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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 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.
A modern kitchen with white cabinets, a built-in microwave, and a large island.
A swimming pool surrounded by lush greenery, a covered outdoor seating area, and a building with a green door.

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
2 bedrooms2 bathroomsSleeps 4

Popular amenities

  • Private pool
  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning

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

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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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property Registration Number 25230-138749
Property # 9577316
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

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.
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
  • Clarence S. Higgs Memorial Beach Park - 17 min walk - 1.5 km
  • Ernest Hemingway Home and Museum - 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

  • ‪Cuban Coffee Queen Waterfront - ‬18 min walk
  • ‪Sandy's Café - ‬5 min walk
  • ‪Circle K - ‬9 min walk
  • ‪Dions Truman & White - ‬3 min walk
  • ‪Pepe's Cafe - ‬18 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.

How much does it cost to stay at SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!?

As of 19 Aug, 2026, prices found for a 1-night stay for 2 adults at SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! on 1 Sept, 2026 start from S$11,182, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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).

About the host

Hosted by Wendy Zintsmaster & Team

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Languages:

English

Premier Host

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