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.
The Space:
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.
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.
For all reservations made through our official website, guests will be required to complete a secure verification process through our third-party partner, Autohost. This process helps us ensure the safety and integrity of all stays. Our full privacy policy, which explains how your information is handled and protected, is available upon request prior to booking.
The Neighborhood:
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!
Other Things to Note:
Pool can be heated for an additional fee of $29 per night. Please contact our customer service team after you have booked your stay to arrange payment.
- Pool heat is not included in the reservation cost. Charges are non-refundable unless the heating system is experiencing issues.
- Pools require a minimum of 48 hours to reach the desired temperature.
- Pool heat must be added for the entire stay; partial pool heat is not allowed due to the high energy costs required to bring the water to temperature.
Note: Cold fronts in the winter months (<60°F) may prevent the electric pool equipment from functioning; this is not considered a mechanical failure, and refunds will not be issued. Homes with heat pumps can generally only raise the water temperature 15–20°F above ambient air temperature.
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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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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. Take the opportunity to explore the area for outdoor excitement like cycling.
Disney's Animal Kingdom® Theme Park - 8 min drive - 5.7 km
Getting around
Kissimmee Station - 24 min drive
Kissimmee, FL (ISM-Kissimmee Gateway) - 31 min drive
Restaurants
Wawa - 3 min drive
Starbucks - 5 min drive
Taco Bell - 19 min walk
7 Brew Coffee - 4 min drive
Olive Garden - 4 min drive
Frequently asked questions
Is Trade Winds Life - Margaritaville pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Trade Winds Life - Margaritaville?
As of 12 May, 2026, prices found for a 1-night stay for 2 adults at Trade Winds Life - Margaritaville on 16 Jun, 2026 start from S$238, 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.
How much is parking at Trade Winds Life - Margaritaville?
On-site parking is available at the property.
What time is check-in at Trade Winds Life - Margaritaville?
Check-in begins at 4:00 PM.
What time is check-out at Trade Winds Life - Margaritaville?
Checkout is at 10:00 AM.
Where is Trade Winds Life - Margaritaville 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.
Great place! very clean and had everything we needed. It was an easy uber ride to Disney parks.
Jennifer S.
Stayed 4 nights in Jun 2023
Response from VrboOwner on 28 Jul, 2023
We are thrilled you have stayed in one of our Grand Welcome homes and would love to invite you back in the future. Please let us know what we can do to make your stay even better for next time!
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
Eric L.
Stayed 4 nights in Aug 2023
Response from VrboOwner on 22 Sept, 2023
We hope you enjoyed your vacation in Orlando and would love to have you back in our home! We appreciate thoughtful guests such as yourself and hope to have you all back for your next trip to Central Florida! Thank you from the Grand Welcome Greater Orlando team.
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.
Stephanie J.
Stayed 5 nights in Apr 2024
Verified
10/10 Excellent
Alice D
13 Mar, 2024
Liked: Cleanliness, property conditions & facilities, communication
Beautiful property. Lots of room for our family of six. Close to island h2o and sunset walk.
Loved this property 1st time staying at Margaritaville but will definitely stay again. Property was amazing loved the pool, beds were really comfy. Great proximity to shops restaurants & of course Disney will definitely book again.
Verified traveller
Stayed 8 nights in Oct 2022
Response from VrboOwner on 22 Jul, 2023
One thing that is in short supply these days are easy guests. WOOHOO! Thank you for making your stay enjoyable for us and we hope that we have payed it forward multiple times to you. Come back to Orlando soon and stay again! Yours in hospitality, the Grand Welcome Greater Orlando team.
The home was just as beautiful in person as the pictures. The house was accommodating to all of our needs. My family will definitely stay at this home again!
property was fantastic, very clean and close to everything
we had a great stay, property was spotless and convenient to everything. m
Timothy M.
Stayed 6 nights in Mar 2023
Response from VrboOwner on 22 Jul, 2023
We are thrilled you have stayed in our home and would love to invite you back in the future. Please let us know what we can do to make your stay even better for next time! Come back to Orlando soon and visit us! - Jay and Christina, the Grand Welcome Greater Orlando team.
Overall a nice place to stay - it was quiet - had almost everything you needed for a stay. Property management responded quickly to questions and was kind enough to drop off some dish towels for the kitchen. Would stay again.
We are thrilled you have stayed in one of our Grand Welcome homes and would love to invite you back in the future. Please let us know what we can do to make your stay even better for next time!
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.
Zac B.
Stayed 5 nights in Apr 2023
Response from VrboOwner on 22 Jul, 2023
Thank you for staying with us and for your review! We are so happy to hear your Grand Welcome Vacation experience and hope to host you again soon, either here or at one of our many locations across the country.
We have traveled to the Kissimmee area for many years. Margaritaville is our all time favorite spot. A week was not long enough. We plan to return again and stay longer. Highly recommend this area.
Sandra K J.
Stayed 7 nights in Jun 2022
Response from VrboOwner on 22 Jul, 2023
Thank you for your review! We are so happy to hear you enjoyed your Grand Welcome Vacation experience and hope to host you again soon, either here or at one of our many locations across the country.
Beautiful new house. Very clean! Minutes from Disney Great being walking distance to sunset strip restaurants. Highly recommend.
Chad B.
Stayed 5 nights in Jan 2023
Response from VrboOwner on 22 Jul, 2023
Thank you for your review. We are so happy to hear you had an overall enjoyable experience and hope you consider us for any future vacations! Orlando already misses you! - Jay and Christina, the Grand Welcome Greater Orlando team.
Super nice, comfortable and clean! Host very responsive to inquiries. Would highly reccommend.
Heather M.
Stayed 6 nights in Feb 2023
Response from VrboOwner on 22 Jul, 2023
We hope you enjoyed your vacation in Orlando and would love to have you back in our home! We appreciate thoughtful guests such as yourself and hope to have you all back for your next trip to Central Florida! Thank you from the Grand Welcome Greater Orlando team.
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.
We really loved this home. So cute, quiet, and close to parks. We couldn't have asked for a better spot. 10/10
Ashley E.
Stayed 5 nights in Apr 2023
Response from VrboOwner on 22 Jul, 2023
Thank you for your review. We are so happy to hear you had an overall enjoyable experience and hope you consider us for any future vacations! Orlando already misses you! - Jay and Christina, the Grand Welcome Greater Orlando team.
Visited during record cold temps. Issue with heat and owner responded ASAP on Christmas Day!! 10/10
Top Notch!!
Carrie B.
Stayed 5 nights in Dec 2022
Response from VrboOwner on 22 Jul, 2023
One thing that is in short supply these days are easy guests. WOOHOO! Thank you for making your stay enjoyable for us and we hope that we have paid it forward multiple times to you. Come back to Orlando soon and stay again! Yours in hospitality, the Grand Welcome Greater Orlando team.
This property is very modern and beautiful. There was plenty of space for our group of 5. The pool was a great place to relax after a long day of walking at the parks. Margaritaville resort has a relaxing tropical vibe that makes you feel like you're at a beach. Lots of great restaurants and shops were super convenient. Disney is just a few minutes away and universal studios is around a 30 minute drive.
This villa is beautiful. Stylishly decorated, spotlessly clean and there was plenty of room for our family of 5. I struggle to say anything negative about this property other than sadly not having access to the Margarittavile facilities as we had hoped. Having said that it has a lovely little pool of its own which we all enjoyed. I wouldn’t hesitate to stay here again 😊
Lesley I.
Stayed 16 nights in Jun 2022
Response from VrboOwner on 22 Jul, 2023
Thank you for your review! We are so happy to hear you enjoyed your Grand Welcome Vacation experience and hope to host you again soon, either here or at one of our many locations across the country.