Beach house holiday rentals in Key West

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Popular amenities for Key West beach house rentals

Beachfront house rentals

Superhost
Home in Marathon
4.85 out of 5 average rating, 26 reviews

(#8)Waterfront 4 Bed 3 Bath Pool Home w Free Dock

MollyRating, 5 stars3 months ago
We had a delightful time. The unit was clean & comfortable and easily accommodated our party of 5 adults. The balcony was very pleasant and had a great relaxing view. The shared beach was also very relaxing with plenty of chairs and a nice covered card table area. This is in addition to the multiple seating options at our private pool. Families were enjoying the provided kayaks of which there were plenty. Susan and Dale were extremely responsive to all of our inquiries including showing up to address an issue within 15 minutes! Overall we had a very pleasant stay.
Top guest favourite
Home in Key Colony Beach
4.98 out of 5 average rating, 123 reviews

Paradise found!Key Colony Beach,Cabana Club.

NathanRating, 5 stars3 weeks ago
We had a great time at Paradise Found. The property was lovely and clean, all very well maintained. The location was beautiful, backing onto the water and enormously peaceful, a great setting. Kari was very communicative and always responded quickly to any queries. Overall, we were very happy.
Superhost
Home in Marathon
4.94 out of 5 average rating, 17 reviews

Pool & Spa, Walk to Beach, Dock, Tiki, Lux Home

Stefan And KarenRating, 5 stars3 weeks ago
The house was spacious and clean, and we got good use out of the pool and hot tub. Bert requires signing a separate contract after booking on AirBnB, but worked with us to tailor the language. Towels are provided but be prepared to bring most other amenities like shampoo, etc yourself. Also, be aware that Sunrise Drive is a private road and you cannot access the beach there - Sombrero Beach is about a 15 minute walk, but definitely worth the walk!
Superhost
Home in Marathon
4.92 out of 5 average rating, 24 reviews

Steps to Sombrero Beach | 4BR w/ Dock, Pool + Dogs

DianeRating, 5 stars3 weeks ago
We thoroughly enjoyed our week at Matt’s place! As a host, Matt was quick to answer our questions and provide what we needed. The location is excellent, with the canal views from the back yard and a few minutes walk to the beach.
Top guest favourite
Home in Cudjoe Key
5 out of 5 average rating, 23 reviews

Tiki Time in Cudjoe Key 136

CourtneyRating, 5 stars3 weeks ago
Highly recommend anyone to stay here! The house is clean, well stocked, cozy, and quiet. The view is absolutely amazing! Sitting on the porch was our favorite way to start the day. Everyone was very friendly too.
Superhost
Home in Key Colony Beach
5 out of 5 average rating, 3 reviews

The Sandcastle - 2bed/1bath half duplex with docka

RachelRating, 5 stars11 months ago
Key Colony Beach is a quaint little village in and of itself. This duplex was exactly as the pictures show. Beds, pillows and sofa very comfortable. The kitchen was the most well stocked of all we’ve stayed in; all cooking, baking, and dining that you have at home and then some. Towels and linens were plentiful and clean. The neighbors were also kind and courteous. Having the boat dock was a big plus as we brought our boat with us. We put-in and pulled-out at the public landing across the street from the entrance, for a $25 fee each occurrence . Short, beautiful ride to our dock. Docking was easy and included an outside cleaning station and shower. Nice outdoor seating and Palms. The retractable awning above the sliding glass door was also perfect for blocking some of the afternoon sun. The location is convenient to dining, grocery and convenience stores. We loved everything about our vacay, other than having to leave. We’ll definitely be back.
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 44 reviews

Tropical Dream Vacation - 3bdrm/2bath CANAL FRONT!

JamesRating, 5 stars6 days ago
The place looked exactly like the pictures. Great location and close to the beach. The pool was the best part. Would definitely stay here again.
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 32 reviews

Viamarhe House-Private beach, Kayak, yard games

LisaRating, 5 stars3 weeks ago
We had a great stay. Enjoyed family time. The only feedback is that we didn’t realize there would be so much natural debris by the water which isn’t anyone’s fault. We just didn’t know so we were not prepared with water shoes.

Beach house rentals with a pool

Top guest favourite
Home in Marathon
5 out of 5 average rating, 39 reviews

Discount Available! 100' Dock, Lots of Amenities!

KatieRating, 5 stars2 weeks ago
We loved our stay here! The house was perfect for our family. Very roomy and comfy. The backyard was our favorite! We enjoyed nonstop days of relaxing on the patio and in the pool and also fishing/kayaking in the canal. They had everything you could think of that you’d need. The location was great too. Down a quiet dead end road, within walking distance to an amazing beach and just over a mile to Publix. We enjoyed evening bike rides down to the beach which were also provided with the house. We have recommended this place to our fiends and family and hope to come back again ourselves!
Superhost
Home in Marathon
5 out of 5 average rating, 7 reviews

Discount Availble! 3BR 2.5BA Direct to Ocean!

SydneyRating, 5 stars3 months ago
This home offers so many amenities!! We thoroughly enjoyed biking, kayaking, the heated pool, grilling, and several games the host had for us. The large kitchen made it easy for our group of 6 to interact and enjoy meals together. The host was very responsive with any questions we had and checked in throughout the stay to ensure our needs were being met. This was our second year staying in Marathon, would stay at this location again.
Superhost
Home in Key West
4.6 out of 5 average rating, 5 reviews

Coastal Comfort; Waterfront Luxury Home with priva

JayRating, 5 stars18 months ago
We all loved the house. Plenty of space, the outdoor patios were a daily hangout, the views were great, what's not to love. The maintenance of the house itself was excellent and it didn't feel like a "rental". Well decorated, not worn down, a bathroom for everyone, it was great. We rented a golf cart to get back and forth from town which was very easy and barely a ten minute drive. We did have a small issue with the pool while there, which apparently is very unusual. It is Key West so it took a few days to get the parts needed. However, Javier was always easy to reach and while he did eventually fix it it was his 'out of the box' thinking and communication on everything that was superbly professional. I understand he manages several properties and we would gladly stay at any of them. With an AirBNB, if something goes wrong and you're far from home all you have to rely on is the owner/manager and you are in excellent hands with Javier. A++ on customer service
Guest favourite
Home in Key Colony Beach
4.93 out of 5 average rating, 14 reviews

Paradise Cove!30ft Dock Pool BBQ

RebeccaRating, 5 stars1 week ago
Loved our rental in Key Colony. The house was beautiful and the kids loved the private pool. The place felt just like home.
Superhost
Home in Key Largo
4.86 out of 5 average rating, 100 reviews

Cary’s Oceanside

KrissieRating, 5 stars3 months ago
We had a great time at Cary’s Oceanside! Beautiful location, beautiful and comfortable accommodations! Maria was very helpful and responsive with our questions. We really enjoyed the pool and outdoor area.
Superhost
Home in Summerland Key
5 out of 5 average rating, 10 reviews

Pelico Palm Villa

KellyRating, 5 stars13 months ago
This home was absolutely beautiful!! It was exactly what we had hoped for, We were a family of 4 with my husband and I, with are two sons, ages 17 & 20, plus ones girlfriend age 16. We wanted a nice family vacation without the spring break chaos & this was it! This home was so clean yet cozy, had all the necessities we needed, everyone had their own room and bathroom which was super!!! This home could definitely accomodate so many more if you wanted to do so. We were the only ones there at the time, so we had the pool area to ourselves which we loved sooooo much! We played bags by the pool daily, swam during day & at night. The home had a great deck with a wonderful grill, we made slushy drinks with the ninja blender, anything you wanted this place had! We traveled to Key West a couple times which was nice and close, about a 30 minute drive. All in all this place is top notch! Don't hesitate to book! It's worth it!! LOVED this Home!! & Nate was a spectacular host!!!
Guest favourite
Home in Marathon
4.88 out of 5 average rating, 24 reviews

Golf Coast Oasis

AmandaRating, 5 stars2 weeks ago
This was the most perfect Airbnb for our vacation. First of all, Marathon is the perfect location if you are looking to explore multiple parts of the Keys. 1 hour to Key Largo, 1 hour to Key West. We could not have asked for a better location. The home looks just like the photos and was perfect for our family of 4 + our pup. The beds were comfortable, the living space had plenty of room for our crew, but the real show stopper was the pool. If we weren't out and about exploring the Keys, we were definitely in/by the pool! A few added bonuses: (1) K-cups for our use for that first morning. This kept us from having to worry about an emergency grocery store trip the evening of our arrival (2) pool floats available for our use (3) bikes & kayaks for everyone (4) EVERYTHING. We couldn't have asked for better - we will definitely be back!
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 112 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

JessicaRating, 5 stars3 weeks ago
Our family of 9 loved the house! The pool, corn hole, and roof deck were all huge hits with the kids. The house is perfectly situated on Marathon, close to all the restaurants. Quick drive to Bahia Honda. We will definitely will be back for another visit to Andy’s place.

Private beach house rentals

Guest favourite
Home in Marathon
4.92 out of 5 average rating, 50 reviews

Luxe Waterfront Keys Cottage- with Jacuzzi

MaxsenaRating, 5 stars1 week ago
Super nice place to stay. Very comfortable.
Superhost
Home in Cudjoe Key
4.89 out of 5 average rating, 36 reviews

Lower Keys Paradise

JasonRating, 5 stars1 month ago
Great location in Cudjoe key. The community has tons of amenities and great fishing!!
Guest favourite
Home in Marathon
4.95 out of 5 average rating, 59 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

ErinRating, 5 stars1 month ago
I can’t say how much we enjoyed this place. So private and clean. Beautiful view. Everything we needed was there. Sad to leave but back to real life. Thank you Thank you!
Top guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 19 reviews

Keys to the Sea + Cabana Club

MarcilleRating, 5 stars1 month ago
Our family of 4 really enjoyed our stay! It really was the perfect getaway spot for us to rest and recharge. The amenities available were so convenient, from a well stocked kitchen, bathroom supplies, laundry, a bait freezer, to even having pool towels and a cooler available to use. Our kids ages 11 and 13 spent hours fishing off of the dock out back. We even caught our meal a couple of times! We also really enjoyed access to the Cabana Club! It had a lovely beach front along with a perfect temperature pool! Drinks and food at the club were very reasonable priced. This is our third year in a row visiting the keys and we always enjoy this area. Next year I will be looking at this rental first! Thank you again for the wonderful stay!
Superhost
Home in Marathon
5 out of 5 average rating, 15 reviews

P87 - New Construction house. 4 bedrooms, open wat

KaitlynRating, 5 stars12 months ago
Such a beautiful home in a beautiful location! 2-3 min walk to Sombrero Beach. Safe, walkable neighborhoods, close to loads of great restaurants and activities. Being centrally located in Keys, plenty of options in Marathon or with a short ride north or south. Would definitely recommend/return.
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 69 reviews

Private 174ft Dock, Boat Launch, Sombrero Beach

ChrisRating, 5 stars1 month ago
We had a great stay here, beds were comfortable and bathrooms were clean. Kids loved fishing off the dock - although the boat ramp was unavailable, we were able to use the ramp at the marina down the block ($30 each drop). Hosts were easy to communicate with and very helpful when we had a question. Wed definitely stay here again next time in Marathon.
Guest favourite
Home in Key Largo
4.95 out of 5 average rating, 44 reviews

Cottage in Paradise

WillRating, 5 stars4 weeks ago
The perfect place to stay while we were visiting our family in the Keys.
Guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 15 reviews

Bohemian Beach Bungalow

SamanthaRating, 5 stars2 weeks ago
This was one of the best experiences we have had in a long time! This amazing boho beach paradise had everything the comfort of home would have plus more! Karen was so responsive to any questions we had and helped me surprise my husband for our anniversary and made this trip even better! We will absolutely be back here for a trip again!

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