Condo vacation rentals in Key West

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Popular amenities for Key West condo rentals

Condo rentals with a pool

Guest favorite
The image showcases a vibrant living space within the Dapper Dolphin condo, featuring a stylish kitchen with granite countertops, a cozy dining area, and a comfortable bedroom with a king-sized bed. The outdoor area displays a large pool surrounded by lounge chairs, highlighting the resort's inviting atmosphere.
Condo in Marathon
4.94 out of 5 average rating, 95 reviews

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

AndreaRating, 5 stars2 weeks ago
Kate was SUPER responsive and available to us if we needed her. The home was beautiful and the decorating was top notch! I loved the interior of the condo and it was sparkling clean! I would definitely stay here again, or at any of her other properties.
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!!
Top guest favorite
Condo in Key West
4.94 out of 5 average rating, 64 reviews

Bright Condo in Paradise

GregRating, 5 stars1 week 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
4.88 out of 5 average rating, 26 reviews

New Listing! Key Lime Paradise/Condo

GordonRating, 5 stars1 week ago
We loved it. The pictures were spot on. Very beautiful unit. Stayed with friends, loved it. Pool was amazing, we spent every day in The pool and went out in the evenings. We would highly recommend this unit
A view from a private balcony showcases the resort pool, surrounded by palm trees and a sun terrace. Lounge chairs are arranged neatly around the pool, while shaded seating areas provide options for relaxation. The bright blue sky enhances the atmosphere of leisure.
Condo in Key West
4.72 out of 5 average rating, 192 reviews

Pool View Suite w/ Full Kitchen | Beachside Resort

SusanaRating, 5 stars1 week ago
I reserved the suite with full kitchen and balcony. The suite was a lot larger than I had expected it to be which was a pleasant surprise! We were on the third floor and we had roof access from our balcony which was a nice touch. Everything was nice and clean. Would definitely return.
Superhost
A spacious balcony overlooks the ocean, featuring blue Adirondack chairs and a dining table. Lush greenery and palm trees frame the view. The sky is clear and sunny, reflecting on the water, creating a serene atmosphere.
Condo in Key West
5 out of 5 average rating, 4 reviews

Southermost Serenity an exclusive 3 Bedroom Ocean

ColleenRating, 5 stars2 months ago
We were 3 couples and Julia’s place was absolutely perfect. Views were gorgeous and the wrap around deck was particularly awesome! Kitchen was well appointed. Check in was easy and Julia communicated throughout the process to make sure it went perfectly. A delight all around!
Superhost
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.
Guest favorite
A clear, inviting outdoor pool is surrounded by lush tropical landscaping. Palm trees are scattered around, softening the edges of the pool area. A multi-story building with a light-colored exterior provides a backdrop, featuring several balconies with white railings.
Condo in Key West
5 out of 5 average rating, 7 reviews

Hyatt Beach House-Quiet Key West Spot!

AnneRating, 5 stars1 month ago
Close enough and not too far away from Key West exploration. The concierge was friendly and very eager to accommodate, front desk staff were helpful and very pleasant. The restaurant next door, Tavern N Town at the Beachside Resort, had a nightly happy hour with great cocktail service from Mr. George and delicious tapas - shrimp tacos, conch chowder, calamari, roasted cauliflower. The rental was fully stocked with all dishes & utensils needed. No issues with parking or anything else. Very enjoyable stay.

Weekly condo rentals

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 stars6 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!
A bright and modern kitchen is showcased, featuring stainless steel appliances and white cabinetry. A large countertop provides ample space for meal preparation. Under-cabinet lighting enhances the work area, while a well-organized pantry is visible in the background.
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
A tranquil pool area is surrounded by lush palm trees and tropical landscaping. Lounge chairs are arranged around the pool, inviting relaxation. A shaded area with a blue awning is visible, along with a pathway leading to a nearby white building.
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.
A serene sunset is captured over the water, with the sun appearing to rest on the horizon. Sailing boats are seen in the distance, with soft hues of orange, pink, and purple dominating the sky. Palm fronds frame the image, adding a tropical touch.
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.
Guest favorite
A modern kitchen showcases white cabinetry and a spacious granite countertop. A dining area features a light wooden table surrounded by matching chairs. The living area is visible through sliding glass doors, enhancing the openness and natural light in the space.
Condo in Key West
4.88 out of 5 average rating, 151 reviews

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

LauraRating, 5 stars1 month ago
This was a treasure in paradise for 2 couples to stay and feel completely relaxed. We enjoyed coffee sunrises, a wonderful sunset walk around the marina and we were in walking distance from anywhere we wanted to go in Old Town. Inside the home was a well appointed kitchen that met any cooking need including salt and pepper. It would have been a pleasure to cook but we ended up reheating our leftovers from all the great restaurants we visited. Coffee sunrise and a cocktail in the evening shade overlooking the marina on that beautiful big balcony were highlights of our time there. Thank you from all of us to our gracious host Jennifer. Laura, Neil, Rich and Deb
Guest favorite
Condo in Key West
4.9 out of 5 average rating, 206 reviews

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

BethRating, 5 stars2 weeks ago
The condo is beautiful and close to everything! We had plenty of room for the whole family.
Top guest favorite
A sandy beach area is framed by palm trees, with two yellow lounge chairs facing the turquoise ocean. A Tiki hut is visible in the background, adding to the serene beach setting and offering a place for relaxation.
Condo in Tavernier
5 out of 5 average rating, 5 reviews

Oceanfront 2 bdrm, 2 bath, View, Pool, Islamorada

MichalRating, 5 stars6 months ago
We stayed here for the Thanksgiving week. The place was nice, clean, and quiet. My kids enjoyed the playroom and the pool. The condo had plenty of board games to keep the kids entertained. The Keys have lots to offer, so there is always plenty to do. Donna was very responsive, the check-in was very simple, and we had a great time. Thank you for hosting us.
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 stars29 months ago
Place was nice and clean. We had a great time.

Condo rentals with a hot tub

Guest favorite
A view of a marina featuring wooden docks lined with boats. Lush greenery, including vibrant pink flowers, frames the foreground. A calm inlet reflects the sky, where fluffy clouds drift above. Palm trees provide shade along the shoreline, contributing to a serene coastal atmosphere.
Condo in Tavernier
4.87 out of 5 average rating, 30 reviews

Sea Side Whimsy Ocean Pointe -06

LadonaRating, 5 stars5 days ago
Swift response and resolution to a broken essential in the condo. Very responsive and timely communication. Would stay again.
Guest favorite
A private beach area is revealed, featuring rows of blue lounge chairs set on soft, sandy ground. Lush greenery borders the beach, while a wooden pier extends into the calm, turquoise water. A thatched gazebo provides shade, and scattered palm trees complete the coastal scene.
Condo in Tavernier
4.94 out of 5 average rating, 98 reviews

Your Happy Place - Oceanfront

JeffreyRating, 5 stars3 weeks 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!!
Top guest favorite
A clear view of the ocean is captured from the balcony, showcasing the shimmering water beneath a bright blue sky. Lush greenery lines the foreground, while a dock extends into the sea. The scene conveys a serene coastal atmosphere.
Condo in Tavernier
4.98 out of 5 average rating, 196 reviews

Ocean Views at Ocean Pointe

PattyRating, 5 stars1 month ago
We had a fantastic stay at this condo in Tavernier! The location was ideal—close to everything we wanted to see and do in the Keys. The unit was clean, comfortable, and well-stocked, with a beautiful view of the ocean that made every morning feel like a dream. The host was extremely responsive and made everything easy from check-in to check-out. Highly recommend this place—we’d love to come back!
Top guest favorite
A light-filled living room reveals ocean views through sliding glass doors. A spacious white couch and armchair offer comfort, while a wooden coffee table rests on a patterned rug. Decorative elements include natural wall art and a bright indoor plant, enhancing the coastal ambiance.
Condo in Tavernier
5 out of 5 average rating, 52 reviews

Tequila Sunrise

HolliRating, 5 stars1 week ago
My husband and I spent two nights at Kathryn's place in Tavernier. We wish we could have stayed longer. The condo is beautiful! I dare any guest to find something Kathryn didn't think of to make your stay incredibly comfortable. The grounds were very nice, the pool and hot tub were especially nice. I would not hesitate to return again.
Guest favorite
A spacious living room features a light color palette with a large flat-screen television mounted on the wall. Comfortable seating is arranged around a coffee table, and large windows provide a view of the ocean and natural light. Coastal decor enhances the atmosphere.
Condo in Tavernier
4.9 out of 5 average rating, 124 reviews

Luxurious Suite+Open Ocean Views+Pool & Cabana Bar

WilliamRating, 5 stars4 days ago
This was a great place to stay in Tavanier! Very close to Key Largo and a short drive to all the charters and activities in Islmarada. Very roomy condo with every at home convenience. Great community pool that had food and drinks available on site from Island Grill. Will definitely consider staying here again. Also.....our host "Largo" was great to deal with. Nice, Friendly, and quick to answer any questions. My boys and I had a wonderful stay!
Superhost
A wooden pier extends over calm waters, leading toward a thatched-roof gazebo. The scene is illuminated by a vibrant sunset, casting warm hues across the sky and reflecting on the water's surface. Lush greenery frames the sides, enhancing the serene atmosphere.
Condo in Tavernier
4.97 out of 5 average rating, 98 reviews

Ocean views at “Sangria Sunrise” 10% off Charters

LaurenRating, 5 stars3 weeks ago
I cannot say enough about how much we enjoyed our stay at Sangria Sunrise! The condo itself is beautiful, the property is awesome, well-maintained, and the staff are friendly and helpful! We spent most of our time at the pool and the beach. The pool bar is great and the pool is clean and refreshing. Plenty of sunny spots and lots of shaded tables, too. It’s right across from the condo so we went multiple times a day. Beautiful landscaping all around. The beach and marina area are really nice. We loved watching the boats from the balcony and seeing the sunrise over the water. Lots of fun things to do in the area within a short drive, but also plenty to do on the property if you prefer to stay put. Tracy is an excellent host and is very helpful and responsive. We will absolutely be back. Thank you for sharing your space with us, Tracy!
Top guest favorite
A light-filled living space features a turquoise sofa with yellow accent pillows, paired with a round glass dining table. Rattan chairs complement the decor, which includes a vibrant tropical wall mural and a circular mirror. Modern appliances are visible in the kitchen area.
Condo in Tavernier
4.95 out of 5 average rating, 190 reviews

Tiki Time! Ocean Pointe Top Floor King 1 Br/1Ba

TimothyRating, 5 stars2 weeks ago
Laurie and Co. were so responsive and welcoming. The place is beautiful and the amenities are lovely. Much like the other reviews, we had a wonderful stay and totally recommend this place!
Guest favorite
A serene ocean view is captured, showcasing calm turquoise waters under a bright blue sky dotted with fluffy white clouds. A lush green shoreline of mangroves frames the scene, creating a tranquil natural setting.
Condo in Tavernier
4.9 out of 5 average rating, 158 reviews

Spectacular 2 Bedroom with a beautiful ocean view.

Brian And MelissaRating, 5 stars1 week ago
My daughter and I stayed her for a long weekend and it was perfect. Very clean and up to date, the beds were very comfortable and an overall nice place to stay. We would definitely stay here again if we were in the area.

Quick stats about condo rentals in Key West

  • Total rentals

    430 properties

  • Nightly prices starting at

    G$18,884 GYD 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
  3. Florida
  4. Monroe County
  5. Key West
  6. Condo rentals