Family-friendly holiday rentals in Henlopen Acres

Guest suite in Rehoboth Beach

A view of the ocean is captured from a fenced front yard, featuring a grassy area and a paved road. The coastline is visible in the distance, where the shimmering water meets the sky, enhanced by a few wispy clouds.

4.97 out of 5 average rating, 156 reviews

Steps From The Ocean & Boardwalk On Surf Ave.

Enjoy a day or week at our unique beach front guest suite. You are only steps from the sand and boardwalk that leads you to the amazing restaurants and shops of Rehoboth Beach. Your private entrance is located just inside the fenced in front yard. The whole first floor and front yard is yours to enjoy. The 1,200 sf. space is PET FRIENDLY and has a back deck, front patio, full bath, 2 bedrooms with 1 queen& king bed, 1 reserved parking space, & kitchenette(no stove). 11.5% tax added at booking.

FamilyKitchenValue

An open-concept kitchen and living area features a large wooden island with a sink, surrounded by modern cabinetry. Natural light floods the space through wide windows, showcasing cozy seating and a vibrant dining area with a round table. Bookshelves line a portion of the wall.

4.97 out of 5 average rating, 102 reviews

Modern Beach House w/ Private Pool

Modern eco-friendly retreat perfect year-round! This salt-box cottage is an open concept 3 bedroom, 2 bathroom filled with natural light. Huge yard with a pool house with dining table and grill, patio with lounge chairs, outdoor shower, and private pool (pool open May 15 - October 15). Located perfectly for Rehoboth Beach or Dewey Beach visitors. It is a 20 minute walk to the shops and restaurants on Rehoboth Ave or to the beach. Three parking spots, beach items, and all amenities included.

KitchenIndoor spacesAmenities

A spacious bedroom is presented, featuring a four-poster bed with a light-colored bedding set. Flanking the bed are two bedside tables, each with a lamp. Natural light filters through the window, illuminating the soft, neutral tones of the room.

4.99 out of 5 average rating, 118 reviews

Coastal Modern Condo • Balcony, 2 Baths, East Rt 1

☀️ Your Rehoboth Beach Escape Why guests love staying here: • Community pool 🌴 • 2 full baths • Private screened balcony 🌿 • East of Route 1 • Strong central AC ❄️ • Split-bedroom layout for added privacy • Beach chairs & towels included 🏖️ • Fast WiFi + smart TVs • Plenty of FREE parking • In-unit washer & dryer • Minutes to beaches, boardwalk, restaurants & shopping • Quiet community close to everything Perfect for couples, families, girls’ weekends, and relaxing coastal getaways.

FamilyKitchenLocation

4.92 out of 5 average rating, 118 reviews

A charming beach cottage in a vibrant blue hue is framed by a black gate and a wooden fence. Lush greenery and blooming azalea bushes add color to the entrance, leading to a pathway illuminated by natural light. A gentle slope of trees enhances the tranquil setting.

Cottage in Dewey Beach

Shady Shore Cottage in North Dewey Beach

Charming Mid-Century beach cottage located in north Dewey Beach. Relax and enjoy one of the original beach cottages built in Rehoboth by the Sea in the 1960s. Only two blocks to the ocean and a short walk to restaurants in downtown Dewey or take a trolley ride to Rehoboth Beach for more restaurants and shopping. No parking pass needed - there's room for 4 cars in the driveway. Feel free to borrow the 3 beach chairs and enjoy the outdoor shower when you get back from the beach.

KitchenIndoor spacesAir conditioning

Cottage in Rehoboth Beach

A screened porch is depicted featuring a round table surrounded by four white, ornate chairs with cushioned seats. A vibrant bouquet of flowers sits at the center of the table, and light filters through the screens, enhancing the airy and relaxed setting.

4.85 out of 5 average rating, 206 reviews

The Good Stuff #2 - One Block to the Beach!

In Rehoboth Beach! Second block from the beach. Newly Redecorated. Come and enjoy these one of a kind vintage Rehoboth Beach cottages in a GREAT LOCATION! Perfectly nestled in a nice, quiet, family friendly neighborhood for relaxing yet close to everything. Walk and explore all Rehoboth has to offer; the beach; boardwalk; restaurants; shops; bike rental and more. Our clean, simple, comfy beach cottages are the perfect classic Rehoboth Beach experience. Come and Enjoy!

FamilyIndoor spacesLong stay

Holiday home in Dewey Beach

A modern dining area features a large white table surrounded by upholstered chairs. A vase with fresh flowers sits at the center, and sliding glass doors allow natural light to enter, providing a view of the outdoor space.

4.99 out of 5 average rating, 124 reviews

Luxury, Ocean Block 4B/3B Condo at Van Dyke Villas

Come stay at our stunning 4 bedroom, 3 full bathroom, ocean block condo with direct ocean views. This rental has every convenience for the perfect vacation. Located on the same block as the beach, you can have your feet in the warm sand within minutes. Newly renovated, this rental features modern amenities, including a fully upgraded kitchen and bathrooms, a gas fireplace, smart TVs throughout and an amazing, oversized screened-in porch with Ocean views.

Indoor spacesFamilyLaundry

The kitchen features modern cabinetry in a soothing blue hue, with stainless steel appliances and a white farmhouse sink. A stylish wooden shelf displays dishware, while unique wall fixtures provide light. The countertop offers ample space for meal preparation, creating an inviting cooking area.

4.99 out of 5 average rating, 99 reviews

Great Location! Bike path, Beach, Shop & Dine

Have fun with the whole family at this brand new, stylish bungalow located directly on the bike trail. Bike to Rehoboth Beach’s many restaurants, shops and the famous beach boardwalk. This custom home features many unique architectural details and is ideal for entertaining with multiple large seating areas. Thoughtfully decorated with local art and elegant furniture, the bungalow is the perfect setting for making lasting family memories in Rehoboth.

FamilyKitchenNearby

Townhouse in Rehoboth Beach

A spacious living area features a modern gray sectional sofa with beach-themed pillows. A round coffee table sits centrally on a vibrant area rug. Light enters through large windows, complemented by flowing curtains adorned with floral patterns. Artwork depicting ocean scenes enhances the decor.

4.9 out of 5 average rating, 377 reviews

Lover's Cove

3 Bedroom Townhouse-Minutes to Rehoboth Avenue and the beach. Rehoboth Avenue is .4 miles away. The ocean is .8. We are on the Ocean side of route 1. Great patio for dining, equipped with Weber propane grill, outdoor shower, beach chairs, tiki bar and patio set with umbrella. Wifi, cable and a dedicated work space. Lover’s Cove offers all modern amenities for your enjoyment and is decorated in modern decor.

FamilyKitchenGetting around

4.9 out of 5 average rating, 105 reviews

OceanfrontJewel|DirectOceanView•NewlyRenovatedPool

Oceanfront Jewel is proudly offered by RedHill Stays. Wake up to unobstructed ocean views from the top floor, just steps from the iconic Rehoboth boardwalk! Sip your morning coffee as the sun rises over the Atlantic, then fall asleep to the sound of waves at night. Designed for both romantic getaways and family escapes, this thoughtfully curated space blends comfort, style, and an unbeatable location.

FamilyIndoor spacesNearby

A round wooden dining table surrounded by eight woven chairs is positioned in a well-lit dining area. Soft natural light enters through large windows adorned with white blinds. A coastal-themed wall art piece enhances the serene ambiance, and a smaller table can be seen in the background.

5.0 out of 5 average rating, 233 reviews

Beautiful Beach House in Rehoboth

Modern spacious house in Rehoboth Beach with a large open floor plan on a quiet street. Five bedrooms/3.5 baths. Walk to town/beach - four blocks from beach right off Rehoboth Ave. Private pool with two levels of decks, grill and table/umbrella on top deck. Big open kitchen/dining/living area, over 3000 square feet of space overall.

FamilyKitchenPool

A single-story house is presented, featuring a welcoming front porch with screened seating. The exterior is surrounded by well-maintained grass and mature trees displaying autumn foliage. A driveway leads to the entry, enhancing the inviting appearance of the home.

4.96 out of 5 average rating, 235 reviews

Pet friendly cottage 4 blocks to Beach

South Rehoboth Beach House located in peaceful country club estates. Fully fenced with outdoor shower, 2 screened porches, gas grill, cable TV, wireless internet, full kitchen, beach chairs, 1 car parking in driveway and garage parking for 1 car. In season Rehoboth Beach parking permits provided DOGS ALLOWED $50 per stay fee

Indoor spacesFamilyView

A charming beach cottage exterior is framed by lush greenery and flower beds. A welcoming path leads to a screened porch, flanked by two large decorative pumpkins. The house features light-colored siding and black shutters, with a flag displayed on the side.

4.96 out of 5 average rating, 144 reviews

Classic Central Rehoboth Beach Cottage

A charming and comfortable beach cottage, walkable to everything-- two blocks to the beach, four blocks to the restaurants and shops of downtown Rehoboth Beach. Chef's kitchen, organic vegetable and herb garden in the backyard, outdoor shower, gas grill, and outdoor seating. Come relax at the beach!

Indoor spacesFamilyHospitality

Popular amenities for Henlopen Acres family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A spacious outdoor pool area features a large swimming pool with a vibrant blue interior and a jacuzzi nearby. Lounge chairs are arranged around the pool for relaxation. Fountains are visible at one end, adding a calming water feature to the setting.

4.96 out of 5 average rating, 112 reviews

Bright condo-On bike trail & 1 mile to boardwalk

KitchenIndoor spacesValue

A private hot tub is set on a paved patio beneath a shaded gazebo. Wooden decking surrounds the area, enhancing the serene outdoor setting. Lush greenery provides privacy, while outdoor lighting can be seen strung above, creating a welcoming space for relaxation.

4.94 out of 5 average rating, 106 reviews

Perfect Rehoboth Beach Getaway with Hot Tub

KitchenIndoor spacesBackyard

4.94 out of 5 average rating, 235 reviews

A cozy sleeping area features a spacious bed with a quilted grey coverlet. Two decorative yellow pillows are positioned at the head of the bed. A small bedside table holds a lamp and books, while a colorful area rug adds warmth to the space.

Tiny home in Lewes

Cozy Woodland Cottage

Indoor spacesFamilyHospitality

The exterior of a large white house is displayed, featuring black and white striped awnings over the windows. A welcoming front porch includes a bench and colorful flower pots. A spacious driveway provides parking, and a garage door is visible on the right.

4.88 out of 5 average rating, 248 reviews

Dodd House Beach Home w/private pool and hot tub

Indoor spacesKitchenView

A dining area is visible, featuring a wooden table surrounded by black chairs with red seat cushions. A pendant light hangs above, illuminating the space. Adjacent to the dining area, a kitchen with light-colored cabinetry and modern appliances is suggested, creating a welcoming atmosphere.

4.94 out of 5 average rating, 191 reviews

Classy Beach Getaway

Indoor spacesKitchenWalkability

4.97 out of 5 average rating, 195 reviews

A two-story beach house is depicted, featuring a spacious front porch with white railings and large deck areas. The structure is raised above a gravel driveway, with outdoor parking space visible below. The facade is painted in muted blue tones, complemented by wooden accents.

Home in Dewey Beach

McAvoy B & B

FamilyIndoor spacesWi-Fi

Cottage in Rehoboth Beach

A cozy sleeping area features a soft blue quilt covering the spacious bed, adorned with colorful dog-themed pillows. A neatly folded stack of white towels rests on the bed, while a bedside lamp provides gentle lighting, enhancing the room's warm ambiance.

4.96 out of 5 average rating, 219 reviews

Dog friendly *HOT TUB* Close to outlets, Sleeps 7

FamilyKitchenLocation

4.9 out of 5 average rating, 144 reviews

The spacious living area features a large sectional couch, designed for relaxation. A central coffee table sits in front of it, surrounded by natural light from multiple windows. A stylish dining area is visible in the background, complete with a wooden table and chairs.

Apartment in Lewes

HUGE bright 5BR, steps from the beach & downtown!

KitchenIndoor spacesParking

Family- and pet-friendly home rentals

The living area features a neutral sofa with decorative pillows, complemented by two armchairs. A wooden coffee table sits atop a colorful area rug. Natural light floods the space through large windows, and wall decor adds a touch of personality.

4.99 out of 5 average rating, 291 reviews

Midway Magnolia-3BR/2BA Home, dog-friendly

FamilyKitchenPets

4.99 out of 5 average rating, 220 reviews

A spacious kitchen with a large central island is featured, complemented by white cabinetry and stainless steel appliances. Natural light fills the room through the window, illuminating the dining area with a wooden table and blue chairs nearby, creating an inviting space for gatherings.

Cottage in Lewes

Ebb & Flow Beach House - Lewes Bay Beach Retreat

FamilyKitchenValue

A spacious dining area features a large wooden table surrounded by eight chairs. A decorative mirror hangs above the table, reflecting warm light from a unique pendant fixture. A doorway leads to a well-lit bedroom, with the bed visible through the open door.

4.88 out of 5 average rating, 185 reviews

Secluded Coastal Cottage • Just 9 Min to the Beach

FamilyIndoor spacesCondition

4.99 out of 5 average rating, 235 reviews

A wrap-around deck overlooks a tranquil waterfront view, featuring lush greenery and calm waters. A seating arrangement includes four chairs with cushioned backs, positioned for relaxation. The scene is punctuated by nearby trees, contributing to a serene atmosphere.

Home in Lewes

Beautiful Waterfront Home-Private, Clean, Relaxing

KitchenIndoor spacesWalkability

Superhost

4.81 out of 5 average rating, 760 reviews

Contemporary 1 Bedroom 2 level home

FamilyIndoor spacesView

4.93 out of 5 average rating, 158 reviews

A blue multi-story beach house features a wraparound porch, large windows, and a screened upper porch. Lush green trees and shrubs surround the front, providing a sense of privacy. The inviting architecture reflects a coastal aesthetic, suitable for family gatherings.

Home in Lewes

Lewes Delaware Beach House

Indoor spacesFamilyBiking

Apartment in Rehoboth Beach

A spacious bedroom features a large bed with dark bedding, complemented by wooden nightstands and lamps on either side. A world map accent wall adds visual interest, while natural light from a window with sheer curtains brightens the room. An adjoining bathroom is visible in the background.

4.97 out of 5 average rating, 668 reviews

Cozy condo / 3,5 miles from the beach.

KitchenFamilyAccuracy

Townhouse in Rehoboth Beach

The entrance to Rehoboth Crossing is framed by neatly trimmed green shrubs and large trees. A stone sign displaying 'Rehoboth Crossing' is prominently featured. Colorful flowers in shades of pink are planted in a decorative arrangement in front of the sign, adding a welcoming touch.

4.98 out of 5 average rating, 248 reviews

Newer townhome in Rehoboth with Pool

FamilyKitchenNearby

Family-friendly home rentals with a pool

A balcony view showcases the ocean, with serene waves and sandy shores. Large glass doors allow natural light to flood the interior, while outdoor seating and potted flowers add a charming touch to the space.

4.94 out of 5 average rating, 198 reviews

Sunrise Studio - Ocean Front, on Boardwalk, Pool!

FamilyIndoor spacesCleanliness

4.99 out of 5 average rating, 179 reviews

Stress-Free Family Beach Stay | Pool + Kid Perks

Indoor spacesFamilyBreakfast

Apartment in Rehoboth Beach

An open-concept living area features a light-colored sectional sofa adorned with textured pillows. A round coffee table sits on a soft area rug. The dining area, equipped with a sizable wooden table and stylish woven chairs, is visible in the background alongside modern kitchen appliances.

4.99 out of 5 average rating, 174 reviews

Cozy Rehoboth Beach Condo w/ 2 bedrooms

KitchenIndoor spacesAccuracy

Holiday home in Rehoboth Beach

A modern living space features a light color palette with wood accents and large glass doors offering ocean views. A sectional sofa, dining table, and stylish chairs are arranged for comfort. A telescope invites exploration of the expansive sea, while natural light brightens the area.

4.96 out of 5 average rating, 110 reviews

Mid century vacation condo newly renovated.

Indoor spacesKitchenView

An overview of the living area showcases a light wooden floor with a neutral-colored area rug. A simple white coffee table is centered between two light grey sofas. A floral decorative pillow rests on one of the sofas, adding a touch of color to the space.

4.94 out of 5 average rating, 147 reviews

Consistent 5-star rating Lakefront 3BR & 2BA condo

KitchenFamilyWi-Fi

Townhouse in Rehoboth Beach

The saltwater pool is surrounded by sun loungers and umbrellas, offering a relaxing space to unwind. Lush greenery borders the area, and a shed is visible nearby. The clear blue water reflects the sky, inviting guests to enjoy leisurely moments.

4.91 out of 5 average rating, 235 reviews

Downtown RB Townhome-Great Location-WALK TO BEACH

KitchenIndoor spacesCheckout

A bright living area is filled with natural light, featuring a spacious light blue couch and a white coffee table decorated with a bowl. A flat-screen TV is mounted on the wall opposite, alongside a cozy reading chair and a dining set for six.

4.98 out of 5 average rating, 235 reviews

Comfy and Convenient 2 bedroom/2 bath condo

Indoor spacesFamilyLocation

A well-maintained, two-story house with light blue siding is set on a landscaped lot. A spacious front porch invites relaxation, and a driveway leads to a two-car garage. Lush greenery complements the exterior, with trees and shrubs enhancing the welcoming atmosphere.