Condo vacation rentals in Key West

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Popular amenities for Key West condo rentals

Condo rentals with a pool

Guest favorite
A spacious living area features a dark sectional couch positioned invitingly, with natural light streaming through glass doors that open to an outdoor deck. The kitchen is visible in the background, showcasing modern appliances and sleek cabinetry.
Condo in Key West
5 out of 5 average rating, 6 reviews

Parking, Deck, Pool, Beach, 2 Blocks to Duval St

JamieRating, 5 stars1 month ago
Karen’s place is the PERFECT home for your stay in Key West! The location couldn’t be more ideal, right in the heart of all Key West has to offer and yet so private and quiet. The space was recently renovated and in great condition. Having a washer/dryer in the unit is a huge bonus. Kitchen has all amenities. Karen is an excellent host, quick to respond and willing to offer local suggestions. We would absolutely stay here again!!
Condo in Key West
5 out of 5 average rating, 4 reviews

2 Bedroom Townhouse Style Condo

KimberlyRating, 5 stars11 months ago
The place was exactly like the pictures. On the water and not far from old town key west. Michael was very responsive and gave us all the information we needed for check in and made sure we were able to check in during a certain time and if not other options were available. Would recommend if you want to stay in key west but far enough away from the busy nightlife and have a quiet night in.
Top guest favorite
Condo in Key West
4.94 out of 5 average rating, 64 reviews

Bright Condo in Paradise

GregRating, 5 stars2 weeks ago
Great place with everything you need and in the perfect location.
Superhost
A modern kitchen space features a marble countertop with bar seating. Open shelves display kitchen essentials, while a spacious living area is visible beyond, furnished with a sofa and armchair. Natural light fills the space, complemented by gentle greenery seen through large sliding glass doors.
Condo in Key West
4.89 out of 5 average rating, 27 reviews

New Listing! Key Lime Paradise/Condo

StevenRating, 5 stars6 days ago
We Definitely would stay again if we are in the area. The place was exactly as advertised and centrally located. we had a nice relaxing time.
Guest favorite
Condo in Key West
4.8 out of 5 average rating, 46 reviews

Casa Arosa

StephanieRating, 5 stars2 months ago
My husband and I thoroughly enjoyed our stay here and have already rebooked. Newly remodeled, private and walkable. Secure, pristine community with lovely grounds. Host was very helpful and prompt in responding.
Top guest favorite
A light-filled living area is visible, featuring a comfortable seating arrangement and a mounted television. A dining table occupies the foreground, adorned with a bowl of oranges. The walls are painted in soft blue, providing a relaxed atmosphere, with a ceiling fan overhead.
Condo in Marathon
4.96 out of 5 average rating, 102 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

AlexRating, 5 stars2 weeks ago
Absolutely perfect for a honeymoon getaway, quiet perfect amount of space for us, the set up was great with 2 bathrooms and a huge walkin closet, the couches were super comfy, the TV was big enough to see from across the room, we enjoyed everything about it. Got to meet some of the neighbors and they were all very welcoming and enjoyed talking to them. Scott had some great local recommendations and we enjoyed everything.
A tranquil swimming pool is surrounded by lush tropical greenery, featuring tall palm trees and vibrant plants. Sun loungers line the pool area, inviting relaxation in a peaceful, secluded setting.
Condo in Key West
5 out of 5 average rating, 10 reviews

2 BR Condo Banyan Tree, Key West,FL

MaureenRating, 5 stars30 months ago
Place was nice and clean. We had a great time.
Superhost
A serene outdoor pool area features a large swimming pool and a hot tub surrounded by tropical palm trees. Umbrellas provide shade over lounge areas. The calm ocean can be seen in the background, enhancing the tranquil setting.
Condo in Key West
4.84 out of 5 average rating, 38 reviews

Henry's Piece of Paradise On The Ocean In Key West

DonaldRating, 5 stars2 months ago
Our stay was great. We had detailed instructions, the unit itself was decorated nicely, and the amenities within the building were great (pool and spa). Also the private beach area and walkability to food, snacks, restaurants was great!

Condo rentals with a hot tub

A vintage Underwood typewriter sits on a wooden table, accompanied by a few books. In the background, a small sculpture is displayed on a side table, adding an artistic touch to the room's decor.
Condo in Key West
4.68 out of 5 average rating, 57 reviews

ENJOY THE BEST DEAL IN THE KEYS!!

AndrewRating, 5 stars2 months ago
Great location in Key West, 2 blocks from Green Parrot, Blue Heaven, and Santiago's Bodega, 3 blocks from Duval, Hemmingway House, Lighthouse etc. Condo is beautiful. Loved sitting outside on balcony. Beds were comfy. Kids loved having their own twin beds.
Superhost
The exterior of a two-story duplex is depicted, featuring a warm yellow facade with a tiled roof. A balcony is adorned with blue railings, while artistic staircase details lead to the upper level. Lush green landscaping is visible in the foreground against a bright blue sky.
Condo in Key Colony Beach
4.57 out of 5 average rating, 7 reviews

P21 - Charming 3 bedroom 3.5 bath duplex in Key C

KevinRating, 5 stars23 months ago
Leslie was very responsive and addressed questions quickly. House was perfect for 6 people with each room having a private bathroom. Very spacious and comfortable.
Guest favorite
An Olympic-sized swimming pool is surrounded by a sun deck, featuring lounge chairs and palm trees. The pool’s clear water reflects the sky, creating a serene atmosphere. The ocean and well-maintained tropical garden can be seen in the background.
Condo in Key West
4.79 out of 5 average rating, 24 reviews

Oceanfront Key West Condo

AlexandraRating, 5 stars4 months ago
This beautiful condo was so much more wonderful than the pictures portrayed! It is the most amazing location and setting with a stunning courtyard garden, ocean views and its own little beach. I felt like I stepped into Paradise! The complex was quiet, respectful and beautifully maintained. The location on the island could not be beat with a short walk to Smathers Beach and Higgs Beach. This was our first time in Key West and it was pure magic! Thank you!
Superhost
The bedroom features a spacious bed with light blue bedding against a red accent wall. A standing lamp provides soft lighting beside a dresser. A mirror reflects the bathroom area, showing a sink and light cabinetry with a contrasting black-and-white tiled floor.
Condo in Key West
4.69 out of 5 average rating, 203 reviews

Sunrise Suites Resort, Key West FL U #408 2bdr2bth

GeorgiaRating, 5 stars1 month ago
Her apartment is in a convenient location in Key West. It is a clean home with all we need for cooking. Sunset is beautiful. Airport is nearby and interesting to us. We enjoied our stay.
The image captures a panoramic view of the waterway between Key West and Stock Island, with lush greenery lining the shore. Boats can be seen gently navigating the calm waters, while the bright blue sky complements the tranquil scene.
Condo in Key West
5 out of 5 average rating, 7 reviews

Superb wtrfrt Coconut Mallory 2 BR, 2 ba w/balcony

TracyRating, 5 stars5 months ago
We had a wonderful time in Key West. The condo was perfect for our family of four, and we enjoyed hanging out on the balcony in the evenings and the complex hot tub. Andre was an awesome host - very responsive and proactive in arranging for our possible late evening arrival. His suggestion of rental bikes to be delivered to the condo was a great one - we used those to bike all over Key West. Would love to return someday!
Superhost
A serene pool area is surrounded by swaying palm trees, with inviting lounge chairs arranged for relaxation. The clear water reflects the sky, creating a tranquil atmosphere. A shaded seating area is visible nearby, adding to the vibrant landscape that leads towards the ocean.
Condo in Key West
5 out of 5 average rating, 6 reviews

Hyatt Windward Point Key West- Two Bedroom

AdisRating, 5 stars2 months ago
We had a great stay here! Everything was clean and had no problem with anything at all. We would definitely stay here again.
Guest favorite
A spacious living area is featured, with comfortable seating arranged around a coffee table. Large sliding glass doors provide a view of the ocean and access to an outdoor seating area. Light-colored walls and soft furnishings create a bright atmosphere.
Condo in Islamorada
4.93 out of 5 average rating, 29 reviews

Just a Few Friends - Ocean View and Bring your Boa

ShawnRating, 5 stars1 month ago
Jonelle was very responsive and helpful! Condo is spacious, clean, and full of kitchen ware. Pool is clean and quiet for when we were there. The location is on the south side of the island so restaurants and shops are a drive. Bedding was clean and comfortable. We would definitely consider staying here again!
A view of the ocean is framed by horizontal blinds. The turquoise water is visible, reflecting the clear blue sky. In the distance, a small island is seen. A dark chair is positioned on the balcony, complementing the relaxed atmosphere.
Condo in Key West
5 out of 5 average rating, 3 reviews

Seaport Serenity-Beach-Pool-King-BBQ-ExtraEntrance

JustinRating, 5 stars41 months ago
I try to always leave a review because I like a lot of people use them pretty much exclusively to make our choice. First off Thomas is first class and is awesome. He communicates well and this place was the perfect location. The place is nice the master suite is great…. The stairs down to the water are great. People are nice location is wonderful… right next to Mallory square and one block from Duval. On the wharf… We travel quite a bit honestly the location is worth the money. Check in was not great BUT that is more due to the times and not the galleon or host fault. ( no one wants to work ) Truly the only thing that is not accurate BUT I am not a geography major is … you cannot see the sunset period from the balcony. You have to get out and around the building. This place is worth all the money and we Travel quite a bit use the VRBO, air etc… and Thomas is the best host we have had honestly. You cannot miss with this place

Weekly condo rentals

Guest favorite
An aerial view showcases the property situated by the ocean, with a private beach area lined with palm trees. The bright blue roofs of the buildings contrast with the lush greenery and the sparkling turquoise water, highlighting the inviting outdoor pool and surrounding lounge areas.
Condo in Key Colony Beach
4.96 out of 5 average rating, 208 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

GinaRating, 5 stars2 weeks ago
Please stop looking and book this spot, you will not regret it! Kim provided a list of full things to do for dining, for fun, and much more. Honestly all you need is this spot and Kim’s recommendations. Walking distance to some amazing restaurants with great views and beautiful live music. Don’t have to drive no where to far because everything is less than 5 miles, sombreo beach is beautiful and is just around the condo. Please don’t even bother driving to Key West stay here and enjoy the Keys:) it’s absolutely beautiful and get your own private beach and the pool is so refreshing and CLEAN. No loud music or rowdy crowds, just bliss of relaxation. I’m so happy I booked this spot for our honeymoon and plan to come back for our anniversary or anniversaries. Had a very romantic dinner at the steak and lobster, again Kim’s recommendation!Which was delicious but don’t forget to make reservations. Kim you place had everything we needed. Service was so prompt for everything we needed.
Guest favorite
A community pool is surrounded by palm trees and lounge chairs. The pool area is paved with light-colored tiles and features a shaded seating area. Several guests can be seen enjoying the water under the bright sky.
Condo in Key West
4.96 out of 5 average rating, 76 reviews

Key West Paradise Poolside

AmyRating, 5 stars7 months ago
I stayed at the Truman Annex last year for the boat races and loved the location. I decided to rent from Wally this year due to his condo was more open and also had a 2nd bath! He was very responsive when I texted him, the house was very clean and everything was perfect, I highly recommend!
Guest favorite
A sandy beach area features lounge chairs arranged neatly under blue umbrellas. Tiki huts provide shaded seating, while picnic tables are available nearby. The calm ocean surface reflects the clear blue sky, enhancing the tranquil environment ideal for relaxation.
Condo in Key Colony Beach
4.97 out of 5 average rating, 241 reviews

Keys Breeze Ocean View Condo & Pool - Key Colony

SamuelRating, 5 stars3 weeks ago
Great location, exactly as advertised! The condo was extremely clean when we checked in. The area was quiet and clean. Perfect location in the middle of the keys. Would definitely stay again!
Superhost
A vibrant rooster stands on a cobblestone surface, showcasing its striking red plumage and an impressive tail of dark feathers. The setting appears to be an outdoor area with tables and chairs dimly visible in the background.
Condo in Key West
4.84 out of 5 average rating, 232 reviews

Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock

DilshadRating, 5 stars2 weeks ago
Absolutely gorgeous place, amazing views, squeaky clean and nicely designed and organized. We enjoyed watching the beautiful sunrise, the yatchs in the marina and the pelicans, from the large balcony! It is right on the water and has all the amenities we wanted, with a great pool and close to many restaurants and main attractions. 5 mins drive to Duval Street. Jennifer was very helpful, friendly and responsive. Will definitely book again and recommend to everyone visiting the area!
Guest favorite
A sandy beach area is showcased, featuring lounge chairs arranged under teal umbrellas. A tiki hut offers shaded seating, while a backdrop of calm ocean waters reflects a bright blue sky dotted with clouds. The scene is framed by lush green palm foliage.
Condo in Key Colony Beach
4.95 out of 5 average rating, 192 reviews

Keys Time Condo Oceanfront Complex Heated Pool

TamaraRating, 5 stars1 month ago
We loved our stay in this beautiful property. Kim was amazing and so friendly I felt like we were friends for years! The condo was immaculate and the property was beautiful and well maintained. Every person on the property was so nice and engaging too. If you are looking for a quiet relaxing place this is it! Perfect location too! I will stay here again for sure !
Top guest favorite
An expansive view of a private beach is captured, showcasing gentle ocean waves lapping at the shore. Lounge chairs are arranged on a green lawn, offering relaxation options while a solitary figure strolls along the sandy beach. Palm trees frame the scene under a partly cloudy sky.
Condo in Key Colony Beach
5 out of 5 average rating, 16 reviews

Private Beach in Marathons Key Colony Beach

KimberlyRating, 5 stars1 month ago
This was a repeat stay with us at Darene's place, and we will come again. Darene is great with communication and responds quickly. Her place is great! The ocean view never gets old. The beach at the condos is perfect, and the proximity to the pool is also perfect! The condo is nice and accomodating. The beds are very comfortable. We had everything that we needed during our stay, and we can't wait to return again! Thank you Darene!
A welcoming living area features a comfortable blue sofa and a rustic wooden coffee table. Light wood flooring extends throughout the space, complemented by a stylish sideboard and updated kitchen in the background, equipped with modern appliances and seating at a spacious kitchen island.
Condo in Marathon
4.88 out of 5 average rating, 25 reviews

Paradise @ MM61 - Waterfront 1 BR / 1 Bath Condo

SusanRating, 5 stars4 months ago
We had a wonderful stay at this location. I recommend it highly. The setting is quiet. Sitting outside on the patio, drinking morning coffee, looking at the ocean, was definately a highlight. The unit was very clean and well stocked with bedding, towels,etc. Duck Key is great for walking. Resturants are easy to get to. We fished most of the time. There is a marina to rent boats less that a 1/2 mile away on Duck Key.
Guest favorite
A modern kitchen is equipped with white cabinetry and a spacious granite countertop. Natural light fills the area, creating a bright environment. The kitchen transitions into an open living space, where views of the water can be seen through large windows.
Condo in Key West
4.88 out of 5 average rating, 153 reviews

Downtown Key West 2BR/2BA•Pool, Dock, Pet "Aruba"

GabriellaRating, 5 stars2 weeks ago
Had a nice time at Jennifer’s place! The space was very well cleaned and looked just like the pics. There must have been some construction going on because it was a bit noisy. Otherwise, it was great!

Quick stats about condo rentals in Key West

  • Total rentals

    430 properties

  • Nightly prices starting at

    $90 before taxes and fees

  • Total number of reviews

    16K reviews

  • Family-friendly rentals

    330 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with a pool

    390 properties have a pool

Destinations to explore

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