Vacation rentals with a pool in Henlopen Acres

4.99 out of 5 average rating, 121 reviews

Coastal Modern Condo • Balcony, 2 Baths, East Rt 1

☀️ Your Rehoboth Beach Escape Why guests love staying here: • Community pool 🌴 • 2 full baths • Private screened balcony 🌿 • East of Route 1 • Strong central AC ❄️ • Split-bedroom layout for added privacy • Beach chairs & towels included 🏖️ • Fast WiFi + smart TVs • Plenty of FREE parking • In-unit washer & dryer • Minutes to beaches, boardwalk, restaurants & shopping • Quiet community close to everything Perfect for couples, families, remote workers, girls’ weekends, and relaxing getaways.

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.

4.9 out of 5 average rating, 135 reviews

4BD 4BA Carriage Home-Fenced Yard | 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 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.

4.94 out of 5 average rating, 202 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 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.

4.98 out of 5 average rating, 226 reviews

Renovated Condo Near Outlets, 3.5 Miles to Beach

Enjoy your stay in this recently renovated and beautifully furnished two-bedroom, two-bathroom 3rd-floor condo conveniently located 3.5 miles from the Rehoboth Beach boardwalk, and 4.5 miles from Lewes Beach. The proximity to the beaches, stores, and restaurants make this condo a great spot to spend a fun-filled vacation at the beach. Our condo amenities include a community pool*( seasonal), free parking, free WiFi, smart TV, washer, and dryer. We supply all the sheets & towels for your stay.

Townhouse in Rehoboth Beach

The saltwater pool is surrounded by sun loungers and umbrellas, offering a relaxing space to unwind. Lush greenery borders the area, and a shed is visible nearby. The clear blue water reflects the sky, inviting guests to enjoy leisurely moments.

Downtown RB Townhome-Great Location-WALK TO BEACH

Great location in downtown Rehoboth Beach-walk everywhere! Tucked away in a quite residential community, yet close to all of RB's favorite attractions: 4 blocks to the beach and boardwalk, less than 1/2 block to Rehoboth Avenue. No need to drive once you arrive-walk to the beach, boardwalk, Funland, and all of the restaurants and shopping in town. Also close to the bike trails. This 2 level townhome overlooks the salt water pool and includes 2 parking spaces and 2 additional parking passes.

4.91 out of 5 average rating, 238 reviews

Apartment in Rehoboth Beach

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.

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.

4.99 out of 5 average rating, 182 reviews

A private hot tub is set on a paved patio beneath a shaded gazebo. Wooden decking surrounds the area, enhancing the serene outdoor setting. Lush greenery provides privacy, while outdoor lighting can be seen strung above, creating a welcoming space for relaxation.

4.94 out of 5 average rating, 109 reviews

Perfect Rehoboth Beach Getaway with Hot Tub

Discover the epitome of coastal comfort in newly remodeled home. Dive into luxury with a private hot tub, where the bubbling warmth provides the perfect escape. Unwind in the chic interiors, adorned with modern furnishings. Stay connected with complimentary Wi-Fi as you plan your outings to the nearby beaches, bustling boardwalk, and local attractions. Steps away from tax free outlet shopping. With convenience at every turn, this home ensures a perfect blend of tranquility and accessibility.

An open-concept kitchen and living area features a large wooden island with a sink, surrounded by modern cabinetry. Natural light floods the space through wide windows, showcasing cozy seating and a vibrant dining area with a round table. Bookshelves line a portion of the wall.

4.97 out of 5 average rating, 103 reviews

Modern Beach House w/ Private Pool

Modern eco-friendly retreat perfect year-round! This salt-box cottage is an open concept 3 bedroom, 2 bathroom filled with natural light. Huge yard with a pool house with dining table and grill, patio with lounge chairs, outdoor shower, and private pool (pool open May 15 - October 15). Located perfectly for Rehoboth Beach or Dewey Beach visitors. It is a 20 minute walk to the shops and restaurants on Rehoboth Ave or to the beach. Three parking spots, beach items, and all amenities included.

A spacious living area is presented, featuring a comfortable green sofa and a matching armchair. A large television is positioned on a low cabinet. Natural light streams through sliding glass doors, leading to a screened-in porch, enhancing the atmosphere with a view of greenery.

4.95 out of 5 average rating, 123 reviews

2BR Coastal Escape with Pool Near Rehoboth Beach

🐋 Whalecome to Condo La Ballena — a quiet, relaxing 2BR/2BA coastal retreat with seasonal pool*, just 10–15 minutes drive from Rehoboth Beach Boardwalk and Lewes beaches. Perfect for beach getaways, outlet shopping, brewery hopping, and exploring Cape Henlopen State Park and the Junction & Breakwater Trail. Walk to local favorites like Fin’s Ale House, Agave, Rosenfeld’s Deli & Rehoboth Diner. Linens/towels included. No pets, no smoking. Enquire about weekly rates. *Pool open seasonally.

4.94 out of 5 average rating, 241 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.

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.

4.94 out of 5 average rating, 188 reviews

Hot tub, Pool, Shop & Dine, Sleeps 8

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.