Holiday rentals with a pool in Dewey Beach

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Top-rated rentals with a pool in Dewey Beach

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Top Guest favourite
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.
Condo in Rehoboth Beach
4.98 out of 5 average rating, 217 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.

Top Guest favourite
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.
Condo in Rehoboth Beach
4.96 out of 5 average rating, 196 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.

Guest favourite
A circular glass table with four woven chairs is positioned on the patio, overlooking a tranquil lake surrounded by greenery. Sunlight filters through the trees, casting soft reflections on the water's surface.
Condo in Rehoboth Beach
4.9 out of 5 average rating, 178 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

Top Guest favourite
Condo in Rehoboth Beach
4.98 out of 5 average rating, 304 reviews

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool

Spring Break Getaway! Fresh New Photos! 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.

Top Guest favourite
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.
Apartment in Rehoboth Beach
4.99 out of 5 average rating, 170 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.

Top Guest favourite
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.
Home in Rehoboth Beach
4.97 out of 5 average rating, 100 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.

Top Guest favourite
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.
Home in Rehoboth Beach
4.96 out of 5 average rating, 103 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.

Top Guest favourite
A spacious bedroom is presented, featuring a four-poster bed with a light-colored bedding set. Flanking the bed are two bedside tables, each with a lamp. Natural light filters through the window, illuminating the soft, neutral tones of the room.
Condo in Rehoboth Beach
4.99 out of 5 average rating, 117 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, girls’ weekends, and relaxing coastal getaways.

Guest favourite
The living area features a light gray sectional sofa with colorful accent pillows, situated within a bright space. A wooden console table is placed against the wall, and light fixtures illuminate the open kitchen area in the background.
Condo in Dewey Beach
4.95 out of 5 average rating, 154 reviews

Luxury water-view condo with high-end finishes

Luxury 2-bedroom condo at The Residences at Lighthouse Cove located in the heart of Dewey Beach. This unit features great views of Rehoboth Bay and is only 1 block from the Atlantic Ocean. Easy walk to Dewey Beach’s shops, restaurants, and nightlife. This unit sleeps up to 6. There is a master bedroom with a king bed and ensuite bathroom. The second bedroom has a queen bed. There are 2 twin-size fold-away beds. Lounge at private rooftop pool, fire pits, & grills for Residences

Top Guest favourite
A private balcony is showcased overlooking the ocean, featuring two comfortable chairs and a small table. The scene is framed by large sliding doors, allowing natural light to brighten the space. Green turf flooring complements the outdoor seating area.
Condo in Ocean City
4.97 out of 5 average rating, 101 reviews

Luxury Oceanfront Oasis!

Welcome to Marigot Beach, one of the most coveted building in OC. This stunning condo boasts 2 spacious bedrooms and 2 bathrooms, ideal for a large family or a large group up to 8 guests. The master bedroom features an en-suite bathroom, while the second bedroom offers two full-size beds. Included: free WiFi, smart TVs in every room, fully equipped kitchen, large-capacity washer/dryer, and elevator. PLUS, take advantage of TWO designated parking spots! Pool/hot tub are now OPEN!

Top Guest favourite
A serene bedroom features a spacious bed draped in a light blue and beige quilt, adorned with nautical patterns. Flanking the bed are two matching bedside lamps on wooden nightstands. A subtle coastal decor, including fish wall art, complements the tranquil atmosphere, with an ensuite bathroom visible in the background.
Condo in Rehoboth Beach
4.96 out of 5 average rating, 109 reviews

Beach condo w/pool! All linens & beach supplies

Renovated and beautifully decorated 3rd floor condo (no elevator) with a comfortable, beachy feel! ALL LINENS AND BEACH SUPPLIES INCLUDED AT NO EXTRA CHARGE. Includes full kitchen with stainless steel appliances, washer/dryer, updated bathrooms, and access to the pool in season. Across from the Tanger Outlets, you are close to tax free shopping, restaurants, bars and numerous activities for the kiddos! Less than 1/2 hour from Sports at the Beach and DE Turf Sports Complex.

Guest favourite
The exterior of a large white house is displayed, featuring black and white striped awnings over the windows. A welcoming front porch includes a bench and colorful flower pots. A spacious driveway provides parking, and a garage door is visible on the right.
Home in Rehoboth Beach
4.87 out of 5 average rating, 246 reviews

Dodd House Beach Home w/private pool and hot tub

Saturday to Saturday bookings from the third week in June through mid August. Large 5 bed 3.5 Bath Luxury Home with pool and hot tub. Parking for six to eight cars. ARRIVE, STOCK UP, AND NEVER LEAVE IF YOU CHOOSE! GET YOUR FAMILY AND FRIENDS TOGETHER SAFELY! This large 4,500 square foot rental unit includes 5 private BR, 3.5 BTH, and sleeps 18! Pool opens May 15th until September 30th. Outdoor fire pit with some wood provided. 25 and older please.

Popular amenities for Dewey Beach rentals with a pool