5 stars5 months ago
Incredible property. Perfect gathering space for my entire family of 6. Private yet close to commerce like Publix and local gym to work out. Great memories made.
Top guest favourite
Home in Marathon
5 out of 5 average rating, 40 reviews

Movie Theater | HotTub | Pool | Boat/RV/EV Parking

AnneRating, 5 stars2 weeks ago
We almost stayed at a hotel, but I saw Christian’s place pop up and it looked like a fun place for the family. It is so awesome! It is exactly as described.and more . He uses every inch of that awesome property for something fun. It’s also a close drive or bike ride to so many things. We took almost all of his suggestions on places to eat and things to do and they were right on. The last night we all chilled outside and projected the Goonies on the outdoor screen and had some good relaxing family time. He is an excellent host and is so helpful. We are all so happy we chose his Airbnb.. Thank you so much, Christian! You are one of a kind and your place is so cool.
Guest favourite
Home in Key Largo
5 out of 5 average rating, 15 reviews

NEW! Oceanside Casa Largo Modern Tropical Getaway

AnnabelaRating, 5 stars1 month ago
amazing stay at Martha's place. it's prestine. she's super responsive and very kind. I'd stay at any of her places because she's on top of it.
Superhost
Home in Key Largo
4.85 out of 5 average rating, 207 reviews

Outdoor Paradise - Beach, Boats, Snorkeling & Sun!

VanessaRating, 5 stars2 weeks ago
mooie RV op een leuke camping die alles te bieden heeft. zwembad en leuke hangmatten die uitkijken op de baai. camper aan te raden voor max. 4 of 5 personen. je hebt in 1 kamer wel stapelbedden. de airco op de ouderslaapkamer werkte wat minder.
Guest favourite
Home in Key Largo
4.93 out of 5 average rating, 75 reviews

Casa Solaris | Key Largo home with Private Pool!

MelissaRating, 5 stars1 week ago
We just came home from our vacation and we had a fantastic time. The house was exactly like it was listed and they were very responsive if we had any questions. The pool and spa were amazing and we spent a lot of time in them. We highly recommended this house and host.
Superhost
Home in Marathon
4.93 out of 5 average rating, 29 reviews

Serenity Bay Estate-FL Keys Best Kept Secret! Beau

JerrieRating, 5 stars6 months ago
Stunning location, very comfortable with plenty of space for 10 people. When we arrived we never felt like leaving. Beautiful pool and hot tub surrounded by palm trees, sandy area with great fire pit, gorgeous outdoor eating area and kayaks to drop from pier. Very private location with spectacular sunsets! Fabulous!!!!
Guest favourite
Home in Key Largo
4.89 out of 5 average rating, 123 reviews

Paradise Palace 3/3 Waterfront Pool Kayak 60' Dock

NathanRating, 5 stars1 month ago
We had a great time visiting the FL keys and staying on Mangrove lane. It was awesome hanging on the dock, using the pool, fishing, and catching the sunsets each night. We also really enjoyed having the screened in porch upstairs and spent our breakfasts and night cap cocktails out there. Great spot on a private street! Looking forward to coming back in the future.

Private beach house rentals

Guest favourite
Home in Marathon
4.96 out of 5 average rating, 25 reviews

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys

CarolRating, 5 stars1 week ago
Sandra’s conch cottage was comfortable and beautiful and very clean. Provided all the necessary items for the week. The location of the house in Marathon is perfect to all amenities. I would definitely come again.
Top guest favourite
Home in Marathon
5 out of 5 average rating, 29 reviews

Luxe Super Snapper-Heated Pool, Tiki, Dock, Lanai

NickRating, 5 stars1 week ago
Book this house! Very comfortable and well stocked with everything you need from pool towels to kitchen amenities! The house is in a quiet area with ample parking and only a couple minute drive from all the restaurants and attractions Marathon has to offer. A few key features to note. The screened in pool and outdoor outdoor shower were such a nice touch after being on the boat all day, the ice machine was priceless to refill the boat coolers everyday and not have to spend a fortune on ice at the bait shop! Beds were comfortable, couch was large and accommodating for my family of 4! The house was clean and bed linens were good quality. Plenty of outdoor seating from chairs to loungers. The fish cleaning station and power plug in station for the boat were a nice touch. Vaca Cut was a short 5 minute boat ride North or you can head South by boat 5 minutes to the 7 mile bridge. We will definitely stay here again!
Guest favourite
Home in Key Largo
4.94 out of 5 average rating, 32 reviews

Keys Paradise 3/3 Waterfront, Jacuzzi, Kayaks+More

RebeccaRating, 5 stars3 weeks ago
We had a fun stay in Key Largo at Gabriel/Stu's place. Plenty of space for 5 adults, and the screened in areas were a nice bonus! There was a slight snafu with the AC, but Stu was very responsive and had it taken care of quickly. We did see a couple manatees cruise through the canal one evening. Overall, everything was clean and enjoyable. Also important to note is, although some of the neighbors had get togethers with loud music, we couldnt hear any of it inside the house. I really can't speak enough to Stu's hospitality and responsiveness!
Guest favourite
Home in Marathon
5 out of 5 average rating, 6 reviews

Casa Chiquita Waterfront Canal Home

ShanaeRating, 5 stars2 weeks ago
My family and I really enjoyed this home the pictures do not do it justice it’s beautiful. The owners are very responsive and we were even able to check in a day early ! The canal was awesome , a boat is a must and so much fun. We saw manatees and iguanas. The private pool was fun all together a great experience.
Guest favourite
Home in Key Largo
4.91 out of 5 average rating, 89 reviews

Great key Largo home with water front and pool

ChrisRating, 5 stars2 weeks ago
We enjoyed our stay, the ground level is a fun place set up very well for children or pets, completely fenced to have no worries. Great view of the canal and direct access to run out of Pennekamp to the ocean side. Alejandro was very responsive and made everything easy
Superhost
Home in Marathon
4.89 out of 5 average rating, 65 reviews

Gorgeous Ocean View Home!

Ashley TaylorRating, 5 stars5 days ago
The pictures of this house, while gorgeous, do not do it justice. Not only was the house immaculate and spacious, it has the most stunning view. It is very close to shops and local beaches, and it's centered in between Key West and Islamorada. Yery, our host, was also very helpful and proactive with the one and only challenge we faced. I really can't say enough about this rental. It was spacious enough and contained all the amenities my family of seven could possibly need, including space for our dog. It has the most amazing view of the turquoise water of the Keys. It quite literally checks every box for a checklist of paradise, and I can't wait to go back!
Guest favourite
Home in Marathon
5 out of 5 average rating, 6 reviews

NEW: Vaca Cut with 60' dock, 4br-4ba, 2 kitchens

BarbaraRating, 5 stars1 month ago
Beautiful home, we come down to fish and dive, couldn't be a better location to keep our boat and get offshore quickly. Everything is within 5 minutes of the home and the bait shop and ice is at the end of the street. Super convenient. Public boat ramp is a 5 minute boat ride away. Definitely recommend
Top guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 23 reviews

Boat Dock+King Beds & Cabana Club

AnnetteRating, 5 stars1 day ago
I was very happy when I walked in the door, it had everything that I needed and more during my stay. Every door or cabinet that I opened had something that could be useful during anyones stay. From the moment that I started inquiring about the rental to the very end of my stay, they were very helpful with all the questions that I had and always responded promptly. I highly recommend renting from them. I look forward to staying in their rental next year.

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