
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.

Nautical Hideaway - Ocean View - Pool - 2 Kayaks
The place was very wonderful and peaceful, perfect for enjoying a relaxing time with beautiful ocean views and relaxing breeze. Plenty of open space right by the water to relax. Apartment was super comfortable with all amenities needed and very clean.

Coconut Mallory. Waterfront & Key West charm.
Very nice condo. Very clean unit. Would stay again. Only inconvenience was no bathroom on the main level. But 2 bathrooms on the upper level. Great value for the price.

Key Largo Treasure at Kawama Yacht Club
Even better then the pictures. Chelsea was so helpful as a Hurricane was coming in on our trip and she offered to let us come early or stay longer. Fast communication and clear instructions in the welcome and farewell email. We would absolutely stay again. We had a wonderful time and the place was perfect! Highly recommend!

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.

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!
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.

Gorgeous lagoon-front 2BR Townhouse with 2 pools
This place is a great place for families. All ages can enjoy this neighborhood. It’s close to everything, but it feels cozy.

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.

key Largo 3 Bedroom Townhouse Gated Community
Everything was great! Nice area, and easy access to local activities. we enjoyed our stay.

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.
Condo rentals with a pool

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

On the water! Marina, Pool, Tiki Bar & Restaurant!
We loved our stay at the Dapper Dolphin! The space was so clean. Kate has everything there for you - from beach chairs to laundry detergent! This apartment is conveniently located to great restaurants, attractions and Sombrero Beach. You are just a short walk to the pool at Skipjack Resort. They have poolside karaoke on Monday nights which was very fun. Highly recommend booking this place - we miss it already!

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!

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.

*NEW* Kokomo Views-Pool/Beach
PERFECTION!!! I have so many great things to say about our stay. First, the condo was beautiful and fully stocked. It even had plenty of soap, toiletries, paper products etc to get you started. Yuni was the perfect host and answered all questions and gave clear instructions. The balcony was huge. It was enough for the family to eat and lounge all while enjoying the beach and pool views! Key Colony Beach is a charming community we walked to the sunset multiple nights. My kids aged 10,8,7 did not want to leave. The complex had very friendly retirees and a handful of families with kids. Everyone was super respectful and friendly. The pool was super clean and warm. The beach was groomed each night and the kid had plenty of room to play on the sand and hunt for shells and hermit crabs. Marathon is a great Key to stay on - close to lots of fun activities. We are already planning our next trip and we will definitely rent this condo again! It’s perfect for families!

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!

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.

2BR Spacious Condo, Balcony, Great Location
Check in/check out was easy! Nice and clean, pool and hot tub area was clean and the pool was nice and warm. We will definitely be check CoolVacay's properties for our next vacation.
Quick stats about condo rentals in Key West
Total rentals
430 properties
Nightly prices starting at
$141 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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