Condo vacation rentals in Key West

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Popular amenities for Key West condo rentals

Condo rentals with a pool

An aerial view of Beachside Resort reveals spacious grounds set against the Gulf of Mexico. The property features multiple buildings arranged around a resort pool, surrounded by lush greenery and access to the marina, highlighting the serene waterfront location.
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
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!!
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
4.89 out of 5 average rating, 27 reviews

New Listing! Key Lime Paradise/Condo

StevenRating, 5 stars4 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.
Superhost
The living room is characterized by wood-beamed ceilings and spacious glass doors framing ocean views. Comfortable seating arrangements include a sofa adorned with colorful cushions. Natural light fills the space, enhancing the warm wood tones and elegant decor throughout.
Condo in Key West
4.92 out of 5 average rating, 24 reviews

Key West's Crown Jewel

JulieRating, 5 stars5 months ago
We had the best time at the Crown Jewel. Property was exactly as described—perfect condition. Bed was super comfortable. Patio view was unbeatable. The property management company was extremely communicative and helpful. Would absolutely recommend!
Guest favorite
Condo in Key West
4.8 out of 5 average rating, 46 reviews

Casa Arosa

StephanieRating, 5 stars2 months ago
My husband and I thoroughly enjoyed our stay here and have already rebooked. Newly remodeled, private and walkable. Secure, pristine community with lovely grounds. Host was very helpful and prompt in responding.
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 stars2 months 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.
Guest favorite
A cozy room features mid-century style furnishings, including two blue velvet chairs adjacent to a small dining table. A queen murphy bed is visible in the background, alongside a television mounted on the wall. Natural light enters through the window, highlighting the vibrant yellow walls.
Condo in Key West
4.91 out of 5 average rating, 86 reviews

Duval Street Suites on Duval Free Parking and heat

KevinRating, 5 stars1 month ago
Don’t go here, I want it to myself! My wife and I stayed here for a few nights and absolutely loved this place. Easy to find and right on Duval St. with great parking. Beautiful room with everything we needed and exceptionally clean. If there’s a better place to stay in key West I’ll never know it! We’re already planning our next trip. Thanks Megan
Top guest favorite
A bright living area features a spacious gray sofa and a light-colored armchair facing a mounted television. Large windows allow natural light to fill the space, with a round dining table set for two nearby. Soft décor and neutral tones create a calming ambiance.
Condo in Tavernier
5 out of 5 average rating, 18 reviews

Heavenly Hideaway Ocean Pointe 3306

AuroraRating, 5 stars2 weeks ago
This place was great. The view was amazing. The recommendation for local restaurants snd things to do by the host were spot on. Always in communication and helpful. Very comfy beds and furniture and well stocked kitchen! Will definitely book again if we come back!

Condo rentals with a hot tub

Guest favorite
A sandy beach area features numerous lounge chairs arranged in rows, each with a blue slatted design. In the background, a wooden pier extends over the water, surrounded by trees and calm waves under a clear sky.
Condo in Tavernier
4.89 out of 5 average rating, 133 reviews

1BR - Key Largo Sun & Sand Hideaway

JosephRating, 5 stars1 month ago
Stayed at Vanessa’s place twice while visiting the Keys. Quiet, clean and private. A great host and would definitely stay again next time a visit. Easy access to everything off the highway and great amenities with the pool and beach nearby. 10/10.
Superhost
A bright living space features a comfortable gray sofa and a recliner, complemented by a white coffee table adorned with decorative items. The dining area, with a white table and several chairs, extends into the modern kitchen equipped with stainless steel appliances and a breakfast bar with stools.
Condo in Tavernier
4.88 out of 5 average rating, 153 reviews

Reel Large END Unit in Ocean Point Suites

RyanRating, 5 stars1 week ago
The place was as described. Check in was easy and Desy even allowed us to check in a bit early due to my son having a fever. The linens and accommodations were clean and the condo set up was very nicely. The property is close to restaurants and supermarkets. The pool was clean and we enjoyed the area that sold food and drinks by the pool. This was a nice place to unwind after being on the water fishing for 6-8 hours. Very comfortable, private, and peaceful.
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 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!!
Guest favorite
A scenic balcony offers an unobstructed view of the sunset over the ocean. Two lounge chairs are positioned for relaxation, while a dining table with chairs is available for outdoor meals. Lush greenery extends to the water's edge, enhancing the tranquil setting.
Condo in Key Largo
4.97 out of 5 average rating, 38 reviews

PENTHOUSE SUITE - OFFERS BEST PANORAMIC OCEAN VIEW

MelissaRating, 5 stars1 month ago
Our stay was everything we could have wanted. The view was incredible. The condo had everything we could need. We will definitely come again and recommend it to family and friends.
Superhost
A spacious living area features a light color palette, large windows with ocean views, and modern decor. A comfortable sofa is complemented by blue accent chairs, while a large flat-screen TV is positioned on a sleek console. Natural light enhances the open layout.
Condo in Key Largo
4.93 out of 5 average rating, 71 reviews

Mariner's Club 522 - Don't worry Beach Happy!

MeganRating, 5 stars1 month ago
The condo was beautiful and perfect for our family of 4 for the week. Lot's of great restaurants and activities near by, including a walking and biking bath right across the street. The pools and hot tub were lovely, and we loved the balcony to watch the sunrise and see the moon at night. Our only comment we be maybe getting some more functional and comfortable patio furniture so we could enjoy that even more! Thanks for a wonderful week :)
Superhost
The bedroom features a spacious bed with light blue bedding against a red accent wall. A standing lamp provides soft lighting beside a dresser. A mirror reflects the bathroom area, showing a sink and light cabinetry with a contrasting black-and-white tiled floor.
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.
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, 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.

Weekly condo rentals

A spacious kitchen area is visible, featuring modern cabinetry and a large countertop with a sink. Behind the counter, an open living space is showcased, complete with comfortable seating and windows that reveal an oceanfront view. Natural light illuminates the room, enhancing its airy feel.
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 sandy beach is bordered by towering palms, creating a serene coastal landscape. Gentle waves lap against the shoreline, while distant figures are seen enjoying the beach. A calm sky features scattered clouds, adding to the tranquil environment.
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
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 stars11 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 favorite
The exterior of a two-story corner property is showcased, featuring light-colored siding and a white picket fence. Lush tropical landscaping surrounds the building, with palm trees and flowering shrubs adding greenery. Two porches are seen, inviting relaxation in a serene setting.
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.
Top guest favorite
A clear view of the Atlantic Ocean is showcased, with sunlight reflecting off the water. A sandy beach with a Tiki Hut and lounge chairs is visible in the foreground. Lush greenery and a pathway lead from the lawn to the beach area.
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!
A tropical setting frames the exterior of a multi-level building, showcasing a charming architectural design with balconies and a decorative staircase. Lush greenery surrounds the structure, providing a sense of tranquility and seclusion against a clear sky.
Condo in Key West
4.75 out of 5 average rating, 163 reviews

Steps from Duval, Shared Pool – Sky Loft Downtown

AmandaRating, 5 stars6 days ago
What a really cool place to stay! Lots of privacy! The beds were comfortable and the shower was nice! Walkable distance to everything and the sky lights were awesome! Very affordable and high quality for the price! We will absolutely stay here again!
Top guest favorite
A wide view of the sandy beach reveals several colorful umbrellas and lounge chairs arranged under palm trees, alongside Tiki huts offering shade. The clear blue ocean extends to the horizon under a partly cloudy sky, enhancing the peaceful beachfront setting.
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.

Quick stats about condo rentals in Key West

  • Total rentals

    430 properties

  • Nightly prices starting at

    R1,613 ZAR 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
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  4. Monroe County
  5. Key West
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