Condo holiday rentals in Key West

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Popular amenities for Key West condo rentals

Weekly condo rentals

Condo in Key West
4.76 out of 5 average rating, 37 reviews

One Bedroom Suite | Beachside Resort

RomanRating, 5 stars3 weeks ago
Everything was solid, would do it again
Superhost
Condo in Key West
4.6 out of 5 average rating, 83 reviews

Beautifully Renovated Summer of 2020 Come and enjo

CristinaRating, 5 stars2 months ago
The experience was so memorable! Just the R&R our family needed!
Guest favourite
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!!
Guest favourite
Condo in Naval Air Station Key West
5 out of 5 average rating, 6 reviews

Palm Garden retreat with Hot Tub & Prime Key West

KimRating, 5 stars2 weeks ago
Small but super nice property. Everything is very new and remodeled.. great location to all fun. Recommended renting bicycles at Island Bicycle- bikes were nice , price was a deal and owners so friendly and accommodating. The property was available to check- in at 9am which allowed us to have the full morning to unpack and relax by the pool. The hottub was amazing!! Will definitely rent again !
Condo in Key West
4.79 out of 5 average rating, 14 reviews

Palm Isle: 2nd-Floor Unit, Shared Heated Pool

TonyRating, 5 stars3 weeks ago
Very nice place,easy to find and plenty to do .great location.very clean and very quiet,and peaceful.Ty
Top Guest favourite
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
Condo in Key West
4.89 out of 5 average rating, 27 reviews

New Listing! Key Lime Paradise/Condo

StevenRating, 5 stars3 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 favourite
Condo in Key West
4.99 out of 5 average rating, 70 reviews

The Palms

gayleRating, 5 stars6 days ago
The listing says no dryer, but there is one. A big plus was the covered balcony, so we could sit out even in the rain. Well appointed and comfortable stay.

Pet-friendly condo rentals

Guest favourite
Condo in Key West
4.94 out of 5 average rating, 18 reviews

Chagall’s Corner | Newly Remodeled!

AshleyRating, 5 stars1 week ago
Woooow, this place was nothing short of amazing!! The exact amount of space we needed because we knew we would be out and about most of the day!! Bed was very comfortable and ushered us right to sleep after our flight! Walking distance from literally everything we had on our list to do! We mingled with the locals, listened to live music during dinner, enjoyed the beach at sunset, and learned a little bit about the Bahamian history! This place is literally 2or 3 blocks from the southern most point and the best Cuban coffee at a local restaurant/food truck! 10/10 would definitely recommend!! Already planning our next visit!!
Guest favourite
Condo in Key West
4.97 out of 5 average rating, 73 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

LesleyRating, 5 stars2 months ago
Carrie's place was absolutely beautiful! it was so clean, the beds were insanely comfortable, and there were tons of linens and towels for everyone. We very comfortably fit 8 people into the home with no problems. The view from the balcony is absolutely amazing and we were all blown away. Carrie was extremely responsive and friendly. We were here for our wedding and had our wedding party stay here so it was extra magical. The pool and hot tub is super close, elevator to help with our bags, and the resort itself is gorgeous. 10/10 would stay again. We loved it so so much! Don't miss out.
Superhost
Condo in Marathon
5 out of 5 average rating, 3 reviews

Beach/Docks Avail/3 Pools/Hot tub/Gym/Restaurants

MichaelneuroRating, 5 stars5 months ago
Great experience, great host and accommodations. Hot tub wasn't working while we were there, but repair was delayed over the holiday week which was out of the hosts' control. Very communicative and responsive.
Guest favourite
Condo in Key Largo
4.94 out of 5 average rating, 108 reviews

Gorgeous lagoon-front 2BR Townhouse with 2 pools

KateRating, 5 stars2 weeks ago
Came down to Key Largo for my beautiful niece’s destination wedding. So nice we could all stay in the same resort. So convenient! Felt totally safe there. It was so clean. Nice to have the back enclosed patio and also the one off the master. Comfortable bed. Slept well. So quiet. Good water pressure in the shower. Just minutes to anything we needed. Would definitely recommend.
Condo in Key West
4.76 out of 5 average rating, 146 reviews

Dog Friendly 1BR | Pool | Easy Beach Access

JeffRating, 5 stars4 months ago
This is an ideal location in the heart of Old Town. But it is relatively quiet, facing into a private courtyard. Having an extra half bath is unusual for a one-bedroom. We enjoyed sitting outside. The kitchen worked well so we didn't have to eat out all the time. There is a great Cuban coffee shop right across the street.
Guest favourite
Condo in Key West
4.81 out of 5 average rating, 165 reviews

Balcony, Pool, & Pet Friendly - St. Martin Suite

NatalieRating, 5 stars5 days ago
Very cozy and clean home, loved how everything was super close.
Guest favourite
Condo in Key Largo
4.87 out of 5 average rating, 85 reviews

Oceanside Key Largo 3/3 kayaks included

StephRating, 5 stars5 days ago
We had a great stay at Rich's place. There were 6 of us (and our dog) so we were able to sleep on the first and third floors and then hang out together, watch TV, eat, etc. on the second floor. There was a lot to do in the complex (e.g., paddleboard the in the lagoon and fish off the jetty), and we were close to a ton of restaurants and places to do other activities as well. Rich was very responsive and checked on us often. We felt very safe. Would return again!
Superhost
Condo in Key West
4.81 out of 5 average rating, 31 reviews

La Maisonnette~ Gated Condominium 1 Block to Duval

KathleenRating, 5 stars3 months ago
This is a BEAUTIFUL condo in a GREAT area with a LOVELY COURTYARD for rest and relaxation. A nice little pool also. Very quiet and easy to get around. It was great to WALK or BIKE RIDE in the area. Would definitely stay there again.

Condo rentals with a pool

Condo in Key West
4.67 out of 5 average rating, 15 reviews

Spacious 2BR Oceanfront | Balcony | Pool

AlettaRating, 5 stars11 months ago
Location Location Location Beautiful condo Excellent view of the sunset and harbor An extra treat was staying next to a military base Be sure to be out on the balcony at 7:55 AM and stay until 8 also be out there at sunset. The only improvement would be to have extra fobs and pool keys for the possible 4 guests on the property Thanks for making your property available guests
Guest favourite
Condo in Tavernier
4.94 out of 5 average rating, 98 reviews

Your Happy Place - Oceanfront

JeffreyRating, 5 stars1 month ago
We thoroughly enjoyed our stay, the property was as described and the pool and bar/restaurant were great! The room in building 4 and floor 4 was perfect for views off the small balcony! Would 100% stay here again!!
Superhost
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!
Condo in Key West
5 out of 5 average rating, 4 reviews

2 Bedroom Townhouse Style Condo

KimberlyRating, 5 stars10 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 favourite
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!
Top Guest favourite
Condo in Tavernier
5 out of 5 average rating, 53 reviews

Tequila Sunrise

ChristinaRating, 5 stars1 week ago
adorable suite! very comfortable beds and couches. home smelled amazing! Kathryn was always responsive to questions. she also would check in on us periodically to make sure we had everything we needed. we 100% recommend this host and will absolutely book with her again.
Condo in Key West
5 out of 5 average rating, 5 reviews

Casa de Bentley

MarjorieRating, 5 stars2 months ago
Wonderful stay. Gorgeous views. I appreciate the thoughtfulness of condo host. We got to hear, feel & see the roar of four Fighter Jets from the nearby US base one morning during our stay. It was quite the treat to see them action. It is a great location to be nearby Key West area - minutes away by car. Would definitely come back to stay there again.
Top Guest favourite
Condo in Marathon
5 out of 5 average rating, 13 reviews

Ocean Potion 1B/2B 3Balconies Ocean View

MelanieRating, 5 stars8 months ago
This has been one of our favorite places in Marathon that we have stayed at. The view from balcony was beautiful, very clean and everything you need for your stay. The pool was amazing and a walk on the dock in the evening was full of sights! Overall we loved our stay and we will be back!!!

Quick stats about condo rentals in Key West

  • Total rentals

    430 properties

  • Nightly prices starting at

    $150 NZD 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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  4. Monroe County
  5. Key West
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