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Middlesex Vacation Rental Properties

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11 Addy Road, Bethany Beach
Community
Middlesex
Location
West of Route 1
Bedrooms
5
Baths
4
Half Baths
0
Sleeps
12

Please call for rates.

Wonderful family rental in the exclusive Middlesex Beach community located in Bethany Beach! This stunning property is perfect for families, with the capacity to sleep up to 12 guests comfortably. With 5 bedrooms and 4 full bathrooms, this spacious retreat is the epitome of comfort. The interior features 4 Queen beds, 1 Single Sofa bed, 2 Bunk beds, and 1 Futon, ensuring that everyone has a cozy place to rest after a day of beachside fun. The amenities in this home are truly top-notch, including a fully equipped kitchen with a dishwasher, microwave, disposal, coffee maker, toaster, and blender. Stay cool with central AC and ceiling fans throughout the property. Entertainment options abound with cable TV, DVD players, and wireless internet. Step outside to enjoy the fresh air on the deck or screened porch, or fire up the BBQ charcoal grill for a delicious cookout. After a day at the beach, rinse off in the convenient outdoor shower. This property is located in a prime spot west of Route 1, providing easy access to all the attractions of Bethany Beach. With 5 parking spaces available, you can bring the whole family along for a beach getaway. Please note that this is a smoke-free property and pets are not accepted. Linens are not provided, so be sure to bring your own. Utilities are included for your convenience. Don't miss out on the opportunity to stay in this fabulous vacation rental with all the comforts of home and more. Book your stay today and create unforgettable memories in Bethany Beach!

139 Evergreen Road, Bethany Beach
Community
Middlesex
Location
West of Route 1
Bedrooms
4
Baths
4
Half Baths
1
Sleeps
12

Please call for rates.

PRIVATE BEACH-Fully updated home! Welcome to Middlesex Beach! Updated and ready for your family to rent this summer. The large private lot is almost a half-acre and is located one half mile from the private beach complete with lifeguards. Middlesex Beach features six blocks of private beaches, a security guard to get into the ocean block parking spots, and beach passes. This large home has a great floor plan with entry foyer, family room with built-ins, laundry room, and first level master suite. The second level features two ensuite bedrooms with their own private bathrooms. The third level features a gourmet kitchen open to dining area and great room with access to a screened porch and deck. There is also a powder room and additional master bedroom suite on this top level. Lots of room for family and friends in this 4 bedroom, 4 1/2 bath home with two separate living areas and lots of outdoor living spaces in screened porch and on trex decks. Also, featuring a one car garage, large driveway, and outdoor shower for after a day on the beach. The new owner have done several enhancements and added new furniture and arranged areas to be more comfortable. Middlesex Beach is convenient to restaurants and attractions in both South Bethany and Bethany Beaches. MaKe this the perfect destination for your family Vacation

24 Bayberry Road, Bethany Beach
Community
Middlesex
Location
West of Route 1
Bedrooms
4
Baths
1
Half Baths
3
Sleeps
12

Rates: $3900.00 - $5100.00

Welcome to tthe sought-after Community of Middlesex Beach in the charming Town of Bethany Beach. This classic Middlesex beach house is a must-see for anyone looking for a perfect beach getaway. With 4 traditional bedrooms and an additional loft set up as a second suite with a half bath, this property can comfortably accommodate up to 12 guests. The sleeping arrangements include 1 king bed, 3 queen beds, 1 double bed, and 2 single beds, ensuring that everyone has a cozy place to rest after a day of fun in the sun. Situated just two blocks from the beach, this home offers convenient access to the private Middlesex beach, allowing you to enjoy the sand and surf with ease. The outdoor space is perfect for al fresco dining, with benches, deck chairs, picnic tables, and 6 umbrellas providing plenty of seating options for your group. Inside, you'll find 4 bedrooms, 2 full bathrooms, and 2 half bathrooms, ensuring that there's more than enough space for everyone to freshen up after a day at the beach. The property is located west of Route 1 and comes equipped with a range of amenities to make your stay comfortable and enjoyable. From a fully stocked kitchen with modern appliances to central AC, ceiling fans, a washer and dryer, and multiple TVs, this property has everything you need for a relaxing vacation. Additional amenities include outside showers, a gas BBQ, a three-season room, and wireless internet access. Whether you're looking to relax on the beach, explore the charming town of Bethany Beach, or simply unwind in a beautiful setting, this property has it all. Don't miss out on the opportunity to make unforgettable memories at this lovely Middlesex beach house. Book your stay today!

27 Dune Road, Bethany Beach
Community
Middlesex
Location
Ocean Block
Bedrooms
4
Baths
3
Half Baths
0
Sleeps
12

Please call for rates.

Escape to the exclusive Middlesex Beach community located just south of Bethany Beach for the ultimate beach getaway! This charming older home offers the perfect blend of comfort and convenience, just steps away from the private beach. Step inside this two-story, 4-bedroom, 3-bath home and be greeted by a spacious living area ideal for unwinding after a day in the sun. The fully equipped kitchen makes meal preparation a breeze with modern appliances including a dishwasher, microwave, coffee maker, toaster, and blender. Accommodating up to 12 guests, this home is ideal for large families or groups. The bedrooms feature a variety of sleeping arrangements including 2 Queen beds, 4 Single beds, 1 Trundle bed, and 1 Pyramid bed, ensuring everyone has a cozy spot to rest. Relax and enjoy the ocean breeze on the screened porch or deck, perfect for your morning coffee or hosting a BBQ with loved ones. Additional amenities include central AC, ceiling fans, cable TV, a washer and dryer, parking for 6 vehicles, and an outdoor shower to rinse off the sand. This smoke-free property does not allow pets, creating a clean and allergy-friendly environment for all guests. With utilities included and wireless internet access, you'll have everything you need for a comfortable stay in this exclusive beach community. Don't miss out on this opportunity to experience the best of beach living in Middlesex Beach, Bethany Beach. Book your stay now and create unforgettable memories by the sea!

32 Bridge Rd., Middlesex
Community
Middlesex
Location
Ocean Block
Bedrooms
4
Baths
3
Half Baths
0
Sleeps
8

Please call for rates.

The charming community of Middlesex, just a stone's throw away from the pristine shores of Bethany Beach. This spacious property is perfect for families or groups, with the capacity to sleep up to 8 guests comfortably. As you step inside, you'll be greeted by 4 inviting bedrooms and 3 full bathrooms, ensuring that everyone has their own space and privacy. The tastefully decorated interiors feature a luxurious King bed, a cozy Queen bed, 3 Single beds, and a convenient Trundle bed, guaranteeing a good night's sleep for all. The well-equipped kitchen is a chef's delight, boasting modern appliances such as a dishwasher, microwave, disposal, coffee maker, toaster, toaster oven, blender, and more. The central AC and ceiling fans throughout the property will keep you cool and comfortable during your stay. Outside, you'll find 2 decks where you can soak up the sun or enjoy al fresco dining with the BBQ gas grill. After a day at the beach, rinse off in the refreshing outdoor shower before heading inside to relax in front of the cable TV or enjoy the rooftop deck with stunning views. This property offers 4 parking spaces, so you can easily bring your vehicles along. Please note that pets are not accepted in this rental. Additionally, the property comes fully furnished with utilities included, so you can focus on making unforgettable memories. With amenities such as a full-size refrigerator, stove, oven, wireless LAN, Smart TVs, and more, this rental has everything you need for a comfortable stay. Just bring your own linens, and you're all set for a relaxing beach getaway. Don't miss out on the opportunity to enjoy private beach access and all the comforts of home in this beautiful Ocean Block property. Book your stay now and experience the best of Bethany Beach living at this fantastic vacation rental in Middlesex.

32 East Errett Road, Bethany Beach
Community
Middlesex
Location
Ocean Block
Bedrooms
4
Baths
4
Half Baths
0
Sleeps
12

Rates: $4800.00 - $6200.00

Perfect in Pink – 32 East Errett Road, Middlesex Beach Welcome to "Perfect in Pink," a spacious coastal retreat located in the highly desirable private guarded beach community of Middlesex Beach in Bethany Beach, Delaware. Ideally situated in the ocean block, this 4-bedroom, 4-bath vacation home places you just a short walk from the beach while offering plenty of room for family and friends to relax together. Designed with an inverted floor plan to take advantage of the coastal setting, the home's upper level features a bright and inviting great room, well-equipped kitchen, dining space for 12, and access to an oversized open open deck. It's the perfect setting for morning coffee, afternoon relaxation, or gathering together after a day on the beach. The home comfortably accommodates up to 12 guests and includes two spacious King suites, making it especially well suited for multiple families or generations vacationing together. Sleeping arrangements include: Bedroom 1: King Bedroom 2: King Bedroom 3: Queen with 1 twin and trundle Bedroom 4: 3 Single beds with 1 trundle With 4 full bathrooms, everyone has room to spread out and enjoy a comfortable stay. Outdoor living is an important part of the experience at Perfect in Pink. Enjoy the screened porch, open sun deck, outdoor shower, and gas grill—ideal for easy summer meals and relaxing evenings after the beach. Additional conveniences include central air conditioning, Wi-Fi, 3 TVs, cable television, washer and dryer, six ceiling fans, a second refrigerator, and parking for up to 6 vehicles. The fully equipped kitchen includes a dishwasher, microwave, Keurig, traditional coffee maker, blender, mixer, toaster, cookware, dinnerware, and plenty of space for preparing family meals. Best of all, guests enjoy the special setting and atmosphere of Middlesex Beach, a sought-after private beach community known for its beautiful stretch of Delaware coastline and relaxed residential feel. For families looking for a spacious Bethany Beach vacation rental close to the ocean, "Perfect in Pink" combines location, comfort, views, and plenty of gathering space for a memorable week at the beach. Property Highlights: 4 Bedrooms • 4 Full Baths • Sleeps 12 • Ocean Block • Middlesex Private Beach Community • 2 King Suites • Ocean Views • Open Deck • Screened Porch • Outdoor Shower • Gas Grill • Central A/C • Wi-Fi • 3 TVs • Parking for 6 • No Tenant Pets • Smoke-Free Check-In: 3:00 PM Check-Out: 10:00 AM

33 Dune Rd, Bethany Beach
Community
Middlesex
Location
Ocean Block
Bedrooms
5
Baths
3
Half Baths
1
Sleeps
13

Rates: $10500.00 - $10500.00

33 Dune Road | Middlesex Beach Located in Middlesex Beach, just south of Bethany Beach, this classic ocean-block beach home is thoughtfully designed for 7-day family vacations and offers only a limited number of summer weeks for rent. With an easy walk to the beach and a layout ideal for multi-generation families, this home delivers the relaxed, traditional beach week families return for year after year. The home comfortably sleeps up to 13 guests and features 5 bedrooms, 3 full bathrooms, and 1 half bath, along with multiple outdoor spaces to enjoy ocean air and coastal breezes. No pets and smoke-free, this property is reserved exclusively for family use. Why Families Love It Ocean Block location – quick, easy beach access Limited summer availability for a quieter, more exclusive experience Two spacious decks for morning coffee and evening relaxation Outside shower for post-beach convenience Parking for 3 vehicles plus street parking Central A/C & ceiling fans throughout Family rentals only | No pets | Smoke-free Sleeping Arrangements 2 King Beds 2 Queen Beds 2 Bunk Beds 1 Trundle Bed Amenities The fully equipped kitchen includes a full-size refrigerator, stove, oven, dishwasher, microwave, coffee maker, toaster oven, and mixer, along with complete cookware, dinnerware, and silverware. Additional conveniences include washer & dryer, iron and ironing board, vacuum, 4 Smart TVs, and comfortable indoor living spaces perfect for family meals and downtime together. If you're seeking a true 7-day family beach vacation in a peaceful ocean-block setting just south of Bethany Beach, 33 Dune Road in Middlesex Beach offers the space, comfort, and location to create lasting summer memories—one perfect beach week at a time.

34 Bridge Rd, Bethany Beach
Community
Middlesex
Location
Ocean Block
Bedrooms
6
Baths
2
Half Baths
1
Sleeps
11

Rates: $4500.00 - $8000.00

Located in the exclusive private beach community of Middlesex Beach, this inviting Ocean Block home at 34 Bridge Road offers the perfect setting for a classic Delaware beach vacation with a private pool. Designed for comfort and flexibility, the property features 6 bedrooms and accommodations for up to 11 guests, making it ideal for extended families or groups traveling together. The home's unique floor plan creates the feel of three smaller cottages combined, offering both shared gathering spaces and private retreats. Two of the sleeping areas are located on the second level with their own exterior entrances, while the main level hosts additional bedrooms along with a warm, open living area and kitchen designed for family meals and relaxing after a day at the beach. Guests will enjoy the covered porch and outdoor living areas, perfect for morning coffee or evening gatherings. Just a short walk from the quiet beaches of Middlesex, this property provides the privacy of a gated coastal community while remaining minutes from the shops, dining, and boardwalk of Bethany Beach.

38 Dune Rd, Bethany Beach
Community
Middlesex
Location
Ocean Front
Bedrooms
6
Baths
5
Half Baths
0
Sleeps
12

Rates: $21000.00 - $23000.00

38 Dune Road – Newly Renovated Luxury Oceanfront Retreat | Middlesex Beach | Sleeps 12 Experience the ultimate Bethany Beach vacation at 38 Dune Road, a beautifully renovated direct oceanfront home located in the exclusive Middlesex Beach community. Featuring updated furnishings, spectacular Atlantic Ocean views, and direct access to the private beach, this spacious coastal retreat offers the perfect combination of comfort, luxury, and an unbeatable beachfront location. This expansive home features 6 bedrooms plus a den, 5 full bathrooms, and accommodations for up to 12 guests. With four king beds, two double beds, and additional twin beds, the home provides comfortable sleeping arrangements for families and multigenerational gatherings. The recent renovations bring a fresh, updated coastal feel throughout the home, complemented by stylish new furnishings and inviting living spaces. One of the home's standout features is its ocean-facing kitchen, allowing guests to enjoy breathtaking views of the Atlantic while preparing meals and gathering with family. The spacious living and dining areas offer plenty of room to relax, entertain, and enjoy time together. A new elevator is scheduled to be installed in January 2027, adding another level of convenience and accessibility for guests. Outdoor living is truly exceptional! An expansive main-level deck wraps around approximately three sides of the home, providing incredible panoramic ocean views and plenty of space for sunbathing, outdoor dining, or simply enjoying the ocean breeze. A second upper-level deck offers another spectacular vantage point for watching the sunrise or relaxing above the shoreline. Located in the desirable private Middlesex Beach community, guests enjoy access to a beautiful private beach with seasonal lifeguard services. Downtown Bethany Beach, with its charming shops, restaurants, boardwalk, and entertainment, is just approximately half a mile away. Additional amenities include central air conditioning, Wi-Fi, cable television, six TVs, a gas grill, outdoor shower, two sets of washers and dryers, and convenient on-site parking. Whether you're enjoying the newly renovated interiors, taking in the ocean views from the kitchen, relaxing on the expansive decks, or spending the day on the private beach, 38 Dune Road delivers an unforgettable oceanfront vacation experience! Property Highlights: Direct Oceanfront | Fully Renovated | Updated Furnishings | Ocean-Facing Kitchen | New Elevator Planned for January 2027 | Private Middlesex Beach | Sleeps 12 | 6 Bedrooms + Den | 5 Full Baths | Expansive Oceanfront Decks | Direct Beach Access | Wi-Fi | Central A/C | Outdoor Shower Non-Smoking | Linens Not Provided | Seasonal Lifeguard Services Offered by Crowley Associates Realty – Serving Bethany Beach vacationers since 1973. Just a 1/2 mile to the town of Bethany Beach offering walkable shops and restaurants.

39 Dune Road, Bethany Beach
Community
Middlesex
Location
Ocean Block
Bedrooms
5
Baths
3
Half Baths
0
Sleeps
10

Please call for rates.

Escape to this stunning 5-bedroom, 3-bath vacation home just south of the Town of Bethany Beach in the Middlesex Beach Community. With the capacity to sleep up to 10 guests, this two-story beach retreat is the perfect coastal getaway for families and friends. Conveniently located just steps away from Middlesex's private beach, this home offers a prime location and a well-thought-out setup. Enjoy the sound of the surf and the salty breeze as you relax on one of the two decks, with the upper deck even providing a glimpse of the ocean. The ground floor of this beach retreat features a full bathroom, two bedrooms, and a cozy den, while the top floor boasts a spacious living room, dining room, a fully equipped kitchen, another full bathroom, and the remaining three bedrooms, including a luxurious master suite. The master bedroom and Bedroom 2 even share a charming screened porch, perfect for enjoying your morning coffee or evening cocktails. This property comes fully equipped with modern amenities, including central air conditioning, a washer and dryer, three flat-screen TVs, a DVD player, a Keurig coffee maker, a gas fireplace, a gas grill, and wireless internet. Additionally, guests can take advantage of the two outdoor showers after a day at the beach. Parking is available for up to 3 vehicles, and please note that this is a non-smoking property with no pets allowed. While the garage is not accessible to guests, the abundance of amenities and the proximity to the beach make this vacation home a true gem in the Middlesex Beach Community. Don't miss out on the opportunity to create lasting memories in this spacious and well-appointed beach retreat. Book your stay today and experience the best of coastal living in this beautiful vacation home!


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