
Beachfront vacation rentals in Islamorada
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Top-rated beachfront rentals in Islamorada
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Popular amenities for Islamorada beachfront rentals
Beachfront home rentals with a pool

Sombrero Beach Getaway
Sombrero Beach Getaway was perfect for our family of 4! The location, pool, well-equipped kitchen, and elevated deck all contributed to a great stay in Marathon.

Islamorada Cay Home. Elegant home
The outdoor space is absolutely fabulous. The heated pool was enjoyed every day. The property is on the corner of two canals that had pretty clean water. We met several manatees who graced us with their presence often. Fishing was not great during the month so our fishermen were rather disappointed. The interior was very pleasant and cooking was easy. The entire third floor is the master sitting room, bathroom and bedroom. The only drawback for me personally is that the master bathroom is an "open concept " design which left me without a sense of privacy. Isa was extremely helpful and responded quickly with our questions. Thank you Isa!

4BR Sombrero Beach House on Canal with Dock & Pool
Matt was super responsive and helpful with any issues we had. The house was comfortable and the proximity to the beach was amazing (5 minute walk). We stayed for a month with a 1 year old and a big dog and found the house perfect for our needs. Manatees even came up to the house on our last day! Super special. Would recommend.

Pool & Spa, Walk to Beach, Dock, Tiki, Lux Home
Great home for a family vacation. Enjoyed the pool and all that Marathon has to offer. Plenty of room for everyone to spread out. Great decks and the tiki hut was a perfect place to hang out when you wanted to be outside but not in the sun. Bert was incredibly helpful and responsive.

Sunset Views, Pool and Dock
We really liked the location. It was peaceful and private and a great neighborhood to walk around and to walk our dog. Yet, a short drive into Marathon for restaurants or any other needs. The house isn’t new but it was exactly as represented and it was perfect for us. Frank was very responsive. There were a couple of issues that he addressed immediately. It wasn’t his fault that because of the location, receiving repair parts can take some time. But Frank took care of our situations.

Paradise Cove!30ft Dock Pool BBQ
My family and I had a great time here! It was the perfect house, super clean and just as described! Yuni was always quick to respond and answer any questions. We had no intentions of renting a boat, but just up the road was an easy rental spot and we were able to tie the boat up right outside the door. Everything we needed was within a few minutes and the location was perfect to take a drive down to Key West! We will absolutely plan to return!

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach
Mary's place was in a very safe and beautiful location. Everyone was friendly and there were endless dining options. There were even local conveniences that I didn't expect nearby such as Dollar Tree, Winn Dixie, Home Depot, etc. Showers had great water pressure, hot water, and had zero sulphur smell. Decor was lovely and ample storage space for your things. A/C and heat works great and no musty smells anywhere. Beds, outdoor furniture and couches very comfortable. Convenient off-street parking. Was too busy to enjoy the cabana amenities but visited it briefly and it looked wonderful. Thank you Mary hope to return in the future!

Sombrero- Waterfront 4 BR Luxury Pool Home- M#9
What a beautiful home! We towed our boat from northeast Florida and were thrilled with how convenient it was to drop the boat in the local marina and keep it right behind the house. Sombrero Beach was down the road and a perfect location for our grandkids to swim and play in the sand. John could not have been more helpful and responded quickly to all of my texts. We are already thinking about reserving again in the spring!
Beachfront home rentals with a hot tub

Huge Swim Spa~ Incredible Special Fall Pricing
We really enjoyed our stay. The host, Sherry, gave timely information and quickly responded to messages. We were pleasantly surprised by the number of amenities that were available to us at the house. The Cabana Club was a real hit with my teenage daughters. It had reasonably priced drinks and lunch type meals. They enjoyed just laying by the pool or beach and sun tanning. We saw manatees one of the evenings right in the backyard of the home.

Seaside Sunrise. Newly remodeled waterfront
Everything was excellent. Only complaint would be the bicycles. One bike was usable but the seat was loose and we didn’t have tools to fix it. The other adult bike’s chain was rusted so bad it wasn’t usable. We still had an excellent experience.

Luxe Waterfront Keys Cottage- with Jacuzzi
We fell in love with the house as soon as we walked in! It was so clean and decorated beautifully! The house had so many special touches....the robes were especially appreciated on chilly mornings outside & to use with the hot tub. We had a manatee & baby visit on several days which was so exciting! The owners were very responsive and helpful. They send you a link to an app for the house which I downloaded. Our only trouble we had was I didn't read everything in the app and thought that the main air conditioning was only controlled by the owners. (We were hot at night) MY FAULT and I can't believe I didn't ask. So please read everything in their app and you will have a lovely stay! It is a gorgeous place to spend your vacation centrally located in Marathon!

Luxurious Suite+Open Ocean Views+Pool & Cabana Bar
We very much enjoyed our stay. Largo was a very kind and helpful host. The ocean views are beautiful and we enjoyed the pool and the private beach. We would love to come back.

Ocean Breeze Home
Pamela’s place was absolutely perfect. She has really thought of every single thing you could need for a comfortable stay. We enjoyed using the bikes in the morning and walking to the private gated beach in the evening. The place is absolutely adorable and so nicely themed. The backyard is an oasis of relaxation. There were several places nearby to eat and go for entertainment. We highly recommend Snappers for a chill vibe by the water with food drinks and live music!! Could not have asked for a better host and stay. Will definitely seek this place out again if we ever stay in the Keys in the future.

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
Jason’s place was a great place to stay in the keys!! Jason is great at responding great location, clean house only the couch could use a cleaning. It would have been nice if there were trash bags, extra hand soap and extra toilet paper. Other then that it was perfect!!

BEAUTIFULLY DESIGNED OCEANFRONT CONDO
Nicole’s condo was beautiful! She has thought of everything, from a well-appointed kitchen to shampoo, conditioner and body wash in each shower. The condo is spotless with up-to-date decor and beautiful bedding. The beds were very comfortable too. We slept like babies! The grounds had a huge pool, hot tub and a small beach. The recent additions of a pool-side bar and beach cafe rounded out the amenities. Thank you, Nicole. We hope to come back soon!

Oceanfront Resort W/Indoor Pickleball - Spacious!
Great place to stay with kids. They loved the pools and game room. Place was clean and spacious! He was a great host, very responsive. Would stay again!
Pet-friendly beachfront home rentals

Sunset Beach Hideaway *Private Beach* *Jacuzzi*
this is a place we will stay at each year for spring break. my kids didnt want to leave - it has everything. we were very impressed. My wife and i had our own house. the kids stayed in their own house. quiet, beautiful grassy areas and trails. We had morning coffee on the private beach and took paddle boards and kayaks out at sunset. thank you Diane for the amazing houses, beach, location etc. We will be back next year :):)

WATER VIEWS ON J. PENNEKAMP Free Kayaks
We had a great time in Key Largo! Home is on a quiet street with excellent water views! We would certainly return in the future!

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!

The Pink Dolphin House.
We had an amazing stay at the Pink Dolphin! Margaret and Phil (hosts) were incredibly nice and so down to earth. We really liked that this Airbnb did not feel commercial at all. It was private and had that “home” feel. A rare find when vacationing. We will definitely go back!

7 Mile Ocean Bliss
We had an amazing stay at this beautiful Airbnb in the Keys! The home was stunning, with all the amenities you could ask for, including a relaxing hot tub. The fishing right on the property made it even better – perfect for enjoying the local marine life. The host was incredibly accommodating and made sure we had everything we needed for a perfect getaway. Highly recommend this spot for anyone looking for a peaceful and fun escape!

Private Ocean Oasis by Key West, Florida
This was the perfect place to meet up for a Christmas gathering with our adult children. The home was so nicely decorated and furnished and had EVERYTHING we could have needed for a three day stay. There was plenty to do on the Venture Out Resort property and anything else you’d want or need is within driving distance. Will definitely stay here again!

Coral House: King Beds & Boat Rental Discount!
Great place to stay for our family of 3 and with a small boat. The home was well stocked with everything our family would need to have endless fun on the water on or shore. The bedrooms were great size. The view was spectacular and the home was well kept. The beds were comfortable and the bathrooms were nice. Plenty of hot water and water pressure. We were able to rent a spot for our boat trailer with the city. We went fishing almost every day in the areas around Key Colony. Enjoyed parks and restaurants in the area in the afternoon and evening. Lots to do. The turtle hospital was great!! Took a day trip to Key West. Very centrally located in the keys. A Publix and WalGreens just down the road. My daughter got something in her eye and we had to go to urgent care. It was less than a mile away and they were great. Called in prescription to Publix and we were back on the water. Hosts were extremely friendly and quick to respond. We would stay again.

Gorgeous Ocean View Home!
This house was in a great central location to Sombrero Beach's other family attractions. All the beds were comfortable, and the upstairs had a stunning view. I only wish the house had more items you could use on a vacation, like beach chairs, an umbrella, more beach towels, etc.
Quick stats about beachfront rentals in Islamorada
Total rentals
280 properties
Nightly prices starting at
$80 before taxes and fees
Total number of reviews
930 reviews
Family-friendly rentals
150 properties are a good fit for families
Pet-friendly rentals
170 properties allow pets
Rentals with a pool
140 properties have a pool
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