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.

KitchenFamilyBathroom

4.94 out of 5 average rating, 135 reviews

In-Town Rehoboth Beach, Walk to Everything!

Comfortable In-Town Rehoboth Beach Home. Walk to all that Rehoboth has to offer! Just one block to Rehoboth Avenue and five blocks to the beach. Host a small party on the large screened porch, grill your dinner, or play in the large back yard. This home has driveway parking for two cars. An additional Rental Agreement is required to rent this home. It is delivered by email following booking, signed and returned to host by email. The agreement may be reviewed before booking, by request.

FamilyKitchenBiking

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, 177 reviews

Cozy Rehoboth Beach Condo w/ 2 bedrooms

This condo is a boho getaway tucked away in a quiet enclave conveniently located on the beachside of Highway 1. It has dedicated parking in front, plus an additional spot for a second car. This condo it is a two bedroom/two bathroom unit. Full kitchen and a dining area that seats up to six. The condo is on the second floor with one stair flight. The beach is a 20 minute walk, 10 minute bike ride, or 5 minute drive Community pool on site provides an extra place to relax and cool down.

Indoor spacesFamilySleep quality

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, 103 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.

FamilyIndoor spacesHospitality

4.96 out of 5 average rating, 228 reviews

Breakfast at Tiffany - Spacious Home w/ Deck

This tastefully furnished home is the perfect getaway in the Midway Estates neighborhood of Rehoboth Beach. Located within 6 miles of Lewes Beach, Cape Henlopen State Park, and Rehoboth Beach this house is centrally located east of Route 1 and has plenty of room for your family vacation. With all amenities included and plenty of entertainment options this is the ultimate carefree retreat. Walkable to many restaurants, movie theater, mini golf, outlets, go-karts, water park and more!

KitchenIndoor spacesTV

4.92 out of 5 average rating, 119 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 spacesNearby

A spacious living area features two large sofas, one being a queen sleeper bed. A wooden coffee table sits on a neutral area rug. A dresser and smart TV are positioned along the wall, with a dining area visible through an open layout.

5.0 out of 5 average rating, 124 reviews

The Loft 2B/2BA minutes to Rehoboth & Lewes Beach

Escape to a stylish coastal 2 bedroom 2 bath condo designed for relaxing beach vacations, family trips, and weekend getaways. Conveniently located just minutes from Rehoboth Beach and Lewes, The Loft offers the perfect combination of comfort, convenience, and coastal charm. Whether you're planning a family beach trip, a couples retreat, shopping weekend, or exploring Delaware’s beautiful coastline, you'll have everything you need for a memorable stay.

Indoor spacesFamilyCheck-in

Cottage in Rehoboth Beach

A charming front porch features white wicker chairs adorned with plush cushions and a round table. Flower pots add a touch of greenery, while hanging planters bloom with vibrant flowers. Lush plants and shrubbery are visible in the background, enhancing the inviting outdoor space.

4.92 out of 5 average rating, 226 reviews

The Good Stuff #1 - One block from the 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; and more. Our clean, comfy, simple, beach cottages are the perfect classic Rehoboth Beach experience. Come and Enjoy!

KitchenFamilyBathroom

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.

KitchenFamilyWalkability

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, 235 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.

Indoor spacesFamilyWi-Fi

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

KitchenIndoor spacesValue

An inviting living space features a plush navy sofa and a light-colored coffee table on a vibrant, circular patterned rug. High ceilings with exposed beams enhance the airy feel. A modern dining area can be glimpsed in the background, with a glimpse of the kitchen visible beyond.

4.98 out of 5 average rating, 123 reviews

Hot Tub, Sheets & Towels and IN TOWN!

Gorgeous, modern, bright and open renovated Rehoboth home with 4 large bedrooms (each with king bed!) and a new HOT TUB, 2 nice bathrooms, fenced yard, parking for 3 cars, FIRE PIT, and grill and on a quiet, tree lined street one block off Rehoboth Ave and 2 blocks to Dogfish Head! Only a 15 minute walk to the boardwalk too.

FamilyIndoor spacesAccess

Popular amenities for Henlopen Acres family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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

Indoor spacesKitchenParking

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

KitchenFamilyGetting around

4.94 out of 5 average rating, 236 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 spacesFamilyValue

Cottage in Rehoboth Beach

The spacious kitchen features a large island with four barstools. Brightly lit pendant lamps hang above the island, and a farmhouse sink is positioned under the window. Cabinets are stylishly finished in navy blue, complemented by light countertops and backsplash.

4.96 out of 5 average rating, 246 reviews

Hot Tub, Fire Pit, Private Back Yard, Relaxing

FamilyKitchenSleep quality

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

KitchenIndoor spacesPool

4.91 out of 5 average rating, 107 reviews

The open living space features light wooden paneling and natural light streaming through multiple windows. A blue sofa faces a flat-screen TV, while a small dining table with stools is positioned nearby. The kitchen area is equipped with modern appliances for convenience.

Cottage in Dewey Beach

Uncle Buck's Cottage

KitchenFamilyPets

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, 249 reviews

Dodd House Beach Home w/private pool and hot tub

Indoor spacesFamilyGetting around

4.9 out of 5 average rating, 145 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!

KitchenFamilyQuiet

Family- and pet-friendly home rentals

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

Indoor spacesFamilyWi-Fi

4.99 out of 5 average rating, 221 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

KitchenFamilyTV

4.95 out of 5 average rating, 323 reviews

Condo in Lewes

Modern & Cozy Retreat | Pool | Close to Beaches

FamilyIndoor spacesHot tub

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

KitchenFamilyAccuracy

Superhost

4.81 out of 5 average rating, 761 reviews

Contemporary 1 Bedroom 2 level home

KitchenIndoor spacesWalkability

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

KitchenFamilyTV

A charming two-story house features a large covered porch with seating and decorative lanterns. The soft green and white exterior is complemented by a manicured garden showcasing colorful flowers and lush greenery. Trees provide shade, creating a peaceful ambiance around the property.

4.98 out of 5 average rating, 107 reviews

Modern Beach House | Walk to Beach & Town

Indoor spacesFamilyLocation

A cozy nook is featured beside a bright window, showcasing a wooden bench adorned with textured cushions. A decorative pillow with the word 'Beach' complements the scene, while natural light illuminates the green backyard visible through the glass. A woven pouf serves as additional seating.

5.0 out of 5 average rating, 99 reviews

The Jungalow - Dog Friendly, Fenced in & Pool

FamilyKitchenLaundry

Family-friendly home rentals with a pool

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 spacesKitchenGetting around

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, 236 reviews

Downtown RB Townhome-Great Location-WALK TO BEACH

Indoor spacesFamilyBathroom

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!

FamilyKitchenCheckout

4.99 out of 5 average rating, 180 reviews

Stress-Free Family Beach Stay | Pool + Kid Perks

Indoor spacesKitchenCleanliness

A dining area is showcased with a grey table set for six, surrounded by vibrant yellow chairs and a metal wire-frame chair. A modern light fixture hangs above, and a decorative wreath adorns the wall, complemented by abstract artwork on either side.

4.98 out of 5 average rating, 221 reviews

Renovated Condo Near Outlets, 3.5 Miles to Beach

Indoor spacesFamilyAccess

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, 119 reviews

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

KitchenFamilyHospitality

4.97 out of 5 average rating, 241 reviews

Two spacious beds with white bedding are positioned against a clean, white wall. A lamp and a small plant rest on a bedside table situated between the beds. Framed botanical artwork is displayed above each bed, adding a touch of nature to the serene space.

Condo in Lewes

Villa Del Sol, Beautiful stay near beaches/outlets

Indoor spacesKitchenCheck-in

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.