House holiday 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

Top guest favourite
Home in Marathon
5 out of 5 average rating, 38 reviews

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

JillRating, 5 stars1 month ago
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 didn’t expect when we arrived on April 16, 2025, was to be blown away. The pictures don’t 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 didn’t move for seven days. Airbnb was right- RARE FIND. Amanda - you are the hostiest host in the world. Your communication was 💯. And we pray to make it back to yo
Top guest favourite
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
Superhost
Home in Key West
4.88 out of 5 average rating, 8 reviews

Mermaid's Retreat at Coral Hammock Key West Islan

BrianaRating, 5 stars2 weeks ago
I loved the stay at this house. Would definitely come again.
Guest favourite
Home in Marathon
4.89 out of 5 average rating, 66 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

RobinRating, 5 stars2 weeks ago
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 didn’t love.❤️
Superhost
Home in Key West
4.93 out of 5 average rating, 30 reviews

Bahamian Reed by AvantStay

DebRating, 5 stars1 month ago
We came to truly appreciate how stellar our townhouse, Reid’s 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.
Superhost
Home in Summerland Key
5 out of 5 average rating, 3 reviews

Waterfront Beach House with Dock & Heated Pool!

HeatherRating, 5 stars1 month ago
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.
Top guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 18 reviews

Bohemian Beach Bungalow

AnnaRating, 5 stars1 week ago
I can’t 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 vibe—exactly what you want for a beach getaway. Whether you’re 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 we’re already dreaming of coming back!
Superhost
Home in Cudjoe Key
4.8 out of 5 average rating, 92 reviews

Palm Breezes! Room for Everyone on the Ocean.

GerritRating, 5 stars1 month ago
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

Guest favourite
Home in Marathon
4.94 out of 5 average rating, 35 reviews

Florida Keys Oceanside Utopia

CaroleRating, 5 stars1 month ago
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!
Superhost
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.
Guest favourite
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.
Top guest favourite
Home in Cudjoe Key
4.96 out of 5 average rating, 26 reviews

Tiki Time in Cudjoe Key 136

TaniaRating, 5 stars3 days ago
Amazing views and ocean breeze! Modern and clean home which I appreciated. Only thing I could ask for but it’s 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! Couldn’t ask for a better stay and vacation in the Keys with my family!
Guest favourite
Home in Cudjoe Key
4.93 out of 5 average rating, 54 reviews

Private Ocean Oasis by Key West, Florida

EricaRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 34 reviews

Viamarhe House-Private beach, Kayak, yard games

AmandaRating, 5 stars1 week ago
Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.
Guest favourite
Home in Key West
4.93 out of 5 average rating, 29 reviews

Poinciana Treetop ~ Casual Second Floor Duplex

ThomasRating, 5 stars1 month ago
Great place. Walk-able to all attractions in the historic district, Duval Street, Sunset Pier and Bahama village.
Superhost
Home in Marathon
5 out of 5 average rating, 3 reviews

Clocked Out 2bed/2.5bath updated open water condo

HelenRating, 5 stars4 months ago
Absolutely outstanding rental. Don’t 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 couldn’t find the place initially. We were following written directions sent by the management company that had not been updated; turns out the ‘turning point building’ no longer existed. The road into the complex looks more like a parking lot. We also initially didn’t 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 wasn’t working well during our stay; however It was fixed a day & a half after notifying the management company.

Private house rentals

Top guest favourite
Home in Marathon
5 out of 5 average rating, 18 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

JohnRating, 5 stars1 week ago
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!!
Guest favourite
Home in Marathon
5 out of 5 average rating, 37 reviews

Waterfront Escape -VACA-23-408

NatalieRating, 5 stars1 week ago
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.
Superhost
Home in Marathon
5 out of 5 average rating, 8 reviews

Sandbox

MikeRating, 5 stars3 months ago
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.
Top guest favourite
Home in Marathon
5 out of 5 average rating, 14 reviews

P36 - Charming and immaculate 2 Bedroom, 2 bathroo

BradleyRating, 5 stars3 weeks ago
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!
Top guest favourite
Home in Marathon
5 out of 5 average rating, 12 reviews

Waterfront Oasis w/Private Pool-Dockage-Beach

DaveRating, 5 stars5 months ago
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.
Top guest favourite
Home in Marathon
5 out of 5 average rating, 40 reviews

Movie Theater | HotTub | Pool | Boat/RV/EV Parking

AnneRating, 5 stars1 week ago
We almost stayed at a hotel, but I saw Christian’s 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. It’s 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.
Superhost
Home in Cudjoe Key
4.9 out of 5 average rating, 30 reviews

Waterfront FL Keys Cottage @ Venture Out

MariaRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Key West
4.91 out of 5 average rating, 11 reviews

Seagull Suite | Inviting Studio, Just Steps From D

RandyRating, 5 stars2 months ago
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

    ₹8,609 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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West
  6. Key Haven
  7. House rentals