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

Millsboro, Delaware
$265 avg/night Minimum Stay 2 Nights
Bed 2

Bed

Bath 2

Bath

Home Condo

Property Type

Sleep 6

Max Sleeps

Night 2 nights

Min Stay

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. We have added 2 bicycles for your use, they are in the garage and there is a picture of them in our listing.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • GENERAL

    Energy-saving Switches Uses Some LED Lighting
  • KITCHEN

    Blender Coffee/tea Maker Dishwasher Ice Maker Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Balcony
  • POOL/SPA

    Hot Tub Pool
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Hair Dryer Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Basketball Nearby Fishing Nearby Golf Nearby Kayaking Nearby Swimming Nearby
  • ENTERTAINMENT

    Smart TV
  • LIVING SPACES

    Fireplace
  • CLIMATE CONTROL

    Air Conditioning
  • FAMILY FRIENDLY

    Children's Games Playground
  • LOCATION HIGHLIGHTS

    Near A Health Or Beauty Spa Near Outlet Shopping Near The Bay
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Rates & Availability

Review Review

  • Tom B.

    Submitted Jan 10, 2026

    Stayed Dec 26, 2025

    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.

  • Bev K.

    Submitted Oct 23, 2025

    Stayed Oct 13, 2025

    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.

  • Karen R.

    Submitted Oct 6, 2025

    Stayed Oct 3, 2025

    What a lovely condo! Comfortable bed, beautifully decorated, and a wonderful host who communicated promptly. Would definitely stay here again

  • Jacquie L.

    Submitted Sep 29, 2025

    Stayed Sep 12, 2025

    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!

  • Stephanie K.

    Submitted Sep 22, 2025

    Stayed Sep 19, 2025

    Absolutely amazing. Lots of thoughful touches, super clean.!

  • Abbie S.

    Submitted Sep 16, 2025

    Stayed Sep 14, 2025

    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!

  • Sweety L.

    Submitted Aug 31, 2025

    Stayed Aug 23, 2025

    The condo was so peaceful and decorated beautifully. Any communication with the host was prompt and courteous. We loved our stay!

  • Meg P.

    Submitted Jul 11, 2025

    Stayed Jul 2, 2025

    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!!!

  • Richard W.

    Submitted May 29, 2025

    Stayed May 27, 2025

    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.

  • GWEN P.

    Submitted May 16, 2025

    Stayed May 8, 2025

    Everything was great. No complaints.

  • Karen B.

    Submitted Apr 9, 2025

    Stayed Apr 4, 2025

    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

  • Cynthia S.

    Submitted Jan 7, 2025

    Stayed Dec 30, 2024

    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!

  • Wendy P.

    Submitted Sep 19, 2024

    Stayed Sep 11, 2024

    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.

  • Megan D.

    Submitted Sep 2, 2024

    Stayed Aug 29, 2024

    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

  • Denise T.

    Submitted Jul 27, 2024

    Stayed Jul 20, 2024

    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!

  • Matt S.

    Submitted Jul 15, 2024

    Stayed Jul 6, 2024

    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.

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Total

Includes taxes and fees
$265+
View details