
Condo holiday rentals in Stock Island
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Top-rated condo rentals in Stock Island
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Popular amenities for Stock Island condo rentals
Weekly condo rentals

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

Parking, Deck, Pool, Beach, 2 Blocks to Duval St
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!!

Oceanfront Breeze, Stunning Views, Beach/Pool
We had a great stay at Kim's for our 25 year anniversary. The spot was even better than the pictures. And Kim was a great host, very proactive and extremely helpful. We'll definitely look to stay there again in the near future.

Palm Isle: 2nd-Floor Unit, Shared Heated Pool
Tina was very responsive. The place was very clean, located only a half mile from Duval Street. Only a few miles from beaches. Host was great & accommodating.

Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock
Absolutely gorgeous place, amazing views, squeaky clean and nicely designed and organized. We enjoyed watching the beautiful sunrise, the yatchs in the marina and the pelicans, from the large balcony! It is right on the water and has all the amenities we wanted, with a great pool and close to many restaurants and main attractions. 5 mins drive to Duval Street. Jennifer was very helpful, friendly and responsive. Will definitely book again and recommend to everyone visiting the area!

Bright Condo in Paradise
Great place with everything you need and in the perfect location.

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.

Superb wtrfrt Coconut Mallory 2 BR, 2 ba w/balcony
We had a wonderful time in Key West. The condo was perfect for our family of four, and we enjoyed hanging out on the balcony in the evenings and the complex hot tub. Andre was an awesome host - very responsive and proactive in arranging for our possible late evening arrival. His suggestion of rental bikes to be delivered to the condo was a great one - we used those to bike all over Key West. Would love to return someday!
Pet-friendly condo rentals

Cozy 2BR 3rd-Floor | Pool | Dog Friendly
The place was very nice and cozy. Great location and atmosphere. I would definitely stay here 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.

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.

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.

Sunrise Condo at Seaside - KEY WEST!
Great place, clean, nice location, and complimentary snacks and water on the fridge, which was a pleasant surprise. The location is well-maintained and strategically situated, providing an overall positive experience.

Carey’s Corner | Updated Studio with Heated Pool
Rick’s place was clean, cozy and in a perfect location for taking in Duval and the sights. The pool was very private and clean.

2BR 4th-Floor | Balcony | Pool |
Great place close to airport close to Smathers beach, 5 minutes to stores shops bars. Great pool and place to stay!

The Osprey's Nest at Sunrise Suites
Victor was truly amazing at making sure we made landed ok and made it save. The place was just as described and extremely clean! Also, the birthday balloon gift was truly sweet. This place makes you feel right at home. Will definitely be back!
Condo rentals with a pool

Rum Cay at Sunrise Suites
Rum Cay was a delightful place to stay. Clean, beautifully decorated, and well designed (e.g., the Murphy bed). I recommend it to other families with a car!

Anchor Drop modern elegance upgrades throughout vi
Exceptional stay. Anchor Drop was a top Airbnb property in our book.,Would definitely look to return to both Key West and the property. Host was responsive, explicit, and helpful. Space was as described and very well appointed, clean, and comfortable. First time to Key West and was very satisfied with our accommodations, location, and area. Thank you!

Private Beach in Marathons Key Colony Beach
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!

Sunrise Suites Resort, Key West FL U #408 2bdr2bth
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.

Coastline Comfort at Coconut Mallory
Loved this space for my family (including 2 toddlers)! We loved eating breakfast outside on the balcony (balcony has a door with a high lock in case you are trying to keep toddlers IN - which was extremely helpful for us). Pool was great with only a handful of people each day. Very peaceful and private area away from the busy downtown area of Key West.

Walk to beach, Duval Street, Mallory Square
Felt right at home from first step inside! Loved watching the iguana and geckos out back and the pool was a welcome cool down. Very close to all the action but peaceful and serene and safe feeling at the homestead! Perfect!!! Great hosts to answer local details on where to go! Fully enjoyed this Airbnb trip!

Oceanview Retreat w/Pool Steps Away From Beach #14
The views of the Atlantic were awesome! Having the pool and beach so close was very nice. We very much enjoyed our stay and would definitely come back.

*NEW* Private Beach, pool & fully loaded kitchen
Our first time visiting the Keys and Celia’s place made it wonderful! Located in a very nice, quiet, and safe community her condo is like new and so well cared for. Perfect size for our two couples. The decor and furniture is very nice, bright and clean. Had all the amenities we needed and then some. We enjoyed the heated pool everyday and the private beach was nice for a more natural experience. The furnished patio had a great view of the pool and ocean. Celia is a wonderful host! Very helpful and a great communicator.
Quick stats about condo rentals in Stock Island
Total rentals
100 properties
Nightly prices starting at
$149 NZD before taxes and fees
Total number of reviews
4.7K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
100 properties have a pool
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