House - Rating 4.6 (18)

Trade Winds Life - Margaritaville

As low as $120.00 / night + taxes & fees

  • Location: Kissimmee
  • Type: House
  • View: Garden View

Bedroom 3 bedrooms
Bathroom 3 baths
Guests 9 guests
Pets Allowed Pets Allowed

Summary Summary
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.
Description Description
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.

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.

This property is non-smoking. You will be fined $500 plus mitigation costs
Please note this home is pet friendly and able to take in your pets for $19/night per pet. The pet fee is NOT included in the rent and needs to be paid before arrival.
Do not exceed the maximum number of cars or occupants.
Do not park automobiles in the grass, as you will be towed/ticketed.
Always observe quiet hours after 9PM, as there are neighbors close by.
Failure to follow these rules/procedures and the rules/procedures stated in the agreed upon rental agreement could result in fines, forfeit of the security deposit, and in some cases being asked to leave without a refund.

Availability Calendar Availability Calendar
Available
Unavailable
Check-In
Check-Out
March 2026
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30 31        
April 2026
Su Mo Tu We Th Fr Sa
      1 2 3 4
5 6 7 8 9 10 11
12 13 14 15 16 17 18
19 20 21 22 23 24 25
26 27 28 29 30    
May 2026
Su Mo Tu We Th Fr Sa
          1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31            
June 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30        
July 2026
Su Mo Tu We Th Fr Sa
      1 2 3 4
5 6 7 8 9 10 11
12 13 14 15 16 17 18
19 20 21 22 23 24 25
26 27 28 29 30 31  
August 2026
Su Mo Tu We Th Fr Sa
            1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 22
23 24 25 26 27 28 29
30 31          
September 2026
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30      
October 2026
Su Mo Tu We Th Fr Sa
        1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
November 2026
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30          
December 2026
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31    
January 2027
Su Mo Tu We Th Fr Sa
          1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31            
February 2027
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28            
Swipe Swipe for Availability

Amenities 56 Amenities
  • Air conditioning
  • BBQ grill
  • Bed linens
  • Blender
  • Body soap
  • Cable TV
  • Carbon monoxide detector
  • Ceiling fan
  • Coffee maker
  • Conditioner
  • Cookware
  • Cycling
  • Dining table
  • Dishes and silverware
  • Dishwasher
  • Downtown
  • Dryer
  • Essentials
  • Free parking on premises
  • Garden or backyard
  • Garden View
  • Golf - Optional
  • Hair dryer
  • Heating
  • Hot tub
  • Hot water
  • Ice maker
  • Internet
  • Iron
  • Kitchen
  • Lake
  • Laptop friendly workspace
  • Long term stays allowed
  • Microwave
  • Museums
  • Oven
  • Pack ’n Play/travel crib
  • Patio or balcony
  • Pets allowed
  • Private entrance
  • Private pool
  • Refrigerator
  • Shampoo
  • Shopping
  • Smoke detector
  • Stove
  • Suitable for children (2-12 years)
  • Suitable for infants (under 2 years)
  • Theme Parks
  • Toaster
  • Town
  • TV
  • Washer
  • Water Parks
  • Wine glasses
  • Wireless Internet

Location Location

Reviews Rating 4.6 (18) Reviews
Rating 4
Everything felt wonderful except if you need help to get something fixed... I communicated via email on our 2nd day that we couldn't figure out how to turn on the pool light and thought that maybe it was broken. Several emails kept going back and forth throughout days 3 and 4 assuring me that management will look into this as soon as they can - basically pacification and promises that never came. Finally on our 5th day, i was able to flag down one of the pool cleaners myself and ask if he can have someone fix our pool light. He instantly got it done - made a quick phone call and within a 1/2 hour, someone came to change out the lightbulb and we were able to have a nice evening swim on our final night there. Owners and management kept repeating that they would accomodate and help in any way possible, however they were only words without action. Just be aware of empty promises here. I felt like this minor issue became a LOT of effort for ME to basically fix it for the next renter
Anonymous - Posted: 2/24/2026
Rating 5
We have stayed in this home before and enjoyed it so we came back. This is one of my favorite layouts in the neighborhood. The pool controls are confusing. Jets only come on when it’s off…. Wasn’t a big deal so we didn’t reach out. There is not a grill on site as pictured. But I’m sure you could ask for it if needed. Master pillows were not great but we stole some additional from another room. We look forward to coming back.
Anonymous - Posted: 2/16/2026
Thank you so much, Katrina, for staying with us again — we’re thrilled to hear you enjoyed the home and layout and that you’re looking forward to returning. We truly appreciate your feedback. Had we known about the pool controls, missing grill, or pillow comfort during your stay, we would have been more than happy to help and make adjustments right away. We always want our guests to have the best possible experience, and your notes are helpful as we continue to improve. We look forward to welcoming you back for another enjoyable experience!
Grand Welcome staff
Posted: 2/22/2026
Rating 5
This is our second stay here and would definitely recommend to anyone looking to stay in Margaritaville. The home looked just like the photos/description. While we had no issues during our stay, the hosts kept in communication before, during and after our stay to make sure everything was going smoothly. Thank you for opening your home to us!
Anonymous - Posted: 2/3/2026
Thank you, Kerry! We’re so glad you enjoyed your second stay and truly appreciate your kind words. It’s always our goal to provide a seamless and enjoyable experience. We’re grateful for your continued recommendation and look forward to welcoming you back to Margaritaville soon.
Grand Welcome staff
Posted: 2/9/2026
Rating 5
We had an excellent time from the moment we pulled up everything was spot on. It was a little chilly, but we sat in a hot tub for a couple hours after going to Disney. The place was extremely well taken care of and beautiful. This is my second time saying at one of their properties and we loved them both.
Anonymous - Posted: 12/12/2025
Rating 3
I have stayed at this property 3 times, every time i have stayed I have had the same concerns and been told they would be handled, and nothing was handled. I specifically have discussed my disappointment but it didn't seem to be a priority to be actually taken care of. The gentleman I spoke with was very kind, understanding but he said he would resolve the issue. I waited 4-5 hours for a maintenance person and no one arrived. We left the property. i unfortunately wont be staying again.
Anonymous - Posted: 12/9/2025
Rating 5
We had a wonderful stay at Trade Winds Life house! We stayed here for 2 weeks and felt right at home. Everything was in great condition, was very clean, and we felt so comfortable! The hot tub & pool was a plus. Our son had a blast! We highly recommend this house, it was perfect!
Anonymous - Posted: 11/17/2025
Rating 5
Es war ein wunderschöner Aufenthalt auf Fragen wurde schnell geantwortet. Das Haus ist sehr schön eingerichtet und gepflegt. Ich werde sicherlich noch einmal wiederkommen.
Anonymous - Posted: 10/6/2025
Thank you, Hartmut! We're thrilled you had a wonderful stay and appreciated our quick responses. Your kind words about the house mean a lot to us. We can’t wait to welcome you back for another visit!
Grand Welcome staff
Posted: 10/12/2025
Rating 5
10/10, I highly recommend booking with Dr Jay & Christina. Their home was very clean and peaceful! Very nice host.
Anonymous - Posted: 9/7/2025
Thank you so much for your kind words, Bianca! We're thrilled you enjoyed your stay and appreciated our home. Your recommendation means a lot to us, and we look forward to welcoming you back soon!
Grand Welcome staff
Posted: 9/22/2025
Rating 5
I would highly recommend Drs Jay and Christina’s place to family and friends. Anytime I had a question and would email them they were quick in responding. Their place is beautiful. Will definitely rent their place again.
Anonymous - Posted: 8/24/2025
Thank you so much, Stacie! We're delighted to hear you enjoyed your stay and found our home beautiful and peaceful. Your kind words mean so much to us. We can't wait to welcome you back for another wonderful visit!
Grand Welcome staff
Posted: 9/5/2025
Rating 5
This is an incredible place! The house was extremely clean, response was timely and we loved our visit - and the pool at the end of the day was an incredible bonus! We would love to come back here next year!
Anonymous - Posted: 8/12/2025
Rating 4
House was great for our stay. Close to the parks and plenty to do in the area. Spacious for our entire family. Had an issue with the code we were given for the door for check in and immediately helped when we called the number provided. Would rent from them again.
Anonymous - Posted: 7/27/2025
Thank you, Walter, for your wonderful feedback! I'm thrilled to hear you enjoyed your stay and found our home spacious and comfortable. Your suggestions are invaluable, and we look forward to welcoming you back soon!
Grand Welcome staff
Posted: 8/11/2025
Rating 4
The house was very clean and good location. Felt right at home . Only issue was the grill was not there when we got there and it took multiple messages back and forth to the manager to get it delivered 24hrs after check in . Beautiful home and would stay there again definitely!
Anonymous - Posted: 7/7/2025
Rating 5
My family and I had a pleasant time together at your Margaritaville cottage. We held our annual family reunion on the grounds and the experience was spectacular. The place was immaculate and the views were great. Thanks for allowing us to stay in your home. Have an excellent day 😊
Anonymous - Posted: 6/30/2025
Thank you so much for your kind words Gary! We're thrilled to hear your family reunion was such a memorable experience and that you enjoyed the immaculate space and beautiful views. It was our pleasure to host you, and we’d be happy to welcome you back anytime. Wishing you an excellent day as well!
Grand Welcome staff
Posted: 7/4/2025
Rating 5
The cottage was beautiful. We usually drive to Orlando once a year and stay in the cottages at Margaritaville. This cottage was one of the nicest that we have stayed in.
Anonymous - Posted: 6/29/2025
Rating 5
I have rented from Dr's Jay and Christina before. Their places are always extremely clean!
Anonymous - Posted: 6/11/2025
Thank you so much for your kind words! We're thrilled to hear that you consistently find our places to be extremely clean. It's always our top priority to ensure our guests have a comfortable and spotless stay, and your feedback lets us know we're succeeding. We truly appreciate your continued business and look forward to hosting you again
Grand Welcome staff
Posted: 6/18/2025
Rating 5
Awesome place to stay lots to do in the area,close to Disney perfect place to unwind for a week. We made great use of the private pool and the available BBQ. Would definitely stay here again, Vince
Anonymous - Posted: 5/19/2025
Thank you so much for your wonderful review! I’m thrilled you enjoyed the location and made the most of the private pool and BBQ — perfect for unwinding after a fun day. It was a pleasure hosting you, and we’d love to welcome you back anytime for another great stay!
Grand Welcome staff
Posted: 6/6/2025
Rating 5
We enjoyed or stay at this home very much! We have stayed at several properties at Margaritaville and this is our favorite! We will not hesitate to stay again.
Anonymous - Posted: 5/18/2025
Rating 3
Courtney P. - Posted:
Swipe Swipe for More Reviews