
Holiday rentals with outdoor seating in Islamorada
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Top-rated rentals with outdoor seating in Islamorada
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Popular amenities for outdoor seating rentals in Islamorada
House rentals with outdoor seating

Paradise in Islamorada
We had a wonderful 5 week stay in Islamorada! The place was really nice; very well supplied. The balcony and areas to chill out by the canal are relaxing, comfortable and well-thought out. With the laundry, ice machine and grill set-up, they have thought of everything you need to feel at home in paradise. The neighbors are terrific/interesting people. And, the beach was a lovely added highlight! We had a great time!!

Cancellation Deal: 08/02 thru 08/09
Had a wonderful stay, would recommend to anyone looking for a convenient, beautiful spot in Marathon. Eddie was an excellent host!

Endless Ocean Views -5 Bedrm/4Bath/Pool Built 2024
We loved the house! Everything was exactly as described. I would even say pictures didnt do complete justoce to the space and views! We had everything we needed at the house with ample dishes and cookware. We drove down to Key West which wasnt too far of a trip. We definitely would always recommend and stay again! Jessieca was an amazing host with great recommendations and general info for the area.

Bohemian Beach Bungalow
I can’t say enough great things about this beach bungalow! From the moment we arrived, we were welcomed with warm hospitality and thoughtful touches that made our stay truly special. The bungalow itself is cozy, clean, and beautifully decorated with a laid-back coastal vibe—exactly what you want for a beach getaway. Whether you’re looking for a romantic escape, a solo retreat, or a peaceful base for beach adventures, this place is a gem. We left feeling refreshed and recharged, and we’re already dreaming of coming back!

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV
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!

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!

Islamorada Waterfront House on Canal w Boat dock
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 ⭐️⭐️⭐️⭐️⭐️

Beach Cottage with pool, Dock and beach access
This house is in a good location and the pool is a definite plus. It was fun watching the neighborhood fishermen bringing in their catches. Being from the west we enjoyed the resident iguanas and the manatee in the channel.
Apartment rentals with outdoor seating

Ocean Breeze Gated Community
The condo and the whole condo complex was beautiful. The pool was great, with an awesome view. Plenty of places to sit at the pool and in the surrounding areas. One thing to note is that the condo has no closets and no place to hang clothes. Wasn’t a huge deal for us, as we were able to put things on shelves. Frank was very responsive when we needed something. The Marathon area has plenty of things to do and it’s close enough for a day trip to Key West.

Beachside Unit 22 - Private Beach on Atlantic
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.

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

Turtles Nest 2 Ocean Point condo
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! 😊

La Casa HMH
I had a lovely stay with my college daughter in the Keys. The place was just what we wanted. The decor was so beautiful and the grounds/pool area were so pretty. We were so sad to leave. Will definitely return. Heather Marie was amazing and such a wonderfully generous human. I can’t recommend this property enough.

Waterfront Studio 2| Couples Oasis | Kayaks | Pool
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!

Little Venice in Marathon (in the Beautiful Keys)
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.

Boho FL Keys Condo
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.
Apartment rentals with outdoor seating

Newly Renovated Piece ofParadise
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!

Oceanfront and Sunrise Views!
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!

2BR - Key Largo Sunshine Getaway
I had a great stay at Vanessa’s place! The Airbnb was exactly as pictured—clean, comfortable, and well-maintained. Vanessa was an excellent host with great communication throughout the entire stay. There was one minor water issue on the last day that affected the whole community, but it was addressed and resolved quickly. Overall, a smooth and pleasant experience. I would definitely stay here again!

Million dollar view in Key Largo!
The condo was very nice. Lots of room, clean and easy to access. We loved the balcony, and spent a lot of time there. We enjoyed the kayaks a couple of different times as well. Our first time to The Keys and we enjoyed this spot.

Islamorada Home 2 Sandy Beaches+Pool+2 Work Areas
Jose's place was perfect for our needs. The central location provided easy access to all the activities we had planned during our stay. The secure compound's private beach provided for some enjoyable time in the sun and--paired with the included water toys--a lot of monkeying around. The wifi and dual-monitor home office setup is a nice touch for those of us who need to remain in-touch with our day jobs during time in the Keys. Should also mention that Jose is one of the most helpfully communicative hosts i have had the pleasure of connecting with. Before the trip, he provided a helpful list of local recommendations tailored to the things we wanted to do during our stay. He also checked in with us routinely once we had arrived. Would be thrilled to stay here again.

Ocean views at “Sangria Sunrise” 10% off Charters
I cannot say enough about how much we enjoyed our stay at Sangria Sunrise! The condo itself is beautiful, the property is awesome, well-maintained, and the staff are friendly and helpful! We spent most of our time at the pool and the beach. The pool bar is great and the pool is clean and refreshing. Plenty of sunny spots and lots of shaded tables, too. It’s right across from the condo so we went multiple times a day. Beautiful landscaping all around. The beach and marina area are really nice. We loved watching the boats from the balcony and seeing the sunrise over the water. Lots of fun things to do in the area within a short drive, but also plenty to do on the property if you prefer to stay put. Tracy is an excellent host and is very helpful and responsive. We will absolutely be back. Thank you for sharing your space with us, Tracy!

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
Host was extremely helpful and communicative. Check in was a breeze and all the amenities needed for a pleasurable stay. Bonus outdoor bait freezer!

🏝 Oceanfront Paradise Awaits You
Great place, adorable beach and plenty to do in the area. Home is perfect and has everything you could possibly need for a short stay.
Quick stats about holiday rentals with outdoor seating in Islamorada
Total rentals
290 properties
Nightly prices starting at
₹3,462 before taxes and fees
Total number of reviews
3.4K reviews
Family-friendly rentals
270 properties are a good fit for families
Pet-friendly rentals
130 properties allow pets
Rentals with a pool
210 properties have a pool
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