Vacation rentals with a pool in Henlopen Acres

4.91 out of 5 average rating, 128 reviews

An aerial view of a community swimming pool is presented, surrounded by neatly manicured greenery. Poolside loungers are visible alongside a gazebo that offers shaded seating. Clear blue water fills the spacious pool, inviting relaxation under the sunlight.

Home in Rehoboth Beach

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 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, 191 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.

A spacious outdoor pool is surrounded by lounge chairs and umbrellas, providing a relaxing environment. A two-story building with a balcony overlooks the pool area, while modern structures stand in the background, emphasizing the setting's inviting atmosphere.

4.95 out of 5 average rating, 153 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.

An aerial view reveals a pair of adjoining units with dark roofs and light-colored exteriors, surrounded by trees. A calm body of water reflects the seasonal foliage, while a parking lot is visible in the foreground. The peaceful setting is enhanced by a winding path leading to the shoreline.

4.89 out of 5 average rating, 155 reviews

Right on Silver Lake walk to the beach and town!

Completely renovated, right on Silver Lake! On the most secluded part of Rehoboth Beach watch the sun rise and wildlife sitting at your patio! Park your car and walk or bike everywhere. Steps from the pool and three blocks across Turtle Bridge to get to the less crowded part of the beach. Five blocks from Rehoboth Avenue, where most restaurants and shops are. Full kitchen, Central heat/air, Smart TV, Cable and High speed internet. Pickleball, Tennis, Basketball and Tennis courts next door

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.

4.91 out of 5 average rating, 218 reviews

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.

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, 403 reviews

Pool, near Shopping, Clean and Comfy

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 spacious outdoor pool area is surrounded by lounge chairs and bright blue umbrellas. The well-maintained pool reflects the clear sky, with a fence ensuring privacy and safety. Nearby, a multi-story building can be seen, contributing to a relaxed community atmosphere.

4.99 out of 5 average rating, 149 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!

4.97 out of 5 average rating, 122 reviews

Modern 2BR/2BA – Beach Pass + Bikes, 5 Min Drive

This spacious, clean, and modern 2-bedroom, 2-bath condo is the perfect place to unwind after a road trip or a sun-soaked day at the beach. With a King bed, Queen bed, beach parking pass, and bikes included, getting to Rehoboth Beach is as easy as it gets. And when you're back home, parking is a breeze — with hundreds of open spots right outside the condo. We even provide you recommendations to restaurants, fun activities and even what to order! Beach, Outlets, Parks and Good Food.

A large, clear swimming pool is bordered by a sunbathing area featuring several lounge chairs. The surrounding area is enclosed by a black fence, with multiple apartment buildings visible in the background against a blue sky with soft clouds.

4.94 out of 5 average rating, 101 reviews

10 mins to beach-2 BR-Sleep Six-Pool-Beach PK pass

The first floor condo. Easy access to the parking. 10 minutes to the beach and close to all the great restaurants. Tanger Outlet is across the street. Beach Bus stop is right by the entrance. A large pool is located right next to the building. A beach parking permit is provided during your stay here. All guests must be 25+ (except for the minors that must be accompanied by a legal guardian). ID’s may be requested. For the security of our property, a Ring camera is on the front door.

Apartment in Rehoboth Beach

A bright bedroom is presented with large windows that offer views of the surroundings. A spacious bed is complemented by decorative pillows, while a white dresser and television add functionality. Light wood flooring enhances the modern aesthetic of the room.

4.99 out of 5 average rating, 234 reviews

The Sandy Starfish - Rehoboth Beach

The Sandy Starfish – Steps from Rehoboth Beach Fun! Enjoy coastal living in this bright, top-floor 3BR/2BA condo in a resort-style community, just 1.2 miles from Rehoboth Beach and the boardwalk. Modern, airy, and family-friendly, it’s the perfect home base for your beach getaway. Walk, bike, or drive to the sand and soak up everything this charming beach town has to offer! Pool is open though the end of September!

4.98 out of 5 average rating, 197 reviews

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.