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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

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 stars5 days 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 stars1 week 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 stars1 month 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.
Superhost
Apartment in Key West
4.86 out of 5 average rating, 99 reviews

Penthouse in Paradise

EllenRating, 5 stars3 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 favourite
Home in Tavernier
4.96 out of 5 average rating, 102 reviews

Sunset Beach Hideaway *Private Beach* *Jacuzzi*

TristaRating, 5 stars1 month ago
We absolutely loved our stay & already can't wait to visit again! We enjoyed the hot tub, kayaks, paddle board, corn hole, wildlife & napping in the chairs under the palms! We dined at the beautiful Marker 88 twice and thoroughly enjoyed it! We also had food and drinks delivered with no problem & had everything (pots, pans, toaster oven, etc) we needed to make breakfast! We primarily used the one bedroom house closer to the street, but loved having access to the house closer to the water for quick bathroom trips & cold water during corn hole and Sun bathing. Diane is so easy to work with and super helpful. Thank you for a beautiful stay!!
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 Summerland Key
4.78 out of 5 average rating, 9 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 Key West
4.83 out of 5 average rating, 6 reviews

Waterfront 4 Bed 4 Bath Home in Key Cove Landings

WilliamRating, 5 stars2 months ago
The location and home were perfect, close to all the action but very private and relaxing at the house. Loved the view and home was very well maintained and comfortable making for a very relaxing time for the family. Will definitely look to stay here again, perhaps making it an annual trip to look forward to for the whole family.
Guest favourite
Home in Sugarloaf Key
4.81 out of 5 average rating, 114 reviews

The Guest House - Sugarloaf Beach Key West

KimberlyRating, 5 stars3 weeks ago
Upon arrival it was very clean, well taken care of and beds were comfortable sleeping 8 guests - which is not easy to find. Location is quiet, private and driving distance to town is minimal. My husband and I enjoyed walking on the private dock and beach. Tom greeted us right away and was exceptionally helpful anytime we had questions or needed anything at all We look forward to returning.
Superhost
Home in Cudjoe Key
4.83 out of 5 average rating, 265 reviews

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

FrankRating, 5 stars1 day ago
We had a great time at Janet and Jerry’s home at Venture Out in Cudjoe Key! We made the short drive down to Key West after some morning pickleball. Our only unexpected (not welcome) surprise was the rotten egg smell all the way down the Keys. The smell is apparently from the over abundant seaweed blooming due to very warm water temps. Unfortunately this is a norm between May and October now? Key West did not have the smell due to wind direction, so overall we really enjoyed our stay!
Top Guest favourite
Home in Key Colony Beach
4.98 out of 5 average rating, 106 reviews

Waterfront House with 37 ft Dock & Cabana Club

CaseyRating, 5 stars6 days ago
Enjoyed the stay! If you’re looking for a low key place to stay this is it. Great location for day adventures in the keys.
Guest favourite
Home in Cudjoe Key
4.91 out of 5 average rating, 34 reviews

Rise And Shine On The Water

FlorianRating, 5 stars1 month ago
There were five of us in the house and we immediately felt 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!

Waterfront condo accommodation

Guest favourite
Condo in Key West
4.95 out of 5 average rating, 39 reviews

Condo de Paradise/Salt Water Pool/Boat Dock

Lori Rating, 5 stars1 month ago
We are absolutely in love with this place. The views are gorgeous. the grounds were immaculately groomed. There are so many colorful trees and flowers. The pool is slightly heated, which is perfect. Everyone we met was so nice and helpful with recommendations. We got to see the jets fly over a few times, so cool. The kitchen has everything you need to prepare meals and snacks. The beds in both rooms are very comfortable. We hope to stay here again in the future.
Superhost
Condo in Key West
5 out of 5 average rating, 6 reviews

Galleon Resort - Walk to Duval & Mallory Square!

PatriciaRating, 5 stars5 months ago
Incredible view! Place was clean and what we expected. Gorgeous unit right on the water. Watching the boats go by was so relaxing. Tiki bar right below us was convenient if we wanted a drink while relaxing. Had a small problem with the dryer and they came to fix it within the hour, so I was more than satisfied with upkeep. Walk to restaurants and hot spots was easy. Great Irish pub a block away (Celtic Conch). Unit is convenient for any type of boating excursion you would like to book as the boardwalk/marina is right there. Chris, our host, was very responsive to any questions we had and very helpful in booking arrangements. We did not have recommendation questions for him, as we’ve been to key west a number of times and have friends who live there, but I’m sure based on the dealings we had with him, he’d be happy to help. One note, this is a timeshare community. I was worried we’d be hounded. We were not.
Top Guest favourite
Condo in Duck Key
5 out of 5 average rating, 38 reviews

Oceanfront and Sunrise Views!

StephenRating, 5 stars3 weeks ago
We had an amazing stay in this wonderful Condominium! The host was absolutely fabulous - super responsive, friendly, and made sure we had everything we needed. The apartment itself was clean, comfortable, and perfectly located. The whole experience was top-notch, and we highly recommend this place to anyone looking for a great stay. Thanks again to the host for making it so special!
Guest favourite
Condo in Tavernier
4.94 out of 5 average rating, 101 reviews

Your Happy Place - Oceanfront

RodRating, 5 stars5 days ago
Sandra's place was very nice and clean. She was very reponsive with any and all questions. The accomodations are as listed. I enjoyed the peace and quiet. I most enjoyed relaxing on the balcony listening to the ocean. All you need is you, clothes, and the memories you will make. The rest is provided. However I will note that I was expecting a "real" beach and it was more of a lagoon. although still nice. Thanks Sabdra I would definitely book again. 🙂
Superhost
Condo in Key West
4.85 out of 5 average rating, 156 reviews

Anchor Drop modern elegance upgrades throughout vi

MoiraRating, 5 stars4 days ago
This was a great condo for 5 of us! PROs- Everything was so nice and clean. The owners are super organized with labeling on sheets, pillows, games, pool toys, etc all clearly marked in bins. The kitchen was well equipped, even though we didn't use it much. The sitting area around the TV was perfect and plenty of room for everyone. The master shower is huge and the bathrooms were very clean. We loved the large balcony. The pool was so nice and plenty of room and chairs, very well maintained. Communication with the property management company was pretty good, although it was more than 12 hours response time on one of the questions we had. They were very helpful and available on a Friday night when we were trying to access the TV and had questions on how to connect, which was great since it was a weekend. CONS- the condo is not situated very close to the Old Town area or restaurants. We took ubers and had a car, so it didn't really bother us. I would definitely book this place again!
Guest favourite
Condo in Tavernier
4.94 out of 5 average rating, 146 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

KatieRating, 5 stars3 weeks ago
This is a top notch airbnb. Excellent communication from the host, extremely clean, well stocked condo, generous supplies beautiful decor. We stayed 8 days in the condo and felt right at home. Loved the large pool. We caught many fish and cooked at the condo all but 2 evenings and had everything we needed to prepare meals. Really appreciated the assortment of coolers provided for day trips. Thank you again, John!
Top Guest favourite
Condo in Marathon
4.96 out of 5 average rating, 103 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

AlexRating, 5 stars3 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.
Guest favourite
Condo in Tavernier
4.95 out of 5 average rating, 128 reviews

BEAUTIFULLY DESIGNED OCEANFRONT CONDO

NicholasRating, 5 stars3 days ago
We really enjoyed our stay Beautiful condo extremely clean clear instructions wonderful place to stay pool and hot tub area are amazing. You can swim anytime which is really nice. Most places the pool closes at dusk. There is a nice poolside little restaurant and also a restaurant right by the beach area really convenient would go back there anytime

Quick stats about waterfront rentals in Key West

  • Total rentals

    460 properties

  • Nightly prices starting at

    $93 AUD 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