
Beachfront holiday rentals in Islamorada
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Top-rated beachfront rentals in Islamorada
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Popular amenities for beachfront rentals in Islamorada
Pet-friendly beachfront home rentals

Endless Summer
We very much enjoyed our stay, the house was as expected based on previous reviews & pictures. The location was perfect for us to access from Key Largo to Key West easily. The pool was nice & the kids had fun snorkeling off the back dock & looking for all kinds of wildlife both on land & in the water with their flashlights after dark. We found the sunsets at the house to be better than what we experienced in Key West. If you need beach chairs and/or beach umbrella, we recommend you rent those.

Beachfront Villa - Florida Keys
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!

Luxury Boating Paradise+Pool+Sailing Kayaks
We had an amazing family weekend here! The home was spotlessly clean, beautifully maintained, and incredibly well equipped with everything we needed. The ping pong table, video games, and sail kayaks were huge hits with the whole family. We also rented a boat, and having a private dock made that experience seamless and unforgettable. The location was quiet, safe, and perfect for quality time—cozy enough to relax, yet close to everything we needed. It truly felt like a home away from home. For all the amenities and the exceptional condition of the property, the price was a fantastic value. We’ve stayed in many vacation rentals, but this one stands out as one of the best. We’re already looking forward to coming back. Highly recommended!

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach
Great place to stay for family vacation or guys fishing trip. Plenty of dock space to park the boat and easy access to the Atlantic. House is clean and all amenities worked as they should. Would definitely recommend to a family or friend. Mary was a great host who provided all information without even requesting it.

Gorgeous Ocean View Home!
We had an amazing time with our family and a beautiful Easter dinner with our friends. The location is perfect to travel all of the keys as it's just over an hour to Key West and Key Largo. The sun rose over the top floor guest bedroom with such a beautiful view of the water every day. Morning coffee with the view was awesome. Evenings spent wrapped on the couch watching movies with really nice big TV and unwinding. Sitting down by the water in evenings before sunset hanging with family watching niece play in sand was great too. Highly recommend.

Little Venice in Marathon (in the Beautiful Keys)
We (two couples) enjoyed a great week here. Being on the canal was nice, outside sitting spots were great. The house had plenty of cooking supplies needed. Was a tad bit smaller than I expexted, but worked out just fine. Remember to bring your shampoo, body wash etc as it's not provided. Comfortable and bright, was quiet even with boats going by. Would definitely stay here again!

Studio apartment in Calusa Resort & Campgrounds
So must say 10/10 we stay in a lot of places and this one we will deff come back to over and over again it was perfect and I must say the price is a steal honestly when we first booked we were nervous because of the price was cheap and I must say dosent reflect at all it is a amazing studio super clean super comfy can’t wait to come back highly recommend

Vibrant Beachfront Villa
Great stay, we all enjoyed our mini vacation. This place is excellent. This is our 2nd time visiting this house and we loved it. Definitely we're coming back.
Beachfront home rentals with a pool

Conch Cottage at Hawks Cay - Chic Tropical Retreat
Loved it! I hope to go again some day in the near future.

PENTHOUSE SUITE - OFFERS BEST PANORAMIC OCEAN VIEW
Our stay was everything we could have wanted. The view was incredible. The condo had everything we could need. We will definitely come again and recommend it to family and friends.

NEW luxury RV, Marina, 6 beds&1.5 baths, 2 pools!
First RV experience, did not expect massage sofa... everything you need to explore the mangroves off the beach, take a paddle and who knows what you'll meet...explore the state parks, snorkel, dive kayak fly...it's what you make it ..wish we were here for longer and Kelly is a top host...🤗

Beach House, Private Pool & Dock, Gulf Sunset view
Our 7 day stay was the most relaxing vacation we’ve had in years. The location was somewhat remote but only a short drive into Marathon. We hope to come back soon!!!

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!

Turtle Nest 1 Ocean Point Condo “Newly Remodel”
This stay was close to absolutely everything you’d want to do and see in Islamorada! The host was friendly, provided easy instructions and a home that felt like home. Was glad to find this amazing, cozy space, will be back soon.

🏝 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.

Studio with Balcony, Kitchen, Open Living Space
My husband and I chose this place for part of our honeymoon, and we were so happy we did! We absolutely loved it, even more than the resort we paid double the price for in Key West. Our room was clean and very comfortable. The pool area was equally clean, never too crowded, and offered a really peaceful atmosphere. Having a full kitchen was a huge benefit for us, it allowed us to save money on meals and enjoy some home-cooked food. We were also incredibly lucky to have a beautiful view of the water from our room. We loved waking up each morning, making breakfast in our kitchen, and eating it on our little patio while enjoying the view. There’s lots of cool stuff to do in Islamorada, and the location of this place made it easy to explore everything. We had such a wonderful experience and would love to return someday!
Private beachfront home rentals

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!!

Florida Keys Oceanside Utopia
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!

Tower 2 Master Suites 2 Kings Beds Marina Pool
Pedro was an amazing host! We got in a little early and thought we were going to need to check in early and he was very accommodating! I had a few questions and he responded almost immediately which is more than impressive! The place is perfectly decorated, had a very homey feeling to it and everything we needed.

KCB Tropical Escape
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.

Villa 5087 on Duck Key BOAT SLIP available
Great stay, would highly recommend, home was clean and quiet. Can’t wait to come back to duck key so I can book again.

P36 - Charming and immaculate 2 Bedroom, 2 bathroo
Great place! Very spacious, nice dock and out door and area to enjoy with the pool! It was nice having a large deep freezer for ice and fish!

Viamarhe House-Private beach, Kayak, yard games
Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.

Seaside Searenity w/ Golf Cart/Kayaks
Diane’s place was very nice and spacious! Super clean and very well stocked with everything we needed. The golf cart was an added plus. The pool for the tower guests was also perfect and never super crowded when we stayed. The location was also close to all the recommended restaurants. We would stay here again if ever in the area.
Quick stats about beachfront rentals in Islamorada
Total rentals
280 properties
Nightly prices starting at
₹6,892 before taxes and fees
Total number of reviews
1K reviews
Family-friendly rentals
150 properties are a good fit for families
Pet-friendly rentals
170 properties allow pets
Rentals with a pool
220 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
- Biscayne National Park
- Cannon Beach
- Conch Key
- Calusa Beach & Loggerhead Beach
- Everglades Alligator Farm
- Theater of the Sea
- Cocoa Plum Beach
- EAA Air Museum
- Far Beach
- Horseshoe Beach
- Sea Oats Beach
- Monkey Jungle
- Long Beach
- Windley Key Fossil Reef Geological State Park
- Long Key State Park
- Keys' Meads