Southard Breezes

Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We inspect our homes multiple times each month and follow the AHLA Stay Safe Guidelines to ensure your stay is safe and comfortable. You will also find an initial supply of cleaning and paper products along with handsoap and toiletries. The home has a private entrance and contactless Check-In/Out.

Need to stay connected during your trip? We offer high speed cable internet.

This upscale home has been meticulously renovated with our guests' complete comfort in mind. Located in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the peaceful tropical landscape and pool while only 2 blocks from the excitement of Duval St. We are just outside the entrance to Ft Zachary Taylor State Park and Beach and so close to many of Key West’s popular attractions. After a full day of taking in many of the island's wonderful experiences, come back to all the comforts of home. This open airy home offers a fully furnished kitchen, eating area, living room and bedroom with a queen size bed and full bath. There are televisions in both the bedroom and living room along with wireless internet access. Two sets of French doors bring in lots of light and open to a large balcony where you can enjoy a meal or relax and sip umbrella drinks on the chaise lounges in your own private tropical paradise. Gated parking lot with one reserved space. (For reviews on our other homes, please see Listing # 877318 Sunset on Southard)

Amenities

- Televisions in bedroom and living area
- 2 Bicycles for Guests to use during their stay
- Bed Linens, Bath & Beach Towels
- Hairdryer
- Beach Chairs & Cooler
- Access to Shipyard Pool
- Partially covered oversize deck
- Reserved parking place
- Secure high speed wireless internet in condo
- Only a few short blocks from Duval Street and Mallory Square
- Short walk to the Fort Zachary Taylor State Park Beach
- Fully equipped Kitchen with Silestone counter and eat in bar- Silverware, Dishes, Cooking Utensils Provided, Stove/Oven, Refrigerator, Microwave, Dishwasher, Coffee Maker & Blender

Vacation Rental Reviews

• Perfect location and great accommodations

  Stayed 7 days ending in October, 2024

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  a guest from Brockton, MA recommends this vacation rental

  Enjoyed every minute of our stay. The condo was very clean and homey. Plenty of space and everything you will need to enjoy your vacation. The location can’t be beat. Easily walkable to everything. If Key West is your destination, this is your location. Highly recommended!

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• Cozy Vacation Home

  Stayed 7 days ending in October, 2024

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  Jennifer V from Parma, Ohio recommends this vacation rental

  We absolutely love this condo and the beautiful property. Location is perfect for walking everywhere .This is our 3rd time renting from Tracy and we again on our next trip to Key West, Our Happy Place.

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• nice week in the Annex

  Stayed 7 days ending in August, 2024

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  charles b from Bordentown, NJ recommends this vacation rental

  A cute condo in Truman Annex that was perfect for 2. The bikes were in very good condition. The pool was refreshing and the location was great. Very clean condo with everything you would need. I would stay here again.

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• Birthday Week Shipyard Condo

  Stayed 7 days ending in June, 2024

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  Skip W from Port Richey, FL recommends this vacation rental

  Spent a week at the Condo to celebrate my birthday. Condo was beautiful, clean, and so close to everything we walked everyday. Would definitely stay here again. Everything was provided even detergent to wash your clothes. Only suggestion, a broom or vacuum to keep the floors clean.

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• Nov 25, 2023

  Stayed 7 days ending in December, 2023

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  Michelle S from Ukiah, CA recommends this vacation rental

  We enjoyed our stay & we'll be back! Property is amazing, condo clean & beautiful, location fantastic.

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• Definitely Recommend

  Stayed 7 days ending in November, 2023

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  Christy T from Hardinsburg, Kentucky recommends this vacation rental

  This was a great property. The layout was very nice with a larger bathroom than most Shipyard condos. Everything was clean and it had all the supplies we needed. I would definitely recommend this condo! Also renting from Tracy is always a good experience!

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• Great stay!

  Stayed 7 days ending in October, 2023

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  a guest from Mechanicsburg , Pennsylvania recommends this vacation rental

  I have nothing but positive things to say! The rental was clean, in a nice location, and comfortable. I would definitely recommend it to anyone and I would stay here again!

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• Key West Trip

  Stayed 9 days ending in September, 2023

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  a guest from Aiken, SC recommends this vacation rental

  This was our second stay at Southard Breezes. We love the location. We are two blocks from Duvall Street and a short bike ride to Truman waterfront park and Zachary Taylor State Park. The sunsets at Truman Waterfront Park are beautiful. We also seen a pod of Manatees. You are a short bike ride to all the restaurants and bars. Tracy was very responsive to any questions we had. Southard Breezes was as described very nice and clean. We will definitely be back to Southard Breezes again.

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• What a Week

  Stayed 7 days ending in September, 2023

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  a guest from Reynoldsburg, OH recommends this vacation rental

  We thoroughly enjoyed our stay at the Key West Condos Truman Annex. The condo was clean, well appointed and in a great location. Only had a couple of questions and the Owner answered promptly and patiently. Definitely would stay there again!

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• Great location and condo

  Stayed 7 days ending in September, 2023

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  Karin W from Jefferson, GA recommends this vacation rental

  We loved our stay here and found the location was perfect as we were able to walk everywhere. The condo was clean and well stocked and had everything we needed. We used the coffee pot daily and enjoyed sitting on the deck in the morning. We appreciated the beach chairs, cooler, and beach towels. We never did get around to using the bikes, but would have been great I'm sure! We found the bed a little uncomfortable (compared to ours's at home) and wish there were more pillows. We had an issue with the air conditioner (it was super hot during our stay) and reached out to Tracy who communicated back immediately and had a service company there in an hour! She was great to work with and we would definitely recommend staying here.

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• Key West

  Stayed 7 days ending in June, 2023

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  linda s from Apollo Beach, FL recommends this vacation rental

  Condo was wonderful! So cute and comfortable with everything you need for your stay. Perfect location in Key West-walked to everywhere we needed to go. A very relaxing vacation. Cant wait to go back and stay!! Thank You!!

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• Southard

  Stayed 7 days ending in May, 2023

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  a guest from Jacksonville, Arkansas recommends this vacation rental

  It was great as usual. We love Tracy's properties. Had to call maintenance regarding not able to regulate the hot water in the shower. They were very prompt to address the issue.

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• Dreaming of a return trip

  Stayed 7 days ending in May, 2023

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  Susan and Philip K from Surfside Beach, SC recommends this vacation rental

  The condo was clean, comfortable, and convenient. Well-stocked and attention to details that made the stay wonderful. Any essential you could think of was there. We walked everywhere, only using our car once. We enjoyed the patio morning and night. In our 60s, it was our first visit to Key West and we would love to return - and we know where we would want to stay again!
  The only downside - the parking space was a little further from the unit than we expected, and we decided that was okay because of the appreciated shade BUT the shade was from a Cuban Mahogany tree that dropped large hard pods that dented our car.

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• Christmas get away

  Stayed 7 days ending in January, 2023

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  Deidre T from Cleveland, GA recommends this vacation rental

  This was our 3rd stay at Southard Breezes and it once again was awesome! Very clean property and walking distance to everything there is to do in Key West. The owners responded quickly to our concerns. I would highly recommend this property to friends. We enjoyed Crusin Tiki and Dry Tourtugas National Park this visit. Breakfast at Moondog and Blue Heaven was delicious as expected.

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• Great Location and Clean!

  Stayed 7 days ending in December, 2022

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  Amber P from West Seneca, NY recommends this vacation rental

  This condo was wonderful! It was in the center of everything and was super easy to get around. It was very clean when we arrived and was perfect for the 2 of us. We enjoyed using the bikes and the chairs to go to the beach! I thought it wouldve been loud being on the main road but it was super quit at night. We had an issue with the AC, but they had someone come within the hour of us reporting it to get it fixed. I would stay here everytime!

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• Perfect Location

  Stayed 7 days ending in November, 2022

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  Eric D from Minooka, IL recommends this vacation rental

  The dimmer light switch in the Kitchen needs to be replaced. Also, bring a cooler in the luggage if going to the pool. We had to purchase a soft-sided cooler because there wasn't one available in our unit 208-10. Otherwise, all was good.

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• Wonderful spot!

  Stayed 7 days ending in October, 2022

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  Stacie B from Newfield, NJ recommends this vacation rental

  We have been to Key West several times and have stayed in this complex most. This unit was our favorite. Great location, cute decorations and huge deck. Also loved the fact that they left bicycles for us to use and beach chairs!

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• Hurricane Ian

  Stayed 7 days ending in October, 2022

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  linda s from Apollo Beach, FL recommends this vacation rental

  We did not come to Key West this week due to Hurricane Ian. Sorry we have no review. Bur the owners are wonderful and properties are beautiful!

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• Amazing central location in Key West

  Stayed 7 days ending in September, 2022

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  Holly C from Virginia Beach, VA recommends this vacation rental

  Our rental in Truman Annex was more then we could have hoped for. So close to all of our favorite places in key west that was a very walkable distance and provided bikes if needed. Seeing the sunset every night at the Truman waterfront was better then being at Mallory. Ft Zachary was also close enough to walk or bike. The accommodations were great and everything was updated and supplied. The back deck was perfect for those little Florida rains that we got a few times. The only downfall that we had was the pool not being opened the whole week because it was being resurfaced. We would definitely stay here again.

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• Perfect Retreat

  Stayed 7 days ending in August, 2022

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  Sonia V from Bay Shore, NY recommends this vacation rental

  Such a relaxing and peaceful week. Walking distance from restaurants, beach, and shopping.Grounds were beautiful and picturesque. Having access to the pool during the hottest time was great. The condo itself was beautifully decorated, cozy and comfy for a couple. Would definitely go back!

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• Loved the fact we did not need to keep track of a key

  Stayed 7 days ending in July, 2022

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  Elisa K from New Lenox, IL recommends this vacation rental

  Very cute with all necessary amenities. The only issue we had was we were not 100% clear that we had a keypad code. Our friends staying in Truman Annex had to get a key. Once we figured it out, it was great. I like not having to worry about a key.

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• Our trip to paradise!

  Stayed 7 days ending in May, 2022

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  Cathy G from Lititz, PA recommends this vacation rental

  Our trip was highlighted with great food, fabulous drinks, good entertainment and a beautiful Condo. We were very happy with the location of our rental and the fact that we were able to bike to the beach was a plus. Of courses the many miles we walked were just an added feature.

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• Birthday Trip of my Dreams

  Stayed 8 days ending in May, 2022

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  Jennifer V from Parma, Ohio recommends this vacation rental

  Simply amazing. Home away from home. Very clean and comfortable. Within walking distance to so many great Island locations. No doubt we will be back soon and Keywestcondos is the only choice for us.

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• Great vacation to end a difficult year!

  Stayed 7 days ending in January, 2022

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  Deidre T from Cleveland, GA recommends this vacation rental

  Amazing week in Key West! 2nd stay at Southard Breezes and will defiantly be back. Location is perfect and property very clean.

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• Southard Breezes

  Stayed 7 days ending in December, 2021

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  Debra K from Southington, CT recommends this vacation rental

  Enjoyed the condo and its wonderful location. Would highly recommend this property it will not disappoint.

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• Staying in paradise

  Stayed 7 days ending in December, 2021

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  David L from N/A, CO recommends this vacation rental

  Great place and great location!

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• Great spacious, sunny and open open condo!

  Stayed 7 days ending in December, 2021

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  Ameilia d recommends this vacation rental

  We’ve stayed at many of KeyWest.condos and this was one of the nicest. Loved the location!

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• Perfect Location

  Stayed 14 days ending in November, 2021

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  Eric D from Minooka, IL recommends this vacation rental

  Within walking distance of...everything in Old Town. Two bikes are available for those that are adventurous enough. Vehicles are not necessary unless they are needed to travel outside of Old Town (grocery shopping at Winn Dixie/Public, or going off-island for restaurants up the Keys). The unit was clean. Stayed two weeks at the Southard Breezes. The only thing that would be a nice addition on-premises would be a slow cooker/crockpot for occasional cooking in the unit...instead of going out to restaurants.

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• A Cute Little Paradise

  Stayed 7 days ending in October, 2021

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  Patricia L from Macomb, MI recommends this vacation rental

  The place was very quaint and in a great location to beaches, bars, food and all things fun. The property owners were prompt in answering back. Only thing is if you have any mobility issues wouldn't recommend for the flight of stairs otherwise outstanding.

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• Key West First Trip

  Stayed 7 days ending in August, 2021

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  a guest from Harpersville , AL recommends this vacation rental

  Cute little condo that met our needs. Convenient to Duval, Mallory Square, and the beach. The tow bicycles came in real handy, and we ended up renting one for my son seeing this is the only way we traveled while in KW. The only complaint I have is there wasn’t extra bedding as far as the pull out couch, or an extra blanket. Just enough towel me for maybe on day of showers, but there is a washer and dryer in the unit, so this wasn’t that big of a deal. I’d definitely rent this little condo again for my family of three. It was updated, clean and we loved the location!!!

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• Wonderful first time Key West

  Stayed 7 days ending in July, 2021

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  Dawn W from Poteau, OK recommends this vacation rental

  Rental was perfect for everything we wanted to do. Perfect location. Bikes were added bonus. Condo spacious and beautifully appointed.

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• Southard Breezes

  Stayed 9 days ending in May, 2021

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  Keith B from Queensbury, NY recommends this vacation rental

  We've stayed with KeyWest.condos for a few years now. We have never been disappointed. Great hosts!

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• Southard Breezes

  Stayed 7 days ending in May, 2021

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  Cathy G from Lititz, PA recommends this vacation rental

  This place is absolutely awesome! We are so happy with the location and the cleanliness of the property. Thank you!!

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• Southard Breezes Vacation in paradise

  Stayed 7 days ending in May, 2021

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  a guest from Jacksonville, Arkansas recommends this vacation rental

  Wonderful. We love Tracy's properties.

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• Fabulous Property!!!

  Stayed 7 days ending in December, 2020

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  a guest from Concord, NC recommends this vacation rental

  This unit is fabulous!! It is the most cleanest property we have ever stayed in!!! The decor is beautifully tastefully done!! The location was great, close to everything. We would definitely stay again.

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• Perfect Location

  Stayed 7 days ending in November, 2020

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  Erica F from N/A, CO recommends this vacation rental

  This was one of the best, most relaxing vacations we've been on. The condo was perfect; had everything we needed and the locations was perfect for us. We loved riding the bikes which were provided to get around town. We would highly recommend this condo.

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• Return Customers

  Stayed 11 days ending in November, 2020

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  Eric D from Minooka, IL recommends this vacation rental

  Easy check in...easy parking (if you have a vehicle. Pool just across the street and another a one minute walk. Right in the middle of everything there is to see/do in Key West. Two bikes available for free usage. Two minute walk to Duval, ten minute walk to Seaport/Mallory Square....ONE MINUTE WALK to the Green Parrot Saloon!

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• Another week in Paradise

  Stayed 7 days ending in October, 2020

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  Alan G from Malvern, PA recommends this vacation rental

  Our second year at Southard Breezes and had a wonderful time in Key West with perfect accommodations. So close to Duval Street, the Beach, and all that Old Town Key West has to offer. Tracy has always been accessible and prompt with any questions and issues- cant wait for our trip next year!

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• Paradise

  Stayed 7 days ending in September, 2020

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  Tony C recommends this vacation rental

  Definitely want to go there again.

  • Manager Responded on 10/29/2020

    Thank you Tony! I hope you return to stay with us for a future stay!

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• December Fun

  Stayed 8 days ending in December, 2019

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  Mary M from Apex, North Carolina recommends this vacation rental

  This is the second property we have rented in the beautiful Truman Annex area from Tracy. The location cannot be beat! Right around the corner from Blue Heaven and two blocks from The Green Parrot. Tracy always outfits her properties with lots of extras-bikes, beach passes and chairs, cooler. She is great to work with. Lovely condo! Thanks Tracy!

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• Destination Wedding and Honeymoon

  Stayed 7 days ending in December, 2019

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  Haley F recommends this vacation rental

  This was our first time renting a condo instead of staying at a hotel and we could not have been happier! Beautiful condo in a great location, within walking distance of some great bars/restaurants, shopping and Fort Zachary Taylor. The one and only disappointment we had during our stay was when it was time to leave!

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• "Will Return"...Correction, are returning (Booked)

  Stayed 8 days ending in November, 2019

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  Eric D from Minooka, IL recommends this vacation rental

  Checked in on November 4th-12th, 2020. We've been going down for vacations to Key West since 1992, and location wise, the Southard Breezes is the most convenient by far. Our unit was clean and well stocked. Two pools close by. Unit also comes with a bicycle which I used on a daily basis. A car is definitely not necessary with the location of Southard Breezes. Beer and wine two blocks away at the Walgreens, hard liquor choices 1 block away at the Green Parrot Bar/Liquor Store. Groceries and well appointed deli/meat shop (if you choose to cook in the unit)...three blocks down the street at Faustos, they also deliver for a small fee of $5.00. Like we said above, we've been vacationer's for going on 30 years and probably visited 60-70 using numerous motels, resorts, Bed and Breakfast establishments, Condos, Airbnb's (for monthly stays). Southard Breezes ranks right up there with the best, and location the top of the list.

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• Key West Getaway

  Stayed 7 days ending in November, 2019

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  a guest from Delanco, NJ recommends this vacation rental

  This was our third year with Keywest.condos and we will definitely be back. You can not beat the location of the condos or the amenities that are included.
  The proximity to Fort Zachary and the Beach can not be beat. Everything you need for a beach day is provided; Bikes, chairs, cooler, towels and the family pass make for a great day. The refreshment stand at the beach serves great food at affordable prices.
  If you are flying in don't worry about renting a car, everything is withing walking distance. Save your money for adult beverages :)

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• At the heart of KW

  Stayed 7 days ending in October, 2019

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  Alan G from Malvern, PA recommends this vacation rental

  So nice, coming back next year!

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• Wonderful experience

  Stayed 7 days ending in October, 2019

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  a guest from Millbury, OH recommends this vacation rental

  The condo and owner awesome. The owner thought of everything to make our vacation a wonderful experience. The condo is in a great location. Would definitely stay again.

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• Great condo in a great location

  Stayed 10 days ending in September, 2019

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  Dana & Rodney S from Macomb, MI recommends this vacation rental

  We had a great experience. Working with Tracy easy and she really just wants to make sure you have a great stay in her property! This location is close to everything and has everything you need!

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• Fantastic Southard Breezes

  Stayed 9 days ending in September, 2019

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  Keith B from Queensbury, NY recommends this vacation rental

  We cannot say enough about our experience at Southard Breezes. This condo was perfect for the two of us. It's beachy decor perfectly suits Key West. The unit was extremely clean with modern fixtures. Every detail was thought of from the kitchen, bath, bedroom, and other amenities. We will certainly look forward to returning!

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