
Waterfront holiday rentals in Key West
Find and book unique waterfront accommodation on Airbnb
Top-rated waterfront accommodation in Key West
Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Key West waterfront rentals
Waterfront apartment accommodation

Beachside Unit 22 - Private Beach on Atlantic
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.

Seaside Vista - Ocean Front 2/1 with dockage
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!

Henry's Penthouse On The Ocean
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.

Waterfront Condo with Slip & Pool in Key West
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 !!

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!

Boho FL Keys Condo
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.

Beachfront Condo w/ Ocean Views in Marathon
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.

Penthouse in Paradise
Enjoyed our stay. The place was beautiful and matched the description. Just disappointed couldn’t use jacuzzi tub. Otherwise no isssues
Waterfront house rentals

Sunset Beach Hideaway *Private Beach* *Jacuzzi*
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!!

Million Dollar View
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.

Sailfish Dream on Cudjoe Key-28 day minimum
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.

Waterfront 4 Bed 4 Bath Home in Key Cove Landings
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.

The Guest House - Sugarloaf Beach Key West
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.

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

Waterfront House with 37 ft Dock & Cabana Club
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.

Rise And Shine On The Water
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

Condo de Paradise/Salt Water Pool/Boat Dock
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.

Galleon Resort - Walk to Duval & Mallory Square!
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.

Oceanfront and Sunrise Views!
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!

Your Happy Place - Oceanfront
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. 🙂

Anchor Drop modern elegance upgrades throughout vi
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!

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach
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!

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
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.

BEAUTIFULLY DESIGNED OCEANFRONT CONDO
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
- Florida Keys Holiday rentals
- Havana Holiday rentals
- Miami Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Bay Holiday rentals
- St Petersburg Holiday rentals
- Seminole Holiday rentals
- Tampa Holiday rentals
- Central Florida Holiday rentals
- Kissimmee Holiday rentals
- Condo rentals Key West
- Beachfront rentals Key West
- Rentals with a fire pit Key West
- Rentals with an EV charger Key West
- Beach house rentals Key West
- Houseboat rentals Key West
- Smoking-friendly rentals Key West
- Kid-friendly rentals Key West
- Rentals with outdoor seating Key West
- Rentals with an accessible height toilet Key West
- Rentals with a patio Key West
- Cottage rentals Key West
- Family-friendly rentals Key West
- Rentals with a hot tub Key West
- Pet-friendly rentals Key West
- Fitness-friendly rentals Key West
- Beach condo rentals Key West
- Townhouse rentals Key West
- Hotel rentals Key West
- Rentals with a washing machine and dryer Key West
- Apartment rentals Key West
- Mansion rentals Key West
- Rentals with breakfast Key West
- Rentals with lake access Key West
- House rentals Key West
- Luxury rentals Key West
- Rentals with a kayak Key West
- Rentals with pools Key West
- Rentals with a fireplace Key West
- Villa rentals Key West
- Rentals with beach access Key West
- Waterfront rentals Monroe County
- Waterfront rentals Florida
- Waterfront rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Things to do Key West
- Sightseeing Key West
- Art and culture Key West
- Tours Key West
- Things to do Monroe County
- Sports activities Monroe County
- Tours Monroe County
- Food and drink Monroe County
- Sightseeing Monroe County
- Nature and outdoors Monroe County
- Art and culture Monroe County
- Things to do Florida
- Wellness Florida
- Tours Florida
- Art and culture Florida
- Sightseeing Florida
- Food and drink Florida
- Entertainment Florida
- Nature and outdoors Florida
- Sports activities Florida
- Things to do United States
- Sightseeing United States
- Food and drink United States
- Nature and outdoors United States
- Sports activities United States
- Tours United States
- Art and culture United States
- Entertainment United States
- Wellness United States