House holiday rentals in Dewey Beach

4.94 out of 5 average rating, 264 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!

4.9 out of 5 average rating, 608 reviews

A charming tiny house features wooden shingles and a welcoming front door. It is framed by colorful flowers in a garden, enhancing the outdoor landscape. A sign above the door adds a personal touch, while large windows allow natural light to fill the space.

Home in Ocean View

Tiny House at Good Earth, near Bethany Beach

A custom 165 sq. ft. "Tiny House" located right between our theater and the garden dining area. True to the show "Tiny House Nation".. cool interior with custom woodwork, stairs to a lofted bed. Fully functioning kitchen. Spacious bathroom & shower. We provide TV and internet in the unit. We have 2 on-site restuarants, market, theater, and parking. Our AIRBNB village consists of 2 tiny houses, 2 cottages, tent sites, a loft appartment, and more! Staying at Good Earth is more than a beach trip!

A cozy living area features a stone fireplace as a focal point. Comfortable leather seating surrounds a coffee table, with a TV visible nearby. Natural light is allowed through multiple windows, and a dining area is positioned in the foreground with elegant lighting.

4.91 out of 5 average rating, 131 reviews

Luxury Carriage House in Rehoboth Beach

Luxury carriage house with 4 bedrooms / 4 baths. Private fenced in backyard with wrought-iron fence and paver patio with iron dining furniture. Great kitchen with Dacor double ovens, built-in gas range in two-tier island, subzero wine refrigerator. First floor is open floor plan with kitchen, living area, TV/sitting area with two sliders leading to furnished screen porch. Floors are mainly stone & hardwood, except two bedrooms. Master - jacuzzi & dual showerhead stone shower. Enjoy firepit

A private pool area features a spacious rectangular pool with a waterfall feature, surrounded by natural stone tiles. A large patio includes a gas grill, shaded seating under an umbrella, and lounge chairs. The home’s exterior showcases a mix of white siding and black railings, offering a modern aesthetic.

5 out of 5 average rating, 19 reviews

Family & Pet-friendly Beach House with Pool

Located on a quiet street less than a mile from the beach, shops, and dining, this 5 bedroom 4.5 bath is ideal for large families. Highlights include open living room/dining room floor plan with large outdoor space and pool. The house is pet friendly, with fully enclosed backyard area. Sleeper sofa in upstairs living room. Sleeps 15. Rents weekly Saturday to Saturday Memorial Day weekend through Labor Day weekend. 3 night minimum during the off season. Must be 25 years old or older to rent.

4.99 out of 5 average rating, 104 reviews

A spacious living room features a comfortable dark sofa, two brown chairs, and a cozy fireplace. Natural light enters through large windows adorned with light blue drapes. A ceiling fan and recessed lighting contribute to a bright and airy atmosphere, complemented by modern decor.

Home in Ocean Pines

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines

Beautifully updated and recently renovated, rancher on a great street in Ocean Pines perfect for families and adults looking for a relaxing stay. We offer 3 bedrooms and 2 bathrooms on one level, with new large flat screen TV's, stainless appliances, and everything you'll need for your stay. We have a large driveway and a screened patio. Ocean Pines boasts over a dozen parks and walking trails, a public Yacht Club, 5 pools, 2 marinas, and a championship golf course - 10 min to the beach!

The living room features two gray sofas and two light wooden chairs surrounding a circular coffee table. A flat-screen TV is wall-mounted above a white fireplace, and natural light filters through the window coverings, creating a bright and open atmosphere.

4.97 out of 5 average rating, 200 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!

A spacious kitchen is highlighted by an 11 ft island with four round bar stools. Pendant lighting above creates a warm ambiance. Modern appliances and a stylish backsplash are featured, enhancing the functionality of the space. Neutral tones and open shelving provide a clean, inviting atmosphere.

4.95 out of 5 average rating, 147 reviews

Hot tub, Relax, Shop & Dine, Sleeps 8, Games

A convenient central location between Rehoboth/Dewey and Lewes Beaches. You can walk to the neighborhood pool (available Memorial Day- Labor Day). Stylish, clean and comfortable, our house is an entertainer's dream. A huge 11 ft island and open concept living space is perfect for gatherings. Each bedroom is curated for comfort. The peaceful, private back deck is perfect to layout. We go above and beyond to ensure the best experience for our guests.

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.

4.87 out of 5 average rating, 240 reviews

Dodd House Beach Home w/private pool and hot tub

Saturday to Saturday bookings from the third week in June through mid August. Large 5 bed 3.5 Bath Luxury Home with pool and hot tub. Parking for six to eight cars. ARRIVE, STOCK UP, AND NEVER LEAVE IF YOU CHOOSE! GET YOUR FAMILY AND FRIENDS TOGETHER SAFELY! This large 4,500 square foot rental unit includes 5 private BR, 3.5 BTH, and sleeps 18! Pool opens May 15th. Outdoor fire pit with some wood provided. 25 and older please.

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, 101 reviews

Hot Tub, Pet friendly, IN TOWN, chic renovation!

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! Dogs are allowed for a $75 fee per stay for 1st, $25/ea for 2nd/3rd (fees for 2 & 3 charged later). Only a 15 minute walk to the boardwalk too.

4.99 out of 5 average rating, 239 reviews

A deck overlooks sandy paths leading to the ocean, framed by lush dune grass and coastal vegetation. The bright blue sky contrasts with the calming sea, creating a serene coastal view. The deck railing offers a defined space for relaxation while enjoying the surrounding nature.

Home in Milton

ON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.

For years, we searched for the perfect beach getaway: secluded, tranquil, yet close to attractions. We found it in Beachwalk. Peaceful. Private. 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 far fewer visitors. The ideal beach retreat where it's just you, the sand, and the sea.

4.99 out of 5 average rating, 212 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

A beautiful and peaceful get-away all year round! Bright and sunny 3 bed/2 bath waterfront home with wrap-around deck. Fully stocked, community pool, walking trails, kayaks and more! Visit Rehoboth or Lewes Beaches (10 miles away), Cape Henlopen and tax-free outlet shopping (6 miles away)! Great for families, water lovers, and bird lovers! Sunday to Sunday weekly rentals *only* from Memorial Day to Labor Day.

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.