Windward Isle | House in Key West

Q: How much does it cost per night to stay in Windward Isle?

Best-rates for the Windward Isle starts from $507 per night with includes Pet Friendly, Security/Safety, Wellness Facilities, Guest Services, Barbecue/Outdoor Cooking, Child Friendly, Hot Tub with all other amenities. Perfect for Weddings is committed to ensuring every guest experiences a comfortable and extraordinary stay, whether planning a romantic getaway, a honeymoon, a pet-friendly stay, or celebrating with the entire wedding party.

| 7.5 (14 Reviews) | Pet Friendly 2 Bedrooms 1 Bathroom 6 Guests

2 Bedroom House in Old Town, Key West

A 4-minute walk from Duval Street in Key West, Windward Isle provides accommodations with access to a hot tub. The property is close to several well-known attractions, a 16-minute walk from Mallory Dock, 0.9 miles from Mallory Square, and a 7-minute walk from San Carlos Institute Casa Cuba. The property is a 10-minute walk from South Beach and within 200 yards of the city center. Providing a patio, this vacation home also provides guests with a satellite TV, a well-equipped kitchen with an oven, a microwave, and a toaster, as well as 1 bathroom with a hot tub and a hair dryer. For added privacy, the accommodation features a private entrance. Popular points of interest near the vacation home include Ernest Hemingway Home and Museum, Southernmost Point, and Key West Aquarium. Key West International Airport is 2.5 miles away.

Windward Isle is located in Key West.

This 2 Bedrooms House is suitable for tourists and travelers. It has several amenities that would guarantee your comfort. These amenities include: Pet Friendly, Security/Safety, Wellness Facilities, and several others. This is a 3 star rated property and has over 14 reviews with the average score of 7.5 . Coming to Key West and needing a place to stay? Be it for work or for leisure, consider staying at this House for your next visit, you will surely love it.

You can check the reviews and description of this 2 Bedrooms House if you want to learn more about this PerfectforWeddings place in Key West. These details are authentic, as they are provided by our partner, booking.com.

This Windward Isle in Key West is well equipped and has all facilities that have been listed below. Please note that these details were shared to us by booking.com for the listed “Windward Isle”. We solely rely on their shared details and are regarded as “accurate”. If you have any concerns about the information or accuracy describing this House, please let us know.

Amenities

Pet Friendly
Security/Safety
Wellness Facilities
Guest Services
Barbecue/Outdoor Cooking
Child Friendly
Hot Tub

Policies

Check-in The minimum age for check-in is 25

Payment Policy Credit card required

Pet Policy Pets are allowed upon request and charges may apply.

Other Policy Guests will receive a rental agreement, which must be signed and returned directly to the property prior to arrival. if the agreement is not received, the guest should contact the property management company at the number on the booking confirmation, please note that only registered guests are allowed at the property, guests shall abide by the property's policy. quiet hours are from 22:00 to 8:00.guests are required to show a photo id and credit card upon check-in. please note that all special requests are subject to availability and additional charges may apply, please inform of your expected arrival time in advance. you can use the special requests box when booking, or contact the property directly using the contact details in your confirmation, this property does not accommodate bachelor(ette) or similar parties.

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Reviews

Darran, United Kingdom Nov 15, 2025 08:00:00 AM

Reviewer Type: Extended Group

Travel Purpose: leisure

Positive: Location

Negative: Very noisy. Property next door hand a party that went on till after 2am. Very little sleep

Jennifer, USA Jul 21, 2025 07:00:00 AM

Reviewer Type: Family With Children

Travel Purpose: leisure

Greg, USA Jul 5, 2025 07:00:00 AM

Reviewer Type: Couple

Travel Purpose: leisure

Positive: Location to state park and other attractions

Negative: Outdated wall finishing

Summary: Relaxing weekend

Paul, United Kingdom May 3, 2025 07:00:00 AM

Reviewer Type: Extended Group

Travel Purpose: leisure

Positive: Location was excellent. Good size rooms.

Negative: Poor state of repairs. Hot tub was filthy, don’t plan on using that. Outside area a mess. Generally very tired property

Summary: A very tired property but in a great location.

Erika, USA Mar 26, 2025 07:00:00 AM

Reviewer Type: Extended Group

Travel Purpose: leisure

Positive: This property is in a great location, one block from Duvall and walking distance to everything we wanted to do. It has its own parking space off the street so we didn’t have to search for parking. The house was clean and perfect for what we needed during our stay in Key West!

Summary: Excellent Location!

Kristina, USA Feb 1, 2025 08:00:00 AM

Reviewer Type: Extended Group

Travel Purpose: leisure

Janie, USA Jan 22, 2025 08:00:00 AM

Reviewer Type: Family With Children

Travel Purpose: leisure

Pamela, USA Sep 20, 2024 07:00:00 AM

Reviewer Type: Couple

Travel Purpose: leisure

Positive: Older house with character. One of the few times we brought our dog instead of putting him in kennel. All of Key West was very dog friendly and this house was perfect for our pooch and us!

Negative: Trip hazards. The patio stones to walk in house. The small step just inside back door, the uneven sidewalk and tight steps in front of house. In all honesty, the entire downtown area is trip accidents waiting to happen! I dont have the best balance and I was on high alert everywhere I walked! But…No fall this trip and I would love to come back for a return trip. There was a maintenance call to repair a ground floor window that would not lock. Management fixed the window super fast. You do have to hand wash dishes. I am used to hand washing, but others may find that unexpected.

Summary: Unexpected classic charm with a wild rooster wake up call!

Grace, USA Jun 17, 2024 07:00:00 AM

Reviewer Type: Family With Children

Travel Purpose: leisure

Positive: The location of this property is absolutely perfect and it includes parking! For this alone, it's worth checking out. It's easily walkable to everything on Duval street and the two bedrooms are both of equal size, so perfect for a couple who is sharing. The house is cute and historic.

Negative: Unfortunately, the house is not well insulated and does not have central AC. It has several portable and mini-split systems that were all running on full blast and failing to significantly cool off the house. The kitchen and bathroom have no AC at all, which was unbearable for our early May trip. Of note: the parking spot is very narrow and uses a shared driveway. Bigger cars will not fit.

Summary: Cheap, perfect location, needs better AC/insulation

SUBRAMANI, USA May 4, 2024 07:00:00 AM

Reviewer Type: Family With Children

Travel Purpose: leisure

FAQ's

Is this Windward Isle pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

What time is check-in & check-out at Windward Isle?

Check-in time for Windward Isle starts counting from 4:00 PM and check-out is until 10:00 AM. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

Does the Windward Isle have a swimming pool?

No, this Windward Isle does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Windward Isle?

Best-rates for the Windward Isle starts from $507 per night with includes Pet Friendly, Security/Safety, Wellness Facilities, Guest Services, Barbecue/Outdoor Cooking, Child Friendly, Hot Tub with all other amenities. Perfect for Weddings is committed to ensuring every guest experiences a comfortable and extraordinary stay, whether planning a romantic getaway, a honeymoon, a pet-friendly stay, or celebrating with the entire wedding party.

Is Windward Isle a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house 3 stars or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Windward Isle wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Windward Isle has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Windward Isle?

Based on the information reported by the owner or manager, the Windward Isle indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Windward Isle?

Based on the information reported by the owner or manager, details for the cancellation policy for the Windward Isle are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

Check House Availability

Nightly rates from:

US $507