
Beachfront vacation rentals in Islamorada
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Top-rated beachfront rentals in Islamorada
Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.
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Popular amenities for Islamorada beachfront rentals
Beachfront home rentals with a pool

Oceanfront Getaway | Kayaks, BBQ & Stunning View!
Enjoyed the stay. Was very well equipped with everything we needed. We had a question about one of the keys and host was very responsive.

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.

Chiquita Waterfront 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.

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!

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!!!

Cary’s Oceanside
We had a great time at Cary’s Oceanside! Beautiful location, beautiful and comfortable accommodations! Maria was very helpful and responsive with our questions. We really enjoyed the pool and outdoor area.

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!

Cozy Waterfront Retreat w/ Private Boat Dock +Tiki
The RV was perfect for my husband, sister and I. We especially loved the tiki dock where we hung out. Watching sunrises with our coffee was a great way to start each day’s adventures. Ramses was very communicative and made sure the check-in form was completed so everything went smoothly for us. All in all a great experience!
Pet-friendly beachfront home rentals

Ocean View Duplex Penthouse | Pool | Vista Two
Beautiful, very clean property with a fantastic location. Excellent proximity to snorkeling, restaurants and other local attractions. Short stroll to excellent walking path that takes you along route 1 with amazing morning views of the beautiful water. Great views all around, in fact. Plenty of soft, plush towels and similarly luxurious bed linens. We had a wonderful family vacation staying at this property.

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 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.

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!

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
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
We spent an amazing week in the house of Kelly and Shane. The location on the waterfront is unbeatable and the house itself is super convenient, nicely remodeled and has a very cozy feel to it. We spent days in a row fishing from the dock, prepared our catch of the day on the bbq on the terrace, and caught shrimp at night which served as bait for the next day. There are great beaches, restaurants, and all kinds of day trips at hand if you wish to leave the property ;). Kelly and Shane are great hosts, with tons of tips - they clearly love the area and put great effort in the maintenance of the house and dock. They are super quick and easy in their communication and all three of us (me, husband and our 12 year old son) look forward to staying at their property again!

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.

Sandbox
The stay experience exceeded our expectations. The only recommendation would be to have a listing of recommended restaurants, beaches, boat rental places, etc to go see in both Marathon and key west. We visited key west and found out afterwards where we should have gone.

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.

Ocean View 2br/2ba w/pool, bar and dockage 28ft
What an amazing location and you can really tell the host has thoughtfully designed the Airbnb, making it an experience. Will be back!

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!

Luxe Waterfront Keys Cottage- with Jacuzzi
Super nice place to stay. Very comfortable.
Quick stats about beachfront rentals in Islamorada
Total rentals
280 properties
Nightly prices starting at
G$16,787 GYD 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
- Theater of the Sea
- EAA Air Museum
- Cocoa Plum Beach
- Everglades Alligator Farm
- Long Beach
- Far Beach
- Sea Oats Beach
- Horseshoe Beach
- Monkey Jungle
- Windley Key Fossil Reef Geological State Park
- Keys' Meads
- Long Key State Park