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Greenwood Family & Kid Friendly Rentals

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    Don't let other travelers get your favorite Greenwood area vacation rental. You're so close to securing your perfect getaway. Book today.
    26 Matching Rentals in the Greenwood AreaView all 33 rentals
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    1,250 Sq Ft BARN RETREAT-2BR,BEACH 17MILES JACUZZI/ PETS1 / 153
    (6)Very good
    Greenwood
    2 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    Sun and Sand Loft- just minutes to the beach:) Hot tub1 / 122
    (4)Excellent
    Greenwood
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    The following rentals are within 25 miles of Greenwood.
    Surfside Oasis on the Sand1 / 23
    (3)Excellent
    Milton
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Delaware Beach Bliss- Steps from the Beach1 / 9
    (4)Excellent
    Broadkill Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 9, 2018
    What an awesome rental in a great location! You will love this 2 story, open home full of windows, a spacious deck & located on a quiet lane. Comfortable beds, WiFi, washer...
    Reviewed June 8, 2018
    Well-kept and beautiful home. Loved the hammock swings outside. Spacious & well-stocked rental. Short walk to the beach.
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    About this property
    Make great family memories at our sunny, contemporary Broadkill Beach home near Lewes and Rehoboth, just steps from the beach. Go back in time. Broadkill is pristine, private, and next to the Prime Hook Nature Preserve. Golf nearby too! Explore the area on our 4 adult and 2 child bikes (bring your...
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    Broadkill Beach, Delaware 19968
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Brandt St 17071 #52061 / 22
    (1)Very good
    Lewes
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 7, 2018
    We stayed at the 17071 Brandt St condo for a week while my son played in the SATB (Sports @ the Beach). It was about a 20 min drive to SATB, straight down I-9. The Lewes town...
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    About this property
    Lewes' most popular luxury resort community. The town center offers pool, tennis courts, bocce ball courts, restaurants, sports bar, grocery store, coffee shop, and salon, all within walking distance. A jogging / bike path encircle the community Welcome to the First Town in the First State-Lewes...
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    Lewes, Delaware 19958
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Summerlyn 3 Bedroom 2 bath condo with pool1 / 11
    (1)Excellent
    Lewes
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 5, 2018
    We definitely recommend this place. First and foremost, it is so clean. Second, they have everything you need - towels, linens, kitchen items, etc. Third, it is close to...
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    About this property
    Luxury Supersuite (Summerlyn) Condo ~ 2000 sq ft of beautiful living space within 5-10 minutes of the Lewes and Rehoboth beaches. Master suite - bedroom & private bath with whirlpool tub/separate shower. Two other bedrooms with shared full bath. Plenty of space in the living room with TV, DVD. and...
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    Lewes, Delaware 19958
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Harbeson
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Balcony
    • DVD Player
    • Terrace
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Single Family home, 1,728 sq ft, 3 BRs, 2 full bathrooms, gas fireplace, screened back porch, fire pit with 6 chairs in the back yard, media room with 65' HDTV with Surround Sound, DirectTV service, WiFi internet is available, 20' iMac & computer table work space in the living room for your usage....
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    Harbeson, Delaware 19951
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Best Value at the Delaware Shore!1 / 15
    (17)Very good
    Lewes
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 10, 2018
    We were pleasantly surprised at how spacious this condo was, it had everything you needed to make our stay very comfortable.. The location was great near everything..The pool...
    Reviewed July 29, 2018
    My family (husband, son, Mom, & 2 dogs) stayed at this property for our first Delaware beach vacation. We all had an amazing time! Plenty of room in the condo (open floor...
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    About this property
    This spacious first floor three bedroom, two bath condominium is ideally located close to wonderful outdoor activities of Cape Henlopen State Park, some of the best restaurants in historic downtown Lewes, shopping at the Rehoboth Beach Outlets, and the fun and excitement of Rehoboth boardwalk as...
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    Lewes, Delaware 19958
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    ROMANTIC PRIVATE APARTMENT GETAWAY- 17 Miles to BEACHES & BAY--Pets!!1 / 140
    (2)Excellent
    Farmington
    1 Bedroom, 1 Bathroom, Sleeps 12 Quick View
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    • Washer
    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Patio
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 23, 2017
    Had a great weekend. Everything was just as pictured and described. Looking forward to returning with my family. They have and awesome Shepard and will bring our pet too
    Reviewed November 20, 2017
    This is the ideal honeymoon location– Totally private and secluded with tons of amenities including, candles and champagne when we arrived. The Jacuzzi was terrific and got...
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    About this property
    Studio apartment getaway private entry w/ jacuzzi and private entrance in wooded rural central De on 80 acre organic farm. Visit beaches, restaurants and shopping during the day and enjoy Delaware's peaceful countryside in the evening. Kids & pet friendly:) This beautiful studio apartment has...
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    Farmington, Delaware 19950
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 12
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    Beach Front- Dog and Child Friendly!1 / 18
    (32)Very good
    Slaughter Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Patio
    • Washer
    • Grill
    • Ocean Views
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 23, 2018
    I recently stayed at this beach house with my husband and toddler and it was a perfect fit. It felt like we had our own private beach! The house is adorable and well kept...
    Reviewed June 26, 2018
    This is like our 6th year staying here and it was wonderful as always. We bring our two Rotties that enjoy it just as much. Everything you need is there especially the peace...
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    About this property
    Charming beachfront cottage nestled in the dunes, with a beach level deck. The cottage is in a quiet residential area bordered by Delaware Bay and the Prime Hook National Wildlife Refuge. Biking, boating, swimming, fishing and bird watching can be enjoyed right outside the front door. There are...
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    Location Information
    Slaughter Beach, Delaware 19963
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lewes
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand new rental for 2018! Plantations is a wonderful established gated community located just behind the Route 1 outlets in Tax-Free Delaware. Lewes Beach (3 miles) has much calmer waves and is good for the younger children. Whether you are looking for fabulous restaurants, want to search for sea...
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    Location Information
    Lewes, Delaware 19958
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Broadkill Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely three-level, contemporary home is situated just a short block back from a quiet beach that's reminiscent of the movie classic 'Summer of '42'. If you're looking for a quiet, relaxing vacation away from the traffic and hectic pace of Rehoboth, Dewey, Ocean City, and other nearby Atlantic...
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    Location Information
    Broadkill Beach, Delaware 19968
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    Lewes
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
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    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kick off your getaway at this pristine 2-bedroom, 2-bathroom vacation rental condo, located just 3 miles from Lewes and Cape Henlopen State Park beaches! After a day of boating, fishing, or sunbathing by the Atlantic Ocean, all of the amenities of home plus prime resort features, including a pool...
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    Location Information
    Lewes, Delaware 19958
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Preston, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
    • Shared Indoor Pool
    • Private Yard
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home has a beautiful fire fly show in our historical wooded back yard. Always enjoy our wildlife our humming birds are the best. Go four leaf clover hunting. The deck is comfortable with lounge chairs for basting in the summer sun. We have goats that get loose... The horse that lives in our...
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    Preston, Maryland 21655
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Lewes
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Housekeeping Included
    • Balcony
    • Air Conditioning
    • Children's Pool
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A second floor three bedroom condo in a family friendly community with access to community pool and tennis courts both a 5 minute walk from condo. Several restaurants located in the community walking distance from condo. Major food market, CVS pharmacy, ice cream parlor, gym, breakfast bar and...
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    Location Information
    Lewes, Delaware 19958
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lewes
    2 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Wi-Fi
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note that this property features a security camera outside the front door* This blissful Lewes getaway beckons you to stay in comfort just 10-20 minutes from the ocean! With 2 bedrooms, 2 baths and accommodations for 10, this vacation rental condo boasts a screened porch and access to the...
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    Location Information
    Lewes, Delaware 19958
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 10
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    Lewes
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful 3 BR/2 BA condo is located in a resort like community just west of Coastal Highway in Lewes. A gated community with lush landscaping and scenic ponds, Plantations East offers a variety of housing styles including single family and townhomes. Convenient walking paths outlining the...
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    Location Information
    Lewes, Delaware 19958
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Lewes
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
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    • Children's Pool
    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relaxing pet friendly 3 bedroom waterfront cottage Paradise awaits in this hidden gem with a newly remodeled kitchen and water just a few feet away, an immaculate life-guarded salt water community pool, basketball courts, tennis and pickle ball courts, a brand new playground that is accessible for...
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    Location Information
    Lewes, Delaware 19958
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Lewes
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • DVD Player
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This comfy 'fun-in-the-sun' two-bedroom condo at the Villages of 5 Points is a wonderful place for a small family or group to enjoy their vacation in Lewes. Our third floor unit has 2 bedrooms, 2 full baths, living & dining areas plus a nice balcony to enjoy your morning coffee. New carpet was...
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    Location Information
    Lewes, Delaware 19958
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lewes
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    • Grill
    • Hot Tub
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    • Porch
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely home located in The Villages of Five Points East with 3300 sq ft, 2 fireplaces and conveniently located to all beaches. Walking distance to fine restaurants, fast food, pool, grocery store, retail stores and more. This house is designed for family living. Large great room with high...
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    Location Information
    Lewes, Delaware 19958
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Lewes
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are a family of five who have enjoyed countless summers here at the beach, swimming every day and going to the boardwalk. Our house is perfect because it is outside of all the action in a quiet, safe, family neighborhood but has easy 10 minute access to things such as Rehoboth, Dewey, Lewes,...
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    Location Information
    Lewes, Delaware 19958
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Preston, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Secure Parking
    • Patio
    • Housekeeping Included
    • Balcony
    • Shared Indoor Pool
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 18 acres large deck over looks historical woods. Nature at its best... Hawks, rabbits, deer, all kinds of birds.... Our hummin birds are fabulous... WE have a complimentary coffee/ tea bar, we can set up a water slide for a fee also manicures and pedicures plus ear candling done on site...
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    Location Information
    Preston, Maryland 21655
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Millsboro
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Private Yard
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    • Shared Indoor Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    OUR HOME IS WITHIN 'THE PENINSULA' A GATED COMMUNITY ON THE INDIAN RIVER BAY JUST MILES FROM REHOBOTH BEACH< DEWEY BEACH AND LEWES BEACH. THE PENINSULA HAS A WORLD CLASS 18-HOLE GOLF COURSE, 1-INDOOR POOL, 1 ADULT POOL, 1 WAVE POOL. THE CLUB HOUSE IS COMPLETE and opened in 2017. the CLUB HOUSE...
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    Millsboro, Delaware 19966
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Slaughter Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Ocean Views
    • Washer
    • Wi-Fi
    • DVD Player
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Slaughter Beach vacation rental chalet is perfect for your next beach experience. There are excellent views of the water, and if you want to take a swim, the town beach is only a 10-minute walk from the property. With 3 bedrooms and 1.5 bathrooms, this secluded property offers a spacious deck...
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    Location Information
    Slaughter Beach, Delaware 19963
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lewes
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the first city in the First State and stay just steps from a peaceful lake in this 3-bedroom, 3-bath vacation rental townhome. Located in a quiet, well-maintained Lewes neighborhood, this recently renovated and furnished home boasts a 2-story interior with contemporary amenities. Relax on...
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    Location Information
    Lewes, Delaware 19958
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Millsboro
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that this property features exterior security cameras on the front porch. These do not look into any interior spaces ** Bring the family along to this 5-bed, 2.5-bath vacation rental that sleeps 14 in Millsboro! Boasting 1,800 square feet, this house promises plenty of wiggle room...
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    Location Information
    Millsboro, Delaware 19966
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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