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Trade Winds Life | Cottage at Amazing Margaritaville Resort

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Trade Winds Life
Outdoor Gas BBQ Grill
Counter seating and full kitchen
Living room with TV
Living room with TV

Reviews

9.6 out of 10
Exceptional
3 bedrooms3 bathroomsSleeps 9168.9 sq m

Popular amenities

  • Parking available
  • Pet-friendly
  • Dryer
  • Washer
  • Hot tub

Explore the area

Map
Kissimmee, FL
  • Island H2O Live!
    ‪20 min walk‬
  • Mystic Dunes Golf Club
    ‪4 min drive‬
  • Disney's Animal Kingdom® Theme Park
    ‪18 min drive‬
  • Kissimmee, FL (ISM-Kissimmee Gateway)
    ‪31 min drive‬

Rooms & beds

3 bedrooms (sleeps 9)

3 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Spaces

Deck or patio
Kitchen
Balcony
Outdoor play area
Garden

About this property

Trade Winds Life | Cottage at Amazing Margaritaville Resort

Dreamin’ about a cheeseburger in paradise? We’ve got you covered at Trade Winds Life, a nautical blue cottage nestled in Jimmy Buffet’s Margaritaville Resort. With a private pool and hot tub, close proximity to major theme parks, and the ability to accommodate a large group, there’s no better place to indulge in every virtue and vice.

Upon entry, it’s obvious this is an adorned home with furniture in pristine condition, tasteful decor, and new furnishings throughout. The main floor is open-concept so there’s a flow between the dining, kitchen, and living areas. The living room is cozy with a couch, TV, and lovely accent wall. From here, guests have access to open up the back door and step out onto the covered patio. An outside oasis awaits with a pool and hot tub.

Back inside, the kitchen is equipped with a suite of stainless steel appliances and everything you may need to whip up delicious meals from home or a quick pre-theme park snack. The large island is simply gorgeous with marble countertops, bar seating for 4, and a stylish light fixture overhead. Steps away, enjoy meals together at the dining table for 6.

The home sleeps up to 9 guests comfortably between 3 suite-style bedrooms and a sofa sleeper in the bonus room. Each space is tastefully decorated and is furnished with cool, crisp linens to ensure everyone has a restful stay.

Bedroom #1, located on the main living floor, features a King bed, TV, and en-suite. The en-suite has dual sinks and a stand-up shower.

Bedroom #2, located upstairs, is configured with 2 Twin beds, a trundle bed, TV, and en-suite. The en-suite has a shower/tub combo.

Bedroom #3, also located upstairs, is decked out with a King bed, TV, and en-suite. The en-suite has a stand-up shower.

In addition to the 3 bedrooms, a bonus space upstairs features a large sectional with a sofa sleeper option. With a TV and plenty of space, this room is ideal for extra sleeping quarters or perfect to snuggle up on the couch and enjoy a movie together.

THINGS TO NOTE:
- Margaritaville has a “no logo” policy for parking on site. If you are driving a vehicle with a company logo, they will not allow you to park on site. If you are unsure, please send us a photo of your vehicle for the HOA to advise us.
- Guests do NOT have access to the Owner’s-Only Margaritaville Resort swimming pools or resort amenities - commonly called "The Fins Up Club."
- Please note this home is pet friendly and able to take in your pets for $35/night per pet. The pet fee is NOT included in the rent and needs to be paid before arrival.
- Patio grills. Your home might have a BBQ grill installed on the patio. If you decide to use the grill, there is a $95 fee. You should request to use the BBQ grill prior to your arrival as we have locks on the grills. After each checkout and before any arrival, our operations team checks the grills by taking pictures and/or videos. If it is determined that you or your guests used the grill, you will receive communication from our guest services team advising you that your card will be charged. BBQ grill fees are non-refundable.
- A washer/dryer is available for guest use.
- Please be sure to read through the check-in details for instructions on trash disposal.
- A Ring doorbell is attached to the main entrance of this unit and is actively recording for security purposes.
-In case of hurricanes or inclimate weather or due to necessary repairs, certain amenities may be closed and unavailable during your stay. We cannot guarantee the availability of each amenity​ in the community.
-Due to unusually high amount of theft and destruction we regret to tell you we no longer supply wash clothes. If this is a “must have” item for you, you may request them ahead of your stay. Thank you for understanding as this helps keep our rent low for you and your family.

Margaritaville Resort is less than 5 miles from Walt Disney World and just 10 miles from Universal Studios. Guests of the resort have access to on-site restaurants, live music, shopping, and comedy shows, to name a few! To ensure every member of the family gets their perfect vacation, you can also find an on-site playground for the kids and a designated dog park for your beloved pets. SunsetWalk, a modern shopping complex offering just about everything under the sun, is .6 miles away and a quick walk. A shuttle is also available with regular rotations of pick-up and drop-off. The SunsetWalk complex features Island H20 Waterpark, over a dozen noteworthy restaurants, a dine-in movie theater, video arcade, live music, farmers market, spa, and if you can believe it SO much more! There’s truly something for everyone!

Please note that requests for late checkout must be received no later than 10:00 AM local time on the day prior to your departure. Early check-in and late checkout are based on availability and require approval, and may be subject to an additional fee of $30 per additional hour requested. Please feel free to contact us if you are interested in arranging.

Property manager

Grand Welcome

Languages

English, Spanish

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washer
Dryer
Pet-friendly

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House Rules

Check in after 4:00 PM
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

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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property

About the area

Kissimmee

Located in Kissimmee, this holiday home is in the city centre and near theme parks. Mystic Dunes Golf Club and Reunion Resort Golf Course are worth checking out if an activity is on the agenda, while those in the mood for shopping can visit Flamingo Crossings Town Center and Old Town. Walt Disney World® Resort and Disney's Blizzard Beach Water Park are not to be missed. Explore all the area has to offer with cycling and hiking/biking trails.
Map
Kissimmee, FL

What's nearby

  • Island H2O Live! - 20 min walk - 1.7 km
  • Mystic Dunes Golf Club - 4 min drive - 3.0 km
  • ESPN Wide World of Sports Complex - 12 min drive - 9.9 km
  • Disney's Hollywood Studios® - 13 min drive - 11.0 km
  • Disney's Animal Kingdom® Theme Park - 18 min drive - 12.6 km

Getting around

  • Kissimmee Station - 24 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 31 min drive

Restaurants

  • ‪Starbucks - ‬5 min drive
  • ‪Wawa - ‬4 min drive
  • ‪Chick-fil-A - ‬4 min drive
  • ‪Texas Roadhouse - ‬4 min drive
  • ‪Bahama Breeze - ‬5 min drive

Frequently asked questions

Does Trade Winds Life | Cottage at Amazing Margaritaville Resort have a pool?

Yes, this property has a pool.

Is Trade Winds Life | Cottage at Amazing Margaritaville Resort pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Trade Winds Life | Cottage at Amazing Margaritaville Resort?

Check-in begins at 4:00 PM.

What time is check-out at Trade Winds Life | Cottage at Amazing Margaritaville Resort?

Checkout is at 10:00 AM.

Where is Trade Winds Life | Cottage at Amazing Margaritaville Resort located?

Located in the heart of Kissimmee, this holiday home is 1 mi (1.7 km) from Island H2O Live! and 2.1 mi (3.4 km) from Walt Disney World® Resort. Mystic Dunes Golf Club is 1.6 mi (2.6 km) away.

Reviews

9.6

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. 34 out of 40 reviews
Rating 8 - Good. 4 out of 40 reviews
Rating 6 - Okay. 1 out of 40 reviews
Rating 4 - Poor. 0 out of 40 reviews
Rating 2 - Terrible. 1 out of 40 reviews

9.6/10

Cleanliness

10/10

Property conditions & facilities

10/10

Check-in

9.4/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Kelly B.

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

Perfect house in a perfect location

House was beautifully appointed, clean and very close to the parks. We had a great time with our adult children during our stay!
Stayed 4 nights in Mar 2025

10/10 Excellent

MARILYN H.

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

PERFECT!

This has to be the best property we have stayed in. The area, pool and hot tub just perfect.
Stayed 5 nights in Mar 2025

8/10 Good

richard s.

Stayed 11 nights in Jan 2025

6/10 Okay

Courtney P.

Liked: Check-in, location, listing accuracy
Disliked: Communication
Stayed 11 nights in Dec 2024

10/10 Excellent

Jennifer O.

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

Another great stay in Margaritaville

We have stayed in the community before, but this is our first time at Trade Winds Life. We were there for the long Veteran's Day weekend - and wish we could have stayed longer. The house is much larger in person than in the photographs. Each en suite bedroom is spacious, yet cozy and well appointed. The house is equipped with terrific bath towels and enough pool towels for a full house. Smart TVs throughout the home as well as WiFi access and the backyard pool and spa made this all an amazing stay! The management company representing the owner were so quick to respond when we decided (last minute) to add BBQ grill use to our stay. The Margaritaville complex is safe, immaculately clean and super convenient to both the airport and attractions in Orlando. The whole family agrees we will definitely be booking another stay at Trade Winds Life again!
Stayed 3 nights in Nov 2024

10/10 Excellent

Stephanie J.

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

Great place for teens and parents

My son had a school trip to Disney. We stayed here with another friend and their kid. Easy to get to the parks, gave us a fun day to rest by the pool and have dinner locally.
Stayed 5 nights in Apr 2024

10/10 Excellent

Loren C.

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

Cheer competition at espn

Very clean and conveniently located to everything we needed to go to. Stores close by. Nice pool at house also
Stayed 5 nights in May 2024

10/10 Excellent

Cindy W.

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

Beautiful Cottage

We had a great stay. Beautiful pool/spa.
Stayed 6 nights in May 2024

10/10 Excellent

Heather Q.

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

Great week long stay!

Property is well kept and in a great location! Plenty of space for our family of 5. Even though we have a pool and hot tub at home, our kids LOVED the little plunge pool and hot tub to play in daily. Able to order groceries and food easily and quickly at Disney’s door (parks, Disney Springs, etc all within 10-15 mins depending on traffic). Would absolutely stay again. Two small issues - 1.) The bedrooms got warm at night. Not sure if there is a duct problem or what, but when the doors are closed the A/C did not work well. Our boys had a ceiling fan but the other 2 rooms didn’t have that relief. 2.) The hot tub didn’t get hot. The jets would turn on but it never heated properly. This was a bit of a bummer because my husband ran 3 Disney races and was hoping to use it for recovery.
Stayed 8 nights in Apr 2024

10/10 Excellent

Alice D

Liked: Cleanliness, property conditions & facilities, communication
Beautiful property. Lots of room for our family of six. Close to island h2o and sunset walk.
Stayed 3 nights in Mar 2024

10/10 Excellent

Brandi P.

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

Paradise away from home!!

The pictures we saw online were representative of the rental unit. The rooms were clean & the beds were super comfortable, which accommodated my family of 6! We loved the whole vibe of the place and the decor. We loved the location, which was close to so many shops, restaurants and parks! The few minor issues that we had were addressed and taken care of right away. The communication was impeccable… so for that, we were very pleased with our stay and would absolutely consider staying at the Margaritaville Cottage again in the future. We would 100% recommend it to anyone! Thanks again for a fabulous stay! ☀️
Stayed 4 nights in Feb 2024

10/10 Excellent

Alfonso T.

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

One of my best experience. Great job!!!!!

Great place. Will definitely recommend. Thank you for a great experience.
Stayed 2 nights in Sep 2023

10/10 Excellent

Eric L.

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

Beautiful Home

This was a beautiful home very clean place to stay. The pool and hot tub was fabulous .This is a nice area for family gated community very safe place to rest
Stayed 4 nights in Aug 2023

10/10 Excellent

Jennifer S., Cypress

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

perfect location

Great place! very clean and had everything we needed. It was an easy uber ride to Disney parks.
Stayed 4 nights in Jun 2023

8/10 Good

Jaime V., Lexington

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

Great house for family or friend group...beware of management co. and host

We LOVE Margaritaville! We have stayed in a different cottage in this resort previously. This house is beautifully decorated, spacious, and clean! We love the layout, spacious bedrooms with ensuite bathrooms, the fully equipped kitchen, and a private pool with a hot tub and grill. When in Orlando for a longer stay with a group, a house is the way to go! It is a short drive to the Disney parks, Disney Springs, and easy to get to Universal. There was an issue during our stay with the A/C in the upstairs king room. The house stayed cool, however, the temp in this upstairs room was always 10ish degrees warmer. It made for a warm night's sleep. We contacted the management co. via email and text so communication was delayed. The host called and I got the impression that this is an ongoing issue that he did not want to deal with it. He lacked proper customer service and communication skills and did not offer any solutions to the problem. A technician was NOT sent out during our stay and we never received any follow-up communication. Also, the pool alarm on the living room door was malfunctioning and was not repaired during our stay. We had to use the door in the half bath to go out to the pool. Overall, we enjoyed our time in this beautiful home while we vacationed in Orlando. Due to the lack of care for guests by the management co and host, we will rent a different house for our next trip. There are plenty of other houses in Margaritaville!
Stayed 4 nights in Jun 2023

8/10 Good

I’d Rather Be O.

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

Margaritaville

Great property and location. My only complaint is that I tried contacting the owner twice and I never received a response. Also, upstairs main bedroom was hot. Other than that lovely property. Keep in mind when renting that you have no access to Margaritaville pools.
Stayed 2 nights in Jun 2023

10/10 Excellent

Traci K.

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

Spring getaway

Beautiful property. Clean and comfortable. Everything is just like the pictures show. We plan to book it again next year!
Stayed 5 nights in Mar 2023

10/10 Excellent

Maria G.

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

Great property

This property did not disappoint. Had everything that is needed for a family to stay. The pool was great after a long day at the parks. This cottage was clean and was located in a great location. Everything was near by, restaurants, grocery store and stores for shopping. We definitely will plan on staying here again for our next family trip.
Stayed 5 nights in May 2023

10/10 Excellent

Ashley E.

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

Perfect!

We really loved this home. So cute, quiet, and close to parks. We couldn't have asked for a better spot. 10/10
Stayed 5 nights in Apr 2023

10/10 Excellent

Zac B.

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

Perfect For Family of 5

We greatly enjoyed our stay at this property. Our youngest boys spent a ton of time in the pool which was a perfect size for us. There was also plenty of space for the whole family for sleeping arrangements and time to relax downstairs and upstairs (teenager). Will look to stay again when in the area.
Stayed 5 nights in Apr 2023

10/10 Excellent

Tyler S.

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

Wasted Away Again in Margaritaville!

If you've ever wanted to experience the Margaritaville property, this cottage is the way to go! Beautifully decorated, easy access, and in good distance to anything on the Disney side of Orlando and the growing Sunset Walk area (even Flamingo Crossings up the road a little bit). Things to think about for renters: Your pool experience can be seen from the cottages to the left and the right so not a lot of privacy and if you get unlucky with screaming children you may not get to relax as much. Also the complex has the required pool door alarm that can be temporarily (30 seconds) silenced when open but NOT shut off (like you may see in other properties in the area). You will hear this noise throughout Margaritaville throughout your stay all day and night because no one is used to them so you end up shouting at neighbors to help them learn. Finally, if you sleep HOT and prefer a cold room do not that the Margaritaville cottage are one unit air conditioners. This means multiple floors must share so the house will never get below 75ish because it is not able to keep up in the Florida sun. The property owners don't really have any control over those two things, but I think it is good to be aware of. We had a lot of fun in the hot tub at all hours of the day. Thanks for the memories!
Stayed 4 nights in Mar 2023

10/10 Excellent

Jeremy V.

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

It was good

Clean property, very spacious.
Stayed 3 nights in Mar 2023

10/10 Excellent

Timothy M.

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

property was fantastic, very clean and close to everything

we had a great stay, property was spotless and convenient to everything. m
Stayed 6 nights in Mar 2023

10/10 Excellent

Heather M.

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

Kissimmee Margaritaville

Super nice, comfortable and clean! Host very responsive to inquiries. Would highly reccommend.
Stayed 6 nights in Feb 2023

10/10 Excellent

Meaghan F.

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

Felt like home!

Wonderful stay! Very comfortable, clean, and convenient location. Property managers Jay and Christina were available to answer all questions. The condo itself was very comfortable and felt like home, we didn’t want to leave! Plenty of parking available in front of the condo and there was a nice area close by for shopping and dining. Just a 10-20 min drive to all parks depending on the traffic/time of day. The pool alarm took some getting used to, but not a big deal! We will certainly be returning to stay on our next trip to Orlando. :)
Stayed 5 nights in Feb 2023

About the host

Hosted by Grand Welcome

Host profile image

Languages:

English, Spanish