Family-friendly vacation rentals in Milton

4.92 out of 5 average rating, 250 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 serene view of a sandy beach leading towards the ocean is depicted. A wooden fence with wire stretches along the path, bordered by patches of tall grass. The gently rolling waves and soft sky create a calming atmosphere.

4.99 out of 5 average rating, 452 reviews

High Tech Hideaway: The modern beach lifestyle

Live the beach lifestyle with every modern convenience! Roomy 2 bedroom, 2 bath condo only 10 mins from Rehoboth, Lewes and Dewey. Surrounded by craft beer, tax-free outlet shopping, and fantastic food. Cleanings exceed CDC guidelines. Three 65" 4k TVs with 221+ channels, Apps, touchscreen Amazon Echos, dimmable LED lighting, and ultra high speed wi-fi. Fully renovated with luxurious flooring, quartz countertops, and new furniture. Free washer/dryer, free coffee, free parking, and water views.

4.97 out of 5 average rating, 111 reviews

The image captures a sandy beach scene with gentle dunes and a wooden fence leading to the ocean. The sun casts a warm glow over the water, illuminating the horizon where the sea meets the sky. Grasses sway softly in the foreground.

Home in Milford

Pet Friendly Home In A Private Beach Community!

Forget your worries in this spacious and serene space. Single-floor home with a very short walk to quiet Bay Beach. Spectacular 4 season Sunroom facing west over Primehook's 10,000-acre National Wildlife Refuge. Stunning sunsets and birding while dining or just relaxing after a day at the beach make this room a favorite. The home offers views of Delaware Bay. There is an outdoor shower for rinsing away the day's salt and sand. The fully fenced backyard includes a grill and space for your dog!

4.92 out of 5 average rating, 260 reviews

A spacious living area features a large L-shaped mahogany leather couch and a brown suede love seat adorned with decorative pillows. An ottoman complements the seating arrangement. A 65" HD flat screen TV is visible, alongside two windows allowing natural light to brighten the room.

Apartment in Dewey Beach

DeweyBeach 1 BR + sleeper sofa. Walk to the beach!

Enjoy all of Dewey Beach at this delightful 1 BR, ground floor, apartment on the north side of town. 1.5 blocks to the beach, and 3 blocks to the start of restaurants and music venues. Quiet, relaxing location on a side street. Perfect for a small family or group of 4 friends! Custom self check-in keypad code for Private Entry sent upon booking. Professionally cleaned + bed made before your stay. 4 beach chairs, 1 on-property parking spot + 1 free Street Parking Passes provided at no charge!

4.97 out of 5 average rating, 634 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)

4.94 out of 5 average rating, 141 reviews

Chestnut-Near Dogfish, DE Turf & Sports at Beach

Weekly Discount Chestnut Retreat is a historic farm style home located in historic town of Milton, DE (12 miles from local beaches). DE Turf is 25 minutes away & Sports @ Bch is 10 minutes. This home has been renovated. Relax in the screened in porch with 2 reclining chairs & swing. Home has 3 bedrooms (1 bedroom down, 2 up) & queen sleeper sofa in living room. Patio has grill and fire pit. Short walk to Dogfish Restaurant. Easy walk/bike ride to downtown. Golf Courses minutes away.

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.

4.83 out of 5 average rating, 263 reviews

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, 186 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 homes 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.

Superhost

4.87 out of 5 average rating, 104 reviews

Cheerful Country Bungalow - Near Dogfish Brewery

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!

4.99 out of 5 average rating, 166 reviews

A modern living room features a large, L-shaped blue sectional sofa accented with bright throw pillows. A round coffee table sits at the center, adorned with a decorative tray. Soft lighting from a nearby lamp complements the colorful wall art and greenery from a potted plant.

Condo in Lewes

Downtown * Walk to the Beach * Free Bikes

Walk & bike everywhere. Explore Lewes (loo-iss) & scenic Coastal Delaware. ✔ Walk Downtown - Restaurants, shops, parks - 2 minute walk ✔ Walk to Lewes Beach - Less than a half mile ✔ Bike Trails - Plenty of options at your fingertips ✔ Cape Henlopen State Park - Less than 2 miles ✔ Easy electronic keypad entry ✔ Fast Gigabit Wi-Fi (950/880 Mpbs) ✔ Roku TV w/ free YouTube tv cable channels ✔ Parking is plentiful & linens are included *Bonus* Two complimentary bicycles provided

4.96 out of 5 average rating, 280 reviews

A cozy living area displays a light blue color scheme. A white sofa is positioned beside a coffee table on a patterned rug, while a dining table is set nearby. Floor-to-ceiling sliding doors open to a balcony, offering views of the ocean.

Condo in Ocean City

Caramar Couples Retreat

This cute little first floor efficiency condo is ocean front for a perfect vacation to the beach. It’s an older building but has been partially renovated and updated. You can get to the beach by a very short walk through a private walkway from the condo building. The view from the private balcony is perfect and relaxing. WiFi provided upon check in- xfinity, Netflix, and internet. Indoor and outdoor dining areas and a full kitchen. Closet and dresser for storage use.

4.96 out of 5 average rating, 195 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

Popular amenities for Milton family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 120 reviews

A thoughtfully decorated living area features a light-colored sofa adorned with several decorative pillows. A coffee table sits on a neutral rug with seashell patterns, while a side table holds a lamp. Natural light enters through a window with sheer curtains, enhancing the beachy vibe.

Home in Rehoboth Beach

Beach Getaway•Hot Tub + EV Charger•4 mi to Beach

4.9 out of 5 average rating, 116 reviews

A comfortable living area features a light-colored table surrounded by ocean-themed upholstered seating. Large glass doors allow natural light to fill the space while offering a view of the balcony and ocean beyond. A flat-screen television is mounted on the wall.

Condo in Ocean City

Oceanfront Carousel building, Swimming Pools!

4.99 out of 5 average rating, 170 reviews

A comfortable living room features a gray sofa across from a wooden coffee table. A large round mirror reflects light, while framed fish prints adorn the walls. Natural light floods the space, highlighting the open layout that connects to the dining area and kitchen.

Home in North Cape May

Hot Tub Holiday Escape! Fireplace + Close to all!

4.99 out of 5 average rating, 312 reviews

The exterior of a quaint house features a black and white design with a front porch adorned by a vibrant American flag. The gravel pathway leads to the entrance, surrounded by small potted plants and a spacious, tree-lined yard.

Bungalow in Town Bank

Romantic Saltbox Bungalow! HOT TUB! Bay Sunsets!

4.84 out of 5 average rating, 258 reviews

A shared outdoor space showcases a large pool with a tiled hot tub, surrounded by lounge seating. In the background, a playset and a whimsical playhouse are visible amid lush greenery, creating an inviting area for relaxation and family fun.

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, 194 reviews

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

4.96 out of 5 average rating, 118 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

5 out of 5 average rating, 145 reviews

Four colorful tiny cottage suites are aligned under a blue sky with fluffy clouds. Each suite features distinct pastel-colored exteriors with round windows and front doors in various hues, complemented by modern railings and landscaping that enhances the welcoming vibe.

Tiny homes in Villas

Coastal Quad: Hot tub | Mini Golf | Arcade | Gym

Family- and pet-friendly home rentals

4.91 out of 5 average rating, 228 reviews

A serene gravel lane is framed by tall trees, creating a natural canopy. Sunlight filters through the leaves, creating a dappled effect on the path below. The surrounding greenery contributes to a peaceful and quiet atmosphere, ideal for relaxation.

Guest suite in Greenwood

Woodsong Suite & Getaway!

4.99 out of 5 average rating, 196 reviews

A charming cottage facade is framed by white columns and features a gabled roof. Two black rocking chairs, adorned with pillows, sit on a brick porch surrounded by colorful potted flowers. Lush greenery enhances the inviting atmosphere.

Cottage in Frankford

19th Century Cottage with Modern Amenities

4.95 out of 5 average rating, 214 reviews

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.

Home in Rehoboth Beach

Pet friendly cottage 4 blocks to Beach

4.97 out of 5 average rating, 287 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!

The exterior of a two-story yellow house is showcased, featuring blue shutters and a welcoming front porch. White rocking chairs are arranged on the porch, surrounded by neatly trimmed bushes and trees, creating an inviting atmosphere for guests.

4.85 out of 5 average rating, 114 reviews

Suds and Sand

4.88 out of 5 average rating, 107 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

Superhost

The exterior of a charming bungalow features soft blue siding, decorative window boxes filled with blooming flowers, and a welcoming black front door. A well-maintained lawn surrounds the home, with stepping stones leading to the entrance and greenery providing a natural border.

Home in North Cape May

4.8 out of 5 average rating, 313 reviews

Beach Bum Bungalow (Dog Friendly)

4.75 out of 5 average rating, 163 reviews

The exterior of a two-story farmhouse is displayed, featuring light gray siding and dark blue shutters. A central entrance with double doors is flanked by two front-facing windows. The well-maintained lawn showcases a vibrant green color, enhancing the welcoming appearance of the property.

Home in Georgetown

The 1934 Farmhouse (close to the beaches)

Family-friendly home rentals with a pool

A serene bedroom features a spacious bed adorned with a textured navy quilt, flanked by two bedside tables with lamps. Natural light enters through a window, illuminating the light blue walls. A dresser and decorative mirror complement the calming atmosphere.

4.99 out of 5 average rating, 158 reviews

Family Friendly Top Floor Condo Near Boardwalk

4.97 out of 5 average rating, 143 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

4.83 out of 5 average rating, 155 reviews

Tiny homes in Millsboro

Farm Cottage - POOL - 30 Min to BEACH

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, 196 reviews

Renovated Condo Near Outlets, 3.5 Miles to Beach

A welcoming living room features a modern design with a circular mirror and stylish light fixture. Comfortable seating includes a round chair and plush sofas configured around a wooden coffee table. Natural light enters through large windows, illuminating the space and providing a view of the outside.

4.97 out of 5 average rating, 129 reviews

Modern 2BR/2BA – Beach Pass + Bikes, 5 Min Drive

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

4.97 out of 5 average rating, 196 reviews

A serene waterfront scene is captured at sunset, with vibrant colors reflected in the calm water. A charming building with large windows is illuminated, surrounded by lush trees, and boats are docked along the waterfront, creating a peaceful atmosphere.

Condo in Ocean Pines

Pines Getaway - Berlin Tree Light & Ice Ice 11/28