
House vacation rentals in Islamorada
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Top-rated house rentals in Islamorada
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Popular amenities for Islamorada house rentals
House rentals with a pool

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

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish
Plenty of room for all the family and their families. We enjoyed all the backyard amenities with pool, kyacks, boat dockage and fish cleaning station. There was sufficient seating for everyone and a great area to hangout. The only things we struggled with was TVs didn’t work properly in some of the rooms, no washcloths or kitchen towels available. With that being said, we will definitely consider renting Ryan’s place again in the future!

4BR 3B, Heated Pool & Spa, 60' Dock
Our stay in Marathon couldn’t have gone any better! I traveled with my three 20-something sons and their wives/significant others. The layout of Gerardo’s home was perfect for our needs. We had plenty of room, places to enjoy together, and space where everyone could find some peace and quiet. The location was ideal. We were within an easy driving distance of all excursions and restaurants and could even walk to Island Fish Company, which was one of our favorites. Gerardo was extremely responsive. He checked in prior to our arrival and touched base a couple of times to make sure there was nothing we needed. An excellent home I recommend to others with no hesitation!!

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

Paradise Cove!30ft Dock Pool BBQ
Had a great week at Yunis place! Her house was extremely clean and had everything we needed and more especially for cooking which was nice. She had probably the most comfortable bed, sheets and pillows I’ve ever used. I loved how it was clutter free and didn’t have any breakable decorations down low around since we had our two toddlers with us. The pool was the perfect size for us and it was great to relax outdoors. We even saw Manatees swim up to the dock. 10/10 would recommend this spot.

Newely Renovated 3/2-private pool/dock/cabana club
Absolutely amazing place to stay! Dennis is amazing and had several great recommendations for us to eat and do! The dock out back was beautiful and we were even able to see manatees! The pool was a GREAT addition and my family wouldn’t have wanted to explore the Keys any other way! The neighbors are also friendly and great to talk to! Overall beautiful place! My family and I would stay again!

P31 - 11785 5th Ave. Ocean
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.

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!
House rentals with free parking

Waterfront Escape -VACA-23-408
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.

Waterfront with Boat Lift/Kayaks and Hot Tub
The place was amazing!! plenty of room for our family of 5. All of the fishing equipment was awesome!! From the rods and tackle, to the deep freezer with bait, the extras made the whole trip more enjoyable. Loved the house. It was perfect!!! Will definately be back in the future!! 10 out of 10 would recommend!!

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

Chiquita Waterfront Canal Home
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.

NEW! Oceanside Casa Largo Modern Tropical Getaway
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.

Anglers Haven- 2 bed 2 bath home in Islamorada
Spent the week of Christmas. Great location. Perfect for our family.

Key Largo Waterfront Home with Tiki & Boat Dock
This is the perfect location for us, we have a small flats boat and there’s great fishing in the area. The weather was not great but were able to find areas to fish sheltered from the wind. When not fishing, hanging out on the dock with Princess, watching the manatees and having a cold drink was absolute paradise. Penny is very responsive and was available anytime needed. This was our second time staying at this location and already talking about booking a longer stay next year.

Great key Largo home with water front and pool
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
Weekly house rentals

Sandbox
⭐️⭐️⭐️⭐️⭐️ 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

Oceanfront with Pool near Sombrero Beach
Absolute Keys Perfection!! This vacation spot won't disappoint. Private, gorgeous, well maintained home with lots provided & to do on site, PLUS a place to dock a decent sized boat. Our 30' Grady White Marlin sat nicely at the bulkhead and we could easily spin it in the canal - it does get shallow but if you stick to the marked channel you're good. Homeowners are extremely responsive, friendly & want you to enjoy your stay. Kitchen is fully stocked & has appliances I wish I had room for at home. HiFee boat ramp and Publix down the street. Bonus, there's a preservation next door where lots of seabirds like Frigates roost and teach their young to fly in front of the house. Wish I had booked a second week! or the whole month lol

Twin Dolphin Marathon Deep Water Canal, 100’ Yard!
This house was perfect for my family of 5. We where all very comfortable and had plenty of space! The kitchen had everything we needed. The waterfront lot across from the house was peaceful and had a wonderful area for the kids! The backyard was my favorite!

Serenity Bay Estate-FL Keys Best Kept Secret! Beau
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!!!!

“La casa azul” step 3’ to a private pool
We spent an amazing week in this home. Very comfortable and quiet. The pool was amazing. Will definitely be back.

Gorgeous Ocean View Home!
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!

Clocked Out
Absolutely outstanding rental. Don’t change a thing. Fabulous location on the water in the center of the Keys. Super comfortable furniture, super well-stocked kitchen. Love that everything in this unit was good quality. Nothing was cheap, we really appreciated that. Quiet & relaxing. Our only gripe was we couldn’t find the place initially. We were following written directions sent by the management company that had not been updated; turns out the ‘turning point building’ no longer existed. The road into the complex looks more like a parking lot. We also initially didn’t receive our entry code, but it came immediately after we notified the management company. Then we got a second (and different) code, but one of them did work. The A/C wasn’t working well during our stay; however It was fixed a day & a half after notifying the management company.

Come Monday: Sombrero Beach Home w private pool
This was the most amazing vacation home! It was open and airy, with comfortable beds, a fully stocked kitchen, games in the living room, and thoughtful touches throughout. We absolutely loved the use of the outdoor space, especially the grill and the salt water pool. One of the best things that we weren’t expecting was what a quick walk to Sombrero Beach it was. Five minutes or less and we were on one of the best beaches in the Florida Keys! We also loved how quiet and nice the neighborhood was. As an added bonus, we were very close to both a few wonderful restaurants (castaway, Isla Bella resort, 7 mile grill, dockside, Irie eats to name a few), Publix, and Walgreens. The location was convenient, and our stay overall was perfection. Looking forward to spending some time down in the Keys again soon!!
Quick stats about house rentals in Islamorada
Total rentals
330 properties
Nightly prices starting at
R1,774 ZAR 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
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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