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Waterfront vacation rentals in Key West

Find and book unique waterfront rentals on Airbnb

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Popular amenities for Key West waterfront rentals

Waterfront apartment rentals

Top guest favorite
Apartment in Marathon
5 out of 5 average rating, 14 reviews

Oceanfront Getaway in Marathon!

TriciaRating, 5 stars2 months ago
Condo was great. Exactly as described. 2 minute walk to the large heated swimming pool and beautiful ocean view. Shuffle board and ping pong available to play near the pool area. Safe, quiet, gated condo community. Within short driving distance to many great restaurants and activities. Frank responded within hours and answered my questions. We would recommend this rental and would gladly stay here again!
Superhost
Apartment in Key Colony Beach
4.85 out of 5 average rating, 114 reviews

Beachside Unit 22 - Private Beach on Atlantic

JamesRating, 5 stars2 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 favorite
Apartment in Key Largo
4.88 out of 5 average rating, 281 reviews

Seaside Vista - Ocean Front 2/1 with dockage

JacquelineRating, 5 stars1 week ago
Nice place. Great access to the ocean. New owners are staying on the upper unit. Very nice people. We loved walking to snappers next door.
Guest favorite
Apartment in Key West
4.89 out of 5 average rating, 36 reviews

Key West Condo with Pool & Boat Slip Access

DougRating, 5 stars1 week ago
Fantastic waterfront condo! Everything about it was exactly as described on the listing! Very comfortable condo! We will be back!
Guest favorite
Apartment in Key Largo
4.79 out of 5 average rating, 145 reviews

Escape to the Seaside!

CarlyRating, 5 stars1 month ago
Perfect spot for a long weekend beach getaway! This was our first time visiting the Florida Keys, and we loved being right on the water with a small beach area to ourselves. The space was ideal for our group of friends, and the location was great—close to local bars and restaurants, some within walking distance or just a short drive away.
Guest favorite
Apartment in Key West
5 out of 5 average rating, 5 reviews

Henry's Penthouse On The Ocean

WilliamRating, 5 stars4 weeks 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 favorite
Apartment in Tavernier
4.95 out of 5 average rating, 197 reviews

Boho FL Keys Condo

MarkRating, 5 stars1 week 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.
Superhost
Apartment in Key West
4.86 out of 5 average rating, 98 reviews

Penthouse in Paradise

EllenRating, 5 stars2 weeks ago
Enjoyed our stay. The place was beautiful and matched the description. Just disappointed couldn’t use jacuzzi tub. Otherwise no isssues

Waterfront house rentals

Guest favorite
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 favorite
Home in Marathon
4.99 out of 5 average rating, 136 reviews

Cancellation Deal: 07/26 thru 08/09

KevinRating, 5 stars5 days 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 favorite
Home in Cudjoe Key
4.97 out of 5 average rating, 159 reviews

Cudjoe Key Home with a View

RobRating, 5 stars2 weeks ago
Everything was great. We enjoyed the pool, pickleball, and the water. The house was perfect for the area. Definitely recommend!
Guest favorite
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 favorite
Home in Summerland Key
4.75 out of 5 average rating, 8 reviews

Sailfish Dream on Cudjoe Key-28 day minimum

DougRating, 5 stars2 months ago
Had a very comfortable and enjoyable stay. Accommodations were excellent. Weather was excellent! Warm balmy breezes most days kept humidity down. Lots to do, explored the keys from Islamorada down to Key West, caught the sunset. Spotted deer on Big Pine Key. A very fine month long vacation. Thank you Jeanene.
Superhost
Home in Cudjoe Key
4.83 out of 5 average rating, 264 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

AlexRating, 5 stars1 month ago
The house was exactly as pictured and in a very peaceful community. The beds were comfortable, as was the couch (two of our group opted to sleep on the couch itself instead of pulling out the sleeper sofa, and said it was pretty comfy!). Several of our group enjoyed using the bikes at night, and while we didn’t use the kayaks, it’s nice they were available. We didn’t get to do everything we hoped to do on our trip to Keys, but we plan to stay here again someday when we come back!
Guest favorite
Home in Cudjoe Key
4.91 out of 5 average rating, 34 reviews

Rise And Shine On The Water

FlorianRating, 5 stars3 weeks ago
There were five of us in the house and we felt immediately comfortable. Everything was super clean. The location right on the water was overwhelming as expected. Everything that is needed was there. The kitchen and terrace were very large and the mattresses were very comfortable. Key West is about 30 minutes away. Check-in and check-out as well as contact were completely unproblematic. We will be back!
Top guest favorite
Home in Marathon
5 out of 5 average rating, 114 reviews

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV

LaurenRating, 5 stars2 months ago
We had a wonderful time staying at Tim’s place! He was an excellent host who was always available if I had a question. The house is in a beautiful location. We enjoyed sitting on and fishing off the dock. The house had everything we needed for a fantastic stay and a very enjoyable vacation. I can’t say enough good things about our experience at the home. We were able to meet Tim and he was a lovely host. Thank you for a great vacation! We hope to come back in the future!

Waterfront condo rentals

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

Oceanfront 3 bed condo Ocean Edge w/ optional slip

LesleyRating, 5 stars1 month 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, 94 reviews

Villa 5087 on Duck Key BOAT SLIP available

JadenRating, 5 stars3 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 Tavernier
4.88 out of 5 average rating, 153 reviews

Reel Large END Unit in Ocean Point Suites

RyanRating, 5 stars1 week ago
The place was as described. Check in was easy and Desy even allowed us to check in a bit early due to my son having a fever. The linens and accommodations were clean and the condo set up was very nicely. The property is close to restaurants and supermarkets. The pool was clean and we enjoyed the area that sold food and drinks by the pool. This was a nice place to unwind after being on the water fishing for 6-8 hours. Very comfortable, private, and peaceful.
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!
Top guest favorite
Condo in Tavernier
4.94 out of 5 average rating, 16 reviews

Salty Mermaid Ocean Pointe 4406

KatherineRating, 5 stars1 week ago
We had a great 4 night stay at the Salty Mermaid with 4 adults and a toddler. Sean was responsive to questions and sent very detailed and helpful information about check in and what was and was not available at the condo beforehand. The location was perfect for us with many parks, beaches, activities, restaurants and groceries within a 20 minute drive. Everything was super clean and well maintained. If you are traveling with small children you’ll want to bring some toys or activities to keep them entertained. Would definitely recommend and stay again in the future!
Superhost
Condo in Key West
4.78 out of 5 average rating, 65 reviews

Casa Papa Del Mar Ocean Front 1800 Atlantic Spectacular

GeorgeRating, 5 stars5 months ago
The sunsets from the balcony are amazing. Overall the place was relaxing and georgious.
Top guest favorite
Condo in Tavernier
5 out of 5 average rating, 53 reviews

Tequila Sunrise

ChristinaRating, 5 stars6 days ago
adorable suite! very comfortable beds and couches. home smelled amazing! Kathryn was always responsive to questions. she also would check in on us periodically to make sure we had everything we needed. we 100% recommend this host and will absolutely book with her again.
Guest favorite
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!!

Quick stats about waterfront rentals in Key West

  • Total rentals

    460 properties

  • Nightly prices starting at

    G$12,549 GYD 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