Vacation rentals with outdoor seating in Delaware

Ranch Stay- Farm Animals, Jacuzzi, Arcade, Beaches

Welcome to the Swedish Cowboy, your ultimate escape! This unique BARNDOMINIUM home is designed to offer a memorable retreat for up to four (4) guests, with the flexibility to accommodate two (2) additional guests for a small fee. Enjoy the charming backyard where you can meet a variety of fuzzy and feathered friends or head inside and play on the arcade or relax in the jacuzzi. Perfectly situated near popular beaches and bustling boardwalks, you'll have plenty of options for fun and relaxation.

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

2 Bedroom Condo Top Floor (3rd Floor) - Waterfront in Lewes/Rehoboth Beach DE Great Scenery Views - The Residence at Rehoboth Bay. Each bedroom has 1 king size bed and 1 queen size air mattress (in closet) *Community Pool available during in-season (8am-8pm) *No cleaning fee Nearby amenities and attractions include: Rehoboth Beach Boardwalk (6 Miles) Cape Henlopen State Park (8 Miles) Dewey Beach, DE (7 Miles) Bethany Beach, DE (18 Miles) Ocean City, MD (32 Miles) Shopping Outlets (4 Miles)

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!

The Beach Cabin, NO WI-FI

This private room is small, basic and rustic. Nestled in the back of the property, it offers a comfy queen bed, AC, small heater, a mini fridge, Keureg style coffee maker, in room toilet, outside shower and sink with hot water, private patio, clean linens and towels. Backyard has sitting areas and chimnea with firewood provided. Quiet neighborhood. Bethany Beach -10 min drive, Rehoboth-25 min. Beach gear available. TY. For current backyard blooms check on insta: glamping_with_the_flowers

Hot Tub, Fire Pit, Private Back Yard, Relaxing

Stylish, beautifully appointed, spacious home with original paintings by local artist, Laura Erickson. 4 Bedroom/2 Bathroom with brand new hot tub & very private large back yard located in Rehoboth Beach 3 miles from the downtown strip. 1 mile to grocery & liquor stores, pharmacies etc. Dewey Beach, Lewes Beach and Rehoboth Beach all within 5 miles. Driveway that can accommodate up to 5 vehicles. We go above and beyond to ensure the best experience. See our reviews on our other properties.

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.

Delightful Skoolie Near Bethany Beach

Try tiny living! Come to the Delaware beach for a unique glamping experience. The Coastal Cruiser is a 1985 Thomas School Bus turned tiny home. Spend your days exploring the Delaware Coast and come home to a rustic Skoolie with a full kitchen & outdoor area. You have access to fire pit, grill, and outdoor seating area. We’ve renovated- there is a bunk bed, and a full bathroom with toilet, shower, and sink. The bathroom is in a separate building about 20 ft from the bus.

King Bed - Center of Historic District

This cute 1 bedroom apartment is located at the HEART of our lovely town. Steps away from some of the most historic places in the entire United States. Come near the weekend and you can tour our informative museums and wayside exhibits while taking in the local culture. We are a close-knit town and are happy to show out-of-towners "the way". On days we are open enjoy a $15/day credit to our cafe next door. Please enjoy your stay! We are so sorry but no pets allowed.

Hobbs & Rose | A Peaceful Cottage Escape

Built in 1941 from historic “clinker bricks,” this restored cottage is a dreamy place to slow down and reconnect. Surrounded by enchanted gardens and close to the beach, Hobbs & Rose is filled with charm—gorgeous living spaces, a carved marble soaking tub, and thoughtful details throughout. Enjoy a romantic getaway and unwind in our Sanctuary meditation room, where birdsong and forest friends welcome you. You relax—we’ve created every detail to help you feel restored.

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!

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

Relax in our stylish 2 BR / 1 BA Rehoboth Beach getaway! This top-floor unit of our duplex home is bright, comfortable, and perfectly located—just 3.7 mi to the beach, moments to outlet shopping and dining. Sip coffee on the sunny deck with lounge seating, then unwind in the hot tub after a beach day. Enjoy a fully stocked kitchen, fast WiFi, on-site laundry, EV charger, free parking, and tasteful décor designed for the perfect coastal escape.

Cottage w/ Fireplace, King Bed & Fenced in Yard

Welcome to The Cottages on Orchard—a restored 1BR/1BA, dog-friendly cottage (king bed) built in 1920 by author Victor Thaddeus. Nestled among trees in whimsical Ardentown, you’re 2 min to I-95 and 10 min to Downtown Wilmington. Enjoy a private fenced backyard, fireplace (wood provided), firepit, and scenic walks to the woods, creek, and nature trails. READ HOUSE RULES.