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Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach

Photo gallery for Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach

Living area
Living area
Living area
Interior
Living area

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
2 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Air conditioning

Explore the area

View in a map
Millsboro, DE
  • Place, beach near Lingo Point
    ‪2 min drive‬
  • Place, 2nd Time Designs
    ‪5 min drive‬
  • Place, Nanticoke Indian Museum
    ‪6 min drive‬
  • Airport, Georgetown, DE (GED-Sussex County)
    ‪26 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 2

1 Queen Bed and 1 Twin Bed

Living Room 1

1 Double Sofa Bed

Master Bedroom

1 King Bed

2 bathrooms

Bathroom 2

Towels provided · Bathtub or shower · Bathtub · Toilet

Master Bathroom

Towels provided · Bathtub or shower · Bathtub · Toilet

Spaces

Kitchen
Balcony
Outdoor play area

About this property

Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach

Come enjoy and relax at The Peninsula - a beautiful and upscale gated country club and golf course community! The East Coast's most award-winning resort community is located on the Indian River Bay close to Rehoboth and Lewes beaches. This perfect blend of sophisticated yet comfortable resort living awaits you! Vacation at The Peninsula in this deluxe two-bedroom, two-bathroom condominium. Enjoy your morning coffee on the screened porch while watching the sun rise. If you prefer to eat in, there is a fully equipped kitchen with gas stove. The condominium comfortably sleeps up to six people. The master suite has a king bed with a sitting area and private bath. The second bedroom provides a queen bed and twin daybed. The Peninsula condominium is excellent for families looking for a worry-free vacation - the 3 indoor/outdoor pools and hot tubs (wave pool and adults-only pool available - from Memorial Day to Labor Day only), game center, playground, tennis, and basketball courts all offer an activity to please the whole group! For the outdoor-loving guests, the private bay beach is a short walk away. Enjoy fishing and crabbing as well as scenic nature trails. Kayaks and SUP (available for an additional charge) are a perfect way to take in the breathtaking views of the bay. The resort also offers pickle ball, bocce courts, volleyball, children's activities, fitness classes and so much more. Take advantage of casual dining at The Terrace Grille or fine dining (not available to rental guests on Friday or Saturday) at The Clubhouse. For the golfers, here is your chance to play a Jack Nicklaus Signature Golf Course for an additional fee. Guests can drive a short distance to the tax-free shopping at Tanger Outlets, downtown Rehoboth Beach with a boardwalk or Historic Lewes. No smoking allowed.
Club Amenity Fees due with final payments. Some Restrictions Apply. Pets are not allowed at this property. Peninsula rules allow for a maximum of 2 cars.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No 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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property

About the neighborhood

Millsboro

Millsboro is home to this condo. While the natural beauty of Cape Henlopen State Park and Rehoboth Beach can be enjoyed by anyone, those looking for an activity can check out Cape May - Lewes Ferry. 2nd Time Designs and Midway Speedway are also worth visiting. With kayaking, fishing, and swimming nearby, you'll find plenty of adventures in the water.
Map
Millsboro, DE

What's nearby

  • beach near Lingo Point - 2 min drive - 1.1 km
  • 2nd Time Designs - 5 min drive - 5.9 km
  • Nanticoke Indian Museum - 6 min drive - 6.5 km
  • Baywood Greens - 7 min drive - 7.2 km
  • Baywood Greens Golf Course - 16 min drive - 18.0 km

Getting around

  • Georgetown, DE (GED-Sussex County) - 33 min drive

Restaurants

  • ‪Wawa - ‬6 min drive
  • ‪McDonald's - ‬6 min drive
  • ‪Royal Farms - ‬7 min drive
  • ‪Dunkin' - ‬6 min drive
  • ‪Yellowfins Bar & Grill - ‬6 min drive

Frequently asked questions

Does Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach have a pool?

Yes, this property has a pool.

How much does it cost to stay at Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach?

As of May 6, 2026, prices found for a 1-night stay for 2 adults at Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach on Jun 1, 2026 start from $248, 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.

Is Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach?

Check-in begins at 3:00 PM.

What time is check-out at Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach?

Check-out is at 11:00 AM.

Where is Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach located?

Situated in Millsboro, this condo building is 2.9 mi (4.7 km) from 2nd Time Designs and within 6 mi (10 km) of Nanticoke Indian Museum and Baywood Greens. Delaware Seashore State Park and Marsh Island Golf Club are also within 9 mi (15 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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Rating 10 - Excellent. 20 out of 20 reviews
Rating 8 - Good. 0 out of 20 reviews
Rating 6 - Okay. 0 out of 20 reviews
Rating 4 - Poor. 0 out of 20 reviews
Rating 2 - Terrible. 0 out of 20 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Tom B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great stay as a family of four (children aged 1 and 3) here! Exceptionally clean, comfortable and equipped with all of our needs. We felt right at home, which is the best you can hope for with a weekend rental. We loved the welcome basket as well. Thank you for a great stay! We will happily book again when we are back to visit family.
Stayed 2 nights in Dec 2025
Verified

10/10 Excellent

Jacquie L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay for us and our toddler! Place was so clean and accessible. The community is so great too! Owner was accessible for questions leading up and during our stay which was very much appreciated!
Stayed 2 nights in Sep 2025
Verified

10/10 Excellent

Karen R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a lovely condo! Comfortable bed, beautifully decorated, and a wonderful host who communicated promptly. Would definitely stay here again
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Sweety L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The condo was so peaceful and decorated beautifully. Any communication with the host was prompt and courteous. We loved our stay!
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

Stephanie K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely amazing. Lots of thoughful touches, super clean.!
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

Abbie S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
I have stayed at many peninsula properties this one has to be one of the best. It was spotless upon arrival. The host was extremely accommodating the kitchen had everything you needed! Can’t wait to come back for an extended stay!! Thanks so much!
Stayed 2 nights in Sep 2025
Verified

10/10 Excellent

Karen B.

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

Wonderful place!

Offseason golf getaway and this condo was the perfect place to stay. The pictures don’t do it justice - very nice layout and furnishings - the owners have thought of everything to make your stay enjoyable!! You will feel very welcome with great communication prior to check-in and during your stay. We hope to be back later this year
Stayed 2 nights in Apr 2025
Verified

10/10 Excellent

Cynthia S.

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

Peninsula vacation rental

This rental is spotlessly clean, very comfortable and beautifully decorated with a chic and fun beach theme. It had everything we needed with thoughtful extra touches. The host was very responsive and happy to help with some additional requests we had. Would definitely stay here again!
Stayed 4 nights in Dec 2024
Verified

10/10 Excellent

Meg P.

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

Wonderful stay in the Peninsula

The condo was immaculate and extremely well-stocked for our stay. The owners were exceedingly responsive to our questions and couldn't have been more flexible. The property is walking distance to the pier, the pool, golf, pickleball/tennis and the clubhouse. 10 stars!!!
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

GWEN P.

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

Stay in DE

Everything was great. No complaints.
Stayed 4 nights in May 2025
Verified

10/10 Excellent

Megan D.

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

Amazing family stay

Condo is perfect for families! Great space and two good size bedrooms. Screened in porch is also added plus and so enjoyable. Walking distance to the clubhouse, which has indoor play area and pool for rainy days, as well as put putt, wave pool, kids activity pool and splash pad for good weather days. We will definitely be back
Stayed 4 nights in Aug 2024
Verified

10/10 Excellent

Matt S.

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

Recommended stay at the Peninsula

We are a family of five with 3 kids under 12, this is our fifth time staying at the Peninsula complex, first time at this location. The apartment was super clean, convenient walk to four pools and the bay, stocked with everything you need to cook your own meals (as we do a lot of), plenty of board games for the whole family, TVs in every room, beautifully decorated, and comfortable for a family of five. The owner was very friendly and most of all, super responsive. We would stay here again and I recommend this to any family of 4 to 5.
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Denise T.

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

Beautiful condo!

As previous reviewers stated, the condo was very clean, smelled great, is well stocked with everything for cooking, and is in a great location: walking distance to the pools, clubhouse, and nature trails. We especially appreciated that one of the pools is adult-only which allowed for a relaxing time. My husband and I along with our daughter and son-in-law had enough space in the condo to enjoy both family time and privacy. The beds were very comfortable. We would surely return here. 5 stars!
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Bev K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
I rarely write reviews, but I feel compelled to submit one in this instance because my husband and I were so impressed. This was actually our first experience with VRBO, and it was an extremely positive one. The owners answered our numerous questions thoroughly and promptly, enabling us to understand the process for booking the unit, for entry, and for preparing to check out. This condo is definitely a cut above others in which we've stayed over the years. It's visually striking, with a beautiful decor and amazing attention to detail. Well-stocked and spotless, it's easy to feel comfortable as soon as you walk through the door. There is a parking space for the unit in the ground floor garage, with a cart available for transporting belongings and groceries up to the unit. As a result, move-in (and -out) is easier and more efficient than it would be otherwise. We had a truly delightful stay and are already planning future rentals of this wonderful property.
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

Wendy P.

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

Wonderful!

Don't hesitate to rent this beautiful home. From the moment you enter, you can see the steps the owners have taken to make your stay comfortable. From comfortable beds and linens, to all of essentials you need in the kitchen, this home is perfect for couples or families. We had one hiccup, and the owners were responsive immediately. If I had anything to say on the negative side it would be that the development is huge, and the first day it took a few extra minutes to locate where the unit was. Once found, it was no problem. Don't hesitate to choose this home.
Stayed 4 nights in Sep 2024
Verified

10/10 Excellent

Doreen L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The Host was easy to communicate with and even let us know when the property was ready for an early check in. This home is stunning in every way. The Peninsula is my favorite community anywhere in Delaware. If you want a resort feeling community this is IT!
Stayed 7 nights in Apr 2026
Verified

10/10 Excellent

lori c.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The Condo was beautiful, everything as pictured. Clean and well appointed. It was also one of the most well stocked rentals we’ve stayed in. I hope to visit again!
Stayed 10 nights in Mar 2026
Verified

10/10 Excellent

Richard W.

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

Beautiful Condo in Fun Community

The property manager/owner was a pleasure to work with. He responded quickly to every question. The community was wonderful and in spite of rain we enjoyed ourselves very much.
Stayed 2 nights in May 2025
Verified

10/10 Excellent

Joseph d.

Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

Robert D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Jun 2025

About the host

Hosted by John Petrosino

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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