Holiday rentals with a pool in Henlopen Acres

A spacious living area features a modern blue sofa facing a white coffee table. On the walls are framed artworks, while a dining area with counter-height seating and a kitchen is visible in the background. Natural light brightens the room through the open layout.

4.94 out of 5 average rating, 151 reviews

Condo Reho -1st fl/2 bed/2 bath, centrally located

Close to everything that Rehoboth has to offer, you'll be within walking distance of numerous restaurants & breweries, a nature trail, and downtown. Even the beach is just a 20 minute walk, 10 minute bike ride, or 5 minute drive! Condo Reho has been renovated to reflect a modern beach lifestyle with crisp, clean lines, hand-crafted details, and Scandinavian-inspired furnishings. Our home away from home has everything needed to make your stay enjoyable, and we look forward to sharing it with you!

4.98 out of 5 average rating, 105 reviews

An open-concept living area features a spacious gray sectional sofa arranged around a casual coffee table. Bar seating at the kitchen island is complemented by stylish stools. Natural light fills the room, highlighting the subtle décor and a wall adorned with decorative fish.

Condo in Dewey Beach

Newly Renovated Modern 2 Bed/2 Bath Condo w/ Pool

Newly renovated and designer decorated 2 bedroom/2 bath beach condo with the most comfortable beds imaginable. Located in the heart of Dewey Beach with an outdoor pool and only 1 block to beach and bay. One bedroom includes a King sized bed with private bathroom. The 2nd bedroom includes a Queen and a Twin sized beds adjacent to the 2nd bathroom. The fully equipped kitchen features stainless steel appliances, granite countertops, an island w/ seating, and washer/dryer. 2 parking spots included.

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.

4.96 out of 5 average rating, 166 reviews

Sunrise Studio - Ocean Front, on Boardwalk, Pool!

Our quiet ocean front studio has all the comforts of home with amazing views, a balcony hovering over a serene stretch of the Boardwalk, and is just steps away from restaurants, shops, arcades, rides and all of the best boardwalk foods! Walkable to everywhere in town! If you want to venture out further, a bike rental shop is just a few doors away! Enjoy a bike ride through town or to Dewey Beach. If you are looking for a scenic ride, enjoy the bike trails to Cape Henlopen State Park and Lewes.

A round blue dining table is set for four, featuring neutral plates and glasses. Surrounding chairs have a classic black design. A large piece of abstract art adorns the wall, while the kitchen area is visible in the background, showcasing light cabinetry and appliances.

4.94 out of 5 average rating, 422 reviews

Clean and Comfy, Close to Beach and Shopping

This newly updated condo is perfect for your next beach vacation. A convenient central location between Rehoboth/Dewey and Lewes Beaches. You can walk to the neighborhood pool. Stylish, clean and comfortable, the unit has two bedrooms, one on either side of the kitchen, an ideal layout for privacy for two couples or a family. Each bedroom has it’s own full bathroom. The screened in porch has a view full of trees. Located right off of Route 1, 3.6 miles from downtown Rehoboth and the boardwalk.

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, 159 reviews

Family Friendly Top Floor Condo Near Boardwalk

Located just 2 miles from the Rehoboth Beach boardwalk, yet nestled in a peaceful community. Condo offers a comfortable & well-equipped space Primary Bedroom: King w/ en-suite bathroom Second Bedroom: Queen w/ en-suite bathroom Living Area: Sofa & comfy chairs for relaxing For the Littles: Pack 'n Play, high chair, & many kid-friendly extras—see the last few photos for all the thoughtful touches! Whether you're here to explore Rehoboth’s charm or simply unwind, this is the perfect home base!

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

Bright & spacious 1st floor, 2 bedroom/2 bath condo (sleeps 6) in Eagles Landing is perfect for families, couples or friends. Recently renovated floors, appliances and countertops, new furniture. We are an easy 5-minute drive from the beach. The community has 3 pools. Our unit includes parking, a full kitchen, living room, dining room (seats 6), washer/dryer, dishwasher, wi-fi. Downtown restaurants, outlet shopping, & boardwalk are all within 2 miles. We provide necessities so you pack less!

An open-concept living area features a light-colored sectional sofa adorned with textured pillows. A round coffee table sits on a soft area rug. The dining area, equipped with a sizable wooden table and stylish woven chairs, is visible in the background alongside modern kitchen appliances.

4.99 out of 5 average rating, 123 reviews

Cozy Rehoboth Beach Condo w/ 2 bedrooms

This condo is a boho getaway tucked away in a quiet enclave conveniently located on the beachside of Highway 1. It has dedicated parking in front, plus an additional spot for a second car. This condo it is a two bedroom/two bathroom unit. Full kitchen and a dining area that seats up to six. The condo is on the second floor with one stair flight. The beach is a 20 minute walk, 10 minute bike ride, or 5 minute drive Community pool on site provides an extra place to relax and cool down.

4.96 out of 5 average rating, 289 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.

Townhouse in Rehoboth Beach

A modern living area is presented with a large sectional sofa, accompanied by two stylish chairs. A vibrant wall art piece enhances the space, while natural light enters through glass doors leading to an outdoor patio. A round coffee table and area rug complete the inviting setup.

4.94 out of 5 average rating, 190 reviews

Modern Beach Vibe - Rehoboth Beach

Step into a beautifully comfortable designer townhome, and relax in style just blocks from the restaurants & beach on Rehoboth Avenue. Much care has been given to all the furnishings in this 2300sq foot, 3 stories, from the Gourmet Kitchen, Great Room, 3 gorgeous bedrooms, 2 full baths, 2 half baths, patio, to the 2 balconys, large 3rd floor indoor & outdoor living, plus a pool. Every detail is of the highest quality to evoke a relaxed upscale modern beach vibe.

The living room features two full couches facing a coffee table, with a Smart TV mounted on a console nearby. A ceiling fan rotates above, while natural light filters through the sheer curtains. A dark accent wall contrasts with light walls, enhancing the space's depth.

4.97 out of 5 average rating, 276 reviews

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool

Perfect location to enjoy the holiday season in Southern DE for upcoming events, such as Polar Bear Plunge, Super Bowl Weekend or Dewey’s Famous Winter Gala! Whether you're planning a beach vacation, a business trip, or a shopping spree at the nearby Outlets, this condo is the ideal retreat. Conveniently located near dining, shopping, scenic trails, and just a short drive to Lewes, Rehoboth, and Dewey by having everything you need for a memorable stay.

4.99 out of 5 average rating, 214 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* and no pets from Memorial Day to Labor Day.

A patio space is displayed, featuring a round table surrounded by four cushioned chairs. Lush greenery frames the scene, offering a view of Silver Lake in the background, where trees stand along the water's edge, enhancing the serene atmosphere.

4.79 out of 5 average rating, 307 reviews

Right on Silver Lake walk to beach!

On the most beautiful and secluded part of Rehoboth. Have breakfast in your patio right on Silver Lake and then go to the pool or walk to the beach, shopping and restaurants downtown or drive 5 minutes to Tanger Outlets! For your peace of mind we comply with Airbnb COVID-19 cleaning and disinfecting guidelines. In addition we follow CDC guidelines leaving more than 24 hour between guests.

Popular amenities for Henlopen Acres rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living area features a comfortable sectional sofa arranged around a central ottoman. A stone fireplace serves as a focal point, complemented by a large HDTV on the wall. Natural light enters through the nearby windows, enhancing the room's welcoming atmosphere.

5 out of 5 average rating, 21 reviews

Spacious Family-Friendly Beach Home w/Hot Tub

The backyard is defined by a well-manicured lawn and a paved pathway leading toward a private pool. Several lounge chairs and an umbrella-covered dining area are positioned around the pool, surrounded by a tall white fence and lush greenery in the background.

5 out of 5 average rating, 18 reviews

Cozy updated cottage with private heated pool.

An open kitchen and dining area are presented, featuring a wooden dining table set with circular placemats and six white chairs. A chic breakfast bar with three black stools is visible. Modern artwork adorns the walls, and plants add a touch of greenery.

4.92 out of 5 average rating, 50 reviews

Artist’s Escape (2-bedrooms/3 beds/3 bathrooms)

A spacious in-ground pool is surrounded by lounge chairs in light blue and white. Lush greenery is visible along the perimeter, creating a refreshing outdoor space. A blue umbrella provides shade, while stone steps lead to an elevated area in the background.

4.95 out of 5 average rating, 110 reviews

Amazing Bay Vista Beauty with Private Pool!

A screened porch features two white rocking chairs with soft gray cushions, positioned facing a cozy seating area adorned with colorful pillows. Natural light pours in through large windows, illuminating the wooden flooring and surrounding greenery.

4.96 out of 5 average rating, 46 reviews

Rehoboth Beach Retreat |4BR Near Beach/Pools/Trail

Superhost

A serene view of a pond is presented, featuring a gentle fountain at the center. Surrounding lush greenery includes tall grasses and trees, and a multi-story condo building is visible in the background, showcasing balconies with light-colored shutters.

4.94 out of 5 average rating, 16 reviews

The Urban Condo @ Creekwood Reho

4.96 out of 5 average rating, 122 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, 44 reviews

A bright bedroom is presented with a spacious bed dressed in crisp white bedding. Natural light streams through several windows adorned with woven shades, revealing views of the lush outdoors. A large mirror and decorative tray add to the room's charming décor.

Home in Lewes

Lewes Carriage House: Spa Hot Tub & Winter Luxury

Condo rentals with a pool

Superhost

The living area features a dark fabric sleeper sofa and a wooden coffee table positioned on a textured area rug. A large flat-screen TV is mounted on the wall, and large glass doors provide access to the balcony, allowing natural light to fill the space.

Condo in Ocean City

4.92 out of 5 average rating, 123 reviews

Oceanfront 1 Bedroom 1.5 Bath-Balcony-Laundry-WiFi

A modern kitchen area features wooden cabinets, stainless steel appliances, and a stone accent wall. A circular glass dining table is surrounded by wicker chairs, providing a cozy space for meals. The overall layout is bright and inviting, with natural light highlighting the contemporary decor.

4.94 out of 5 average rating, 122 reviews

Cozy Condo on Silver Lake - Walk to the beach!

4.99 out of 5 average rating, 163 reviews

A balcony view captures a wide expanse of lush green fields and dense trees, framed by a soft gray sky. The natural landscape offers a serene backdrop, highlighting a peaceful atmosphere. A railing can be seen in the foreground, providing a sense of depth.

Condo in Lewes

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

A decorative wooden sign with a blue background and black lettering stating 'LIFE IS BETTER IN FLIP FLOPS' is placed on a neutral-colored surface. A small metallic sailboat sculpture is visible in the background, adding a nautical accent to the scene.

4.91 out of 5 average rating, 137 reviews

Salt Air Retreat - Rehoboth Beach

A spacious bedroom features a large bed with a patterned comforter and multiple decorative pillows. Natural light floods the room through a glass door leading to a balcony. A bedside table with a lamp and a potted plant add to the calming atmosphere.

4.94 out of 5 average rating, 115 reviews

Cozy condo, 3 pools, and 4 beds in Rehoboth Beach

White Adirondack chairs are positioned along a lakeside path, offering a view of calm waters surrounded by vibrant autumn foliage. The ground is covered with fallen leaves, and a large tree casts gentle shade nearby.

4.9 out of 5 average rating, 101 reviews

1 Bedroom 1 Bath Condo on Silver Lake

4.99 out of 5 average rating, 155 reviews

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.

Condo in Lewes

Mimi’s Place @ The Villages of 5 Points in Lewes

4.95 out of 5 average rating, 121 reviews

A corner sectional sofa is arranged in a cozy living area, accompanied by a rectangular coffee table placed on a patterned area rug. Two framed art pieces adorn the wall above, and soft natural light filters through the space.

Condo in Lewes

Cozy condo in the Villages of Five Points, Lewes

Other holiday rentals with a pool

A bright living area features light blue walls with decorative sailboat artwork. A ceiling fan circulates air above a comfortable seating area. The open floor plan connects to a dining space with wicker-style furniture and a view of the kitchen, showcasing modern appliances.

5 out of 5 average rating, 14 reviews

Loft Penthouse 8 min Drive to Beach & Boardwalk

Two white Adirondack chairs are positioned on a patio overlooking a serene lake. Lush green grass surrounds the area, while trees offer shade. The calm water reflects the greenery, creating a peaceful outdoor setting.

4.9 out of 5 average rating, 63 reviews

Lakefront condo blocks from the beach

A view of the sandy beach and ocean is visible in the background, with a clear blue sky above. A group of colorful umbrellas can be seen set up on the beach. In the foreground, parked cars are arranged along a open area, with a person walking nearby.

4.91 out of 5 average rating, 55 reviews

Blue Skies

4.93 out of 5 average rating, 42 reviews

A charming studio cabin, nestled among tall trees, features a brown exterior with white trim. Large windows allow natural light to fill the interior. A stone pathway leads to a main entrance, framed by a serene woodland setting.

Guesthouse in Lewes

Studio Bedroom in the Woods

A modern dining space is depicted with a round table set for four, featuring light blue plates and glasses. Contemporary bar stools line the kitchen counter, which showcases stainless-steel appliances. Adjustable lighting illuminates the area, enhancing the welcoming atmosphere.

5 out of 5 average rating, 53 reviews

Velo Condo-2 BR, 2 BA, Pool view

A screened-in porch features a round table with two chairs and a decorative sun motif on the wall. Soft outdoor lighting is visible overhead, and a plant adds a touch of greenery. A view of the surrounding buildings is also present.

4.96 out of 5 average rating, 52 reviews

2BR/2BA Rehoboth Beach Condo with Pool/Tennis!

A modern living room is showcased with a leather sectional sofa featuring decorative pillows. Large glass doors open to a balcony, revealing ocean views. The space is complemented by light wood flooring and stylish artwork on the walls. A TV entertainment center is positioned against a white cabinetry unit.

4.92 out of 5 average rating, 93 reviews

Oceanfront Jewel-Direct Oceanview*Romantic Getaway

A spacious balcony offers views of the ocean and beach. White chairs are positioned around a round table, while people can be seen enjoying the sandy shore below. The horizon meets clear blue skies, enhancing the tranquil atmosphere.