Family-friendly holiday rentals in Milton

4.94 out of 5 average rating, 271 reviews

A light and airy deck features a rectangular dining table surrounded by aqua-colored chairs. A calm water view is visible beyond the railing, with flags gently waving in the breeze. Soft lighting is provided by string lights overhead, enhancing the inviting atmosphere.

Home in Ocean City

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

4.93 out of 5 average rating, 258 reviews

A cozy bedroom features a full-sized bed covered with a nautical-themed quilt. A nightstand and a dresser with multiple drawers are situated against the walls. Decorative wall art adorns the yellow walls, while soft lighting creates a welcoming ambiance. A plush area rug adds warmth to the space.

Guest suite in Lincoln

Nicencozy, near DE Turf, Bayhealth, beaches, AFB

Stay in peace at this smoke-free, quiet abode. Within 10 mins of Milford (Bayhealth Sussex, Walmart, shopping, pharmacies, restaurants, etc.). 15 mins: DE Turf, Milton, breweries. 20-30 mins: Bowers Bch, Pickering Bch, Sports at the Bch, Dover & Georgetown, theaters & casinos. 30-45 mins: other beaches and outlets. Please review Guide Book and House Manual after booking, and call us after a last minute booking, so we can tell you how to get in. Snacks, water, etc. provided while supplies last.

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.

4.99 out of 5 average rating, 200 reviews

Renovated Condo Near Outlets, 3.5 Miles to Beach

Enjoy your stay in this recently renovated and beautifully furnished two-bedroom, two-bathroom 3rd-floor condo conveniently located 3.5 miles from the Rehoboth Beach boardwalk, and 4.5 miles from Lewes Beach. The proximity to the beaches, stores, and restaurants make this condo a great spot to spend a fun-filled vacation at the beach. Our condo amenities include a community pool*( seasonal), free parking, free WiFi, smart TV, washer, and dryer. We supply all the sheets & towels for your stay.

4.97 out of 5 average rating, 644 reviews

The exterior of a two-story wooden structure is presented, featuring a staircase leading to a covered balcony. The building is surrounded by trees displaying fall foliage, creating a serene outdoor atmosphere. A gravel area is noted at the base, with a vibrant red and white camper positioned nearby.

Apartment in Greenwood

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

4.99 out of 5 average rating, 103 reviews

Home in Milton

Beach Path Access. PET-FRlENDLY. LlNENS lNCLUDED

Peaceful, secluded, tranquil, yet close to attractions. Our home has beach path access directly across the street. Enjoy views from both the front and back, including the Prime Hook Wildlife Refuge from our back deck. Conveniently located at the quiet southern end of Broadkill Beach. While the north side is denser with homes and more crowded, the southern end provides a more private beach experience with fewer visitors. The ideal beach retreat where it's just you, the sand, and the sea.

4.83 out of 5 average rating, 265 reviews

The exterior of a historic blue home is captured in this image. The house features two levels, with a gable roof and a welcoming front door. Brick accents are visible near the foundation, complemented by a neatly maintained yard and surrounding greenery.

Home in Milton

Glennie's Place Quiet Historic Street/Town

A small historic home in the city of Milton, De. Milton offers small USA hometown charm that is close the world famous Delaware beaches. This home was lovingly upgraded, renovated by Glennie's grandson. Enjoy the sunshine off of the back deck while preparing your BBQ. Take a short walk to Milton's city park which is a few minutes from the house off of the Broadkill River. Check out some of the gift shops, eateries, The Milton Theatre, or a tour of the world renown Dogfish Head Brewery.

4.95 out of 5 average rating, 188 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

Enjoy the sounds of nature when you stay in this unique place. Located less than 5 miles from downtown Lewes and Delaware Beaches. The cottage guest house is nestled in the woods adjacent to a tree house overlooking a tranquil pond with a calming fountain sounds. On the main property guests have access to a in ground swimming pool (seasonal) with a 60 foot lap lane and slide, schedule times with hosts.. The backyard also includes an organic garden, playground and 🐔 chickens.

4.87 out of 5 average rating, 107 reviews

Home in Milton

Cheerful Bungalow- Near Dogfish + Milton Theatre

Welcome to our charming retreat on the outskirts of Milton, where comfort meets simplicity! Perfect for families and friends, our home features two inviting bedrooms, a cozy sofa bed, and a bathroom for a peaceful escape from city life. Just a short walk or bike ride away, you’ll find downtown Milton's attractions, including Dogfish Head Brewery, great dining options, and the historic Milton Theatre. Enjoy a delightful blend of relaxation and adventure in this inviting haven!

4.96 out of 5 average rating, 198 reviews

A blue decorative anchor rests on a white surface, featuring a rustic rope detail. The soft lighting highlights the anchor's design, creating a nautical theme. A blurred background suggests a bright and airy space, complementing the apartment's beach-inspired decor.

Apartment in Milton

Beachin' Inn Milton

Welcome to Beachin' Inn Milton! This cozy apartment located in the quaint, historical town of Milton, DE is the perfect getaway. Our apartment is light and airy with a beach theme. Enjoy the entire apartment to yourself with a keyless private entrance, full bath, washer/dryer, free Wifi and stocked assorted coffee pods. There is no stove/oven, however, we offer a microwave, toaster oven, Air Fryer and induction burner.There is private parking right out front

4.97 out of 5 average rating, 207 reviews

A spacious common area features tall ceilings and large windows, allowing natural light to fill the room. Bookshelves line the walls, filled with a diverse collection of books. A comfortable white sofa and glass coffee table create a cozy seating area, with a TV positioned nearby.

Guesthouse in Milton

The Book Nook - A Private Downtown Retreat

In the heart of downtown Milton, you will find a newly renovated guest cottage less than 10 miles to the beach! If you plan on staying local, simply park your car at the designated off-street parking space and travel by foot to the many shops, restaurants, and attractions offered in historic Milton. Whether you're walking the few short blocks to Dogfish Head Brewery or spending an evening at the theater, The Book Nook will serve as the perfect location!

Guest suite in Rehoboth Beach

A single-story home is set amidst a grassy lawn, featuring a light exterior and a welcoming front porch. A large tree provides shade in the foreground, while a paved driveway leads to the garage. The surrounding area is landscaped with a mix of greenery.

4.98 out of 5 average rating, 158 reviews

*Radcliffe Retreat* Studio, Pool & RB Parking Pass

Spacious pet friendly guest suite with Rehoboth parking permit provided. The suite is near outlets, beaches, dining, & Rehoboth boardwalk. Large community pool next door. Charming neighborhood that is a great base to explore all the nearby attractions! Rehoboth boardwalk & beach- 4 mi Outlets- 1 mi Lewes downtown- 4 mi Cape Henlopen State Park- 6 mi 1 dog is allowed with permission.

A light-filled living area features a comfortable seating arrangement with two red chairs and a cozy couch, accompanied by a round coffee table. A wall-mounted TV is situated above an electric fireplace, enhancing the space's inviting atmosphere. Large windows offer views of the outside.

4.94 out of 5 average rating, 294 reviews

Spacious| Modern & Cozy| Pool| Close to the Beach

Perfect getaway conveniently nested just off the Costal Highway and just few minutes from the Nassau Valley Vineyard. Less then 5 miles to Lewes Beach and 7 miles to Rehoboth and Dewey Beach to enjoy the Ocean! Cape Henlopen State Park, Great Restaurants, Breweries, Historic Downtown Lewes, Tax free shopping at the Tanger Outlets and much more.

Popular amenities for Milton family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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, 179 reviews

Classy Beach Getaway

4.99 out of 5 average rating, 156 reviews

A spacious living room features a large sectional sofa and a floor-to-ceiling gas fireplace. Natural light filters through the plantation shutters, highlighting decorative plants and a round mirror. A large TV is mounted above a white-brick fireplace, creating a cozy gathering space.

Home in Villas

Hot Tub Backyard Oasis, Private Beach, Local Pool

4.84 out of 5 average rating, 258 reviews

The shared pool area features a clear blue pool surrounded by a spacious deck. Lounge chairs are placed near the water, sheltered by large umbrellas. Lush greenery and trees provide a natural backdrop, creating a relaxing outdoor environment.

Apartment in Lincoln

Waterfront Studio • Pool • Near DE Turf & Beach

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.

4.95 out of 5 average rating, 198 reviews

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

4.96 out of 5 average rating, 122 reviews

An outdoor space features a heated swimming pool surrounded by a concrete patio. Comfortable seating options include several couches and chairs. A large umbrella provides shade, while a hot tub is positioned nearby. String lights and greenery enhance the backyard ambiance.

Home in Lower Township

Relaxing Getaway

Superhost

The living area is furnished with a light-colored sofa and armchairs, complemented by a white coffee table. A flat-screen TV is positioned near a dining table with seating for four. Views of the ocean can be seen through expansive glass doors, leading to a private balcony.

Condo in Ocean City

4.83 out of 5 average rating, 131 reviews

Oceanfront 2 Bed/2 Bath, Sleeps 6, Pools, Gym, Etc

4.76 out of 5 average rating, 107 reviews

An aerial view showcases a large swimming pool area surrounded by lounge chairs and umbrellas, with a smaller kids' pool adjacent. Tennis courts and well-maintained landscaping are visible, alongside additional buildings and open green spaces in the distance.

Townhouse in Selbyville

Bayside - Best Deal in Bayside!

4.99 out of 5 average rating, 150 reviews

An open-concept living area is featured with beach-inspired decor, a spacious sofa, and a dining table for six. Large sliding glass doors provide access to an oceanfront balcony with stunning views. A ceiling fan is installed for added comfort.

Condo in Ocean City

🌊Carousel Oceanfront 2 Bedroom Amazing Amenities

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 144 reviews

The living area features a light gray sectional sofa with colorful accent pillows, situated within a bright space. A wooden console table is placed against the wall, and light fixtures illuminate the open kitchen area in the background.

Condo in Dewey Beach

Luxury water-view condo with high-end finishes

4.95 out of 5 average rating, 151 reviews

The interior of the bus features a cozy layout with wood paneling and large windows providing natural light. A comfortable seating area, equipped with pillows, is situated next to a compact kitchen with a stove and cabinets. A small dining table with two placemats is visible.

Bus in Frankford

Delightful Skoolie Near Bethany Beach

Guesthouse in Rehoboth Beach

The structure features a modern design with a wooden exterior and large glass windows. A spacious deck is accessible from the upper level, surrounded by lush greenery. The ground floor includes a stone facade with garage doors, creating a harmonious blend with the natural surroundings.

4.87 out of 5 average rating, 343 reviews

The Winkler

4.85 out of 5 average rating, 105 reviews

The living room features large windows adorned with floral-patterned drapes, allowing natural light to fill the space. Two comfortable chairs, including a recliner and a plush seating option, are positioned next to a coffee table. A television rests on a light-colored media unit, enhancing the room's functionality.

Home in Ocean City

Ocean City Townhome by Beach Bayside

A dining area features a wooden table surrounded by six chairs, situated on a patterned rug. A woven pendant light hangs above the table. Large windows provide a view of the outdoors, with sheer curtains softly filtering the natural light.

4.85 out of 5 average rating, 192 reviews

Elegant 3-Bedroom Condo in Lewes with Pond Views

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, 146 reviews

Steps From The Ocean & Boardwalk On Surf Ave.

4.97 out of 5 average rating, 298 reviews

A compact kitchen area is visible, featuring white cabinetry and modern appliances. Two bar stools are positioned at a small island. The cozy sitting area includes a light blue chair and a striped sofa, with light streaming in from the nearby window.

Condo in Dewey Beach

Sweet getaway - beach block, steps from the beach!

4.89 out of 5 average rating, 151 reviews

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.

Home in Rehoboth Beach

Secluded Coastal Cottage • Just 9 Min to the Beach

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 301 reviews

The living area features a modern design with a sleek Italian leather sofa and a wall-mounted flat-screen TV. An electric fireplace is installed beneath the TV, while a coffee table and a single chair complement the space. Ample natural light enters through a nearby window.

Condo in Ocean City

Bluewater Couples Escape

A circular glass table with four woven chairs is positioned on the patio, overlooking a tranquil lake surrounded by greenery. Sunlight filters through the trees, casting soft reflections on the water's surface.

4.9 out of 5 average rating, 162 reviews

Right on Silver Lake walk to the beach and town!

A balcony view captures a wide expanse of lush green fields and dense trees, framed by a soft gray sky. The natural landscape offers a serene backdrop, highlighting a peaceful atmosphere. A railing can be seen in the foreground, providing a sense of depth.

4.99 out of 5 average rating, 165 reviews

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

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.

4.97 out of 5 average rating, 219 reviews

Villa Del Sol, Beautiful stay near beaches/outlets

4.88 out of 5 average rating, 108 reviews

The kitchenette area includes a sleek countertop with two black bar stools, a microwave, coffee maker, and a countertop oven/toaster. A black refrigerator is situated nearby, and a wall-mounted TV is visible above the counter in this open-concept space.

Guest suite in Milford

Studio apt near DE turf, beaches, &hospital

A bright living area features a comfortable sofa and a blue accent chair, complemented by a wooden coffee table. A large flat-screen TV is positioned on a white media unit. Natural light enters through sliding glass doors, leading to a small balcony with outdoor seating.

4.99 out of 5 average rating, 155 reviews

Mimi’s Place @ The Villages of 5 Points in Lewes

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, 215 reviews

Comfy and Convenient 2 bedroom/2 bath condo

A corner sectional sofa is arranged in a cozy living area, accompanied by a rectangular coffee table placed on a patterned area rug. Two framed art pieces adorn the wall above, and soft natural light filters through the space.