
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

2 Bedroom Oceanfront Complex Heated Pool KCB
We had a great time! Awesome community with walkable restaurants and bars. We loved the local beaches. The people at the complex were super nice. Our four boys loved running from the pool to the beach. Everyone we met was very nice. Great instructions and recommendations. Loved it!

Parking, Deck, Pool, Beach, 2 Blocks to Duval St
This condo was perfect for my wife and I. The location was great for exploring all the downtown areas of Key West by foot. We enjoyed walking around Duval street, the waterfront and the beaches. We booked a fishing charter and caught some delicious Mahi and went on a fantastic sunset cruise. The condo had all the amenities that we needed and the pool was very refreshing to go to after a long day at the beach.

Fair Winds @ The Foundry~ Frolic On Duval St
Comfortable, spacious space with all we needed to feel right at home. We loved the neighborhood! Peaceful, beautiful and quiet, yet so close to any restaurant, shop, museum or beach we wanted to go to. We ditched the rental car and walked or rode bikes to get around. The rental is beautiful with floor to ceiling windows to let afternoon sunshine in as well as the garden views from the front porch. The artwork and decor brought in the island vibe … very cozy and carefree. And the Historic Key West Vacation Rental staff were great to work with … responsive and professional. This vacation rental checked all the boxes for us!!

Oceanfront Key West Condo
This beautiful condo was so much more wonderful than the pictures portrayed! It is the most amazing location and setting with a stunning courtyard garden, ocean views and its own little beach. I felt like I stepped into Paradise! The complex was quiet, respectful and beautifully maintained. The location on the island could not be beat with a short walk to Smathers Beach and Higgs Beach. This was our first time in Key West and it was pure magic! Thank you!

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!

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
Great little place for our family of 4! Very clean and the location was perfect for us. Would definitely stay again!

2 BR Condo Banyan Tree, Key West,FL
Place was nice and clean. We had a great time.

Sundown Refuge by AvantStay | Week-Long Stays
The location couldn't be better. Large deck with view of the ocean in distance, very nice large pool just steps away, very quiet (except occasional airplanes - well, it's a small island after all) and the 5:00 pm fog horn last-boarding-warning from the cruise ship in port... kind of appropriate since the building's architecture looks a bit like a cruise ship - added to the vibe. Oh the SUNSET VIEW!! Within walking distance to the best part of Duval, the best restaurants and less than 15 minute bike ride to the best (Ft Zachary) beach. We Will be back if we can!!
Pet-friendly condo rentals

La Dolce Vita, Old Town Steps to Duval! 3 blks bch
Great location and accommodations, friendly and prompt communications.

Chagall’s Corner | Newly Remodeled!
What a great spot! We were blown away by the value. Clean, comfortable and close to literally everything we wanted to do in Key West. They even picked us up at the airport even though our flight was 30 minutes late. Amazing place in an amazing town. We will definitely stay with Rick again!

Balcony, Pool, & Pet Friendly - The Trinidad
Nice area near the airport away from Duval but easy to get to everything. Kids liked the pool (water was warm and hot tub was hot), comfortable beds and good sized kitchen.

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.

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access
A very well appointed condo with everything supplied. A great view over the marina. However, close to a main route into Central Key West made it a slightly noisy location. Also next door to a bar/restaurant,this made sitting on balcony a not so peaceful experience. For those interested in watching TV the wifi was awful. The pool area was predominantly in the shade come the afternoon. The host was very responsive and helpful. All in all, we enjoyed our stay as we loved Key West.

Orchid Suite @ the Old Town Villas, steps from
The orchid suite was just what we were looking for. We knew we weren’t going to be there much but was quiet and cozy when we were there. Plenty of towels and the fact they had beach towel was a great addition so we didn’t have to pack those. The location was perfect being one block away from Duval st. There is a CVS right across the street and we were able to grab a few grocery items there. Would definitely stay here again!

Lovely 2BR | Pool | Hot Tub| Tennis | Dog Friendly
Great Stay in Key West. The unit was very clean, comfortable and the kitchen was well appointed. Safe neighborhood for runs or walks and the place had a nice pool. Quick Uber/Lyft to Duval St. Would definitely recommend and stay again.

Sunrise Condo at Seaside
The place was nice and easy to find. The hosts were very responsive. The only thing that could be better is the WiFi and the options for the TV but not a big deal if the goal is to spend time in the Key West town.
Condo rentals with a pool

1BR with pool, patio, sundeck & great location
This place was absolutely stunning! The complex was well taken care of and the pool was awesome. I loved the location of this property, as it was close to everything. Would absolutely recommend and would stay here again!!

Marathon-waterfront 2Br with pool & boat slip
The condo was perfect and like a home away from home. We were given recommendations on things to do and any questions we had were answered quickly. I loved kayaking in the canals and was able to see a sea turtle, dolphins, and manatees. Would love to return!

Key West Paradise Poolside
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!

Bright Condo in Paradise
John’s condo is a great place to stay to enjoy Key West. It’s spacious, clean, and tastefully decorated. He has decks on both sides. We didn’t cook there, but the kitchen was fully supplied. The pool was very nice as well. The absolute best thing is that it’s in a gated community so it is quiet even though it’s close to the action. Nothing was further than a mile walk, and most things were just a few blocks like Mallory Sq, the Old Seaport area, and Fort Zachary Taylor State Park. John readily answered any questions I had. He was very nice to deal with.

Updated 2/2 on the Ocean with private Beach & Pool
Enjoyed the great room location with cold a/c, quiet atmosphere, perfect saltwater pool, and beautiful views. We got to enjoy seeing manatees, dolphins, and iguanas from the property. There are quite a few great places right near for a quick good sandwich or bait for fishing. Will definitely be back!

Beachfront Condo on Coco Plum Beach w/heated pool
This was a beautiful place to stay that was off the busy road and afforded less traffic and noise. It was still very convenient to all restaurants and activities in Marathon. The condo was very clean, beds comfortable, updated kitchen, and just great overall. There is a pool available and you are just a few steps from the beach. We would definitely recommend it to others, and stay here again.

EYW Getaway
Edward's place was great! we really enjoyed the home like vibe. It had everything we needed during the stay. The sunset view from the balcony was beautiful.

Corner Unit 2BR | Deck | Pool | W/D
Great place to stay ! The listing should include that it is upstairs, didn’t notice that or I would have looked for something else. Very clean and nicely decorated.
Quick stats about condo rentals in Stock Island
Total rentals
100 properties
Nightly prices starting at
$140 AUD 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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