Entire condo

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

An indoor swimming pool with clear lanes, a sunlit roof, and lounge chairs along the sides. - Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach (Millsboro)
A wooden boardwalk leading to a dock with boats and a clear view of the water. - Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach (Millsboro)
A modern living room with a dining area, kitchen, and a clock on the wall. - Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach (Millsboro)
An aerial view of a sports complex with multiple tennis courts, a swimming pool, and a large covered area. - Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach (Millsboro)
An aerial view of a golf course with a lake, surrounded by residential areas and a clubhouse. - Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach (Millsboro)
At Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach, you can look forward to a playground, laundry facilities and a gym. For some rest and relaxation, visit the hot tub. Stay connected with free in-room WiFi.

Reviews

10 out of 10
Exceptional

Entire condo

2 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Add dates for prices

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! There is a separate amenities fee for use of the pools and other amenities that is paid to the community association at the Concierge Desk in the Activity Center. 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. We have added 2 bicycles for your use, they are in the garage and there is a picture of them in our listing. Our Community Association requires a 7 day stay from Memorial Day to Labor Day. The rest of the year there is a 3 day minimum stay.

Property amenities

Pool/Spa

  • Hot tub
  • Pool

Internet

  • Available in the condo: Free WiFi

Parking and transport

  • Wheelchair-accessible parking available
  • Onsite parking options include a garage

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 2 accessible parking spaces
  • Area rugs in public areas
  • Front entrance ramp
  • Hardwood flooring in public areas
  • Lift
  • Pool hoist on site
  • Thin carpet in public areas
  • Wheelchair-accessible parking
  • Wheelchair-accessible path of travel
  • Wheelchair-accessible path to lift
  • Wheelchair-accessible pool
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a health/beauty spa
  • Near an outlet shopping centre
  • Near the bay

Things to do

  • 4 outdoor pickleball courts
  • Bicycle parking
  • Bicycles
  • Gym
  • Tennis
  • Basketball nearby
  • Fishing nearby
  • Golfing nearby
  • Kayaking nearby
  • Swimming nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)

General

  • Bicycle parking
  • Bicycles
  • Recycling
  • Some LED lighting used

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Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

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
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 is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

About the area

Millsboro is home to this condo. Shoppers can check out Tanger Outlets, while everyone can enjoy the natural beauty of Lewes Beach and Rehoboth Beach. 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. Visit our Millsboro travel guide
View more Condo rentals in Millsboro
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
  • Royal Farms
    7 min drive
  • McDonald's
    6 min drive
  • Dunkin'
    6 min drive
  • American Legion - Post 28
    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.

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

On-site 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?

Checkout is at 10:00 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 miles (10 km) of Nanticoke Indian Museum and Baywood Greens. Delaware Seashore State Park and Baywood Greens Golf Course are also within 12 miles (20 km).

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Reviews

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

10

Exceptional

10

Cleanliness

10

Location
Rating 10 - Excellent. 25 out of 25 reviews
Rating 8 - Good. 0 out of 25 reviews
Rating 6 - Okay. 0 out of 25 reviews
Rating 4 - Poor. 0 out of 25 reviews
Rating 2 - Terrible. 0 out of 25 reviews

Reviews

Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a very enjoyable stay. The condo is tastefully and beautifully decorated and fully equipped. We were ideally located to all the resort amenities. Communications with our hosts were excellent.
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

10/10 Excellent

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 review

10/10 Excellent

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

Stay in DE

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

Stayed 7 nights in Aug 2025
Verified review

10/10 Excellent

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