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
Key West, FL
Key West Naval Station
Place, Key West Naval Station
5 min walk
Duval Street
Place, Duval Street
15 min walk
Ernest Hemingway Home and Museum
Place, Ernest Hemingway Home and Museum
18 min walk
Key West, FL (EYW-Key West Intl.)
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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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.
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
Languages:
English
Premier Host
They consistently provide great experiences for their guests