Experience Luxury.

Welcome to Win-le Vacation Rentals

The vacation rental company you deserve

Longing for the days when you could pick up the phone and book your vacation with passionate locals who know the area and the homes they rent, Win-Le Vacation Rentals was founded by three of the beaches’ top realtors who are determined to take back what makes the Delaware shore so special: the heart and soul of the locals. We have dedicated our livelihoods to sharing our passion and love for the Eastern Shore with everyone who visits – whether they’re here for a weekend, a week, or a lifetime.

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Our Featured Properties

View some of our Best Properties selected just for you

Bay Breeze Retreat

2 bedrooms

2 baths

7 guests

Sandcastle Retreat

4 bedrooms

4 baths

12 guests

Casa del Sol

2 bedrooms

2 baths

6 guests

Coastal Blue

4 bedrooms

3 baths

12 guests

Beachcomber's Paradise

4 bedrooms

2 baths

10 guests

Relaxing Ocean Retreat

3 bedrooms

2 baths

6 guests

Flip Flop Stop

3 bedrooms

2 baths

8 guests

Grill & Chill Cottage

3 bedrooms

2 baths

9 guests

Sea Colony Estate

5 bedrooms

4 baths

16 guests

Recent Client Testimonials

Hear what some of our clients have said about us

Just got back from a golf trip with the guys and we had the time of our lives thanks to Win-Le! Top notch staff who were always available when I needed them… and I needed them a lot. The wives are so much better at organizing these things than us men are, and we relied a lot on Win-Le for all our questions – most of which, it turns out, were all provided in the packet they emailed to us, but we didn’t read it. They even took the time to text us some great places for happy hour and let us in on a few locals’ secret spots for great live music and food. The starter kits they provide as a courtesy are life savers! And the free linens were the best surprise because we thought we were supposed to bring our own – and we all forgot. My wife is laughing and rolling her eyes as I write this, amused at how lost we are without them… but the folks at Win-Le stepped in and saved the day! Several times…

Nathaniel G.

We found Win-Le after beginning a desperate search to get away from our current management company who have been a total nightmare. We looked up our property on Vrbo to see what guests were saying about it, and we were disgusted by the reviews. Constant complaints about maintenance issues never being handled – including backed-up toilets that couldn’t be used the entire stay. Nearly every guest complained about the home not being cleaned properly. We have a 6-bedroom home in one of the most popular communities in Bethany and our rates were being dropped to under $100 a night in the middle of the summer without us even knowing about it! Win-Le has been the dream come true we needed after the nightmare we’d experienced with the previous company. When they say they care for your home as if it were their own, they truly mean it.

Tracy T.

We rented one of Win-Le’s properties in South Bethany for a girls getaway with my daughter before she heads off to college, and the people at Win-Le made the trip extra special for us. We brought my elderly mother along who’s in a wheelchair, and they went above-and-beyond to send us places to go and things to do that would make her feel comfortable and included – and when we arrived, there was even a sweet greeting card from them, wishing my daughter luck as she enters college! We’re used to vacationing in Ocean City – and we would have never gotten this kind of treatment from any of the companies there. We’re diehard Win-Le fans through-and-through now!

Moriah J.

Win-Le was recommended to us by our realtor after we purchased our home in Bayside. After hearing horror stories about some of the bigger names in the area for rental property management, we were worried we’d be tasked with managing this on our own. Win-Le was so new, we thought they wouldn’t be experienced enough, but we were wrong! It was almost ‘love at first sight’ when we met Colleen and Alex. These 2 ladies know their stuff! And they aren’t new to the area or industry at all. Every question we had was answered honestly and in full detail – they even gave us recommendations of other companies to interview because they truly believe homeowners need to find who is right for them. They never pushed us, never harassed us, and let us take our time making our decision without any pressure. We did interview with 2 other companies (1 they recommended and another a neighbor recommended), and our first instincts to go with Win-Le ended up being correct. We couldn’t be happier with our decision and we love working with the team at Win-Le!

Stacey D.

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