Family-friendly vacation rentals in Milton

Tiny house w/ Pool on water near Beaches / turf

Enjoy a peaceful waterfront stay in our custom-built tiny house, located on Cedar Creek just off Route 1. Conveniently situated only 10 minutes from Delaware Turf and 15 minutes from the beach. The home comfortably sleeps four and includes hot tub access. We live on-site and are happy to assist throughout your stay. Ideal for families, pets (please review rules under “The Space” section), contractors, and long-term renters. Perfect for travel nurses & remote workers – Monthly stays welcome!

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)

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.

Teeny's Place: A Historic Milton Home.

Family friendly get-away filled with fun. All the amenities of a single family home, plus a backyard made for life at the beach. Proudly offering an in-ground pool, air-conditioned pool house with changing room, 3 season entertainment space, fire pit and deck spaces. The Pool is opened May 1st-October 1st. Walking distance to Downtown Milton's shops, restaurants, and -of course- Dogfish Head Brewery. Just a short drive to the Delaware Beaches. Newly renovated Pool House in 2024.

Broadkill Beach, seafood, fishing, beach, birds

If you have never been to Broadkill, this is a must. If you are looking for a quiet place to relax, read your favorite book on an empty beach, fish or crab, visit the famous Rehoboth Boardwalk or shop at the outlets, this is the place for you. Located only 1 1/2 block from the beach. Bird watchers paradise. Home on dead end street with very little to zero traffic. Located next to Prime hook National Wildlife Refuge. The extra person charge is for adults only exceeding 4 guest.

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.

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!

1 Bedroom 1 Bath Condo on Silver Lake

Newbold Square is tucked away in Rehoboth Beach on Silver Lake. It is a quiet, sleepy, 40 unit complex with a lakeside pool that offers sun and shade among towering trees. This condo has one bedroom and one bathroom. There is also a queen size sleeper sofa. There is a well stocked kitchen with plenty of storage space. We supply linens, bath towels, four beach towels, four beach chairs, a beach wagon, and a gas grill. No pets are permitted. Our space is allergen free.

BeachHaven: STEPS TO SAND, Pet-Friendly, +Linens

Peaceful, secluded, tranquil, yet close to attractions. Our home is located at the more private (i.e. no crowds) southern end of Broadkill. The boardwalk in front of our home leads to the beach path access across the street. You will enjoy views from both the front and back decks: including the beach & Prime Hook Wildlife Refuge. If this property is booked or you need multiple homes for a group, we host several nearby beach homes. Click on my host profile to see them.

"Mary's Place" Sunsets, walks on the beach , bird watching & more

Welcome to Mary's Place! Wait until you see the amazing views from the roof deck, which overlooks the Prime Hook Wildlife Refuge. The Sunsets are spectacular, and it's a bird watchers dream! Mary's Place has a large screened porch and a large outdoor shower. Enjoy walks on the beach along the Delaware Bay, which is directly across the street. Bikes are available for your enjoyment. Dogfish Brewery and several restaurants are less than 10 miles away in the town of 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

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!