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

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TV - SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! (Key West)
Fridge, microwave, oven, stovetop - SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! (Key West)
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A heated pool - SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! (Key West)
Fridge, microwave, oven, stovetop - SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! (Key West)
Escape to a tranquil island ambiance in this elegant refuge within the desirable district of The Meadows. Welcome to an inviting open floor plan with vaulted ceilings, hardwood floors and wooden beams, perfect for entertaining. Unwind in the bright living space with cozy furnishings or enjoy your outdoor oasis by relaxing in the heated pool or dining al fresco under lush foliage.

Reviews

9.8 out of 10
Exceptional

Entire home

2 bedrooms2 bathroomsSleeps 4106 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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 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…

Property amenities

Pool/Spa

  • Heated pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Jetted bathtub
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Gas grill
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • Pet friendly

Suitability/Accessibility

  • Hardwood flooring in public areas
  • Smoke-free property

Services and conveniences

  • Concierge services
  • Iron/ironing board

Location highlights

  • Near a hospital
  • Near the marina
  • Near the sea

Things to do

  • Heated pool
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Swimming nearby
  • Water skiing nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Unit size: 1,142 square feet

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TROPICAL PROPERTIES VACATION RENTAL-KEY WEST
  • Pool
  • Kitchen
  • Washing machine
  • Dryer
TROPICAL PROPERTIES VACATION RENTAL-KEY WEST
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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Property Registration Number 25230-138749

Property is also known as

2450-214090

About the area

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 Fort Zachary Taylor Historic State Park and Florida Keys Beaches. The Kite House and Sails To Rails Museum at Flagler Station are also worth visiting. 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
View more Holiday homes in Key West
Map
Key West, FL

What's nearby

  • #TroveOn A couple miles north of Key West, on the right is Boca Chica Rd, follow that road as far as you can and you'll get to the beach at Geiger Key. The road comes to an abrupt stop, the rest of it was destroyed in a hurricane years ago but you can park there and walk out. The beach is secluded and quiet, except when the Navy is holding flight practices. The planes are so close, you can see the pilots!
    Key West Naval Station
    4 min walk - 0.4 km
  • Duval Street featuring signage
    Duval Street
    15 min walk - 1.3 km
  • South Beach featuring a sandy beach and general coastal views as well as a small group of people
    South Beach
    16 min walk - 1.3 km
  • Southernmost Point featuring signage
    Southernmost Point
    17 min walk - 1.5 km
  • Ernest Hemingway Home and Museum featuring heritage elements and a house
    Ernest Hemingway Home and Museum
    18 min walk - 1.6 km

Getting around

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

Restaurants

  • Circle K
    9 min walk
  • Dions Truman & White
    3 min walk
  • Sandy's Café
    6 min walk
  • The Dive Bar Shirt Club - Grub House
    15 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. Ernest Hemingway Home and Museum and Florida Keys Beaches are also within 1 mile (2 km).

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

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers 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
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

Cleanliness

10

Location

Reviews

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Anonymous

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.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

John R.

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!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

John M.

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.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

A guest from Montreal, Quebec

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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Melissa S.

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!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Page W.

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.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Alicia W.

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 🤙.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Dwight U., Bourbonnais, IL

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!

8/10 Good

Timothy D.

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