Vacation 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 favorite
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, 195 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 favorite
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, 161 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.

Top guest favorite
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.
Condo in Rehoboth Beach
4.99 out of 5 average rating, 155 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!

Top guest favorite
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.
Condo in Rehoboth Beach
4.98 out of 5 average rating, 214 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!

Guest favorite
A modern living area features a striped sofa adorned with colorful cushions and an adjacent neutral-toned loveseat. A wooden dining table is positioned in the foreground, while a well-equipped kitchen is visible in the background. Natural light fills the space through large windows.
Condo in Dewey Beach
4.94 out of 5 average rating, 101 reviews

Luxury at the Beach.

Luxury accommodations at the beach, walkout to the pool from your sliders to your gated private patio with poolview. Hardwood floors, fireplace, TV, WIFI, Enjoy the rooftop outdoor pool, fire pits & propane grills on the veranda for use only by The Residences at Lighthouse Cove tenants & owners. Access to indoor pool & fitness room along with the hotel guests. Breathe the salt air, bay views and one block to ocean. Restaurants walking distance too. Walking distance to ocean and bay.

Top guest favorite
A welcoming living room features a modern design with a circular mirror and stylish light fixture. Comfortable seating includes a round chair and plush sofas configured around a wooden coffee table. Natural light enters through large windows, illuminating the space and providing a view of the outside.
Condo in Rehoboth Beach
4.97 out of 5 average rating, 128 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.

Superhost
Condo in Ocean City
4.84 out of 5 average rating, 216 reviews

Beachfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with a breathtaking view of the beach and ocean.

Guest favorite
A spacious living area features a comfortable sectional sofa with decorative pillows, complemented by a large area rug. A television is positioned on a stylish media console, while large glass doors provide access to a private patio, framed by blue curtains. A ceiling fan is present above.
Condo in Lewes
4.97 out of 5 average rating, 112 reviews

1st Floor Beach-town Condo in Lewes

Come stay at our favorite little beachtown condo in Lewes! This 1st floor 2 bedroom, 2 bath condo has everything you need for an enjoyable and relaxing vacation! You will be just a few miles to the beach and outlet malls, have access to the community pools (May-Sept), park, and sport courts, and will be within walking distance to several great restaurants and shops. While we are "pet friendly" only 1 pet (dog or cat, 40lb maximum) is allowed per the HOA rules.

Guest favorite
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
4.92 out of 5 average rating, 250 reviews

Sun, Sand & Sea | Your Cozy Oceanfront Hideaway

-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! **2025 guests: Our pool and hot tub are in the process of being renovated and will be closed during your stay. This does not impact our condo, but you will not be able to use these amenities.**

Top guest favorite
A modern living area features a spacious gray sofa and a wooden coffee table, complemented by a cozy area rug. Large glass doors open to a private oceanfront balcony, allowing natural light to fill the space. Decorative accents include a wall-mounted surfboard and a round mirror.
Apartment in Ocean City
4.98 out of 5 average rating, 260 reviews

OceanFront-Fireplace-sleeps4-Balcony-King-Disney+

Welcome to Salty Shark - direct oceanfront studio! This remodeled studio sleeps 4 and is in North Ocean City near great restaurants, bars, and 58 acre North Side Park. The park has sports fields, a recreation center, a walking/biking path, crabbing pier, playground, and outdoor fitness area. Building has outdoor pool in summer too! The unit features a King Murphy bed, and a Queen sofa bed. There's also an outdoor pool open in summer months!

Guest favorite
An open-plan kitchen and living area feature a light wooden counter with three stools. A fully equipped kitchen is visible, including a refrigerator, while a comfortable seating area with a cream-colored armchair and a coffee table is also present. Natural light enhances the inviting space.
Condo in Ocean City
4.89 out of 5 average rating, 157 reviews

Water Front Condo w/Pool Short Walk to Beach

FIRST FLOOR UNIT Bayside Condominium Sleeps 4 - 6 max Walking Distance to Northside Park Walk to the Ocean , don't worry about beach parking NON SMOKING 1 Bedroom 1 Bath condo, First floor unit with an outside deck This Air Conditioned, One Bedroom Condo has a fully equipped kitchen, washer/dryer, full refrigerator. There is a Queen bed and a full bed along with 1 Queen Sleep sofa in the living room *MUST BE 21 OR OVER* No Pets!

Top guest favorite
An in-ground pool is set within a stone patio, surrounded by a lush garden featuring various plants. Two lounge chairs are positioned beside the pool, and a tree provides natural shade, enhancing the backyard's inviting atmosphere.
Home in Rehoboth Beach
4.87 out of 5 average rating, 141 reviews

Hot Tub + Pool, Fire Pit, Cottage by Dogfish Head

This adorable beach cottage has it all, and it's bigger than it looks! With 3 full-size bedrooms, 2 full baths, and an enormous back yard with an IN-GROUND POOL, big back deck, huge HOT TUB, gas fire-pit, and dual charcoal and gas-burning BBQ, this home has everything you need for an unforgettable beach trip. You'll love the 3 KING SIZE BEDS, two of which are tempur-pedic, plus the two twin beds are great for kids.

Popular amenities for Dewey Beach rentals with a pool