Condo holiday rentals in Stock Island

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Popular amenities for Stock Island condo rentals

Weekly condo rentals

Guest favourite
Condo in Marathon
4.94 out of 5 average rating, 95 reviews

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

AndreaRating, 5 stars3 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 favourite
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!!
Guest favourite
Condo in Key Colony Beach
4.92 out of 5 average rating, 238 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

MikeRating, 5 stars3 weeks ago
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.
Condo in Key West
4.8 out of 5 average rating, 15 reviews

Palm Isle: 2nd-Floor Unit, Shared Heated Pool

WilhelminaRating, 5 stars1 week ago
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.
Superhost
Condo in Key West
4.84 out of 5 average rating, 232 reviews

Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock

DilshadRating, 5 stars2 weeks ago
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!
Top Guest favourite
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.
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.
Condo in Key West
5 out of 5 average rating, 7 reviews

Superb wtrfrt Coconut Mallory 2 BR, 2 ba w/balcony

TracyRating, 5 stars5 months ago
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

Condo in Key West
4.56 out of 5 average rating, 130 reviews

Cozy 2BR 3rd-Floor | Pool | Dog Friendly

JrRating, 5 stars3 weeks ago
The place was very nice and cozy. Great location and atmosphere. I would definitely stay here again.
Superhost
Condo in Marathon
5 out of 5 average rating, 3 reviews

Beach/Docks Avail/3 Pools/Hot tub/Gym/Restaurants

MichaelneuroRating, 5 stars5 months ago
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.
Guest favourite
Condo in Marathon
5 out of 5 average rating, 6 reviews

Seashells Getaway - Boat Slip, Ramp, Pool

TaraRating, 5 stars7 months ago
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.
Superhost
Condo in Key West
4.81 out of 5 average rating, 31 reviews

La Maisonnette~ Gated Condominium 1 Block to Duval

KathleenRating, 5 stars3 months 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 in Key West
4.25 out of 5 average rating, 8 reviews

Sunrise Condo at Seaside - KEY WEST!

BrendaRating, 5 stars1 month ago
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.
Superhost
Condo in Key West
4.75 out of 5 average rating, 8 reviews

Carey’s Corner | Updated Studio with Heated Pool

MattRating, 5 stars4 months ago
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.
Condo in Key West
4.42 out of 5 average rating, 191 reviews

2BR 4th-Floor | Balcony | Pool |

WillRating, 5 stars2 months ago
Great place close to airport close to Smathers beach, 5 minutes to stores shops bars. Great pool and place to stay!
Superhost
Condo in Key West
4.88 out of 5 average rating, 8 reviews

The Osprey's Nest at Sunrise Suites

Amanda Rating, 5 stars2 months ago
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

Superhost
Condo in Key West
4.86 out of 5 average rating, 28 reviews

Rum Cay at Sunrise Suites

JenniferRating, 5 stars1 week ago
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!
Superhost
Condo in Key West
4.85 out of 5 average rating, 155 reviews

Anchor Drop modern elegance upgrades throughout vi

ElizabethRating, 5 stars1 month ago
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!
Top Guest favourite
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!
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.
Superhost
Condo in Key West
4.92 out of 5 average rating, 39 reviews

Coastline Comfort at Coconut Mallory

DanielleRating, 5 stars2 months ago
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.
Guest favourite
Condo in Key West
4.9 out of 5 average rating, 42 reviews

Walk to beach, Duval Street, Mallory Square

WendyRating, 5 stars2 weeks ago
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!
Condo in Marathon
5 out of 5 average rating, 4 reviews

Oceanview Retreat w/Pool Steps Away From Beach #14

AdamRating, 5 stars2 months ago
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.
Top Guest favourite
Condo in Marathon
5 out of 5 average rating, 20 reviews

*NEW* Private Beach, pool & fully loaded kitchen

JamesRating, 5 stars1 month ago
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

Destinations to explore

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  2. United States
  3. Florida
  4. Monroe County
  5. Stock Island
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