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Tradewinds - Beautiful, Private Backyard, XL Porch. Canal, Pool Club, 2 Kayaks.

Photo gallery for Tradewinds - Beautiful, Private Backyard, XL Porch. Canal, Pool Club, 2 Kayaks.

Interior
Living area
Living area
Living area
Dining

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
3 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Kitchen
  • Washing machine
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Explore the area

View in a map
Key Colony Beach, FL
  • Place, Sunset Park Beach
    ‪8 min walk‬
  • Place, Great White Heron National Wildlife Refuge
    ‪15 min walk‬
  • Place, Sombrero Beach
    ‪13 min drive‬
  • Airport, Marathon, FL (MTH-Florida Keys Marathon)
    ‪7 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Queen Bed

Living Room 1

1 Queen Sofa Bed

2 bathrooms

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo

Bathroom 2

Soap · Towels provided · Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen

About this property

Tradewinds - Beautiful, Private Backyard, XL Porch. Canal, Pool Club, 2 Kayaks.

Beautifully appointed DUPLEX is renovated & has ALL NEW furniture & new, high quality mattresses + new Plank-style flooring. A must-see

Cabana Club - Private pool & beach club is included free!

Enjoy 37 feet of dock space on a new step-down dock. New ladder too!
2 KAYAKS in backyard

Enjoy the extra large screened-in porch with a TV. Canal, Dock and full set of amenities, this home has it all!

Air Conditioning throughout the house.

So much privacy outside as there is a 6 to 9 foot privacy fence separating both sides of this duplex in the backyard, plus tropical foliage! It is really a serene setting.

Comes with access to the CABANA CLUB, a private swim club with a temp controlled pool & Beach. 8 blocks away.

BOTH sides of this Duplex are available for rent!

The home features an enormous 15' x 20' screened porch complete with lighting, ceiling fans and table.

Beyond the porch is the patio featuring a couch and 3 New cushioned chairs plus 2 chaise loungers .

For those wanting to fish or boat there is fishing at the dock and at the ready are hoses, electric, fish cleaning table and lighting.

2 KAYAKS here! 1 Double seat and 1 Single seat - Sit On Top style
***(Renters using kayaks agree to the following: 1) Recognize that there are certain
inherent risk associated with using kayaks and assume full responsibility for personal
injury to themselves or others and further dismiss the Homeowner and Property
Manager for injury, loss or damage arising out of the kayak's use. 2) Renter is
responsible for any damages to kayaks and cost to replace, if stolen, including kayak
paddles. ***

This home is fully stocked with amenities! Love to cook? The kitchen includes everything you need to prepare and enjoy your fresh catch.

Large-screen Smart TVs (Netflix, Hulu, Amazon) are located in the family room

The home's open floor plan with French doors overlooking the screened porch and canal provide a bright and airy setting. Plenty of living space inside and out to relax and enjoy the boaters, kayakers and wildlife traversing the waterway.

For those wanting a well-rounded beach experience, take a trip to the CABANA CLUB where you'll have access to an Olympic-size pool, full bar & restaurant as well as a beach. Your rental comes with free passes to the CABANA CLUB for the length of your stay and it's located seven blocks from the house!

Additional Details:
* Master bedroom with king bed, private full bath, Smart TV, large closet, desk area, two dressers, and AC unit
* Guest bedroom with king bed, two closets, large dresser, Smart TV

* All bedrooms are private, you do not need to walk through a bedroom to reach other areas of the home & each has a flat screen TV.
* Hall bath with separate sink & shower areas
* Full BRAND NEW master bath and Shower located in master bedroom
* WiFi
* Fully stocked kitchen
* Ceiling fans throughout the home
* Abundance of linens, pillows, bath towels and pool/beach towels
* 50" Smart TV in family room + a tv in each bedroom + BONUS TV on back porch!

* Canal offering direct access to the ocean and gulf
* Beautiful 15' x 20' screened porch
* Fish cleaning table (with water at the table)
* Dock with electric and water
* Bait freezer
* Weber Gas grill with all accessories

** ASK property manager about BIKES to rent, cheap!

If you enjoy the beach, fishing, boating, island living, amazing food and a warm and inviting community, you’ll love Key Colony Beach! It's a magical place for all ages. Key Colony Beach is a walking and biking community with easy access to must-sees such as Sunset Park (12th and Ocean). Your home is also within walking distance of Key Colony’s three restaurants (Key Colony Inn, Sparky's Landing, Havana Jack's). For fishermen/women Key Colony also boasts sport fishing, a fully-stocked bait shop, rental and charter boats, and a dive shop. For sports enthusiasts, Key Colony has tennis and basketball courts, bocce and pickle ball courts, a playground for kids, and a par-3 golf course!!!

We truly appreciate your consideration of our property and hope you enjoy your time in the Florida Keys!

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House Rules

Check in after 3:00 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

No pets allowed
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Smoking

Smoking is not permitted
1 boat trailer allowed and has to be set back off the street at least 6 feet.
No plastic Bags of any kind or styrofoam allowed in Recycle Bin.. Renter may incur up to a $50 sorting fee for violations
Trash + recycle bins cannot go to street before 12noon on day prior to pickup. Also, they must be brought back to house the day of pickup. $50 fine

Important information

You need to know

Property # 2538575vb
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 not indicated whether there is a smoke detector on the property

About the area

Key Colony Beach

Located in Key Colony Beach, this holiday home is on the waterfront. Captain Hooks Marina and Dive Center and Florida Keys Country Club are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Sombrero Beach and Curry Hammock State Park. Kayaking, snorkelling and waterskiing offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours nearby.
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Map
Key Colony Beach, FL

What's nearby

  • Sunset Park Beach - 8 min walk - 0.7 km
  • Great White Heron National Wildlife Refuge - 15 min walk - 1.3 km
  • Curry Hammock State Park - 4 min drive - 3.1 km
  • Sombrero Beach - 13 min drive - 13.3 km
  • Seven Mile Bridge - 18 min drive - 20.1 km

Getting around

  • Marathon, FL (MTH-Florida Keys Marathon) - 8 min drive

Restaurants

  • ‪Brass Monkey - ‬10 min drive
  • ‪McDonald's - ‬10 min drive
  • ‪The Island Fish Company - ‬5 min drive
  • ‪Circle K - ‬6 min drive
  • ‪Wendy's - ‬11 min drive

Frequently asked questions

Does Tradewinds - Beautiful, Private Backyard, XL Porch. Canal, Pool Club, 2 Kayaks. have a pool?

Yes, this property has an outdoor pool.

How much does it cost to stay at Tradewinds - Beautiful, Private Backyard, XL Porch. Canal, Pool Club, 2 Kayaks.?

As of 10 May, 2026, prices found for a 1-night stay for 2 adults at Tradewinds - Beautiful, Private Backyard, XL Porch. Canal, Pool Club, 2 Kayaks. on 19 Aug, 2026 start from S$290, 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 Tradewinds - Beautiful, Private Backyard, XL Porch. Canal, Pool Club, 2 Kayaks. pet-friendly?

No, pets are not allowed at this property.

How much is parking at Tradewinds - Beautiful, Private Backyard, XL Porch. Canal, Pool Club, 2 Kayaks.?

On-site parking is available at the property.

What time is check-in at Tradewinds - Beautiful, Private Backyard, XL Porch. Canal, Pool Club, 2 Kayaks.?

Check-in begins at 3:00 PM.

What time is check-out at Tradewinds - Beautiful, Private Backyard, XL Porch. Canal, Pool Club, 2 Kayaks.?

Checkout is at 10:00 AM.

Where is Tradewinds - Beautiful, Private Backyard, XL Porch. Canal, Pool Club, 2 Kayaks. located?

Situated on the waterfront, this holiday home is 0.3 mi (0.5 km) from Sunset Park Beach and within 3 miles (5 km) of Marathon Visitor Center and Curry Hammock State Park. San Pablo Catholic Church and Captain Hooks Marina and Dive Center are also within 3 miles (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 31 out of 33 reviews
Rating 8 - Good. 1 out of 33 reviews
Rating 6 - Okay. 1 out of 33 reviews
Rating 4 - Poor. 0 out of 33 reviews
Rating 2 - Terrible. 0 out of 33 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Jerri O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The location was excellent with great location to sunset beach park, pool, weekly farmers market and number of good restaurants. The back yard and back porch were so nice for us to hang out on and watch the boats go out to sea. The neighborhood was safe and quiet - great area for walking and biking.Greg, the owner, was very responsive to our questions and concerns. If we ever return to the Marathon area we wouldn’t hesitate to stay there again.
Stayed 28 nights in Jan 2026
Response from VrboOwner on 19 Mar, 2026
Thank you Jerri. We appreciate it!
Verified

10/10 Excellent

Kelly S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Had a great week!

Great location , relaxing stay
Stayed 7 nights in May 2025
Verified

10/10 Excellent

Chadwick C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Really Enjoyed the back porch and fishing off the dock!
Stayed 7 nights in Sep 2025
Verified

10/10 Excellent

Teresa S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The place is beautiful and they have a lot of little items like kayaks and games
Stayed 7 nights in Jul 2025
Response from VrboOwner on 4 Aug, 2025
Thank you Teresa. We appreciate your comments and hope to see you back here next year! Gregg www.keys2joyrentals.com
Verified

10/10 Excellent

Kimberly F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything about Tradewinds was amazing!! Meals on the screened in porch can’t be beat. Plus plenty of room for rods, reels, and fishing gear if you fish.
Stayed 17 nights in Oct 2025
Response from VrboOwner on 19 Mar, 2026
Thank you for your comments Kim.
Verified

8/10 Good

Melvin S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

Great location and layout. Lots of amenities for fishing kayaks and plenty of outdoor seating.
Stayed 28 nights in Mar 2025
Verified

10/10 Excellent

Kerri M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful house

This house was just as described online. It was clean, nicely decorated and had everything we needed! Lovely location on a canal and close to everything. We had a great stay!
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Rachel M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nice house, comfortable, with all the amenities. Good location, nice neighborhood, canal access, big screened porch.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Elizabeth B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Tradewinds was absolutely perfect!

The location, access to the Cabana Club, and relaxing on the beautiful porch....everything was better than we expected. As annual visitors to St Croix, we found we loved this option ao much more.
Stayed 8 nights in Apr 2024
Verified

10/10 Excellent

Lisa H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful! Perfect location! The property is very well-maintained & impeccably clean! Kitchen was stocked with everything we could have needed! Plenty of space for our son & daughter in law & grand babies to join us for a few days. We loved the outdoor space, had a fun ride on the kayaks & watching the boats go by. Even saw a shark & spotted eagle ray swim past! Enjoyed the beach at Sunset Park & happy hour at Sparky’s is the best! Gregg was super helpful & engaged! We can’t wait to go back!
Stayed 7 nights in Oct 2025
Verified

6/10 Okay

Christina D.

Liked: Check-in, communication, listing accuracy
Disliked: Cleanliness
Unfortunately the linens were all blood stained and required removing (so unacceptable) and washing in advance of using the beds! I highly recommend you connect with your cleaning service as it was an OBVIOUS miss on their part. It was also very disappointing as the neighbor to the left built up the divider between the two homes eliminating the view up the canal. We have been visiting KCB for 30 years yearly and have never encountered this situation. In addition there are very few pans to cook with and the fridge had a very strong fish odor which also required additional cleaning as it was "gross" every time you opened the fridge.
Stayed 14 nights in Feb 2026
Response from VrboOwner on 19 Mar, 2026
Thank you for your comments and we apologize for not seeing the stain on the bed sheet, though the sheet was cleaned, the stain should have been removed. There has not been any changes to the fence but we will post more photos of the backyard on the website today. The fence dividing the properties to the left and right gives terrific privacy. I know some people do a lot of cooking so we will get more, quality pans.
Verified

10/10 Excellent

Shana S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful place

Nice updated house with great outdoor area. Love key colony. We will be back.
Stayed 7 nights in Apr 2023
Verified

10/10 Excellent

Katy H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best Rental Ever

We stayed at Tradewinds for a week-long getaway. We brought our boat and the amenities for boating were more than we could have asked for. We had everything we needed in the house. The location is perfect and the home itself is absolutely beautiful. There is a privacy fence on both sides of the back deck area so your outdoor space is completely private. The screened in back porch was probably our most favorite part. We will definitely be back!
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

amy k.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

We loved our stay at tradewinds. We had everything we needed and more. Location was great. House was perfect and very spacious. Newly updated. Thank you for the hospitality! We will be back.
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Sarah S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Homey little suite

Had a comfortable stay at Gregg’s place. It was our first time here but we felt right at home. We especially enjoyed the dock, yard and screened in patio though working remotely from the desk a couple of days in the master suite was also comfortable. The cabana club was a fun addition and we will definitely be back!
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Susan G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house!

Perfect house on the canal. Updated furnishings and great location. All the amenities. Loved sitting out back on the canal and in the screened in porch. Highly recommend !
Stayed 7 nights in Feb 2023
Verified

10/10 Excellent

Michele D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Friends Getaway

It was the perfect key location, in the middle of everything. The screened porch was a wonderful place to relax. The fellas enjoyed being able to fish in the canal. The pool and the beach at the Club Cabana were perfect.
Stayed 7 nights in Oct 2022
Response from VrboOwner on 23 Oct, 2022
Thanks Michele and glad you had a nice time here. Hope you can come back soon.
Verified

10/10 Excellent

Ulrich B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cute Place

The House is wonderful and the area quite. All met our imagination and over. We definitely recommend to stay there. We have had a nice holiday, relaxing all the time. Many Thanks to the owners. Family from Germany
Stayed 9 nights in Oct 2023
Verified

10/10 Excellent

Andrew P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Brilliant stay at Key Colony Beach

There is nothing not to like about this property. Good room sizes, well equipped kitchen, the simple access process, the membership of the Cabana Club, the kayaks.... I could go on. I would highly recommend it.
Stayed 7 nights in Oct 2024
Verified

10/10 Excellent

Diana H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfection in KCB

This sparkling, brand new house was ideal for our family of 5 adults! We were working remotely, but also made use of the kayaks and went daily to the Cabana Beach Club. We are watched the Super Bowl on the screen porch and celebrated Valentines Day oceanfront at Havana Jacks. Gregg was very accommodating and we had a great time!!
Stayed 7 nights in Feb 2022
Verified

10/10 Excellent

Krista K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfection in Paradise

Property is as pictured and described. After staying on Key Colony 4 times, this is by far the most well appointed and tastefully decorated rental. Attention to detail was paid to every aspect. The screened in back patio, complete with a dining set, comfortable lounging furniture, and TV was the perfect way to unwind every evening! Our time at Tradewinds was extremely enjoyable and this is definitely my first choice for my next visit to town!
Stayed 7 nights in Dec 2024
Verified

10/10 Excellent

Paul S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Vacation at Tradewinds

The house was as advertised online and in photos. Very open and airy and great lanai. Looked like a brand new fridge plus an outdoor bait freezer. Step down dock was new as well. Lots of bedding and extra towels. Washer and Dryer were new as well. Very well equipped and great location near sunset park. Highly recommended.
Stayed 28 nights in Feb 2025
Verified

10/10 Excellent

Crissie W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Small, but mighty

We stayed at Tradewinds during our recent Spring Break trip. I have teen boys so it was nice to have 3 bedrooms so they could have some time apart. While the home itself isn't as big as other 3 bedroom homes on KCB everything about Tradewinds was done right. The kitchen utensils were nicely made (although the knives could use sharpening- but I've NEVER stayed anywhere that has sharp knives so I do not hold that against them), the linens were plush and great quality. There is both a Keurig and a drip coffee pot. We had all the pots/pans we could need and many other renters left spices behind (as did we) so make sure to check the supply before you go to the grocery store. Gregg was easy and great to communicate with. We did not have any problems during our stay, so the only communication we had was leading up to our visit and he was always prompt in answering any questions I had. I would highly recommend this property.
Stayed 7 nights in Mar 2024
Verified

10/10 Excellent

Sherri L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a great house! It was very clean and had everything we needed and then some. Quiet, relaxing neighborhood and fun to see the wildlife in the canal, including big tarpon and manatees. Gregg's communication was excellent and he showed up to the house in 10 minutes with a tall ladder when we had a chirping smoke alarm. We thoroughly enjoyed staying here. Thank you!
Stayed 7 nights in Apr 2026
Verified

10/10 Excellent

james r.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful quiet location to relax and enjoy the Keys.

The house was nice and clean. Check in was easy and the property management company was quick to respond to a minor unforeseen issue on the property. We had three couples in the house and it was a good size for all of us. Plenty of towels and kitchen items for everyone to stay comfortably. The back patio area was a great spot to hang out and relax. We rented a boat locally and docked it to load up for the day. Very convenient. The owner has a light in the water by the dock so you can see fish and sharks at night when you sit on the back deck area. The beach club was nice and easy to access and use. It was a nice benefit to have accessible to us. There is a good restaurant in the community and it is very safe with its own small police force. It is centrally located in the Keys so we drove to Islamorada one day and to Key West another. Grocery stores are close for supply runs. I would highly recommend staying here for a relaxing getaway.
Stayed 7 nights in Nov 2022

About the host

Hosted by Gregg

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Languages:

English

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