Tradewinds

Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK
Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK
Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK

Cabin in Key West, Florida

Guests
12 Guests
Bedrooms
4 Bedrooms
Bathrooms
2 Bathrooms
Pets allowed
Pets allowed

Locally Owned & Operated

Florida Keys

Florida Keys

Casago Franchise Owner

Locally Owned & Operated
Rating4.39

What our guests are saying...

AI-generated from guest reviews for this property

Tradewinds is especially well suited for groups, with side by side cottages that give guests plenty of space, comfortable bedrooms, and a layout that balances togetherness with privacy. Guests frequently describe the homes as cute, charming, cozy, and comfortable, with roomy interiors, comfortable beds, and a well stocked setup that had what they needed for a pleasant stay. Cleanliness stands out consistently, with many guests noting that Tradewinds was clean, neat, orderly, and well kept. The location is a major highlight, with guests praising Tradewinds for being close enough to walk to shops, restaurants, bars, and popular attractions while still feeling tucked just off the busiest areas. Guests also appreciated convenient access and the ease of parking, especially for larger groups and those bringing cars or golf carts. Repeatedly enjoyed features included the hot tubs, grill, outdoor shower, porch, backyard spaces, and strong air conditioning in much of the property.

Overview

Rustle up your favorite people for a memorable trip to Key West with these two homey cottages. Sitting side-by-side in a great location, each house features two bedrooms and one bathroom, a private parking space, dog-friendly accommodations, and a tranquil garden with a private hot tub in the back - what's not to love?

Located half a block from all the excitement of Duval Street, you can walk to historical landmarks like the Key West Lighthouse and The Ernest Hemingway Home and Museum, then stroll south to look out to sea from Southernmost Point. A short walk north will reveal more bars and restaurants than you could hope for on an island this size!

Fuel your day with a home-cooked breakfast in your fully equipped kitchen, sip coffee in the tropical garden, and get a morning soak in the hot tub for some extra relaxation. Freshen up using the outdoor shower, have a barbecue using the gas grill, and kill some time browsing the free WiFi or surfing the flatscreen cable TV. A dog is welcome for a small nightly fee.

Put life on hold for a moment and settle into paradise with these two cottages on Key West - book today!

You must be 25 years or older to rent this property.

Amenities

Central AC
Central AC
Internet
Internet
Cable
Cable
TV
TV
Microwave
Microwave
Fridge
Fridge
Stove
Stove
Gas grill
Gas grill
Hot tub
Hot tub
Dog-friendly
Dog-friendly

Sleeping Arrangements

Bedroom 1

sleeps 2

Beds
1 king bed

Bedroom 2

sleeps 2

Beds
1 king bed

Bedroom 3

sleeps 2

Beds
1 king bed

Bedroom 4

sleeps 2

Beds
1 king bed

Location

Key West, Florida, Home

(Exact address will be provided after booking)

Location

Rating

4.39
66 reviews
5 Star
61%
4 Star
27%
3 Star
6%
2 Star
3%
1 Star
3%
search
Tracy C2026-03-14

Great clean place to stay for a group. Close to most things.

Kimberly W2026-02-10

The cottages windows are not sealed at all; in the right cottage there is a huge whole in the windowsill of one of the bedrooms. Not family friendly. There is also termite damage and holes in the home on the right. The cottage on the left was nice and had been updated... but to the bare minimum. Also the hot tub on the left side did not work and water was gross and stagnant. Be aware that there is no heat on the units on the right cottage, only on the left cottage. Also neither bath tubs plugs worked so be mindful of that. There is no dishwasher on either side. Also no access to a washer and dryer, they have the area locked up so you can't use it while you are staying here. We called to get assistance to ask for any additional linens or heaters since there was a baby with us, but the person on the other end was rude and dismissive and basically said it's not policy to provide anything more than what is there.

William C2026-01-24

This property was good for my group because we have an early group and a late night group. So we were able to divide up the houses based on that. The houses were fine, a little outdated but the two houses worked out and having parking was great for our golf carts. I would stay here again. We had one little issue with a shower not draining but the management company fixed it immediately. High marks for that.

Sally K2025-11-26

The location was excellent. What just what we needed. We loved walking leisurely around all of the stores.

Sherri T2025-11-16

Close to Duvall St

Jennifer R2025-10-17

This was a lovely way to go to Key West with friends side by side twin cottages only a block from Duval!

$1501
avg / night
Rating4.39

You won't be charged yet