Close to Duval Street and Ernest Hemingway Home and Museum, SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! provides amenities like laundry facilities. Stay connected with free in-room WiFi.
Reviews
9.89.8 out of 10
Exceptional
Popular amenities
Pool
Kitchen
Washer
Dryer
Pet friendly
Free WiFi
Add dates for prices
About this property
SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!
CATCH YOUR SECOND WIND… Unplug in this newly renovated and elegant refuge, a place of tranquility with an island ambiance. Equipped with 2 bedrooms and 2 bathrooms, this home welcomes you into a peaceful setting within the desirable district of The Meadows. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE
DETAILS & AMENITIES… Welcome in to an inviting, open floor plan boasting vaulted ceilings, hardwood floors and stunning wooden beams ready to entertain your crew for your getaway to Paradise. A fully equipped kitchen allows for seamless meal prep to enjoy together at the dining table for 6. Enjoy the bright and cheery living space with cozy furnishings and a TV for your lazy days in with gorgeous views beyond pocket doors of your outdoor oasis. This home is equipped with Youtube TV for live steaming.
SLEEPING ARRANGEMENTS… Sleep tight in one of two cozy bedrooms both equipped with storage space and flat screen TVs. The primary king suite comes with an en suite bathroom with a double sink vanity and jet tub/shower combination. The second bedroom has a Queen Murphy bed and desk so the room can also be used as an office space. The second bathroom lies in the hallway with a shower/tub combination.
OUTDOOR LIVING… Soak up your surroundings as you head out to your private backyard dream tucked within lush and vibrant foliage. Cool off in the pool which comes heated in the winter month and dine al fresco in the island breeze equipped with a gas grill. Lounge on your private front porch over your morning cup of coffee as you dream of your days adventures ahead. The Meadows district is a charming and convenient location to downtown Key West, yet tucked away for a peaceful evenings rest.
PARKING... There is one parking space making coming and going a breeze.
PETS... Dogs are considered at this home and a pet fee is required. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests.
MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable)
BOOKING DATES... This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.
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!
CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund.
Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).
YOUR SLICE OF PARADISE AWAITS… Virtual Tour Url: https://my.matterport.com/show/?m=Sq73xtcNES3
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Key West Historic District
PINEAPPLE BREEZE ~ JUST RENOVATED Home in The Meadows with Pool!
Located by the sea, this vacation home is in Key West Historic District, a neighborhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby. Visit our Key West travel guide
Does SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! have a pool?
Yes, this property has a pool. Pool types include heated pools.
Is SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! pet-friendly?
Yes, pets are allowed at this property.
How much is parking?
Onsite parking is available at the property.
What time is check-in at SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!?
Check-in begins at 4:00 PM.
What time is check-out at SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!?
Check-out is at 10:00 AM.
Where is SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! located?
Located in Key West Historic District, this vacation home is within a 15-minute walk of The Unitarian Universalist Fellowship of Key West and Duval Street. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 1 mi (2 km).
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Reviews
SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! Reviews
9.8
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.More informationOpens in a new window
6.0
Cleanliness
10
Location
Rating 10 - Excellent. 8 out of 9 reviews
10 - Excellent
8
Rating 8 - Good. 1 out of 9 reviews
8 - Good
1
Rating 6 - Okay. 0 out of 9 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 9 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 9 reviews
2 - Terrible
0
Reviews
From a partner site
10/10 Excellent
John R.
Sep 2, 2024
Perfect house for the summer
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 rented this house for 3 months, and was close enough to all the action, and also super convenient for parking and access to the park to walk our dogs twice a day. We loved it. Not to mention a pool to cool down in!
From a partner site
10/10 Excellent
Anonymous
May 8, 2025
Great experience
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:
I spent two months at this property and loved it. It is a peaceful neighborhood, and the property is beautiful—just as advertised in the pictures. I recommend it highly. Also, the property manager and management company are first rate and very responsive.
From a partner site
10/10 Excellent
John M.
Dec 23, 2023
A pleasant stay at Second Wind
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was more than satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
We're having a terrific time. We've been here for 7 weeks with 10 days to go. The location is perfect for us, in a quiet neighbourhood (the Meadows) but an easy walk or bike ride to anything we want to do. The house itself is bright and airy. The housekeeping and pool/landscaping services are excellent. The property management team has been very helpful and are quick to respond. If we could make some minor suggestions, they would be: to add towel racks to the principal bathrooms and more dishware, especially saucers for the cups, in the kitchen (which is very well-appointed otherwise). The addition of a light over the dining room table would be helpful. We find the living room sofa a bit too deep to be comfortable for TV viewing. These are relatively minor issues and we've loved our stay here.
From a partner site
10/10 Excellent
A guest from Montreal, Quebec
Feb 17, 2023
Best vacation!
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:
Brian was helpfull I loved my stay and I even rebooked for next year
From a partner site
10/10 Excellent
Melissa S.
Jun 25, 2022
Wonderful trip
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:
Second Wind property was a wonderful respite from the cold climes of Wyoming. The location and proximity was perfect for us. The neighborhood was quiet, neighbors lovely, house was comfortable. Team Truman and Company are excellent!
From a partner site
10/10 Excellent
Page W.
Apr 5, 2023
March 2023 Second Wind Stay
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:
Beautiful cottage in great location in Key West. Rental team superb throughout, property manager Brian was great and immediately responded to any issues or concerns. Highly recommend.
From a partner site
10/10 Excellent
Alicia W.
Jul 7, 2022
Wonderful Retreat
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:
Everything was exactly as we hoped it would be. Good location with off street parking (a definite plus). The one problem that we had (lock problem) was quickly and efficiently solved by Brian. Definitely would recommend to friends 🤙.
From a partner site
10/10 Excellent
Dwight U.
Mar 20, 2023
Second Stay at Second Wind.
Rating Details:
The property manager was very helpful.
The vacation rental was very clean.
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 was our second stay at this deluxe house on Albury Street. The perfect home in Key West. We brought our bikes and never drove our car again for the month. You are an easy bike ride from Duval Street and all it has to offer. Once you are home in this private little oasis the fun really begins. The back yard and pool are very secluded and very beautiful. A tropical heaven!
Verified review
8/10 Good
Timothy D.
Dec 11, 2021
Liked: Check-in, location, listing accuracy
Misses
No garbage disposal or ice maker. The freezer would stay open after you shut the fridge.
The landscapers came once during our stay and they were there on the day we left. The yard and street were a mess.
The lack of curtains in the living room provided NO privacy. It was like we were in a fish bowl.
The light over the stove did not work.
The front gate is falling apart.