
House holiday rentals in Key West
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Top-rated house rentals in Key West
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Popular amenities for house rentals in Key West
House rentals with a pool

Sandbox
⭐️⭐️⭐️⭐️⭐️ Absolute Paradise in the Heart of the Keys! Our stay at this vacation house in Marathon was nothing short of incredible. From the moment we arrived, we felt like we had found our own private slice of paradise. The house was spotless, beautifully decorated, and had all the comforts of home—plus the added bonus of breathtaking ocean views and island vibes. The location couldn’t have been better. Tucked away in a peaceful part of Marathon, we were just minutes from everything—the beach, boat rentals, amazing restaurants, and the iconic Seven Mile Bridge. The property itself was incredibly well-equipped: a fully stocked kitchen, super comfortable beds, high-speed WiFi. What really made this place stand out was the outdoor space. The private dock was perfect for fishing and sunset cocktails, and the pool made it hard to ever want to leave. We even spotted dolphins just off the dock one morning—unreal! The hosts were friendly, responsive, and went out of their way to make sure we

Endless Summer
We very much enjoyed our stay, the house was as expected based on previous reviews & pictures. The location was perfect for us to access from Key Largo to Key West easily. The pool was nice & the kids had fun snorkeling off the back dock & looking for all kinds of wildlife both on land & in the water with their flashlights after dark. We found the sunsets at the house to be better than what we experienced in Key West. If you need beach chairs and/or beach umbrella, we recommend you rent those.

Oceanfront with Pool near Sombrero Beach
Absolute Keys Perfection!! This vacation spot won't disappoint. Private, gorgeous, well maintained home with lots provided & to do on site, PLUS a place to dock a decent sized boat. Our 30' Grady White Marlin sat nicely at the bulkhead and we could easily spin it in the canal - it does get shallow but if you stick to the marked channel you're good. Homeowners are extremely responsive, friendly & want you to enjoy your stay. Kitchen is fully stocked & has appliances I wish I had room for at home. HiFee boat ramp and Publix down the street. Bonus, there's a preservation next door where lots of seabirds like Frigates roost and teach their young to fly in front of the house. Wish I had booked a second week! or the whole month lol

Oceanfront, Resort-like luxury home with private p
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!

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!

Funky Chicken Cottage with Shared Pool
Thank you soo much for hosting us Irene! We truly appreciate you having us. We had an amazing Key West! You were a wonderful host. I’d definitely recommend anyone book here!

P31 - 11785 5th Ave. Ocean
I knew that I was limited on what I could do during the week stay bc of a knee injury and it was just fine bc I was quite happy just being at the house for most of my stay. Just loved it and didn’t want to leave. Even though this is an active boating location and boating route l, I still felt quite peaceful staying there. The pool was great and the hot tub was quite beneficial for my knee. Just be careful climbing into the pool. The ladder going up is quite steep. I would’ve preferred some true stairs. But that’s coming from someone with a hurt knee too so take it with a grain of salt. And if you don’t feel like going out to eat, seriously order the steamed shrimp by the pound at FishTails on the corner. It is within walking distance. Will definitely be back for another stay in the future.

Catherine House: A charming Old Town Key West
We thoroughly enjoyed our stay at the Catherine house and it was a perfect location to explore Key West. Beautiful space and well thought out. Perfect for two couples! A welcome retreat when you wanted to get out of the Key West hustle and bustle. We loved our time there!
Weekly house rentals

Waterfront Escape -VACA-23-408
we were a family of 6 staying and had more then enough room. the house was perfect and had everything you needed. we enjoyed fishing off the deck and watching the manatees everyday day swimming by. the backyard was absolutely perfect to hang out and relax. Carmen is a great host and communicates fast. would absolutely stay here again.

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys
Sandra’s conch cottage was comfortable and beautiful and very clean. Provided all the necessary items for the week. The location of the house in Marathon is perfect to all amenities. I would definitely come again.

Florida Keys Oceanside Utopia
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!

Private Ocean Oasis by Key West, Florida
Just what our family needed. As a new Florida resident it’s safe to say the Keys rank up there as one of my favorite places to visit. Rhonda’s home felt like our home. We enjoyed the pool and bikes. A local restaurant The Bent Prop bar and grill was a treasured find. My husband and I met the owner who is from the same area as us in Maryland. If you’ve ever wondered what Maryland Cream of Crab soup taste like… that’s the place to get it from! Can’t wait to book us again for next year!

Waterfront Private Home w/Pool-Family&Pet Friendly
The location and access to the beach and canal was amazing! We had such a fun time with the kayaks while being able to see all the wildlife and sail boats. The house was exactly what we needed. Jose was very helpful and flexible throughout our stay.

“La casa azul” step 3’ to a private pool
We spent an amazing week in this home. Very comfortable and quiet. The pool was amazing. Will definitely be back.

Viamarhe House-Private beach, Kayak, yard games
Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.

Serenity Bay Estate-FL Keys Best Kept Secret! Beau
Stunning location, very comfortable with plenty of space for 10 people. When we arrived we never felt like leaving. Beautiful pool and hot tub surrounded by palm trees, sandy area with great fire pit, gorgeous outdoor eating area and kayaks to drop from pier. Very private location with spectacular sunsets! Fabulous!!!!
Private house rentals

KCB Tropical Escape
This was better than I expected. A very spacious 2 bedroom with large kitchen, family room. The screened in porch was huge, and a great place to have meals and watch TV and the sunrise. The fully equipped kitchen was awesome for those like us that love to cook. It was a great home away from home. This place was so comfortable and was the best we ever rented.

Waterfront Oasis w/Private Pool-Dockage-Beach
Incredible property. Perfect gathering space for my entire family of 6. Private yet close to commerce like Publix and local gym to work out. Great memories made.

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.

Oasis in The Keys-Kayaks-Paddle Boards-Cabana Club
Beautiful, well appointed home in the middle of the keys within driving distance to all the tourist attractions and restaurants. We are a 3 generation trip with grandparents and kids, and this house had it all! 3 bedrooms, each with excellent ocean views, great kitchen, kayaks and bikes in the garage, and incredible outdoor seating area! Highly recommended for families.

Casa Calypso 3bed3bath sleeps 8 beautiful decorate
The house was nice, clean and spacious. we loved the huge bathtub in the master bath, it was that was very inviting. it had all the things that we need, and it was accessible to many places on the island. The host was responsive and helpful. we would book again.

Gorgeous Ocean View Home!
The pictures of this house, while gorgeous, do not do it justice. Not only was the house immaculate and spacious, it has the most stunning view. It is very close to shops and local beaches, and it's centered in between Key West and Islamorada. Yery, our host, was also very helpful and proactive with the one and only challenge we faced. I really can't say enough about this rental. It was spacious enough and contained all the amenities my family of seven could possibly need, including space for our dog. It has the most amazing view of the turquoise water of the Keys. It quite literally checks every box for a checklist of paradise, and I can't wait to go back!

Boat Dock+King Beds & Cabana Club
I was very happy when I walked in the door, it had everything that I needed and more during my stay. Every door or cabinet that I opened had something that could be useful during anyones stay. From the moment that I started inquiring about the rental to the very end of my stay, they were very helpful with all the questions that I had and always responded promptly. I highly recommend renting from them. I look forward to staying in their rental next year.

Waterfront Heated Pool 120 ft Boat Dock
A Hidden Gem – Perfection in Every Way! Truly! This was, one of the best Airbnbs we have been to in Marathon! We have traveled down for many years and could not ask for a better place!!! From the moment we arrived, everything was absolutely perfect. The space was spotless, it slept 8 of us comfortably! Stocked with every single thing we could need! Location itself was Unbeatable! Peaceful, picturesque, and close to everything, yet somehow still felt like our own private escape! The dock cutting board and easy water hose worked perfect for any catch! The wrap around deck was the biggest hit! Seeing manatees and Tarpon sightings really made my kids day! It truly was magical experience! The pool to cool off and the mini splits in each room without it being manually controlled was the ultimate! Milton was phenomenal to communicate with! You can tell he genuinely cares about his guests♥️. Our family has already booked for next year and we highly recommend!
Quick stats about house rentals in Key West
Total rentals
640 properties
Nightly prices starting at
$77 SGD before taxes and fees
Total number of reviews
10K reviews
Family-friendly rentals
550 properties are a good fit for families
Pet-friendly rentals
310 properties allow pets
Rentals with a pool
440 properties have a pool
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