Holiday rentals with a pool in Rehoboth Beach

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

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 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, 170 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, 423 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!

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, 125 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.

A private deck features a round glass table surrounded by four striped chairs. A potted plant with pink flowers adorns the center of the table. The wooden railing provides a sense of privacy while allowing for an outdoor dining experience.

4.82 out of 5 average rating, 401 reviews

2 Bedroom Condo Rehoboth Beach w/ No Chores

2 Bedrooms Condo. Great for families or couples. Walking distance to restaurants, beach, bars & other entertainment. Driving distance to 5 different golf courses within 15 minutes. Walking distance to water park & amusement park. Pool on site. Bike & running trail behind the condo. Roku on every TV with Xfinity app for local TV & a Spectrum app for premium channels. We have MGM +& you can add any of your own streaming services during your stay. Smoking area on deck. No chores for you to do!

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, 113 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, pickle ball 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.

Townhouse in Rehoboth Beach

An open living space features a cozy seating area with a light-colored sofa and a coffee table. A round dining table with white chairs is positioned nearby. Natural light filters through sliding glass doors, which lead to a screened porch.

4.91 out of 5 average rating, 129 reviews

Cute Townhouse in Rehoboth

Cute Townhome Duplex located in Rehoboth Beach. A short 5 min drive to the beach or 15 minute bike ride. Located 5 minutes from downtown Rehoboth Beach and 5 minutes from downtown Dewey beach. A quick drive to the Tanger Outlets and endless restaurants. Our property is located within a private, quiet community with a large gated pool. There is a screened in private back porch to enjoy during your stay. We our located just minutes from restaurants and attractions on Coastal Highway.

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 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.

4.99 out of 5 average rating, 166 reviews

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

2 Bedroom Condo Top Floor (3rd Floor) - Waterfront in Lewes/Rehoboth Beach DE Great Scenery Views - The Residence at Rehoboth Bay. *Community Pool available during in-season (8am-8pm) *No cleaning fee Nearby amenities and attractions include: Rehoboth Beach Boardwalk (6 Miles) Cape Henlopen State Park (8 Miles) Dewey Beach, DE (7 Miles) Bethany Beach, DE (18 Miles) Ocean City, MD (32 Miles) Shopping Outlets (4 Miles)

4.92 out of 5 average rating, 260 reviews

A serene ocean view is presented from a private balcony, featuring two teal chairs. The sandy beach stretches into the distance, with gentle waves lapping at the shore. A clear sky completes the tranquil coastal scene, creating a peaceful atmosphere.

Condo in Ocean City

Oceanfront Paradise | Pool | Hot Tub | Beach

-Oceanfront -Indoor pool & Hot tub -Walk to local dining and shopping -Elevator accessible plus luggage carts -Full kitchen for cooking meals -Fast Wifi and Streaming TVs -Fully Stocked Home: Clean linens, towels, toilet paper, paper towels & more! **2026 guests: Our pool and hot tub are in the process of being renovated and will be closed during your stay. They will re-open after Memorial Day**

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 Rehoboth Beach 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

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)

5 out of 5 average rating, 106 reviews

The exterior of the single-family home is shown, featuring a welcoming entrance with a striped awning. A well-maintained front yard with shrubs and a tree provides shade, while the attached garage is visible on the left.

Home in Frankford

Quiet 3BR Coastal Home Minutes to Bethany Beach

A spacious living room is furnished with a light-colored sofa and two round armchairs, complemented by accent pillows. A modern electric fireplace is mounted on the wall, beneath a large smart TV. Natural light filters through sliding glass doors, leading to the outdoor area.

5 out of 5 average rating, 35 reviews

Modern 3b/2.5 Townhouse w/ Pool & Tennis

4.94 out of 5 average rating, 227 reviews

A spacious living area is furnished with two dark leather sofas, providing ample seating. A ceiling fan enhances airflow. The open layout connects to a dining area featuring wooden chairs, while the kitchen is visible in the background, showcasing modern appliances and cabinetry.

Home in Ocean City

Right behind Alley Oops & Crab Bag. Walk to beach

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.

5 out of 5 average rating, 216 reviews

Beautiful Beach House in Rehoboth

A two-story beach house features a welcoming front porch with white railings, surrounded by well-maintained landscaping. Large windows allow natural light to brighten the exterior, while pathway steps lead up to the entry. The home is situated in a peaceful community setting.

5 out of 5 average rating, 80 reviews

Spacious Living in Rehoboth, with a Pool

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

Condo rentals with a pool

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!

4.88 out of 5 average rating, 189 reviews

A circular swimming pool is surrounded by sun loungers and shaded umbrellas, inviting relaxation. The beach lies in the background, with a stretch of sandy shore and blue umbrellas, while guests enjoy the sun and water nearby.

Condo in Bethany Beach

Beautiful Beach-View Condo

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

A light-filled living area features a comfortable seating arrangement with two red chairs and a cozy couch, accompanied by a round coffee table. A wall-mounted TV is situated above an electric fireplace, enhancing the space's inviting atmosphere. Large windows offer views of the outside.

4.94 out of 5 average rating, 296 reviews

Spacious| Modern & Cozy| Pool| Close to the Beach

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

4.84 out of 5 average rating, 177 reviews

Condo in Ocean City

Love Above the Waves-Best Ocean View & Heated Pool

Other holiday rentals with a pool

4.97 out of 5 average rating, 99 reviews

Lovely 2BR Condo - Rehoboth/ Dewey

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

4.98 out of 5 average rating, 62 reviews

A spacious living room features a comfortable blue sofa, a wooden coffee table, and a media console with a TV. Large windows provide natural light and showcase distant views. A decorative rug adds texture underfoot, while a small table with plants enhances the inviting atmosphere.

Condo in Dewey Beach

Stunning views from Beautiful 2 BR Condo

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

4.93 out of 5 average rating, 43 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

4.87 out of 5 average rating, 15 reviews

The Salty Seahorse | 1st-Floor, Pools & Near Beach

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 bright living area features a spacious sofa paired with accent chairs. Natural light floods through large windows, enhancing the serene atmosphere. A wooden coffee table rests on a textured rug, while a wall-mounted TV adds modern convenience.