Condo holiday rentals in Key West

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Popular amenities for Key West condo rentals

Weekly condo rentals

Superhost
Condo in Key Colony Beach
4.75 out of 5 average rating, 158 reviews

2 Bedroom Oceanfront Complex Heated Pool KCB

JillRating, 5 stars2 weeks ago
Thoroughly enjoyed our stay! The private beach area was well equipped with chairs and shade. It was so peaceful and relaxing. What a nice community! The area was safe, well maintained , and walkable. Friendly people live and vacation here. Sunset Park was the best part of each evening each the sunset with the community. Would definitely stay again.
Guest favourite
Condo in Tavernier
4.88 out of 5 average rating, 145 reviews

Reel Large END Unit in Ocean Point Suites

MichelleRating, 5 stars1 week ago
Felt at home! Very cozy spot. The kids loved the pool and the beach. They especially loved that they had pool toys there for us.
Guest favourite
Condo in Key Largo
4.86 out of 5 average rating, 43 reviews

Nautical Hideaway - Ocean View - Pool - 2 Kayaks

JessicaRating, 5 stars9 months ago
The best stay we’ve had yet. We will be coming back yearly. The condo was perfect and the grounds were perfect. The best place to stay in key largo. See you next year!
Superhost
Condo in Key West
5 out of 5 average rating, 11 reviews

Coconut Mallory. Waterfront & Key West charm.

ChristineRating, 5 stars11 months ago
Perfect place to stay! The kitchen is fully equipped. The location is ideal. The place is clean and updated. Lots of closet space and comfortable beds. We had a great family stay!!!
Superhost
Condo in Tavernier
5 out of 5 average rating, 3 reviews

Gone Coastal @ Ocean Pointe

GaryRating, 5 stars2 months ago
Nice place….exactly as described…..great location….easy access to restaurants….activities….great view….would stay again!
Superhost
Condo in Marathon
4.8 out of 5 average rating, 5 reviews

Reel Escape 2 - Lovely 2nd Floor Condo/Shared Pool

MeleneRating, 5 stars2 months ago
The condo was a perfect place for my husband and me to stay during our week in the Keys. Comfortable and all the amenities we needed. Less than a mile from beach access and good area for walking. Close to good restaurants and things to do. Loved the Turtle Hospital and Crane Museum. Pool was wonderful too. Confirm the unit number before you go. So thankful Tina answered the phone on Christmas night to help us out. Would definitely stay here again.
Superhost
Condo in Key West
4.62 out of 5 average rating, 240 reviews

Sunrise Suites Resort Key West, FL U #111 2bdr2bth

ElmerRating, 5 stars1 month ago
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.
Superhost
Condo in Key Colony Beach
4.85 out of 5 average rating, 108 reviews

Beachside Unit 37 - Come Relax on the Atlantic!

CharlesRating, 5 stars1 month ago
This is located in a great area of Marathon, Fl . A nice and safe area . The building is older but it has been updated and looks great. The beach area is awesome, a very nice beach with lots of sand with a few steps down to the ocean , this is a great private beach

Pet-friendly condo rentals

Superhost
Condo in Key West
4.83 out of 5 average rating, 268 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

KarenRating, 5 stars1 month ago
Beautiful condo-we loved the colors & Wolfgang’s artwork!! So pleasant to sit outside on the comfortable Adirondack chairs enjoying the breeze at night with a glass of wine, or our morning coffee. We loved the location, just a half block off of Duval St. It was easy to walk to many of the great restaurants & recommendations that Debbie had in her welcome book. Clean & comfortable. The ice machine wasn’t working & Debbie was quick to respond with a repairman. When he couldn’t fix it, she had her manager deliver a couple big bags of ice to us. Much appreciated. Parking is a bit dicey as the open/available spots do get taken, but we always managed to get a spot, if we drove somewhere for the day. Very walkable-we’d stay there again!
Guest favourite
Condo in Key West
4.93 out of 5 average rating, 14 reviews

Chagall’s Corner | Newly Remodeled!

ShirleyRating, 5 stars1 day ago
Our room was small, but that was in the listing. The room served the purpose as it was a place to sleep. The place is located very close to the Hemmingway House and the Lighthouse. It was also close to Duvall Street.
Guest favourite
Condo in Key West
4.99 out of 5 average rating, 69 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

JimRating, 5 stars3 weeks ago
The condo is just like the pictures and the views shown are from the deck. We had an unbelievable time here during our family vacation. We were far enough from the craziness of downtown Key West but close enough for a quick Uber ride when we wanted to see the sites, shop, or enjoy restaurants. The condo had everything we could possibly need, just bring your personal stuff, place a delivery grocery order from Winn Dixie and we were set for the week. The condo is part of a resort so you get all those amenities along with the more private condo only pool and hot tub. We enjoyed walking around the marina and looking at the large boats along with enjoying the tranquility of the views of just water from the deck. Carri was the best host I’ve had the opportunity to deal with. Extremely responsive and helpful at every turn. We will absolutely be back and will base our timing around staying at Carri’s place again.
Condo in Key West
4.64 out of 5 average rating, 86 reviews

Balcony, Pool, & Pet Friendly - The Trinidad

KelvinRating, 5 stars6 months ago
Clean and comfortable stay with all the basics needed for a fun stay in Key West. Located 10-12 min away from Duval St and just a few minutes from the southernmost point of the US. Would definitely stay again!
Condo in Key West
4.71 out of 5 average rating, 146 reviews

Walkable 1BR | Deck | Pool | Dog Friendly

KimRating, 5 stars2 weeks ago
I really enjoyed this place. We have been to Key West many times over the years and this one was in the top 3. Peaceful and quiet. Lovely surroundings within the villas . And yet it was close to everything. Very walkable which in Key West is important. The villa we stayed in was comfortable and clean. We rented mopeds from the business next door and they provided free shuttle back to the airport👍
Top Guest favourite
Condo in Key Largo
5 out of 5 average rating, 13 reviews

Key Largo Condo

PamRating, 5 stars2 months ago
Michael’s home is amazing. It was just perfect - from the cleanliness to the quality of the furnishings to the spectacular view!! Everything about this property was better than we hoped. Michael was very nice and responsive. I could sit on the deck and enjoy the view for days!!
Guest favourite
Condo in Key Largo
4.97 out of 5 average rating, 34 reviews

key Largo 3 Bedroom Townhouse Gated Community

MaryRating, 5 stars3 weeks ago
this was a great spot for our group of 6. The property, lagoon and was lovely. thank you for taking care of us👍
Guest favourite
Condo in Key West
4.86 out of 5 average rating, 29 reviews

La Maisonnette~ Gated Condominium 1 Block to Duval

KathleenRating, 5 stars3 weeks 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

Guest favourite
Condo in Tavernier
4.83 out of 5 average rating, 23 reviews

Sea Side Whimsy Ocean Pointe -06

EricandToniRating, 5 stars1 week ago
As Airbnb Superhosts, we pay really close attention to cleanliness and all aspects of the space. This condo was impeccably clean!! Thank you. The description was also very accurate. We loved the location and the small beach area for afternoon cocktails after our daughter's dive trips. Everything is close by, from groceries to restaurants, yet you feel like you are worlds away from everything. The condo was quiet, and the floor plan was great. We will definitely stay here again.
Guest favourite
Condo in Marathon
4.93 out of 5 average rating, 87 reviews

On the water! Marina, Pool, Tiki Bar & Restaurant!

BrieonnaRating, 5 stars3 weeks ago
We really enjoyed our stay! It was in a great location. The guide that Kate left extremely helpful when it came to where we went to eat and what we did.
Guest favourite
Condo in Key West
4.94 out of 5 average rating, 36 reviews

Condo de Paradise/Salt Water Pool/Boat Dock

ErinRating, 5 stars2 months ago
Peaceful location just a short drive to Key West. The views were beautiful and the condo was just like the pictures! Very spacious and comfortable with everything you'd need. It was the perfect space for our family of four. Cynthia was great. Very responsive and friendly!
Superhost
Condo in Key Largo
4.83 out of 5 average rating, 35 reviews

Relax in Key Largo

AnthonyRating, 5 stars6 months ago
Paradise, I stayed for five weeks. July 27th-Sep 3rd. Entire Moonbay Is a condominium resort. It is huge and has everything you could ask for. The grounds are meticulously kept. The pool is gorgeous and brand heated. No one is there in August so I had the entire place to myself. The snowbirds don't return until October. kid's were in school and I was in heaven. Thank you Arthur for sharing your little slice of paradise. I will be back permanently ASAP.
Top Guest favourite
Condo in Marathon
5 out of 5 average rating, 11 reviews

*NEW* Kokomo Views-Pool/Beach

EmilyRating, 5 stars2 weeks ago
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!
Guest favourite
Condo in Key Largo
5 out of 5 average rating, 12 reviews

Key Lime Breeze Ocean Retreat | Waterfront Oasis

AnnRating, 5 stars6 days ago
Looks exactly as photographed. Perfect spot for our family of five which includes older teens - space for everyone to spread out. The girls loved the balconies for those Insta worthy pics. Kitchen was well stocked. We enjoyed the amenities including the pools and gym. Thanks for a great stay.
Condo in Key West
5 out of 5 average rating, 4 reviews

2 Bedroom Townhouse Style Condo

KimberlyRating, 5 stars8 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.
Guest favourite
Condo in Marathon
5 out of 5 average rating, 5 reviews

2BR Spacious Condo, Balcony, Great Location

JohnRating, 5 stars1 month ago
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

    440 properties

  • Nightly prices starting at

    $143 AUD before taxes and fees

  • Total number of reviews

    16K reviews

  • Family-friendly rentals

    340 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with a pool

    400 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West
  6. Condo rentals