House vacation 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, 131 reviews

Sea Ray Cove, Mini Lobster week NOW OPEN!

MeganRating, 5 stars1 week ago
Our stay at Searay Cove was amazing! The house was perfect and had all the amenities and then some! Easy walking distance to the beach and close to many things to do. The highlight was the manatee visitors in the evening. Can’t wait to come back!
Superhost
Home in Key West
4.6 out of 5 average rating, 5 reviews

Coastal Comfort; Waterfront Luxury Home with priva

JayRating, 5 stars17 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 Marathon
4.89 out of 5 average rating, 63 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

BarbaraRating, 5 stars1 week ago
You won’t find a better set up than this with family. Playground, beach, pool , sidewalks for walking everywhere, and great kayaking area as well. And the owner makes sure his guests have all they need.
Guest favourite
Home in Key Largo
4.94 out of 5 average rating, 66 reviews

Casa Solaris | Key Largo home with Private Pool!

AllisonRating, 5 stars2 weeks ago
Had a great time and the house was perfect for our group!
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 Marathon
4.93 out of 5 average rating, 29 reviews

Serenity Bay Estate-FL Keys Best Kept Secret! Beau

JerrieRating, 5 stars4 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!!!!
Superhost
Home in Summerland Key
4.88 out of 5 average rating, 34 reviews

Pelico Palms Sunset Suites

TimRating, 5 stars5 days ago
fantastic cottage and pool with plenty of privacy, close to the water. basically 3 master suites with adjoining bathrooms, one living area and a kitchen. really big pool deck with seating and cornhole, Webber grill and outdoor dining table. (bring bug spray). we had a great time, close to key West and Bahia Honda, a great cottage!
Superhost
Home in Islamorada
4.86 out of 5 average rating, 7 reviews

Venetian Tropics private heated pool at 82 degrees

JessicaRating, 5 stars7 months ago
I’d like to start this review with JoAn is amazing and super responsive. If you need anything, she will ensure that you will get it. This house is the epitome of what you would expect for a Florida keys home. If you’re looking for a house with a lot of character, in a phenomenal location for Atlantic access and fuel, this is the place. We throughly enjoyed our time staying here and will be back next year. The pool was nice to get into after diving every day, there was a fresh water hose on the dock, a freshwater outside shower and even a fish cleaning station. There is a deep freezer for ice and a tiki bar outside with a sink. Couldn’t be any happier with the house or the host. Thanks again JoAn for letting us use your house.

Weekly house rentals

Superhost
Home in Cudjoe Key
4.84 out of 5 average rating, 50 reviews

Keys getaway

ElizabethRating, 5 stars1 month ago
House was perfect for my family of 3- including my 15 month old. There was some trouble with the AC thermostat at first but Jana was very responsive and immediately took care of it. We walked to Morning Joint and My New Joint/Square Grouper. My son loved the pool. All neighbors were super friendly, as well as security guards. The grill was perfect for dinner at home one night and the kitchen was fully stocked!
Superhost
Home in Key Colony Beach
4.74 out of 5 average rating, 23 reviews

Private Beach, Deep Water Dockage, Cabana Club

GregRating, 5 stars8 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!
Superhost
Home in Key West
4.71 out of 5 average rating, 7 reviews

Serene Lily~ Luxurious 2 bed, 2.5 bath home

RoyRating, 5 stars1 month ago
Beautiful home and we enjoyed our stay. We felt right at home and the pool was a nice walk. The kitchen had anything you would need to make a meal. We will definitely come back again. Thank you.
Guest favourite
Home in Marathon
5 out of 5 average rating, 40 reviews

Yellowtail Getaway with Boat Dock and Pool 2

HopeRating, 5 stars3 weeks ago
We absolutely loved the place , it was spacious , clean and had all the extras you would need. So convenient with the boat dick and loved having the pool. Would definitely return.
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 69 reviews

Blue Ocean Bungalow Spring discounts-NOW available

HixRating, 5 stars1 month ago
The house was really nice, clean and a real home away from home. It accommodated my family of 5 with 3 bedrooms and 3 baths. It was located on a canal where we were able to enjoy the manatees and pelicans. It was centrally located and only a short distance from the beaches, snorkeling, wind surfing and excellent restaurants. We will definitely stay again if we visit the keys
Guest favourite
Home in Key Colony Beach
4.91 out of 5 average rating, 134 reviews

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

MelissaRating, 5 stars4 weeks ago
Had a wonderful, peaceful stay. We fished off the dock area, enjoyed time at the cabana, walked every morning enjoying the views and participated in the sunset community almost every night at the park! Great vacation for our multigenerational needs!
Guest favourite
Home in Key West
4.83 out of 5 average rating, 64 reviews

Historic Key West - Turtle House - Sleeps 6

BrockRating, 5 stars6 days ago
Turtle house was great and as advertised. It was well furnished and clean. The location was perfect, so close to great restaurants and shopping. The grounds were beautiful and well maintained. I would definitely stay here again and recommend to anyone traveling to Key West!
Superhost
Home in Cudjoe Key
4.86 out of 5 average rating, 103 reviews

Island Oasis ~ YOUR Paradise Awaits!

PamRating, 5 stars2 weeks ago
As soon as we walked in we felt right at home. We were celebrating my 65th bday week.Bonnie even had me a bday cake in the freezer .Power was destined to be out for several hours one day they brought us a small plug and play generator to run coffee pot hair dryer etc. My only disappointment was we could not use the Kayak's due to the sludge in the canal. That was not any fault of Bonnie or Joe's just mother nature. We had the pleasure of meeting the awesome host and hostess very nice people indeed. Loved their home and hospitality. If we ever come back will stay here again. Very comfortable bed. Clean and comfortable very relaxing.Nice resort and amenities very nice pool.

Private house rentals

Superhost
Home in Key West
4.86 out of 5 average rating, 59 reviews

Key West Paradise

BharatRating, 5 stars1 week ago
Sharon was an excellent host that answered any of our questions promptly. The place was even better than what the photos showed. Comfortable enough for 7 people to stay for a long weekend. We didn't use the pool, but it was nice to have the option. Easy to get into the gated community, and we didn't struggle to find parking with our rental car. Easy to get to many different popular spots around Key West with rideshare. Convenient to have some convenience stores like CVS within walking distance, and a Publix not too far via car. Only thing I would improve is having more toilet paper and hand soap refills in each bathroom, especially with 7 people staying over a long weekend.
Guest favourite
Home in Marathon
5 out of 5 average rating, 17 reviews

Seaside Sunrise. Newly remodeled waterfront

JonathynRating, 5 stars1 month ago
Everything was excellent. Only complaint would be the bicycles. One bike was usable but the seat was loose and we didn’t have tools to fix it. The other adult bike’s chain was rusted so bad it wasn’t usable. We still had an excellent experience.
Guest favourite
Home in Marathon
4.92 out of 5 average rating, 135 reviews

Marathon Star - home with hot tub

RandallRating, 5 stars2 months ago
Cecilia’s place was just wonderful! Amenities abounded. Spotless. Being close to mile marker 50, it was the halfway point in the Keys and easy to get anywhere. Beaches close by. Highly recommend!
Guest favourite
Home in Marathon
4.98 out of 5 average rating, 91 reviews

4BR 3B, Heated Pool & Spa, 60' Dock

RobbieRating, 5 stars4 days ago
Amazing house. Beautiful surroundings. Plenty of room for 3 families and kids. Everything we needed.
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 stars3 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
4.95 out of 5 average rating, 111 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

JessRating, 5 stars4 days ago
We loved our stay! The house was super clean and the back patio was beautiful. We loved the back canal area and saw lots of very cool wildlife and enjoyed fishing right there. Having the kayaks to use was also great. Beds were very comfy and the rooms were spacious. The house had everything we needed. We loved the key colony area. The cabana club was a great space and the house is in walking distance to Sunset Beach, which was beautiful. The whole area is super close to fun things to do and great restaurants. We would absolutely stay here again!
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 68 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 Colony Beach
5 out of 5 average rating, 6 reviews

Key Colony Beach Waterfront 321

JeanneRating, 5 stars9 months ago
Great place right in the heart of Key Colony. House had all we needed and more to make our 8 day stay comfortable. Great boat dock with plenty of room for 2 31 ft boats.

Quick stats about house rentals in Key West

  • Total rentals

    640 properties

  • Nightly prices starting at

    $83 CAD 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

Destinations to explore

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