
Holiday rentals with a pool in Dewey Beach
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Dewey Beach
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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.

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.

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

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.

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.

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.

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.

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.

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

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!

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.

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
House rentals with a pool

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

Family & Pet-friendly Beach House with Pool

4BD 4BA Carriage Home-Fenced Yard | Rehoboth Beach

Coastal Cottage! Walk to Beach!

Lewes Carriage House-Hamptons Style Pool & Hot Tub

Private Pool! Charming 4bdrm, BayVista Beach House

Gorgeous 5BR, 4.5BA, in town, pool, hot tub, beach

Fenced yard, shared pool, hot-tub, fire pit
Condo rentals with a pool

Luxe Oceanfront 1BR | Pool, Hot Tub, Sun Deck

Stress-Free Family Beach Stay | Pool + Kid Perks

Bluewater Couples Escape

Cozy Condo on Silver Lake - Walk to the beach!

Beautiful waterview 2B condo w/Dock&Close to Beach

Consistent 5-star rating Lakefront 3BR & 2BA condo

Modern & Cozy Retreat | Pool | Close to Beaches

WraparoundBalcony-2 Bed-Sleeps 8-Pool-Laundry-WiFi
Other holiday rentals with a pool

Lux Dewey: Rehoboth Bay Front*1Block 2 Ocean! Pets

The Post House

Spring Lake Escape | Dog-Friendly by Trail & Beach

Bayview Oasis-Pool/Free Parking

Luxury Bay & Oceanview Condo in the Heart of Dewey

Cozy Lakeview Stay by the Beach

Condo at Eagles Landing

Perfect Location in Dewey Beach!
Destinations to explore
- New York City Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Ocean City Holiday rentals
- Pittsburgh Holiday rentals
- Virginia Beach Holiday rentals
- Raleigh Holiday rentals
- Jersey City Holiday rentals
- Baltimore Holiday rentals
- Newark Holiday rentals
- Richmond Holiday rentals
- Outer Banks Holiday rentals
- House rentals Dewey Beach
- Family-friendly rentals Dewey Beach
- Beach house rentals Dewey Beach
- Apartment rentals Dewey Beach
- Beachfront rentals Dewey Beach
- Condo rentals Dewey Beach
- Villa rentals Dewey Beach
- Cottage rentals Dewey Beach
- Pet-friendly rentals Dewey Beach
- Beach condo rentals Dewey Beach
- Rentals with pools Sussex County
- Rentals with pools Delaware
- Rentals with pools United States
- Cape May Beach NJ
- Assateague Island National Seashore
- Wildwood Crest Beach New Jersey
- Ocean City Beach
- Broadkill Beach
- Rehoboth Beach
- Ocean City Boardwalk
- Cape Henlopen State Park
- Bethany Beach Boardwalk
- Assateague State Park
- Willow Creek Winery & Farm
- Northside Park
- Dover Motor Speedway
- Wildwood Boardwalk
- Stone Harbor Beach
- Delaware Seashore State Park
- Jolly Roger Amusement Park
- Fenwick Island State Park Beach
- Roland E Powell Convention Center
- Wildwoods Convention Center
- Ocean Pines Golf Club
- Mariner's Arcade
- Funland
- Hawk Haven Vineyard & Winery





