House holiday rentals in Key West

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Popular amenities for Key West house rentals

House rentals with a pool

Top Guest favourite
Home in Marathon
4.99 out of 5 average rating, 129 reviews

Sea Ray Cove, 75' boat dock, 1 block from beach!

NicholasRating, 5 stars6 days ago
We had a wonderful time. The house was comfortable, and the amenities such as the pool and grill added to the experience. The location, specifically the proximity to the beach, made this house the perfect property in Marathon. Would gladly stay again!
Guest favourite
Home in Key West
4.93 out of 5 average rating, 90 reviews

Just steps to Duval- Sleeps 10- Pool House

TwanRating, 5 stars1 month ago
This property has the beach house feel and sits on the same block as the Hemingway House and is perfectly located to walk or cart to all the attractions of Key West. All of the resorts were booked so we went with this property last minute, and it was perfect for our little family party of 6. Although we could never get the heated pool heated during our stay, we were mostly out and about exploring and Corey and extremely accommodative. Thank you Corey for supporting our family's awesome Key West experience and hope to be back!
Superhost
Home in Key West
5 out of 5 average rating, 3 reviews

3 BR 2BA + Private Pool + Waterfront

DavidRating, 5 stars2 weeks ago
Amazing oasis from the cold up north and from the bustle of town when you need a peaceful moment by the pool. The outdoor kitchen is incredible and the boat dockage is great.
Guest favourite
Home in Key Largo
4.94 out of 5 average rating, 63 reviews

Casa Solaris | Key Largo home with Private Pool!

LeviRating, 5 stars2 weeks ago
Excellent place to stay in Key Largo. Yet perfect location between Islamorada and Key Largo to make traveling to either a breeze. Kids loved the pool / hot tub combo, and the parents enjoyed having a deck with umbrella to enjoy at the same time. Accommodations were perfect for two small families to split, and yet have enough shared spaced for the group. Would definitely come back when traveling to the area again.
Superhost
Home in Summerland Key
4.87 out of 5 average rating, 31 reviews

Pelico Palms Sunset Suites

LindaRating, 5 stars1 month ago
Nate’s place was very comfortable and well equipped. We really enjoyed the pool area. Hosts were most responsive and helpful.
Guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 79 reviews

“La casa azul” step 3’ to a private pool

AnthonyRating, 5 stars1 month ago
We really enjoyed our stay at La Casa Azul. Key Colony beach is quiet and has lots to do. Being on the channel was fun, sitting in the pool and watching neighbors fish or the boats strolling by. The house was perfect and spacious for two and would be equally roomy for 4 (but we left the kids at home!) The host was extremely responsive and helpful throughout our stay and made us feel right at home. Thanks Janine!
Superhost
Home in Key Colony Beach
4.83 out of 5 average rating, 12 reviews

P22 - Updated 3 bedroom 2 bath duplex with private

BrittanyRating, 5 stars29 months ago
We had six adults in our group and the house was a perfect location to go out fishing or to the beach. The house was well stocked and with plenty of linens and beach towels. We rented a boat for three days from Tropical boat rentals and the canal location made fishing super easy. Access to the ocean or the bay was convenient. We even caught several fish in the canal. We saw manatees, sharks, manna rays and tons of fish while enjoying the swimming pool. We can’t wait to make a return trip.
Guest favourite
Home in Marathon
4.89 out of 5 average rating, 19 reviews

Golf Coast Oasis

DanaRating, 5 stars2 weeks ago
Very nice place with excellent amenities. The heated pool was awesome! Worked out great for our family. The only minor issue was the noise from the nearby airport was loud at times and there were frequent construction trucks driving by. We live in rural area with no noise, so we were probably more sensitive to it, but we did get used to it and it wasn't a major problem. We would definitely stay here again.

Weekly house rentals

Superhost
Home in Key Colony Beach
4.74 out of 5 average rating, 23 reviews

Private Beach, Deep Water Dockage, Cabana Club

GregRating, 5 stars7 months ago
Roberto is by far the most thorough and conscientious host. We were so pleased with our accommodations and immediately felt at home. The use of The Cabana Club was a real bonus on the hottest days. Will most certainly return to Marathon!
Guest favourite
Home in Key West
5 out of 5 average rating, 19 reviews

Nautical Wheeler: Waterfront Home with private Poo

KaydrianneRating, 5 stars3 months ago
The house is beautiful and well stocked. Javier provided ample information to facilitate a smooth check in process and to help my family plan for our stay. Would 100% recommend this listing to a friend!
Superhost
Home in Key West
4.6 out of 5 average rating, 5 reviews

Serene Lily~ Luxurious 2 bed, 2.5 bath home

EdRating, 5 stars11 months ago
Excellent experience. The property was immaculate and the host 5 star. We would definitely rent from this host again.
Guest favourite
Home in Marathon
5 out of 5 average rating, 38 reviews

Yellowtail Getaway with Boat Dock and Pool 2

JohnRating, 5 stars1 month ago
We agree with all the other 5-star reviews. We had an awesome stay at the Yellowtail Retreat. Carlos was an awesome host and communication was exceptional. The house was one of the cleanest we’ve stayed at and had absolutely no issues. The beds were very comfortable, unlike many other rentals. Few houses on the canals have pools and even less have heated ones – this was a big bonus. Open water in Florida Bay is about a 2-minute boat ride and the industrial ice machine came in very handy. We didn’t use the detached Mother-in-Law room, but would be perfect for a couple or kids to have some privacy. Plenty of parking, TV’s all worked without issues and well-equipped kitchen. This was easily one of the best vacation rentals we’ve stayed at and would stay here again without hesitation if we visit Marathon again. Thanks Carlos!
Guest favourite
Home in Marathon
4.81 out of 5 average rating, 59 reviews

7 Mile Ocean Bliss

JenniferRating, 5 stars4 months ago
We had an amazing stay at this beautiful Airbnb in the Keys! The home was stunning, with all the amenities you could ask for, including a relaxing hot tub. The fishing right on the property made it even better – perfect for enjoying the local marine life. The host was incredibly accommodating and made sure we had everything we needed for a perfect getaway. Highly recommend this spot for anyone looking for a peaceful and fun escape!
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 67 reviews

Blue Ocean Bungalow Spring discounts-NOW available

NicholeRating, 5 stars1 month ago
Stay was good…we were able to get to everything we wanted to do in 15-30 minutes; except the day we spent in key west. Place is close to beaches and lots of good restaurants. We had an almost 6 month old with us and the place allowed for her to have her own place to play and sleep which was important to us. We also saw manatees in the canal right in front of the house.
Superhost
Home in Tavernier
4.84 out of 5 average rating, 19 reviews

Waterfront Home Near Key Largo | Long-Term Stay

ChristopherRating, 5 stars2 months ago
My group and I had an amazing stay! Corey and Armando were amazing hosts; super responsive to any questions and flexible to my requests. They even provided great recommendations for things to do in the area. Home was beautiful and in a great area. I would definitely stay here again!
Guest favourite
Home in Key Colony Beach
4.91 out of 5 average rating, 133 reviews

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK

AnneRating, 5 stars1 month ago
Looks just like the photo’s. Unfortunately weather was a little chilly the first couple of days. When it warmed up we enjoyed the local cabana club with the heated pool, beach and restaurants. The accommodations were spacious and clean.

Private house rentals

Superhost
Home in Key West
4.88 out of 5 average rating, 56 reviews

Key West Paradise

AndreaRating, 5 stars2 weeks ago
This was a fantastic location with a great pizzeria nearby as well as a fabulous French pastry and coffee cafe. This location is very near to nearby downtown and residence was cozy and provided all the comforts. We highly recommend!
Guest favourite
Home in Marathon
5 out of 5 average rating, 16 reviews

Seaside Sunrise. Newly remodeled waterfront

ToddRating, 5 stars1 month ago
This place was perfect for 3 couples. The backyard is amazing and the hot tub was great. The outdoor cooking area worked wonderfully. The dock area was great for our boat rental. The kitchen had all the appropriate amenities that could ask for. We truly enjoyed our stay.
Guest favourite
Home in Marathon
4.92 out of 5 average rating, 134 reviews

Marathon Star - home with hot tub

MichaelRating, 5 stars1 month ago
Good place to stay. Good space for the Keys. hot tub and everything was clean. My only complaints are the shower heads have no water pressure and the patio door is god awful. I would stay here again when visiting the Florida Keys Cecilia was a great host!
Guest favourite
Home in Key Largo
4.91 out of 5 average rating, 160 reviews

Blue House Marine in Key Largo

RhitikRating, 5 stars2 weeks ago
Nancy was a great host and her place was very accommodating! Great private location with amazing views of the water
Top Guest favourite
Home in Key Largo
4.94 out of 5 average rating, 78 reviews

Large Waterfront Home, w/Efficiency, Pool, Kayaks

CindiRating, 5 stars1 month ago
Stu’s place was not only beautiful but it had all the amenities we could have asked for. The location was perfect for all the things we wanted to do. It truly was a home away from home. If I could give more than 5 stars I certainly would. Loved it! Stu was extremely easy to communicate with.
Guest favourite
Home in Key Colony Beach
4.94 out of 5 average rating, 49 reviews

Waterfront House - 30' Dock & Pool at Cabana Club

LauraRating, 5 stars2 months ago
We will be back! We loved it! Clean, comfortable with lots of room. We loved being able to keep our boat behind the house and the trailer in the driveway. We loved walking around Keys Colony. The Cabana Club and Sparkys Restaurant were both within walking distance. The kitchen had every gadget you could imagine. The dining table was perfect for dinners and card playing. The beds were comfy. No allergies whatsoever! Thank you so much!!
Guest favourite
Home in Key Colony Beach
4.94 out of 5 average rating, 107 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

AllisonRating, 5 stars6 days ago
The house was just as described. Loved having meals on the screened in porch each morning while watching the boats and wildlife float/fly by. Very peaceful setting. Modern bathrooms and kitchen. Also the Cabana Club pool and beach was a wonderful place to relax. We enjoyed meeting other Key Colony residents/visitors at the pool and at Sunset Park. They have concerts on Sunday afternoons in the park.
Superhost
Home in Marathon
4.93 out of 5 average rating, 29 reviews

Serenity Bay Estate-FL Keys Best Kept Secret! Beau

JerrieRating, 5 stars3 months ago
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!!!!

Quick stats about house rentals in Key West

  • Total rentals

    580 properties

  • Nightly prices starting at

    $112 AUD before taxes and fees

  • Total number of reviews

    8.6K reviews

  • Family-friendly rentals

    500 properties are a good fit for families

  • Pet-friendly rentals

    270 properties allow pets

  • Rentals with a pool

    380 properties have a pool

Destinations to explore

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  2. United States
  3. Florida
  4. Monroe County
  5. Key West
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