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

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip
If I could rate this stay a 20, I would. We came across the listing last June, after wanting to try something different on our annual trip to Marathon. It looked perfect for our family. What I didnât expect when we arrived on April 16, 2025, was to be blown away. The pictures donât do it justice. The house is STUNNING. I felt like we were walking in/staying at a brand new house as the very first guests. The colors, the furnishings, the level of coziness brought to this luxury beach house was unmatched. The towels (bath and beach) were plush and soft. Pool speakers. The bar! I mean everything. The kitchen was stocked with what you need - high end gadgets, utensils that actually work, and every pot and pan (organized). Immaculately cleaned. And then the views. Holy guacamole. My dad parked himself on the main floor deck and didnât move for seven days. Airbnb was right- RARE FIND. Amanda - you are the hostiest host in the world. Your communication was đŻ. And we pray to make it back to yo

Cancellation Deal: 08/02 thru 08/09
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

Mermaid's Retreat at Coral Hammock Key West Islan
I loved the stay at this house. Would definitely come again.

Beautiful Beachfront Villa w/ Pool/Tiki/Dock
This home is even more than the pictures show! It is an extraordinary home for people who love the sun, shade, beach, and the beautiful home just makes it a luxurious vacation. I could not find one aspect I didnât love.â¤ď¸

Bahamian Reed by AvantStay
We came to truly appreciate how stellar our townhouse, Reidâs Bahamian Stay was once we got our bearings in Key West. The location within the tranquil Truman Annex could not have been more ideal for a great week in Key West. A nicely updated townhome with private porches and back yard and located near the association pool (but not too close!) Avant Stay was wonderful to work with from prompt advance communications to providing a very clean and nicely stocked unit to get us started. As a rental management company, I highly recommend them and we will look them up again for our next stay. A 5 star experience for a nice family vacation.

Waterfront Beach House with Dock & Heated Pool!
House was very clean, host very responsive, beautiful location, pool was perfect and the view was amazing. Definitely recommend and will be staying there again.

Bohemian Beach Bungalow
I canât say enough great things about this beach bungalow! From the moment we arrived, we were welcomed with warm hospitality and thoughtful touches that made our stay truly special. The bungalow itself is cozy, clean, and beautifully decorated with a laid-back coastal vibeâexactly what you want for a beach getaway. Whether youâre looking for a romantic escape, a solo retreat, or a peaceful base for beach adventures, this place is a gem. We left feeling refreshed and recharged, and weâre already dreaming of coming back!

Palm Breezes! Room for Everyone on the Ocean.
10 out of 10 stay. Beautiful, serene property where we often felt we had the mangrove and key to ourselves. Several days were spent on a recurring rotation of kayaking, pool, hot tub, repeat. Perfect distance from Key West for adventuring there, but plenty on Cudjoe Key and Big Pine if you don't want to venture to the hustle and bustle. Sincerely hope to return!!
Weekly house rentals

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!

Indulge yourself. It's heavenly in Little Torch
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.

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.

Tiki Time in Cudjoe Key 136
Amazing views and ocean breeze! Modern and clean home which I appreciated. Only thing I could ask for but itâs strictly on my wishlist is an elevator. I was dealing with a knee injury so the steps were tough but worth it when you get to the balcony and enjoy that view! Couldnât ask for a better stay and vacation in the Keys with my family!

Private Ocean Oasis by Key West, Florida
Just what our family needed. As a new Florida resident itâs safe to say the Keys rank up there as one of my favorite places to visit. Rhondaâs 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 youâve ever wondered what Maryland Cream of Crab soup taste like⌠thatâs the place to get it from! Canât wait to book us again for next year!

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

Poinciana Treetop ~ Casual Second Floor Duplex
Great place. Walk-able to all attractions in the historic district, Duval Street, Sunset Pier and Bahama village.

Clocked Out 2bed/2.5bath updated open water condo
Absolutely outstanding rental. Donât change a thing. Fabulous location on the water in the center of the Keys. Super comfortable furniture, super well-stocked kitchen. Love that everything in this unit was good quality. Nothing was cheap, we really appreciated that. Quiet & relaxing. Our only gripe was we couldnât find the place initially. We were following written directions sent by the management company that had not been updated; turns out the âturning point buildingâ no longer existed. The road into the complex looks more like a parking lot. We also initially didnât receive our entry code, but it came immediately after we notified the management company. Then we got a second (and different) code, but one of them did work. The A/C wasnât working well during our stay; however It was fixed a day & a half after notifying the management company.
Private house rentals

Waterfront with Boat Lift/Kayaks and Hot Tub
The place was amazing!! plenty of room for our family of 5. All of the fishing equipment was awesome!! From the rods and tackle, to the deep freezer with bait, the extras made the whole trip more enjoyable. Loved the house. It was perfect!!! Will definately be back in the future!! 10 out of 10 would recommend!!

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.

Sandbox
The stay experience exceeded our expectations. The only recommendation would be to have a listing of recommended restaurants, beaches, boat rental places, etc to go see in both Marathon and key west. We visited key west and found out afterwards where we should have gone.

P36 - Charming and immaculate 2 Bedroom, 2 bathroo
Great place! Very spacious, nice dock and out door and area to enjoy with the pool! It was nice having a large deep freezer for ice and fish!

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.

Movie Theater | HotTub | Pool | Boat/RV/EV Parking
We almost stayed at a hotel, but I saw Christianâs place pop up and it looked like a fun place for the family. It is so awesome! It is exactly as described.and more . He uses every inch of that awesome property for something fun. Itâs also a close drive or bike ride to so many things. We took almost all of his suggestions on places to eat and things to do and they were right on. The last night we all chilled outside and projected the Goonies on the outdoor screen and had some good relaxing family time. He is an excellent host and is so helpful. We are all so happy we chose his Airbnb.. Thank you so much, Christian! You are one of a kind and your place is so cool.

Waterfront FL Keys Cottage @ Venture Out
What a beautiful cottage. Loved how it was decorated. We had everything that we needed. Loved the outside back patio. Peaceful and quiet. The bed was super comfortable. Very clean and a plus, it had a washer and dryer. Thomas and Lindsay were so nice, communicative and very responsive. Gave us some great recommendations on restaurants and things to do in the area. A little piece of paradise. Island Life. We will DEFINITELY be back. Highly recommend.

Seagull Suite | Inviting Studio, Just Steps From D
Rick's place is in a great location! Lot's of peace and quiet while close enough to walk anywhere. Close to the bus and trolly stops. there's a general store next door, a bar across the street with live music all week and an ice cream shop (a favorite of mine) next to the bar. You "might" be able to find a better place, but you would have to spend a lot of time finding one. If this place is available for your trip to Key West........book it!
Quick stats about house rentals in Key Haven, Key West
Total rentals
60 properties
Nightly prices starting at
âš8,609 before taxes and fees
Total number of reviews
900 reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
50 properties have a pool
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