Waterfront vacation rentals in Key Haven, Key West

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Popular amenities for Key Haven, Key West waterfront rentals

Waterfront apartment rentals

Superhost
A modern kitchen features white cabinetry and a granite countertop. Stainless steel appliances, including a refrigerator and oven, are present. A coffee maker and additional kitchen equipment are visible on the counter. Soft grey curtains adorn the window, allowing natural light to enter.
Apartment in Big Pine Key
4.97 out of 5 average rating, 34 reviews

New Deluxe Duplex Unit, 2 Queen Beds, Unit H-5

BarbaraRating, 5 stars1 month ago
I had an absolutely incredible experience! From start to finish, everything was flawlessly organized, making the journey to the location a total breeze. The host was incredibly welcoming, instantly making me feel right at home. This was precisely the getaway I had been craving for my three-night escape! I'm already counting down the days until I can return! Without a doubt, I’ll be sharing this hidden gem with all my friends and family!
Top guest favorite
An aerial view captures the layout of the Ocean Isles Fishing Village, showcasing multiple light blue condos with white roofs positioned along winding roads. The Atlantic Ocean glimmers in the background, surrounded by lush greenery and residential areas, illustrating the tranquil setting of the Florida Keys.
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
A shaded tiki hut with a thatched roof stands on the sandy shore, overlooking the calm, blue waters of the Atlantic Ocean. Two palm trees frame the structure, creating a serene beach environment, with gentle waves lapping at the rocks in the background.
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.
Superhost
The property is positioned near the shoreline, featuring a modern design with multiple balconies. Lush palm trees frame the exterior, while a landscaped garden adds greenery. The serene ocean can be seen in the background under a twilight sky.
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 favorite
A spacious pool area features a large swimming pool surrounded by lounge chairs and vibrant blue umbrellas. Lush palm trees provide shade, and ocean views are visible in the background, enhancing the tranquil atmosphere of the outdoor space.
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
A waterfront view captures a serene canal lined with tropical greenery and residential boats. The white boat is positioned on the dock, with steps leading to an inviting home painted in a soft yellow. Clear blue skies enhance the tranquil atmosphere.
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 favorite
A welcoming living area features a dark gray sofa and armchair, complemented by patterned cushions. A light wooden coffee table sits atop beige tile flooring. A large flat-screen TV is mounted on the wall, and natural light filters through window coverings, creating a bright atmosphere.
Apartment in Marathon
4.97 out of 5 average rating, 62 reviews

Dock POOL Kayaks Bikes Beach2mi WalkToStores

jennifer Rating, 5 stars1 month ago
My husband, myself and 3 adult children stayed for a week. Place was super well equipped with everything imaginable. Very Spacious inside and out. Danielle was great at answering any questions we had. It was an amazing family vacation and will definitely rent again. - Jennifer
Superhost
A refreshing pool area is surrounded by green palm trees and blue umbrellas. Lounge chairs are arranged neatly around the pool, while tables with chairs provide seating for guests. The clear blue sky enhances the inviting atmosphere of the community space.
Apartment in Key West
4.86 out of 5 average rating, 98 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 favorite
A two-story waterfront home is situated under a clear blue sky, surrounded by palm trees and lush greenery. The property features a bright white exterior with a balcony, along with a manicured yard of decorative rocks and native plants.
Home in Cudjoe Key
4.9 out of 5 average rating, 52 reviews

Keys Island Villa - Venture Out Home 354

ClaudiaRating, 5 stars1 month ago
Fantastic stay w great views. House made us feel right at home. place was in gated community. it felt safe and well maintained. Fun to walk around in the evenings.
Superhost
A serene canal view is captured from the deck, lined with palm trees and houses in the background. Boats are moored along the waterway, with a well-maintained deck and white fence visible in the foreground, inviting a sense of tranquility.
Home in Little Torch Key
4.8 out of 5 average rating, 15 reviews

Indulge yourself. It's heavenly in Little Torch

CharlesRating, 5 stars3 months ago
Clean and neat home on a quiet canal. Neighbors were even friendly! Good amount of parking. Home is clean and well laid out. Airy living room just off the open kitchen. Large master bedroom and bathroom. We felt very comfortable there.
Top guest favorite
A sparkling in-ground pool is visible in the foreground, surrounded by a spacious patio. Lounge chairs are positioned along the deck, offering views of the lagoon. Lush palm trees provide shade, while a clear sky enhances the tranquil atmosphere of the waterfront setting.
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 favorite
An inviting living area features a cozy sectional sofa adorned with patterned pillows. Large windows provide ample natural light, while a TV stands on a wooden console. A dining area with a light fixture and a view of the balcony is visible in the background.
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.
Guest favorite
A spacious porch extends along the exterior, featuring two comfortable chairs with cushions and a small side table. The tranquil waterfront view is framed by lush greenery and distant trees, enhancing the serene atmosphere. Sunlight brightens the area, highlighting the white railings and wood flooring.
Home in Key West
4.92 out of 5 average rating, 13 reviews

Oceanfront, Resort-like luxury home with private p

OliviaRating, 5 stars3 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!
Superhost
A serene view of a waterfront canal is captured from a covered porch. The calm water reflects the sky, with boats docked along the edges. Palm trees gently sway in the breeze, enhancing the coastal setting. Nearby structures suggest a vibrant community atmosphere.
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!
Top guest favorite
A sandy beach is lined with lounge chairs under tall palm trees, facing a calm turquoise sea. A pier extends into the water, and a few beachgoers are sunbathing on the shore. The sky is partly cloudy, providing a serene atmosphere.
Home in Key Colony Beach
4.98 out of 5 average rating, 105 reviews

Waterfront House with 37 ft Dock & Cabana Club

MarciaRating, 5 stars1 month ago
This was a great place for our family. We had plenty of space to relax. The home is well stocked with linens, kitchen items and paper goods. We only had to buy groceries. The tvs had streaming services and there are two types of coffee makers!
Top guest favorite
A private wooden dock extends over calm waters, featuring a boat with a blue canopy and a small table with colorful umbrellas nearby. Palm trees line the waterfront, and a series of pastel-colored homes are visible across the canal, creating a serene setting.
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

An aerial view of Beachside Resort reveals spacious grounds set against the Gulf of Mexico. The property features multiple buildings arranged around a resort pool, surrounded by lush greenery and access to the marina, highlighting the serene waterfront location.
Condo in Key West
4.76 out of 5 average rating, 37 reviews

One Bedroom Suite | Beachside Resort

PhilipRating, 5 stars3 days ago
Stay was clean and in a great location. Lots of amenities in the resort property.
Guest favorite
The balcony offers stunning views of the turquoise waters and sandy beach, framed by palm trees. A resort-style pool can be seen nearby, and the expansive outdoor space invites relaxation under the sun, enhancing the beachside atmosphere.
Condo in Key West
4.97 out of 5 average rating, 36 reviews

Windswept Palms at The Beach

JenniferRating, 5 stars4 months ago
Windswept Palms was beautiful and we enjoyed the setup. The pool and beach were very clean and quiet. The views are absolutely amazing!! We were able to walk in the ocean one day and it was so clean and clear. Victor, the host, was very nice and helpful!! Beds were comfy and so was the couch.
An open-concept kitchen and living area features wooden cabinetry and sleek granite countertops. Stainless steel appliances, including a refrigerator and oven, are visible. The living space includes comfortable seating and decorative plants, with a dining area set against the backdrop of large windows providing natural light.
Condo in Stock Island
4.75 out of 5 average rating, 395 reviews

Private Parking & Waterfront - Grand Marina Suite

JRating, 5 stars1 month ago
Fantastic stay in a fantastic place! Highly recommended! Thank you very much
Superhost
A large pool area is surrounded by lounge chairs, inviting relaxation in a tranquil setting. Lush palm trees and greenery frame the scene, while a covered seating area is present nearby. The multi-story building provides a view of the resort's amenities and landscape.
Condo in Key West
4.71 out of 5 average rating, 7 reviews

Vista Fresco at Oceanside Condo Community

MissyRating, 5 stars11 months ago
Pictures were exactly how the home looked upon arrival. Staff were very helpful and friendly. Location was quiet yet close enough to walk. Beach in either direction. The home had everything you need for the beach and was spacious. Bed in master is very comfortable. Great place and great company. Will use again.
Superhost
A spacious balcony overlooks the ocean, featuring blue Adirondack chairs and a dining table. Lush greenery and palm trees frame the view. The sky is clear and sunny, reflecting on the water, creating a serene atmosphere.
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!
Guest favorite
A balcony view overlooking the Gulf of Mexico features a railing framing the scenic water below, where sunlight glimmers on the surface. Lush greenery is visible nearby, enhancing the serene coastal atmosphere.
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 favorite
A light-filled living area is visible, featuring a comfortable seating arrangement and a mounted television. A dining table occupies the foreground, adorned with a bowl of oranges. The walls are painted in soft blue, providing a relaxed atmosphere, with a ceiling fan overhead.
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 favorite
Lounge chairs are positioned on the grass near the ocean, surrounded by palm trees. A soft gradient of colors in the sky, transitioning from pale pink to light blue, is visible above the tranquil waters. Rocky shoreline meets the beach, creating a peaceful environment.
Condo in Key Colony Beach
4.98 out of 5 average rating, 41 reviews

Paradise found! Sea-Esta Condo beach and pool.

RichardRating, 5 stars4 weeks 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.

Quick stats about waterfront rentals in Key Haven, Key West

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ551 before taxes and fees

  • Total number of reviews

    690 reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    30 properties have a pool

Destinations to explore

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  4. Monroe County
  5. Key West
  6. Key Haven
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