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Waterfront holiday rentals in Key West

Find and book unique waterfront accommodation on Airbnb

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Popular amenities for Key West waterfront rentals

Waterfront apartment accommodation

Guest favourite
Apartment in Marathon
4.93 out of 5 average rating, 14 reviews

*NEW* Sea La Vie - Pool & Beach

MargaretRating, 5 stars3 weeks ago
We just spent 6 days at Yuni's airbnb. Our family of four(all adults) could not have been happier with the peace and quiet this place offered us. The private beach and pool had plenty of chairs and umbrellas. We loved the balcony overlooking the pool and beach. We enjoyed how close it was to Havanna Jack's for a quick bite to eat and drink. Yuni's place was exceptionally clean. Plenty of bath towels and beach towels. The kitchen was fully stocked with all of our needs. She quickly responded to our questions and our needs. Yuni is one of the best hosts we have had throughout the years of using airbnbs. We definitely will go back!
Superhost
Apartment in Key Colony Beach
4.84 out of 5 average rating, 115 reviews

Beachside Unit 22 - Private Beach on Atlantic

JamesRating, 5 stars3 weeks ago
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.
Guest favourite
Apartment in Key Largo
4.88 out of 5 average rating, 282 reviews

Seaside Vista - Ocean Front 2/1 with dockage

JeremyRating, 5 stars1 day ago
We had to make a very last-minute booking for a two-night stay and were thrilled to find this boat- and pet-friendly spot with space to park our boat trailer. Justin was incredibly quick to respond and made the whole process seamless. The accommodations were clean, comfortable, and exactly what we needed. There was more than enough room for our 24-foot boat, which stayed well-protected from wind and waves. A freshwater hose was conveniently available to rinse the boat off after a day on the water, and the on-site fish cleaning station was a great bonus. The property is just three doors down from Snappers Bar & Grill, where we enjoyed live music, great food, and drinks. We even had the pleasure of meeting the property owners during our stay—truly some of the nicest people you could hope to meet. Overall, a great stay. We’ll definitely be back!
Guest favourite
Apartment in Key West
5 out of 5 average rating, 5 reviews

Henry's Penthouse On The Ocean

WilliamRating, 5 stars1 month ago
The Condo was spacious, beautiful, well furnished, very clean and the location was perfect. Henry was great to work with. We rented a golf cart and traveled almost everywhere in Key West by golf cart.
Guest favourite
Apartment in Key West
4.91 out of 5 average rating, 66 reviews

Waterfront Condo with Slip & Pool in Key West

CarolineRating, 5 stars4 days ago
We stayed a week at the apartment. The place was spacious and clean. It was 6 of us and we didn t feel crowded at all. It has a full kitchen and we were able to cook some nights. The porch has an amazing view and the pool is plenty big to have thew kids happy. It is the perfect location if you like fishing and come with your boat (no problem with a 29' ). The Marina to launch is right there and the gas pump as well. Walking to Duval street takes about 10-15 minutes. It is a pretty walk. We ended up renting a golf cart because after a day of fishing, we were tired, but Uber is cheap and fast and bicycles can be rented too if walking is not what you want. I would stay again at Sloan s place !!
Superhost
Apartment in Marathon
4.86 out of 5 average rating, 51 reviews

Little Venice in Marathon (in the Beautiful Keys)

AlisonRating, 5 stars3 weeks ago
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!
Guest favourite
Apartment in Tavernier
4.95 out of 5 average rating, 197 reviews

Boho FL Keys Condo

MarkRating, 5 stars2 weeks ago
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.
Guest favourite
Apartment in Marathon
4.97 out of 5 average rating, 105 reviews

Beachfront Condo w/ Ocean Views in Marathon

AnneRating, 5 stars1 month ago
This was our first family trip to the Keys and this location in Marathon was ideal! The condo was welcoming, beautiful and spacious for our family of 3. The balcony was our favorite place, which overlooked the pool and the seashore. The beach was lovely for shorter walks and just "being" with the ocean. Fun seashells & hermit crabs at low tide! Lots to do in the area -- definitely hoping to return next year. Mike was fantastic host & super helpful with questions.

Waterfront house rentals

Guest favourite
Home in Marathon
4.94 out of 5 average rating, 35 reviews

Florida Keys Oceanside Utopia

CaroleRating, 5 stars1 month ago
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!
Top Guest favourite
Home in Marathon
4.99 out of 5 average rating, 137 reviews

Cancellation Deal: 08/02 thru 08/09

KevinRating, 5 stars1 week ago
The house was very clean and inviting upon arrival. Nice location short drive to great restaurants and local grocery stores also less than 5min walk to the beach. Mr Eddie responded in a timely manner when we had questions. All in all we had a great time and very much enjoyed our stay! Thanks Mr Eddie
Guest favourite
Home in Cudjoe Key
4.97 out of 5 average rating, 159 reviews

Cudjoe Key Home with a View

RobRating, 5 stars3 weeks ago
Everything was great. We enjoyed the pool, pickleball, and the water. The house was perfect for the area. Definitely recommend!
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 26 reviews

Million Dollar View

JohnRating, 5 stars1 month ago
This home was everything we expected and more. Stunning location with absolute privacy. The extra long dock was amazing, the pool was fantastic, and the grounds were meticulous. It’s literally your own private resort. Roman, the host, was very quick with communication. He and his wife actually met us when we checked in to see if we had any questions and provided us with an arrival gift. If you have looked at the listing and are thinking of renting it, do it. You will not be disappointed at all. Excellent value all around.
Guest favourite
Home in Marathon
4.89 out of 5 average rating, 66 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

RobinRating, 5 stars2 weeks ago
This home is even more than the pictures show! It is an extraordinary home for people who love the sun, shade, beach, and the beautiful home just makes it a luxurious vacation. I could not find one aspect I didn’t love.❤️
Guest favourite
Home in Key West
4.92 out of 5 average rating, 13 reviews

Oceanfront, Resort-like luxury home with private p

OliviaRating, 5 stars4 months ago
Was such an amazing place. My family loved it. My dad was thrilled with it which he’s normally the one that’s the one we need to impress. He’s never really liked going to Keywest because of how busy it is. This spot and location he absolutely LOVED. Which made all of us happy. The house is gorgeous and massive. The pictures don’t do the place justice. Super peaceful, relaxing and just a beautiful layout. We were 10min from town and sooo much to do around our area if we didn’t feel like going into the main town. Very pleased! We will be back for sure. Even my father’s words! He has a new appreciation for Keywest! Thank you Javier for everything!
Top Guest favourite
Home in Marathon
5 out of 5 average rating, 51 reviews

Luxury Boating Paradise+Pool+Sailing Kayaks

RickRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Marathon
4.92 out of 5 average rating, 12 reviews

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

HansRating, 5 stars3 weeks ago
Loved every minute of our time here. Communication was excellent before during and after our stay and the house was superb. Highly recommended

Waterfront condo accommodation

Guest favourite
Condo in Key West
4.97 out of 5 average rating, 73 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

LesleyRating, 5 stars2 months ago
Carrie's place was absolutely beautiful! it was so clean, the beds were insanely comfortable, and there were tons of linens and towels for everyone. We very comfortably fit 8 people into the home with no problems. The view from the balcony is absolutely amazing and we were all blown away. Carrie was extremely responsive and friendly. We were here for our wedding and had our wedding party stay here so it was extra magical. The pool and hot tub is super close, elevator to help with our bags, and the resort itself is gorgeous. 10/10 would stay again. We loved it so so much! Don't miss out.
Superhost
Condo in Duck Key
4.85 out of 5 average rating, 95 reviews

Villa 5087 on Duck Key BOAT SLIP available

JadenRating, 5 stars4 weeks ago
Great stay, would highly recommend, home was clean and quiet. Can’t wait to come back to duck key so I can book again.
Superhost
Condo in Key West
4.85 out of 5 average rating, 155 reviews

Anchor Drop modern elegance upgrades throughout vi

ElizabethRating, 5 stars1 month ago
Exceptional stay. Anchor Drop was a top Airbnb property in our book.,Would definitely look to return to both Key West and the property. Host was responsive, explicit, and helpful. Space was as described and very well appointed, clean, and comfortable. First time to Key West and was very satisfied with our accommodations, location, and area. Thank you!
Superhost
Condo in Key West
5 out of 5 average rating, 4 reviews

Southermost Serenity an exclusive 3 Bedroom Ocean

ColleenRating, 5 stars2 months ago
We were 3 couples and Julia’s place was absolutely perfect. Views were gorgeous and the wrap around deck was particularly awesome! Kitchen was well appointed. Check in was easy and Julia communicated throughout the process to make sure it went perfectly. A delight all around!
Top Guest favourite
Condo in Tavernier
5 out of 5 average rating, 54 reviews

Tequila Sunrise

AaronRating, 5 starstoday
Exactly what we were looking for. Clean, cozy and great location with an amazing view of the ocean and sunset. Pool area with hot tub was clean and a nice bonus, as well as the small beach and pier. Highly recommend and would definitely book again
Guest favourite
Condo in Tavernier
4.84 out of 5 average rating, 154 reviews

Bright & Sunny Suite w/ Magnificent Ocean Views

LisaRating, 5 stars1 month ago
Everything was as expected from the description and the pictures. Comfy beds. TVs are older and not many apps available to stream other than Netflix. Overall it was a great location and we had a great time. The poolside restaurant is open now so that was a bonus I wasn’t expecting after reading the previous reviews.
Guest favourite
Condo in Tavernier
4.94 out of 5 average rating, 127 reviews

BEAUTIFULLY DESIGNED OCEANFRONT CONDO

MandyRating, 5 stars1 week ago
This condo is perfection! Close to the pool and private beach. Amazing views too! We felt right at home when we walked in. Highly recommend this place for 2 couples or a family looking for the perfect Keys getaway. Nicole was super responsive to any questions we had before and during our stay. 10/10!!
Guest favourite
Condo in Key West
4.79 out of 5 average rating, 28 reviews

Walking on Sunshine at The Beach

StacyRating, 5 stars3 months ago
The host met us at check in which was nice. He showed us the building, parking, keys, etc. The condo was ready for us even for a little bit of early check in if we needed. It was very clean and well decorated. There were plenty of extra towels and beach towels. They had beach chairs and the kitchen had everything from a juicer to a fondu set. Beds were very comfy and everything was just really comfortable and just right. We felt right at home and hated to leave. We would for sure stay again. We really loved the unit. We had two 14 year old boys who had plenty of exploring they could do and everything was really close for us. Loved the unit and our stay!

Quick stats about waterfront rentals in Key West

  • Total rentals

    460 properties

  • Nightly prices starting at

    $99 NZD before taxes and fees

  • Total number of reviews

    11K reviews

  • Family-friendly rentals

    320 properties are a good fit for families

  • Pet-friendly rentals

    130 properties allow pets

  • Rentals with a pool

    410 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West
  6. Waterfront rentals