Condo vacation rentals in Stock Island

Find and book unique condos on Airbnb

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Popular amenities for Stock Island condo rentals

Weekly condo rentals

Superhost
Condo in Key Colony Beach
4.75 out of 5 average rating, 164 reviews

2 Bedroom Oceanfront Complex Heated Pool KCB

RobertRating, 5 stars3 weeks ago
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!
Condo in Key West
5 out of 5 average rating, 4 reviews

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

AndersonRating, 5 stars1 week ago
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.
Superhost
Condo in Key West
5 out of 5 average rating, 6 reviews

Fair Winds @ The Foundry~ Frolic On Duval St

KathleenRating, 5 stars8 months ago
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!!
Condo in Key West
4.78 out of 5 average rating, 23 reviews

Oceanfront Key West Condo

AlexandraRating, 5 stars3 months ago
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!
Condo in Key West
5 out of 5 average rating, 7 reviews

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

TracyRating, 5 stars4 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!
Top guest favorite
Condo in Marathon
4.96 out of 5 average rating, 100 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

JenneyRating, 5 starstoday
Great little place for our family of 4! Very clean and the location was perfect for us. Would definitely stay again!
Condo in Marathon
4.8 out of 5 average rating, 5 reviews

Reel Escape 2 - Lovely 2nd Floor Condo/Shared Pool

MeleneRating, 5 stars3 months ago
The condo was a perfect place for my husband and me to stay during our week in the Keys. Comfortable and all the amenities we needed. Less than a mile from beach access and good area for walking. Close to good restaurants and things to do. Loved the Turtle Hospital and Crane Museum. Pool was wonderful too. Confirm the unit number before you go. So thankful Tina answered the phone on Christmas night to help us out. Would definitely stay here again.
Condo in Key West
5 out of 5 average rating, 10 reviews

2 BR Condo Banyan Tree, Key West,FL

MaureenRating, 5 stars28 months ago
Place was nice and clean. We had a great time.

Pet-friendly condo rentals

Superhost
Condo in Key West
4.83 out of 5 average rating, 272 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

JudieRating, 5 stars2 weeks ago
Great location and accommodations, friendly and prompt communications.
Guest favorite
Condo in Key West
4.94 out of 5 average rating, 16 reviews

Chagall’s Corner | Newly Remodeled!

AnneRating, 5 stars3 weeks ago
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!
Condo in Key West
4.65 out of 5 average rating, 88 reviews

Balcony, Pool, & Pet Friendly - The Trinidad

BillRating, 5 stars1 month ago
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.
Guest favorite
Condo in Marathon
5 out of 5 average rating, 6 reviews

Seashells Getaway - Boat Slip, Ramp, Pool

TaraRating, 5 stars5 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.
Guest favorite
Condo in Key West
4.74 out of 5 average rating, 95 reviews

Orchid Suite @ the Old Town Villas, steps from

MichelleRating, 5 stars1 month ago
I would rerun to this rental and recommend it. Spent a week here with my nephew and the property was perfect for our vacation. Every detail was thought of. We needed nothing. The location was great!!
Condo in Key West
4.64 out of 5 average rating, 61 reviews

Lovely 2BR | Pool | Hot Tub| Tennis | Dog Friendly

JohnRating, 5 stars1 month ago
This Airbnb was the perfect balance of distance and quiet to staying in Key West. There isn't a whole lot to do around the place but that was fine since we were out most of the day and stayed here to mostly sleep. The place, beds, shower all made us very comfortable to take on another day exploring in Key West.
Condo in Key West
4 out of 5 average rating, 6 reviews

Sunrise Condo at Seaside

Juan AlejandroRating, 5 stars1 week ago
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 in Key West
4.44 out of 5 average rating, 188 reviews

2BR 4th-Floor | Balcony | Pool |

WillRating, 5 stars1 week ago
Great place close to airport close to Smathers beach, 5 minutes to stores shops bars. Great pool and place to stay!

Condo rentals with a pool

Condo in Marathon
4.8 out of 5 average rating, 10 reviews

1BR with pool, patio, sundeck & great location

KristaRating, 5 stars6 months ago
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!!
Guest favorite
Condo in Marathon
4.94 out of 5 average rating, 16 reviews

Marathon-waterfront 2Br with pool & boat slip

AshleyRating, 5 stars5 months ago
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!
Guest favorite
Condo in Key West
4.96 out of 5 average rating, 76 reviews

Key West Paradise Poolside

AmyRating, 5 stars5 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!
Superhost
Condo in Key West
4.85 out of 5 average rating, 55 reviews

Ocean front 1BR/1BA Suite w/ kitchen & living rm

NoraRating, 5 stars1 week ago
We had an amazing few days to disconnect. The resort exceeded my expectations - the property is on a private beach with beach chairs, umbrellas, primitive shower to rinse off, a decent size pool, and tall coconut palm trees. So dreamy! The property is very clean, staff is friendly. The apartment is well stocked with kitchen essentials like plates, cups, silverware, pots, etc. We are definitely coming back!
Condo in Marathon
4.78 out of 5 average rating, 9 reviews

Updated 2/2 on the Ocean with private Beach & Pool

KarlyRating, 5 stars21 months ago
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!
Guest favorite
Condo in Marathon
4.83 out of 5 average rating, 6 reviews

Beachfront Condo on Coco Plum Beach w/heated pool

JenniferRating, 5 stars9 months ago
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.
Top guest favorite
Condo in Key West
5 out of 5 average rating, 24 reviews

EYW Getaway

RootwaRating, 5 stars1 week ago
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.
Guest favorite
Condo in Layton
5 out of 5 average rating, 10 reviews

Oceanfront, gated 3 bedroom condo with boat slip.

GabrielaRating, 5 stars9 months ago
very charming and spacious place. the master bedroom (captains quarters) is massive, and my two friends and I had more than enough room to spread out. There were plenty of towels and items for daily living (well stocked kitchen, laundry items, grilling utensils). the pool is separate from a condo but a short walk away. We had a hard time initially locating our condo b/c we didn't see a unit # outside the door itself, and went up/down the flights of stairs a few times before we found it. But once we did, it was smooth sailing. (2nd floor, take a right.) Gorgeous views and spacious patio!

Quick stats about condo rentals in Stock Island

  • Total rentals

    100 properties

  • Nightly prices starting at

    ﺩ.ﺇ331 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

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Stock Island
  6. Condo rentals