SO MUCH FUN! Key West Style Waterfront Home w/Dock; Huge Screened Lanai w/TV, Pool & Hot Tub; WiFi

Winterberry Whimsy
$212.05 - $396.05 / night   in Marco Island  
3 Bedrooms 2 Bathrooms Sleeps 6
Sleeping Arrangements
Master   King  
Guestroom 1   Queen  
Guestroom Loft (Twin w/trundle)   Twin (2)  

THIS is the vacation destination you've been longing for!! Every square inch of this home - indoors and out - is the epitome of Southwest Florida living that will leave the whole family yearning to return year after year! There is plenty of space for everyone to gather, stay, and play in this comfortably furnished Key West style waterfront home which includes:

- Master ensuite with king bed and flat screen TV

- King bed in the second bedroom and flat screen TV

- Third-level loft space (very private) with twin trundle bed (no TV)

- 2 full bathrooms

- Fully-equipped kitchen with drip coffee maker and Keurig machine

- Indoor dining area

- Grand covered lanai with bar area, TV/lounge area, outdoor dining, fire pit, propane grill/smoker

- Huge screened-in pool

- Wrap around second-level balcony with lounge seating and outdoor dining

- Open air decking and lounge space on the water

- Brand new boat lift installed June 2020

- Single-person kayak

- Tandem Bike

- Pool floats and towels

- Beach cart, 6 beach chairs and umbrella

- Fairy gardens and whimsical details

You could spend almost your entire vacation outdoors in this amazing home! The ground level is a screened-in lanai, much of which is covered, so even on a rare rainy day, you can still be "outside" enjoying cable TV, libations at the bar, or just relaxing to the sound of tropical showers. Chances are, you'll have many sunny days, which is a good thing, because you'll have so many ways to enjoy it - splash in the waterfall pool in the two-story lanai, enjoy the canal/pool view from the second level balcony, or take a cruise around the canals in the double kayak provided. You may even encounter a dolphin, manatee, or other Florida wildlife. If you're a fisherperson, bring your gear and fish/crab right from the dock while enjoying a cool beverage. A combo gas/charcoal grill is available to cook your catch or take it to one of the many restaurants on the island that will cook what you catch. And if you prefer fishing at the local supermarket, the Publix is only 0.6 miles from the house!

The second floor, which is accessible by two different sets of stairs (both are outdoors), is the main living area that includes a large living room, dining room, sitting area, kitchen and two private bedrooms. The third floor boasts a great loft space that can accommodate two additional guests. There are ample linens and towels provided, and the the kitchen is fully stocked and ready for any cooking endeavor. You'll want for nothing on this vacation!!

Restaurants, shopping, a movie theater, miniature golf, public beach access, and much more is only 1.5 miles down Winterberry Drive. Mackle Park is less than a mile away and offers walking paths, shuffleboard, bocci ball, undercover basketball and an amazing kids play area with splash park. So much to see, so much to do...or just relax!!

Still wondering if this is the place for you? Then reach out to iTrip Vacations Marco Island and we will be delighted to answer any questions you have and to make sure we put you and your family in the home that best suits your reason(s) for traveling. Also, take advantage of the iTrip app to help you prepare for your trip and to make the most of your time on our beautiful island. With so much to see and do, we are confident you will want to return year after year and tell your friends about this hidden jewel in SW Florida.

1660 Winterberry Dr Marco Island, FL 34145

To purchase a vacation home like this one, Siobhan St. Amour with Coldwell Banker or click here to see properties for sale.

Property Type: Home Beds: 3 Accommodates: 6 Check In: : 4pm Bedrooms: 3 Check Out: : 10am Bathrooms: 2.0 Pet Friendly: No
Air Conditioning Balcony Beach Cart Beach Chairs Beach Towels Beach Umbrella Big Screen TV Bikes Blender Boat Dock Boat Lift (12K lbs) Cable Canal home Clothes Dryer Coffee Maker Covered Patio Dishwasher Fire Extinguisher Fire Pit Free Parking Full Kitchen Gas grill Hair Dryer Hangers Hot Tub Ice Maker Internet Internet Access Iron and Board Jacuzzi Keurig Coffee Maker Kitchen Laundry Microwave Open Patio Patio Private Boat Dock Private Hot Tub Private Pool Refrigerator Satellite or Cable Screened Patio Smoke Detector TV Toaster WIFI Washing Machine Water Filter Water View Waterfront toaster Disinfected Enhanced Cleaning Wifi
Check the FAQ
Unavailable Days
Select your trip dates.
Contact Manager

Toll Free (833) 556-2726
Reviews - 4.7 stars based on 9 reviews
Winterberry Whimsy
5/5 stars
Really enjoyed our stay at the Winterberry House. Quite unusual and very fun place. Enjoyed the pool and deck. Caught fish in the channel. Made sure we ran the dishwasher while we were away from the house (a bit noisy). A great vacation for us. Thanks so much!
Reviewed on Mar 1, 2021 by Michael, Mattawan, MI   Report

You summed up Winterberry Whimsy perfectly! It is a unique home that has so many great things to offer. Glad you enjoyed fishing off the dock and caught your share. If the owner wasn’t moving back in, I would encourage you to book the house again! To see all the houses we manage, go to:

Manager Response
Winterberry Whimsy
5/5 stars
This place is all about expectations. If you're looking for a fun house, great pool and spa with an excellent location its perfect. Our kids range from 9 to 15 and all three loved the pool and spa. We loved being on the canal which provides an added level of relaxation and escape. I knew our son would like to fish in the canal but it was a cool surprise to learn that our daughters did too. We spent quite a few hours fishing from the dock as well as the bridge located feet away from the house. For those interested in fishing we had good success. We caught sheepshead, snapper, Spanish mackerel, and a 15" pork fish which was beautiful! The house itself was comfortable and clean. The kitchen was adequate to cook in and we loved having breakfast sitting under the wrap around lanai. It's not often we'll get to watch the Super Bowl from a hot tub while the kids swim in the comfort of our own house. Great memories! We knew going in that the upstairs was separated by outside stairs from the downstairs. Honestly the only time it felt inconvenient was bringing the luggage in when we arrived and out when we left. Otherwise it didn't seem like a big deal. Keep in mind that the home, like most in Marco has neighbors who might be retired. We respected them by keeping noise to a reasonable level and they were very gracious in return. Mark was on the spot with questions or concerns and is genuinely committed to making sure your experience is as great as it can be. We would definitely stay here again and hope to some day.
Reviewed on Feb 14, 2021 by Brandon, Waunakee, WI   Report

Wow! What a wonderful review and we are so glad you enjoyed everything the house, and the canal, have to offer. The outdoor living space is truly exceptional and a wonderful place to read, relax, watch TV, grill, chill by the gas firepit, eat, swim and the list goes on! Thank you so much for being respectful of the neighbors as it is important we observe their right to the peaceful enjoyment of their home. Please be sure to book with us again!

Manager Response
Winterberry Whimsy
5/5 stars
We had a great stay at this house with our family including 3 teenagers. It was our first time to Marco Island and we were a bit worried about the trip due to COVID. Both the house and the property manager far surpassed our expectations. The house is fully equipped with everything you might need. We cooked every meal in the fully stocked kitchen and spent hours lounging in the AMAZING pool and bar area. We biked all around the island and rented multiple sea kayaks (delivered to the house before we arrived) so we could paddle to the tropical islands not far from the dock. Saw dolphins jumping each time we ventured out on the water. We have already tried to rebook this house for future trips. The 3 bedroom house is above the pool area, so yes there are stairs but the benefits of the view and the pool area make the steps plenty worth it! Note that the 3rd bedroom is small, right at the top of the stairs off of the living room/kitchen so it functions like a loft bedroom. Perfect for teenagers but could be a little loud for light sleepers, was great for our group. The 2nd fridge/freezer downstairs was also a great bonus! Marco Island is a beautiful place and they take COVID seriously. We saw masks every time we ventured outside. Thanks Mark for making our vacation great!
Reviewed on Dec 20, 2020 by Jennifer, Decatur, GA   Report
Winterberry Whimsy
5/5 stars
We had a great vacation at this house. We spent so much time in the pool, hot tub and tv area. We also rented a boat and the lift worked perfectly. There are some cool beaches to boat to. We also enjoyed the kayak. We were able to see some dolphins in the canal as well! The house was clean and the beds were comfortable. The layout of the house is a little interesting but for a vacation home it didn’t matter. We would definitely recommend this house and Marco Island in general!
Reviewed on Dec 9, 2020 by Mandy, Mohnton, PA   Report

What a wonderful review! The house has a lot to offer guests and you pointed out many of them: hot tub, pool, outdoor TV area, gas firepit, kayak, boat lift, fishing off the dock and free dolphin "tours" in the canal this home is situated on. We are so glad you enjoyed the home's location, along with its comfortable beds and thank you for giving future guests ideas on how they can make the most of their time in this house and on Marco Island. We hope you will book with us again!!!

Manager Response
Winterberry Whimsy
4/5 stars
The home at Winterberry almost got 5 Stars but a few things kept it from a 5 Star review. First I want to thank Mark at iTrip for checking in with us upon arrival and being on top of every text or request I sent him. He was truly awesome. The Pros of this house are definitely the pool level and entertainment area. We probably spent 90% of our waking time in this area. The pool and spa are wonderful and well maintained. The dock deck area was wonderful! My husband and brother-in-laws loved the TV in the pool entertainment area. They could watch all of the sports right from the pool or sitting area. When the refrigerator was working in this area it was awesome. Mark was right on the spot when he brought us a cooler for all of our items when the refrigerator was not keeping our items cold. The house concept itself was very nice and clean. However, the Cons of this house were what kept me from giving a 5 star review. There are updates and repairs that are needed to the home. The pool level refrigerator quit keeping our drinks cold 2 days into the stay. The kitchen sink began leaking BUT Mark had a repairman there within 15-20 minutes to repair, however the repairman said the whole disposal and sink drain were not installed properly. Luckily his drain repair was good for the rest of our stay. The one prado door in living area would not open for us, but there are 2 other prado doors that work so we were good. I do believe you should reveal in the listing that the stairways are exterior from the pool level to main living area. This was not a terrible issue for us as we only had rain one evening, but both the spiral stairs and stairs off the dock area are slippery when wet. So just be aware. Also installing a 1/2 bath either in the laundry area or back by the garage area in the ground level would be a huge improvement as you had to go upstairs to use the bathroom. The tandem bike was ok, but needs some updating (maybe leave a wrench in the storage area to be able to adjust the seat height). But when we needed the handle bars fixed Mark came over himself and repaired them. Overall our trip was wonderful and I probably would say this house is a 4.5 stars mainly because while we had some issues, Mark was amazing at taking care of all our needs. Just need to make some updates and repairs. We have been coming to Marco Island for several years and it is always a wonderful trip! Thank you for another great vacation!
Reviewed on Oct 19, 2020 by Laura, NEW ALBANY, OH   Report

Thank you for that very thorough review! Apologies for the downstairs fridge and the kitchen sink. Regarding the former, I am working with the owners to see if they will repair or replace it so we have taken it out until a decision has been made. In the interim, we purchased a large cooler for guests to put drinks and food in so they don't have to go upstairs to the kitchen. Speaking of the stairs, we updated the listing and clarified the two sets of stairs are exterior so thank you for that. Love your idea about a half bathroom on the ground floor. Unfortunately, Marco Island will not issue a permit for one because it's in a flood zone, otherwise I am sure the owners would do it. Great suggestion about the bike and we left an allen wrench there so guests can tighten and adjust the seats and handlebars. I checked all the doors in the living area and confirmed they are working. We have instructions taped to the windowpane for the french doors to the wraparound balcony as there is a trick to locking it. We are so glad you enjoyed your time on the Island and in the house and we hope you will book your next trip to Marco Island with us.

Manager Response
Winterberry Whimsy
5/5 stars
This house is a perfect getaway.Mark is a pleasure to book through.Simple and easy check in and check out. Will definitely recommend to all my friends.
Reviewed on Aug 16, 2020 by Charles, Canton North Carolina   Report

Thank you for recommending us to your friends! Glad the checkin/out was to your liking. We appreciate how clean you left the place and that you followed the checkout procedures to the letter. We hope you will book with us again :-)

Manager Response
Winterberry Whimsy
5/5 stars
Beautiful place and perfectly clean. All was great. Looking forward to another stay here.
Reviewed on Dec 30, 2019 by Steven, Owings Mills, MD   Report

Thank you for your review. So glad to hear you enjoyed your stay and we look forward to having you back!

Manager Response
Winterberry Whimsy
5/5 stars
We really appreciated all that Mark did to ensure we had a wonderful stay! We will definitely use iTrip again! Thank you!
Reviewed on Aug 18, 2019 by Jennifer, Hebron, KY   Report

Thank you so much, Jennifer!!! You and your family were an absolute pleasure to host and we would love it if you booked with us again. All our best!

Manager Response
Winterberry Whimsy
3/5 stars
Location was wonderful and if everything that was advertised worked it would have been great. 1) House had bugs. Need to hire an extrerminator. 2) Advertized a boat lift. We brought our own boat and expected to use the lift but spent 4 hours and had to run and get parts the first day of vacation to get it to work. 3) Advertised Hot Tub and Pool. Spa never worked properly and Pool was dirty. Spent at least 3 or 4 days trying to get the spa to work. I the plumbing is messed up. Over all I think this house was put up for rental and forgotten about. Seems rental money is taken and there is no maintenance program and it is in desperate need of of some Maintenane. This location is great and centeraly located with eaisy gulf acess but really needs some tender love and care.
Reviewed on Jul 27, 2019 by Jon, Naples, FL   Report

Thank you for your feedback and we are glad you were happy with the house’s wonderful location. We pride ourselves on making sure our guests have a wonderful experience in each of the properties we manage and are sorry that was not the case for you. I will respond to each of your points in this review since it will be informative for future guests looking to book this home: 1) Can you tell me where and what kind of bugs? We have not seen any before or after your stay; however, an exterminator will be going to the house to check for any signs of them. (You can reply to the July 27th email I sent you in response to your review.) 2) We did not advertise a boat lift. While the pictures show one, given its age and lack of use, we chose not to list it as an amenity anywhere in our description. I apologize it did not work and appreciate your initiative to fix it. We will update our description to let future guests know it is an “as-is” amenity. 3) We did not advertise “Hot Tub and Pool.” Our description references the pool twice: “Huge screened-in pool” and “splash in the waterfall pool in the two-story lanai.” We purposely omitted “hot tub/spa” because the system only allows for one temperature to be set. As for the pool being dirty, it is on a weekly cleaning schedule with a professional pool company. You checked in at 3:30pm on July 18, I emailed you at 4pm on July 22 and your reply at 7pm said: “So far so good!“ when I touched base to see how things were going. Perhaps these issues occurred between your reply and your checkout the morning of July 25; however, our first time hearing of them is when we received your review after you checked out. Had you told me about these issues during your stay, I would have addressed them immediately.

Manager Response

Similar Properties

Copyright © 2008 - 2021 iTrip LLC