
Condo holiday rentals in Key West
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Top-rated condo rentals in Key West
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Popular amenities for Key West condo rentals
Weekly condo rentals

2 Bedroom Oceanfront Complex Heated Pool KCB
We had a great time! Awesome community with walkable restaurants and bars. We loved the local beaches. The people at the complex were super nice. Our four boys loved running from the pool to the beach. Everyone we met was very nice. Great instructions and recommendations. Loved it!

Reel Large END Unit in Ocean Point Suites
Nice, clean and quiet place. pool was nice. Nice view off the balcony is of the mangroves. Beach area is nice but pretty rocky once you get into the water.

Key West Pool View
Bonnie's place was just what we had hoped it would be. Comfy, plenty of room for 2 friends and not tripping over each other. Ice maker in fridge was a great plus. We loved it and if we're ever in Key West again, we'll ask for this location.

Key West and Hyatt Windward Pointe
Wonderful resort. Staff super friendly. Loved the pool, and location. Would absolutely recommend!

Den Suite Two Balconies- Islamorada
Great spot to spend days for vacation. Great service by office staff. They took care of all requests we had in the most friendly manner. The hotel is located right on the water, so views were great. Nice pool and great vibe. Would highly recommend.

Gone Coastal @ Ocean Pointe
Nice place….exactly as described…..great location….easy access to restaurants….activities….great view….would stay again!

2-story condo w/ panoramic bay views and balconies
Words can't really express the beauty of this rental inside and out. Fully stocked with whatever your needs are. Full sized washer and dryer were perfect. Absolutely spotless inside. Beach towels were ready to go as well. The two porches were wonderful for relaxing and taking in the breathtaking views. We saw a family of 7 manatee several days in a row. A family of parrot fish almost every day (several times a day). We saw a VERY LARGE sea turtle just hanging out in the bay. Lots of tarpon, several sharks, pinfish, yellow snapper and several conches (even one queen conch). It is worth it to snorkel feet from the porch. My daughter even caught a shark. The pier was perfect for fishing and watching all the wildlife. The landscape is beautiful. The pool is amazing (I used it almost every day for a bit and no one was down there). I cant say enough good things about this space. It's worth every single penny. We will DEFINITELY be back!

Sunrise Suites Resort Key West, FL U #111 2bdr2bth
Very nice place to stay without breaking the bank. Lyft and Uber are always available to get you to where you want to go or rent a golf cart. Very responsive host, we will definitely be back.
Pet-friendly condo rentals

La Dolce Vita, Old Town Steps to Duval! 3 blks bch
Great location and accommodations, friendly and prompt communications.

Chagall’s Corner | Newly Remodeled!
What a great spot! We were blown away by the value. Clean, comfortable and close to literally everything we wanted to do in Key West. They even picked us up at the airport even though our flight was 30 minutes late. Amazing place in an amazing town. We will definitely stay with Rick again!

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

Balcony, Pool, & Pet Friendly - The Trinidad
Nice area near the airport away from Duval but easy to get to everything. Kids liked the pool (water was warm and hot tub was hot), comfortable beds and good sized kitchen.

Seashells Getaway - Boat Slip, Ramp, Pool
Hello. We Booked this place so I could be in the sun on a lounge chair and husband could fish. It was exactly what we wanted. We were able to hang out together and both get what we wanted. He caught fish like crazy! Place is beautiful and exactly how described. Getting an Uber/lyft was easy. Sombrero Beach was beautiful. Ana was excellent to communicate with. Condo bed was very comfy and the bedroom dark. The use of a cooler and beach chairs was appreciated. Would not hesitate to book again.

Key Largo Condo
This condo was everything it said it was. Very clean. Great location, clean and serviceable furnishings and an awesome view. One thing that really struck out for me was that the kitchen had everything that you would need without being stuffed with a lot of extra stuff you don’t need. Also the pots and pans were very clean and almost new. Michael was very responsive to all our questions and made sure that we were happy with everything. We would definitely stay here again and recommend it to anyone interested in staying in Key Largo.

La Maisonnette~ Gated Condominium 1 Block to Duval
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.

Orchid Suite @ the Old Town Villas, steps from
I would rerun to this rental and recommend it. Spent a week here with my nephew and the property was perfect for our vacation. Every detail was thought of. We needed nothing. The location was great!!
Condo rentals with a pool

Sea Side Whimsy Ocean Pointe -06
Great view, easy check in, comfortable stay

Key West Paradise Poolside
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!

Condo de Paradise/Salt Water Pool/Boat Dock
We could not have been more grateful for the stay at Cynthia’s. The setting is perfect - quiet, secluded, right on the water, but a 5-10 minute drive to anything you would want or need (attractions of Key West, Publix groceries, CVs). We did day trips to Key West, Marathon, Bahia Honda, and more. The place is just lovely. The two bedrooms are perfect for a family of four. Our children were very happy and cozy in the room with two single beds. The master looks right onto the ocean. The place is outfitted with everything you need (kitchen needs, etc). The bathrooms are new and nicely redone. The pool is pristine and we often had it to ourselves, but on the occasions we got to say hi to the neighbors they were warm and lovely. One thing that made it extra special was Big Coppit is close to Naval Air Station Key West, so (only during appropriate hours, like 8-9am), we got to see amazing fighter jets fly over head. Cynthia is a great host and was responsive and understanding. Thank you!

Parking, Deck, Pool, Beach, 2 Blocks to Duval St
This condo was perfect for my wife and I. The location was great for exploring all the downtown areas of Key West by foot. We enjoyed walking around Duval street, the waterfront and the beaches. We booked a fishing charter and caught some delicious Mahi and went on a fantastic sunset cruise. The condo had all the amenities that we needed and the pool was very refreshing to go to after a long day at the beach.

A place in the Sun
We really enjoyed our stay. The place was very nice. There are a lot of activities nearby ranging from kayaking, to snorkeling, to boating. The pool in the complex was great! We would definitely stay there again.

Key Lime Breeze Retreat!
We had a great stay with our kids - the condo was well furnished, clean, and easily walkable to the pool, game room, and tennis courts. We appreciated the condo was stocked with “kid things” - pack and play, high chair, pool toys, and games. Would recommend to others!

Oceanfront condo in the keys
This location is the jewel of the Keys. Private, safe and with an incredible view of the ocean and sunrise. I’ve stayed many times in the area and this is absolutely the best. Owner is extremely helpful and available for any questions. Condo has a well stocked kitchen for cooking with great restaurants nearby. Big, fluffy oversized towels are provided. Being on the second floor near the stairs made that the easiest route in and out. Great group of people we met at the pool, many returning every year for extended stays. Just a wonderful place and hoping to return again next year. Thank you so much, Jeanette!

2 Bedroom Townhouse Style Condo
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.
Quick stats about condo rentals in Key West
Total rentals
430 properties
Nightly prices starting at
$140 AUD 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
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