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, 133 reviews

Sea Ray Cove, Mini Lobster week NOW OPEN!

MauraRating, 5 stars2 days ago
We had an incredible week at Eddie’s place! The listing description and pictures matched our experience. Our favorite places to hang out were the screened in area, Tiki Hut, and by the dock. We fished off the dock daily and caught a great number of fish! We were also visited by a manatee. Eddie’s place is easily walkable to Sombrero Beach. The kitchen was well stocked and had everything we needed! We truly enjoyed this beautiful spot and would definitely book again on a future stay!
Guest favourite
Home in Marathon
4.89 out of 5 average rating, 63 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

BarbaraRating, 5 stars3 weeks 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, 69 reviews

Casa Solaris | Key Largo home with Private Pool!

JeffRating, 5 stars1 week ago
I am typically not an Airbnb person, as I prefer a hotel. This home was better than any resort we could’ve stayed at. Check in was simple. The home was beautiful. The location was perfect. Our favorite part was the second space that was separate from the main house. We are a family of four (mom, dad and two kids) who were traveling with my sister. She was able to have her own space with a private bathroom and entrance and could “go home” when the craziness of two kids was enough. Both units were adequately stocked with towels and linens. The kitchens had anything you could need including coffee maker, blender, toaster, pots and pans. The pool and hot tub were incredible! So much so, that we took two full days and only left for dinner! Sean and Denise were great hosts and super responsive! We will be back.
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 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.
Superhost
Home in Key West
4.9 out of 5 average rating, 10 reviews

Southern Comfort: Luxury Waterfront Home with priv

HillaryRating, 5 stars3 months ago
House was clean, spacious, and as pictured. While it is near the Home Depot, there is plenty of foliage that is if completely obscured. The street was very peaceful and quiet. Lovely water views! Lots of Ubers available that arrived quickly - nothing in the island is more than 15 mins away!
Top guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 83 reviews

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

KarenRating, 5 stars3 weeks ago
We throughly enjoyed our stay. We especially loved the private pool and watching the wildlife and boaters in the canal. It was very relaxing and the Florida spring weather was awesome!
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 stars31 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.

Weekly house rentals

Superhost
Home in Cudjoe Key
4.84 out of 5 average rating, 51 reviews

Keys getaway

JamiRating, 5 stars2 weeks ago
We were there to celebrate my husband's 50th birthday. The master bed, pillows and linens were very comfortable. The screened in porch with plenty of comfortable seating was our favorite amenity of the property. We hope to rent there again when we are back in the area. Very comfortable and very clean. 😁
Superhost
Home in Key Colony Beach
4.74 out of 5 average rating, 23 reviews

Private Beach, Deep Water Dockage, Cabana Club

GregRating, 5 stars9 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 Marathon
5 out of 5 average rating, 11 reviews

Endless Ocean Views -5 Bedrm/4Bath/Pool Built 2024

ElaineRating, 5 stars2 weeks ago
Jessieca and her team are by far the most responsive and kindest hosts I've ever had on a rental. Beyond that, the place is beautiful and the sunset water views amazing. I see the price has gone up but if we can afford it, we will definitely return! You will have guests next to you and if they have children, you will probably be disturbed but that goes with the territory. Highly recommend this rental.
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 stars1 month 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, 135 reviews

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

NicoleRating, 5 stars1 week ago
We didn't know anything about Key Colony so based our reservation strictly on reviews and price. Well worth every penny that was spent. What a wonderful tropical getaway! Can't wait to visit the Keys again with my 4 children and husband. If you're looking for a great place to spread out and enjoy family this should be your rental.
Superhost
Home in Cudjoe Key
4.87 out of 5 average rating, 104 reviews

Island Oasis ~ YOUR Paradise Awaits!

AbbyRating, 5 stars3 weeks ago
Bonnie was a nice, responsive host and even brought us additional kayaks to use. We had a great stay!

Private house rentals

Superhost
Home in Key West
4.87 out of 5 average rating, 61 reviews

Key West Paradise

BryanRating, 5 stars1 week ago
Very convenient location for our scheduled golf outing and fishing trips! Just a short distance to old town KW for all the crazy fun, which meant we got to leave the noise behind when we were ready to relax and just spend time with the family on the large back porch and the pool. The place was very clean and felt like home to us for the week that we spent there. Thank you to Sharon for everything.....my entire family is already asking when are we coming back!!!!
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 Key West
4.9 out of 5 average rating, 70 reviews

Casa Loca

ElizabethRating, 5 stars2 months ago
Casa loca was Absolutely beautiful! So close to everything in the keys. Host super friendly and helpful. The house was very clean! 10/10 stay LOVED IT!
Guest favourite
Home in Marathon
4.98 out of 5 average rating, 91 reviews

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

RobbieRating, 5 stars2 weeks 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 stars4 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, 112 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

JessRating, 5 stars2 weeks 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, 69 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.
Superhost
Home in Marathon
4.93 out of 5 average rating, 29 reviews

Serenity Bay Estate-FL Keys Best Kept Secret! Beau

JerrieRating, 5 stars5 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

    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

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