House holiday rentals in Islamorada

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Popular amenities for house rentals in Islamorada

House rentals with a pool

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.
Superhost
Home in Key Largo
4.91 out of 5 average rating, 150 reviews

Tiny Home on Waterfront | Bay Views | Deck | Pool

VikranthRating, 5 stars2 weeks ago
Great great getaway place to relax. Right on the waterfront. You can get your boat, Jet ski and enjoy your stay. I loved watching sunrise with my cup of coffee.
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, 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.
Top guest favourite
Home in Islamorada
5 out of 5 average rating, 5 reviews

Anglers Haven- 2 bed 2 bath home in Islamorada

BenRating, 5 stars5 months ago
Spent the week of Christmas. Great location. Perfect for our family.
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.
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 114 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

JasonRating, 5 stars3 weeks ago
We really enjoyed this home in Marathon. Sitting by the canal for morning coffee, swimming in the pool on a hot afternoon, having dinner on the covered porch, or plying corn hole on the roof… it was all super enjoyable. Andy even dropped off some wonderful bagels one morning! The location is super close to all that Marathon has to offer. We would recommend this home to anyone
Top guest favourite
Home in Marathon
5 out of 5 average rating, 32 reviews

Coco Plum Paradise - Marathon 5 BR 4 BA Waterfront

JesseRating, 5 stars3 weeks ago
Jay’s home was perfect for our large family, very clean, and in a great location. We loved the outdoor area and were able to see several manatees from the dock!

Weekly house rentals

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.
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!
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.
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
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 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 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.
Superhost
Home in Marathon
4.88 out of 5 average rating, 17 reviews

P31 - 11785 5th Ave. Ocean

PattiRating, 5 stars2 months ago
I knew that I was limited on what I could do during the week stay bc of a knee injury and it was just fine bc I was quite happy just being at the house for most of my stay. Just loved it and didn’t want to leave. Even though this is an active boating location and boating route l, I still felt quite peaceful staying there. The pool was great and the hot tub was quite beneficial for my knee. Just be careful climbing into the pool. The ladder going up is quite steep. I would’ve preferred some true stairs. But that’s coming from someone with a hurt knee too so take it with a grain of salt. And if you don’t feel like going out to eat, seriously order the steamed shrimp by the pound at FishTails on the corner. It is within walking distance. Will definitely be back for another stay in the future.

Private 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.
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
4.96 out of 5 average rating, 52 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

LoganRating, 5 stars3 weeks ago
The location and access to the beach and canal was amazing! We had such a fun time with the kayaks while being able to see all the wildlife and sail boats. The house was exactly what we needed. Jose was very helpful and flexible throughout our stay.
Top guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 85 reviews

“La casa azul” step 3’ to a private pool

RickRating, 5 stars3 weeks ago
We spent an amazing week in this home. Very comfortable and quiet. The pool was amazing. Will definitely be back.
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!
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.
Top guest favourite
Home in Marathon
4.98 out of 5 average rating, 56 reviews

Waterfront Heated Pool 120 ft Boat Dock

Gwen And JustinRating, 5 stars1 week ago
A Hidden Gem – Perfection in Every Way! Truly! This was, one of the best Airbnbs we have been to in Marathon! We have traveled down for many years and could not ask for a better place!!! From the moment we arrived, everything was absolutely perfect. The space was spotless, it slept 8 of us comfortably! Stocked with every single thing we could need! Location itself was Unbeatable! Peaceful, picturesque, and close to everything, yet somehow still felt like our own private escape! The dock cutting board and easy water hose worked perfect for any catch! The wrap around deck was the biggest hit! Seeing manatees and Tarpon sightings really made my kids day! It truly was magical experience! The pool to cool off and the mini splits in each room without it being manually controlled was the ultimate! Milton was phenomenal to communicate with! You can tell he genuinely cares about his guests♥️. Our family has already booked for next year and we highly recommend!

Quick stats about house rentals in Islamorada

  • Total rentals

    330 properties

  • Nightly prices starting at

    ₹8,657 before taxes and fees

  • Total number of reviews

    2K reviews

  • Family-friendly rentals

    310 properties are a good fit for families

  • Pet-friendly rentals

    160 properties allow pets

  • Rentals with a pool

    210 properties have a pool

Destinations to explore

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