STRIPES ~ Delightful Condo w/Shared Pool in the Heart of Old Town Key West!

Key West, Florida
$811 avg/night
Bed 4

Bed

Bath 2

Bath

Home Condo

Property Type

Sleep 10

Max Sleeps

When you don't need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key West.... rent Stripes, the second and third floor condo with tree top views and beautiful balconies!
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE

INSIDE AND SLEEPING ARRANGEMENTS...
The unique layout of this property allows your group to be together under one roof but have separate levels offering privacy and your own space!

The second level offers aliving room, dining for eight where one four top table is located inside and the other four top table is outside on the back balcony. There is a full gourmet kitchen and a large bathroom with walk-in shower.

The second level bedrooms include a room with a full size bed, another room with two twin beds, and a bunk room with a trundle that's perfect for a kids room! The bunk room top mattress is a twin, the bottom mattress is a full, and the trundle is a twin mattress. All rooms offer storage for clothing and a flat screen TV. 

The third level is equipped with a small living room with flat screen TV, full kitchen, full bath with shower/ tub combo and a bedroom. The bedroom offers a queen and a twin, as well as a dresser for storage and a flat screen TV. 

Should you want only one adult per double bed there is a sleeper sofa on each floor but we do not allow more than 10 guests in the condo at one time as there are only two baths. 

OUTDOOR LIVING...
The compound has a heated pool that is shared by the other condo on the premise (Stars; level one). All guests have access to the laundry area, grill and grounds.

PARKING...
One parking space is available that is first-come-first-serve with the unit below. You can find non-residential parking spaces in the surrounding area, or there is also The Old Town Garage a few blocks away. But this home is in an ideal location, and you don't need a car as you can walk or bike to almost anywhere you will want. If you need a ride, Ubers and Lyfts are readily available. The grocery is just a couple of blocks away, and you can also have groceries delivered or the fridge stocked by our concierge prior to arrival!

DISTANCES TO BEACHES...
Simonton Beach is 0.4 mi
Fort Zachary Taylor Beach is 1.4 mi
South Beach is 1.1 mi
Higgs Beach is 1.3 mi
Smathers Beach is 2.3 mi

CANCELLATION...
Bookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.

CONCIERGE SERVICES...
Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!

PARADISE AWAITS...

Read More Expand
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Unit Size: 2128 Sq Ft (198 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Ice Maker Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Not Required Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill
  • POOL/SPA

    Heated Pool Shared/communal Pool
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Hair Dryer Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Basketball Nearby Birdwatching Nearby Cycling Nearby Ecotours Nearby Fitness Facilities Nearby Jet Skiing Nearby Sailing Nearby Scuba Diving Nearby Snorkeling Nearby Windsurfing Nearby
  • ENTERTAINMENT

    Flat-screen TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning
  • LOCATION HIGHLIGHTS

    In The City Center Near A Hospital Near The Sea
  • SERVICES AND CONVENIENCES

    Concierge Services Iron/ironing Board Limited Housekeeping
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Availability

Review Review

  • Kathy

    Submitted Apr 2, 2025

    Stayed Mar 31, 2025

    This property was amazing! Whitney was incredible with her communication!

  • May B.

    Submitted Apr 15, 2026

    Stayed Apr 6, 2026

    A nice, clean house in good location, close to restaurants and shops.

  • Thomas H.

    Submitted Apr 8, 2026

    Stayed Apr 2, 2026

    Extremely walkable location. The pool was great! The beds are very very comfortable!

  • Miranda P.

    Submitted Apr 4, 2026

    Stayed Mar 31, 2026

    ACTIVE TERMITE infestation! We noticed several piles of what seemed to be sand on the floor & on the kitchen counter & stove, we cleaned it up thinking it was sand leftover from the previous guest, but the piles returned the next day. We contacted the property manager & she said they were already aware of the termite problem. I feel like if they were aware of the termites that should have been disclosed to us before we arrived at the property. They termites were dropping on the stove & kitchen counter, so we were not able to use the kitchen area. Not an enjoyable stay!

  • Janice S.

    Submitted Mar 3, 2026

    Stayed Feb 27, 2026

    The host was very responsive. House was very nice and clean. Nice pool area.

  • Mike C.

    Submitted Feb 27, 2026

    Stayed Feb 23, 2026

    Great location

  • ryan m.

    Submitted Feb 22, 2026

    Stayed Feb 17, 2026

    Supurb location, house was in great condition, and the host made the rental process very easy for us.

  • AMANDA T.

    Submitted Feb 16, 2026

    Stayed Feb 12, 2026

    Beautiful house close to everything with great decor and living spaces. Lots of beds for sleeping options. Lovely decor. Very comfy beds.

  • Debbi R.

    Submitted Feb 12, 2026

    Stayed Feb 9, 2026

    House was very accommodating. Had a great stay. Plenty of room great location. Home was clean and beds were comfortable. Would definitely stay here again.

  • Barry P.

    Submitted Feb 7, 2026

    Stayed Feb 1, 2026

    Host was very welcoming! The place had a great location and was clean and comfortable

  • Angie C.

    Submitted Feb 2, 2026

    Stayed Jan 27, 2026

    The host, amenities and location are all 5 star!

  • felicia d.

    Submitted Jan 21, 2026

    Stayed Jan 19, 2026

    My party of 6 absolutely enjoyed our stay. Plenty of room for all of us. House is in a great location.

  • Michael P.

    Submitted Jan 18, 2026

    Stayed Jan 15, 2026

    Great location, super clean, turn key!

  • Brandon B.

    Submitted Jan 8, 2026

    Stayed Dec 21, 2025

    Fantastic property in a perfect location. Very clean and spacious. Owner very responsive.

  • Tracy M.

    Submitted Dec 19, 2025

    Stayed Dec 13, 2025

    Stripes was super clean and she provided plenty of towels and beach towels. The street was quiet, plenty of coffee shops nearby and the harbor bars and shops were 2 blocks away. Would definitely stay here again. Thanks Wendy!

  • Susan P.

    Submitted Nov 6, 2025

    Stayed Nov 2, 2025

    Good communication from the property manager. Super location.

  • HG W.

    Submitted Sep 17, 2025

    Stayed Aug 11, 2025

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Amazing experience at this home. Everything was clean and comfortable. The use of the pool was an added bonus after hours of walking around Old Town. The location is ideal. Close to everything you would want to see or do in Key West. The family and I will be back soon!

  • Loren Marie K.

    Submitted Sep 6, 2025

    Stayed Aug 28, 2025

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Stripes was a great stay! Clean and perfectly situated in downtown Key West, and still a quiet neighborhood. The balcony/porch was a perfect place to start our day with coffee or prosecco. Harpoon Harry's, the best breakfast diner in town, was steps away around the corner. The party of Duval was just a few blocks away. Perfect location for a fun getaway without the loud neighbors. Highly recommend!

  • Christian M.

    Submitted Aug 25, 2025

    Stayed Aug 22, 2025

    Great house in a great location! Had an absolute blast and had everything we needed

  • Elizabeth M.

    Submitted Aug 11, 2025

    Stayed Jul 22, 2025

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This place was great. We were with friends who had a boat in the AB Marina and this was very convenient. It was a very short walk to the marina, lots of great resturaunts and shopping. There is only one parking space for both units on this property but we found other parking for the first part of our stay. The pool is shared which was a little awkward at first but then we got to know the other renters. The pool was surprisingly very refreshing for our stay in July. It stays pretty shaded but still gets some sun. Rooms were small but we didnt spend much time in them. I loved the upstairs (3rd floor). My twin sons stayed up there and I was only a little jealous....

  • Patrick W.

    Submitted Jul 24, 2025

    Stayed Jul 18, 2025

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Whitney was a great host/manager. Property was fantastic!!

  • Lindsay D.

    Submitted Jul 16, 2025

    Stayed Jun 23, 2025

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had an incredible stay at this beautiful Key West home! Our group of 9 had more than enough space across the two spacious floors — everyone was comfortable, and we never felt crowded. The house was clean, beautifully maintained, and thoughtfully stocked with everything we needed. We especially appreciated how quiet the streets were, which made it easy to relax and feel like locals for the week. The management company was absolutely lovely: responsive, professional, and always quick to answer any questions we had. We couldn’t have asked for a better experience. Highly recommend this home for any group looking for comfort, space, and a true Key West vibe!

  • Josefa R.

    Submitted Jul 14, 2025

    Stayed Jul 11, 2025

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: My family and I loved our stay! It was very comfortable and serene. We had so much fun at the pool. Beautiful house in the heart of Key West, close yo everything.

  • Christina S.

    Submitted Jul 3, 2025

    Stayed Jun 19, 2025

    We loved this house, it was cozy, yet had enough space for everyone. The management team was very responsive and there to answer any questions we had. I loved the location of the house, walking distance from Duval St, but not right in the middle of the nightlife.

  • Moleana H.

    Submitted Jun 12, 2025

    Stayed May 30, 2025

    It was awesome close to everything.

  • Robyn G.

    Submitted May 27, 2025

    Stayed May 23, 2025

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a group of 9 and stayed at Stripes for a 4 day long Memorial Day weekend trip. The house was very clean. Check in was super easy. They even allowed us to check in a bit early which was great because we took the Key West Express ferry and didn’t want to tote our luggage around. The pool was clean, private, and very enjoyable ! The house layout was perfect for our group and you couldn’t beat the location in proximity to everything! The only thing I would have added was a bigger ( or additional) living room couch in the common area but we weren’t home enough to worry about it. We Definitely will stay there again!

  • Kalani P.

    Submitted May 16, 2025

    Stayed May 2, 2025

    This property is in one of the best locations in Key West. It was very comfortable for a group of seven to stay at. We love the pool and the management was on top of everything. Although the kitchen was nice, it was pretty poorly well stocked (minimal pots and pans, no baking sheet) in order us to cook dinner for a group. The shampoo that they provided was also pretty poor.Otherwise would love to stay again.

  • Jon S.

    Submitted Apr 4, 2025

    Stayed Mar 24, 2025

    My family of 6 loved this place. The location was close to the ferry which was how we arrived on the island so that started everything off on the right foot. We very much appreciated the central location of the house. It was an easy walk to the piers, Mallory Square, Duval Street, and all the restaurants and shops you could want. But, it was off the main drags so you didn't get a lot of night time noise and disturbance. The best of both worlds. The house has a great patio for night time relaxing and the pool was a welcome feature for our kids. We would definitely stay here again.

  • Mike H.

    Submitted Mar 8, 2025

    Stayed Mar 5, 2025

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Had a great time. The place is very clean,lots of room and close to all the fun on Duval.Front porch for coffee in the morning too!

  • Heather H.

    Submitted Feb 5, 2025

    Stayed Jan 29, 2025

    We had an amazing stay at Stripes for a girls trip. The house was clean and lovely and perfect for a group. We enjoyed the heated pool and the second floor balcony was a great place to enjoy a coffee in the morning or happy hour. The street was quiet but an easy walk to all of the entertainment of Duval Street. There is a great coffee shop around the corner which we enjoyed everyday. Everyone on the trip commented that they would stay there again. 10 out of 10!

  • John K.

    Submitted Jan 23, 2025

    Stayed Jan 16, 2025

    Loved our visit, the house was beautifully maintained, great details and instructions to know how to work lights, tvs, etc. location was excellent for the key west 1/2 marathon.

  • Craig L.

    Submitted Dec 2, 2024

    Stayed Dec 31, 1969

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Attended a destination wedding in Key West and stayed at Stripes with members of my family. Lodging was great, location was perfect.

  • Stephanie L.

    Submitted Nov 4, 2024

    Stayed Oct 20, 2024

    I almost want to give this property a bad review so that I can keep it as my own little secret. This place was AMAZING. Location, AMAZING. Clean house, AMAZING. Communication from property manager, AMAZING. This house was incredibly comfy and spacious. Pool is shaded and a wee small to have to share… but if you’re like my group, there’s too much to do out and about to stay in.

  • Brenton R.

    Submitted Sep 23, 2024

    Stayed Sep 19, 2024

    Place was awesome, would definitely stay there again

  • Nancy W.

    Submitted Sep 11, 2024

    Stayed Sep 4, 2024

    Great location! Great service!

  • Allison B.

    Submitted Jul 31, 2024

    Stayed Jul 16, 2024

    We absolutely adored this stay! It is such a great location, and housed all 8 of us with ease. The side pool was such a great addition for the heat! The stay was clean, and the property manager was so helpful! This was one of the best stays we have had!

Your dates are Available!

Total

Includes taxes and fees
$700+
View details