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SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!

Photo gallery for SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!

A spacious living room with a white sofa, a wooden coffee table, and a view of a lush garden through large windows.
A swimming pool surrounded by lush greenery, a covered outdoor seating area, and a building with a green door.
A modern kitchen with white cabinets, a built-in microwave, and a large island.
A modern kitchen with white cabinets, a central island, and a dining area with a wooden table and chairs.
A tropical garden with a gravel path, various plants, and a white building with a porch.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Duval Street

Popular amenities

  • Patio
  • Private pool
  • Gas barbecue
  • Air-conditioning
  • Pet-friendly
  • Refrigerator

Explore the area

View in a map
Key West, FL
  • Place, Key West Naval Station
    ‪5 min walk‬
  • Place, Duval Street
    ‪15 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪18 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪7 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 King Bed

Bedroom 2

1 Double Murphy Bed

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only · Jetted bathtub

Spaces

Deck or patio
Porch or lanai
Kitchen
Office
Dining area

Add dates for prices

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About the area

Key West

Located by the sea, this holiday home is in Key West Historic District, a neighbourhood 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 cycling and ecotours nearby.
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Map
Key West, FL

What's nearby

  • Key West Naval Station - 5 min walk - 0.4 km
  • Duval Street - 15 min walk - 1.3 km
  • Ernest Hemingway Home and Museum - 18 min walk - 1.6 km
  • South Beach - 18 min walk - 1.6 km
  • Southernmost Point - 20 min walk - 1.7 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 7 min drive

Restaurants

  • ‪Circle K - ‬9 min walk
  • ‪Square Grouper Key West - ‬17 min walk
  • ‪Harpoon Harry's Restaurant and Bar - ‬17 min walk
  • ‪Sandy's Café - ‬5 min walk
  • ‪El Siboney Restaurant - ‬11 min walk

Frequently asked questions

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 at SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!?

On-site 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!?

Checkout 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 holiday 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 mile (2 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 8 out of 9 reviews
Rating 8 - Good. 1 out of 9 reviews
Rating 6 - Okay. 0 out of 9 reviews
Rating 4 - Poor. 0 out of 9 reviews
Rating 2 - Terrible. 0 out of 9 reviews

6.0/10

Cleanliness

10/10

Check-in

6.0/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

From a partner site

10/10 Excellent

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
Response from VrboOwner on 18 Feb, 2023
Thank you for your wonderful review Merci! We are so thrilled to hear how much you loved this Key West retreat and we are looking forward to hosting you again next year. Thank you for being our guest!
From a partner site

10/10 Excellent

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!
Response from VrboOwner on 28 Jun, 2022
Thank you for your incredible review Melissa! We are so thrilled to hear how much you loved this Key West retreat and we are looking forward to hosting you again next time you visit the island. Thank you for being our guest!
From a partner site

10/10 Excellent

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!
Response from VrboOwner on 2 Sept, 2024
Thank you for your wonderful review John. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!
From a partner site

10/10 Excellent

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.
Response from VrboOwner on 8 Apr, 2023
Thank you for sharing a review of your recent experience John. Our team here at Best of Key West Rentals is committed to providing high-quality guest service, and we’re thrilled to hear that we made a good impression on you. We hope you’ll visit us again soon.
From a partner site

10/10 Excellent

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.
Response from VrboOwner on 9 May, 2025
Thank you so much for your kind words Peirce! We're thrilled to hear you had such a great experience during your two-month stay. It’s wonderful to know the home and neighborhood met your expectations and that our team could make your time here even more enjoyable. We truly appreciate your recommendation and hope to welcome you back anytime you're in Key West!
From a partner site

10/10 Excellent

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 🤙.
Response from VrboOwner on 16 Jul, 2022
Thank you for this great review Vincent! We are thrilled you enjoyed the property and hope to host you again in the future!
From a partner site

10/10 Excellent

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!
Response from VrboOwner on 22 Mar, 2023
Thank you for your wonderful review Dwight. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!
From a partner site

10/10 Excellent

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.
Response from VrboOwner on 20 Jul, 2024
Thank you for your feedback on your winter stay Alan. We are so glad that you enjoyed your time spent at this home. We appreciate your feedback that we will rely back to the owners for consideration. Thank you again and please reach out to us for your next Key West vacation!
Verified review

8/10 Good

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.
Stayed 29 nights in Nov 2021
Response from VrboOwner on 11 Jan, 2022
Dear Timothy, we are sorry you felt short of your expectations, however the home isn't advertised as having a garbage disposal or an ice maker. The landscapers come twice a month, unfortunately your stay was right in the middle of the time when the tree in the front was shedding its leaves so unless they came everyday, the grounds were never going to be free of leaves. The lush surrounding vegetation provides a lot of privacy, it is a shame you felt like a fish in a bowl., most of our guests enjoy the indoor/outdoor feel. We are addressing the other issues you mentioned and would love the get a second chance at finding you the perfect property next time you visit the island!
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