Family-friendly holiday rentals in Lewes

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, 458 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.

4.95 out of 5 average rating, 114 reviews

Guesthouse in Lewes

Crow’s Nest • 1 BR Lewes Guest Apt – Bike to Beach

Lovely 1 bed/1 bath detached upstairs guest apartment. The space provides privacy & convenience to Lewes activities with serene garden landscaping. It boasts beachy decor with locally sourced touches, a fully stocked kitchen, and a beautiful bedroom complete with a desk and a canopy bed to provide guests with the perfect escape. Enjoy al fresco dining under a pergola & lawn games. Just 3.7 mi to Lewes beach: walk or bike to Old World Bread Bakery, Beach Time Distilling & Lewes Brewing Company!

A shaded outdoor seating area features light-colored sofas with coordinating cushions, arranged around a dark table. An umbrella provides additional shade, while a small shed and a hose are visible in the background, complementing the tranquil setting.

4.86 out of 5 average rating, 313 reviews

A bit of Paradise

Charming end unit secluded in the heart of Lewes. Shady sitting area for viewing the waterfowl & enjoying the peace & quiet. Lewes marina is across the street so is Quest where can rent Kayaks etc. Over the bridge you will enjoy the historic district, town shops, eateries, food market; kiddy park, canal front park; trolley into Rehoboth Beach Henlopen State Park 1 mile; surfing, fishing & nature trails; Bay Beach 1/4 mile w Walk to everything We offer a %15 discount for 7 days or more

4.84 out of 5 average rating, 277 reviews

The sleeping area features a spacious bed with soft linens and decorative pillows. A patterned accent wall adds visual interest, while two bedside lamps provide warm lighting. A piece of framed artwork depicting boats hangs on the wall, complemented by light filtering through a window with white blinds.

Apartment in Lewes

Charming Studio in Downtown, Historic Lewes

Newly renovated second floor studio apartment located in downtown historic Lewes. - Glassware/dishes/utensils/bowls/etc.) - Keurig Coffee Maker - Microwave - Toaster Oven - Dishwasher - Flat screen tv - Wifi - King sized bed - High count linens - Plush bath towels - Plush bathrobes Apartment is on the second floor and is not handicapped accessible. No on site parking, but plenty of public parking in our historic town of Lewes. Check in time : 3 p.m. Check out time : 11 a.m.

4.97 out of 5 average rating, 202 reviews

Home in Rehoboth Beach

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!

4.97 out of 5 average rating, 284 reviews

A tranquil garden path leads to the cottage entrance, flanked by lush greenery and vibrant flowers. A small fountain gently flows, surrounded by well-manicured grass and white gravel. The serene ambience is highlighted by the dappled sunlight filtering through the leaves.

Cottage in Lewes

Charming, Historic Lewes Cottage

This charming cottage is a great romantic getaway. It is cozy and an easy walk into the historic town of Lewes ~ many great restaurants are nearby. Lewes is a fascinating & historic town with so much to do: biking, canoeing, birding, beach time, museums, and more. The doors of the Cottage have low head jams and the stairs are compact. There is some noise from the nearby road ~ a white noise machine is provided. The cottage is compact, the refrigerator for the Cottage is a small one.

A light-filled living area features a comfortable gray sofa and two modern chairs. A coffee table sits in the center, and a large TV is mounted on the wall, providing entertainment options. A painting of a serene beach scene is displayed above the sofa.

4.96 out of 5 average rating, 334 reviews

Beach Camp * Free Bikes * Top Restaurants

The perfect in-town Lewes (loo-iss) location. Explore scenic Coastal Delaware. ✔ Walk Downtown - Restaurants, shops, parks - 2 minute walk ✔ Walk or bike 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 Speed Wi-Fi (950/880 Mpbs) ✔ Roku Smart TV with free YouTube tv cable channels ✔ Parking is plentiful *Bonus* Two complimentary bicycles provided

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.

4.91 out of 5 average rating, 158 reviews

An open living space features a comfortable gray sectional sofa and a light coffee table, creating a cozy seating area. A dining table set for six is visible near large windows, while modern kitchen appliances are seen in the background, contributing to a bright atmosphere.

Apartment in Lewes

Bright 2BR, steps from the beach & downtown Lewes!

Relax and escape to this beautiful space, mere steps to the beach! This open, bright two-bedroom features brand-new construction and furnishings, and has everything you need for a fantastic getaway. ✔ One block from the beach! ✔ 10-15 minute walk to the charming restaurants, bars, shops and parks in downtown Lewes ✔ Lots of bike trails nearby, including through gorgeous Cape Henlopen State Park ✔ A quick drive to the neighboring DE beaches: Rehoboth, Dewey and Bethany.

A bright living area features a light-colored sofa and armchair with coastal patterns. A wooden coffee table sits on a textured rug, while a mounted television is visible on the wall opposite. The open layout allows for glimpses of a dining area with a table set for six.

4.98 out of 5 average rating, 112 reviews

First Floor Comfort and Convenience

This first floor condo is conveniently located in a family-friendly community with all you need within walking distance, including several restaurants and a grocery store. A short and easy 3-mile drive to Lewes Beach and the charming town of Lewes makes this an ideal location. Amenities include access to two pools, tennis courts and kids play area. The Georgetown Lewes Biking/Walking Trail, that connects to the town of Lewes, is literally steps from our front door.

A spacious living area features a comfortable sectional sofa with decorative pillows, complemented by a large area rug. A television is positioned on a stylish media console, while large glass doors provide access to a private patio, framed by blue curtains. A ceiling fan is present above.

4.97 out of 5 average rating, 116 reviews

1st Floor Beach-town Condo in Lewes

Come stay at our favorite little beachtown condo in Lewes! This 1st floor 2 bedroom, 2 bath condo has everything you need for an enjoyable and relaxing vacation! You will be just a few miles to the beach and outlet malls, have access to the community pools (May-Sept), park, and sport courts, and will be within walking distance to several great restaurants and shops. While we are "pet friendly" only 1 pet (dog or cat, 40lb maximum) is allowed per the HOA rules.

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.

Popular amenities for Lewes family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 175 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 Backyard Oasis! Private Beach, Local Pool

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, 323 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!

4.88 out of 5 average rating, 128 reviews

A partial view of the ocean is visible from the balcony, showcasing the sandy beach and a section of the pool below. Beach umbrellas and chairs are arranged along the shore, set against a clear blue sky.

Condo in Bethany Beach

Featured on HGTV! Bethany Beach Ocean Front Condo

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

4.88 out of 5 average rating, 120 reviews

An inviting saltwater pool is bordered by lounge chairs, with colorful floats resting on the water's surface. Surrounding scenery features lush greenery and a vibrant sunset sky, casting warm hues over the space. The area is designed for relaxation and enjoyment.

Home in Cape May

Mimosa Salt Water Pool & HOT TUB Oasis, Sleeps 8

4.99 out of 5 average rating, 148 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

4.95 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, 342 reviews

The Winkler

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, 145 reviews

Steps From The Ocean & Boardwalk On Surf Ave.

4.99 out of 5 average rating, 266 reviews

The living area features a neutral sofa with decorative pillows, complemented by two armchairs. A wooden coffee table sits atop a colorful area rug. Natural light floods the space through large windows, and wall decor adds a touch of personality.

Home in Rehoboth Beach

Midway Magnolia-3BR/2BA Home, dog-friendly

Guest suite in Rehoboth Beach

A spacious studio apartment features a queen-size bed dressed in blue and white bedding, and a double twin trundle bed that functions as a couch. The kitchen area is equipped with modern appliances. Light streams in through a window, enhancing the airy atmosphere.

4.86 out of 5 average rating, 384 reviews

Rehoboth Beach Farmhouse Studio *Pet Friendly*

4.99 out of 5 average rating, 243 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.

Apartment in Rehoboth Beach

An aerial view of the property features a spacious building surrounded by lush greenery. A gravel path leads to the entrance, and ample outdoor space offers room for relaxation. Nearby, a small shed is visible, nestled among the trees, enhancing the natural setting.

4.88 out of 5 average rating, 395 reviews

Timmy's Treeside Studio Pets Welcome Peeps #420

4.96 out of 5 average rating, 113 reviews

Home in Milford

Pet Friendly Home In A Private Beach Community!

Family-friendly home rentals with a pool

4.94 out of 5 average rating, 82 reviews

The living room features a high ceiling and light-colored walls, creating an open atmosphere. A large flat-screen TV is mounted on the wall opposite a comfortable dark leather couch. Natural light fills the space through large windows, alongside a stylish coffee table and accent chair.

Home in Lewes

Baby friendly, walk to pool and bakery town home

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 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

An inviting living area features a dark grey couch complemented by a decorative blue pillow. A wooden dining table accommodates six chairs, positioned near a softly lit ceiling fixture. A television rests on an earthy-toned cabinet, while an open kitchen area is visible in the background.

4.84 out of 5 average rating, 137 reviews

2b 2b condo! 2 master bedrooms! rehoboth beach

Apartment in Rehoboth Beach

An open living area showcases a modern kitchen with dark cabinets and a marble countertop. A wooden dining table is set for six, and large windows allow natural light to fill the space. The seating area features a comfortable sofa and a small side table.

4.92 out of 5 average rating, 128 reviews

Sand & Surf Condo with Pool

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 living area is presented with a gray sofa and wooden coffee table, featuring decorative items. A flat-screen television rests on a wooden console, while a clock and window with sheer curtains provide a bright atmosphere. A doorway leads to an adjacent bedroom.

4.97 out of 5 average rating, 105 reviews

Beach Escape Condo w/ Pool - Lewes Beach 3.5 Miles

A balcony view showcases the ocean, with serene waves and sandy shores. Large glass doors allow natural light to flood the interior, while outdoor seating and potted flowers add a charming touch to the space.