Some info is shown in its original language. Translate

Waterfront holiday rentals in Key West

Find and book unique waterfront accommodation on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Key West waterfront rentals

Waterfront apartment accommodation

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 Islamorada
4.99 out of 5 average rating, 67 reviews

Hidden Gem Islamorada | 1st Floor

AngelaRating, 5 stars3 days ago
We had a great stay here with our kiddos. The Hidden Gem had everything we needed for a relaxing and fun stay. Close to everything - a great middle keys location. Host sent several texts checking on us throughout our stay. We saw so many cool fish right at the back of the property on the sea wall - barracuda, grouper, parrot fish, Angel fish, and crabs to name a few. We hope to visit and stay again soon!
Top Guest favourite
Apartment in Marathon
5 out of 5 average rating, 20 reviews

#1 Island Hideaway 89 - OCEAN FRONT

SamanthaRating, 5 stars2 weeks ago
It was the perfect location that we wanted away from a high tourist area. The neighbors were very nice and welcoming. Everything was clean and beautiful. I would stay here again! It was perfect for us exploring both the southern and northern keys and beaches since it's about middle of the 2. Loved it!
Superhost
Apartment in Key West
5 out of 5 average rating, 4 reviews

Hyatt Windward Pointe! Great Location!

MelissaRating, 5 stars2 months ago
Beautiful place with a well stocked unit…close enough to all the places we wanted to visit, yet far enough away for a quiet, relaxing day. We loved the area and our stay here. Thank you, Chris.
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 !!
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.
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 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
5 out of 5 average rating, 28 reviews

Luxe Super Snapper-Heated Pool, Tiki, Dock, Lanai

KashRating, 5 stars1 month ago
This property was everything and more. Clean, all amenities provided as advertised and the perfect location in Marathon. Randy was very responsive and went out of his way to provide us with top notch service. We had a wonderful time and will definitely be returning again.
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
4.91 out of 5 average rating, 11 reviews

Endless Summer

LisaRating, 5 stars3 weeks ago
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.
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!

Waterfront condo accommodation

Superhost
Condo in Duck Key
4.88 out of 5 average rating, 107 reviews

Villa 5027 on Duck Key BOAT SLIP available

AlexisRating, 5 stars1 month ago
The place was perfect. The patio views were amazing to just sit and watch the sunset. The marina across the street was very convenient to launch our boat from. Very peaceful location. Angler and ale restaurant across the street was delicious
Superhost
Condo in Key West
4.78 out of 5 average rating, 65 reviews

Casa Papa Del Mar Ocean Front 1800 Atlantic specta

GeorgeRating, 5 stars5 months ago
The sunsets from the balcony are amazing. Overall the place was relaxing and georgious.
Top Guest favourite
Condo in Tavernier
5 out of 5 average rating, 5 reviews

Oceanfront 2 bdrm, 2 bath, View, Pool, Islamorada

MichalRating, 5 stars6 months ago
We stayed here for the Thanksgiving week. The place was nice, clean, and quiet. My kids enjoyed the playroom and the pool. The condo had plenty of board games to keep the kids entertained. The Keys have lots to offer, so there is always plenty to do. Donna was very responsive, the check-in was very simple, and we had a great time. Thank you for hosting us.
Guest favourite
Condo in Marathon
4.95 out of 5 average rating, 43 reviews

2-story condo w/ panoramic bay views and balconies

LisaRating, 5 stars1 month ago
We live Marathon and this condo is in the perfect location and minutes away from shopping, restaurants and activities.
Top Guest favourite
Condo in Marathon
4.96 out of 5 average rating, 102 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

AlexRating, 5 stars2 weeks ago
Absolutely perfect for a honeymoon getaway, quiet perfect amount of space for us, the set up was great with 2 bathrooms and a huge walkin closet, the couches were super comfy, the TV was big enough to see from across the room, we enjoyed everything about it. Got to meet some of the neighbors and they were all very welcoming and enjoyed talking to them. Scott had some great local recommendations and we enjoyed everything.
Top Guest favourite
Condo in Key Colony Beach
4.98 out of 5 average rating, 41 reviews

Paradise found! Sea-Esta Condo beach and pool.

RichardRating, 5 stars1 month ago
Gorgeous well kept condo. Grounds were amazing. Views and pool were great. Would definitely recommend and stay again. Everything and everywhere was totally clean.
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!
Top Guest favourite
Condo in Marathon
5 out of 5 average rating, 20 reviews

*NEW* Private Beach, pool & fully loaded kitchen

JamesRating, 5 stars1 month ago
Our first time visiting the Keys and Celia’s place made it wonderful! Located in a very nice, quiet, and safe community her condo is like new and so well cared for. Perfect size for our two couples. The decor and furniture is very nice, bright and clean. Had all the amenities we needed and then some. We enjoyed the heated pool everyday and the private beach was nice for a more natural experience. The furnished patio had a great view of the pool and ocean. Celia is a wonderful host! Very helpful and a great communicator.

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