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

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, remote workers, girls’ weekends, and relaxing getaways.
4.99 out of 5 average rating, 121 reviews
Spacious, Conveniently Located Townhouse
Beautifully updated townhouse located in quiet community of Eagle Point offers 4 bedrooms, 2.5 bathrooms and 2,500 SF. The 1st floor offers open concept layout with living and dining rooms, large set up kitchen with breakfast area, 1/2 bath, laundry room, and master suite with king bed. The 2nd floor offers 3 bedrooms (2 queen beds and 1 full size bunk bed) and full bath. In addition, the 2nd floor presents another living space with TV and pullout sofa. Plenty of room for cozy family gatherings!
4.98 out of 5 average rating, 105 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.
4.98 out of 5 average rating, 224 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.
4.98 out of 5 average rating, 310 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.
4.99 out of 5 average rating, 180 reviews
Villa Del Sol, Beautiful stay near beaches/outlets
This bright and beachy 3 br/2 bath stay in Lewes, De comfortably sleeps 6 to 8 people. Just a short drive (10-15 min) to Lewes Beach and Cape Henlopen Park. Villa del Sol is a great beach escape with plenty of parking, as well as a community pool (open 5/27 - 9/5). Rehoboth Beach is also just 5 miles away, or you can go shopping at the nearby outlets. Walk to Bushel’s or Crooked Hammock for dinner, or cook something up with enough room to seat the whole family! At least 25 years old to book.
4.97 out of 5 average rating, 243 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.
4.94 out of 5 average rating, 108 reviews
The Jungalow - Dog Friendly, Fenced in & Pool
Centrally and peacefully located. Find yourself immersed in a thoughtfully designed vacation space where the relaxing days don’t end at the beach. Dog friendly (2), community pool, walkable to restaurants, bus stop, outlets, and local bars! Fenced in yard perfect for kiddos and pups while grownups can relax on the porch! Also, a comfortable space to enjoy a movie night in or relax outside under the stars. Our little slice of paradise is waiting for you, your guests and well behaved doggies!
5.0 out of 5 average rating, 101 reviews
Modern & Cozy Retreat | Pool | Close to Beaches
Enjoy a relaxing Lewes getaway nestled just off Coastal Highway, with easy access to beaches, dining, and local attractions. Less than 5 miles to Lewes Beach and less than 7 miles to Rehoboth and Dewey Beach, making it easy to enjoy the ocean, boardwalk, and everything the area has to offer. Just minutes from Nassau Valley Vineyards, Georgetown-Lewes Trail, Cape Henlopen State Park, historic downtown Lewes, great restaurants, breweries, and tax-free shopping at Tanger Outlets.
4.95 out of 5 average rating, 326 reviews
Beautiful Updated Condo Waterfront, Pool, Sunsets
WATER FRONT VIEWS AT LEWES HARBOUR! This newly renovated condo is a unique gem as it sits right between town and the beach on the canal in the heart of Lewes. Waterfront views welcome you into a large, modern kitchen; the sitting room has an electric fireplace and the condo includes its own washer/dryer. After a hot day at the beach cool off in the pool, walk into town for dinner or shopping. Or stay home and enjoy happy hour on the waterfront decks; the sunsets are unbeatable.
4.91 out of 5 average rating, 100 reviews
Cozy Woodland Cottage
Enjoy the sounds of nature when you stay in this unique place. Located less than 5 miles from downtown Lewes and Delaware Beaches. The cottage guest house is nestled in the woods adjacent to a tree house overlooking a tranquil pond with a calming fountain sounds. On the main property guests have access to a in ground swimming pool (seasonal) with a 60 foot lap lane and slide, schedule times with hosts.. The backyard also includes an organic garden, playground and 🐔 chickens.
4.94 out of 5 average rating, 239 reviews
The Little house W/ Pool & Spa
Nestled in the woods and just steps from cedar creek, The little house is a charming, pet-friendly tiny house that offers a magical escape from the everyday. Thoughtfully designed and comfortably sleeping up to 6 guests, this unique hideaway is perfect for couples, families, or friends looking to unwind and relax. 10 Minutes from DE turf, 20 minutes from the beach, directly beside yogi bear. Perfect for travel nurses & remote workers – Monthly stays welcome!
4.9 out of 5 average rating, 116 reviewsPopular amenities for Sussex County rentals with a pool
House rentals with a pool

The Big Chill at Bethany Beach
4.98 out of 5 average rating, 105 reviews
A Bethany Beach Gem 1.5 miles to Ocean Pickle Ball
4.94 out of 5 average rating, 218 reviews
Bright Open Floor Plan Family Beach Retreat
4.91 out of 5 average rating, 149 reviews
Modern Beach House w/ Private Pool
4.97 out of 5 average rating, 103 reviews
Bay Pearl House! (grill, screened porch, crabbing)
4.93 out of 5 average rating, 121 reviews
Ruby's Retreat at the Beach
4.84 out of 5 average rating, 32 reviews
Gorgeous 5BR, 4.5BA, in town, pool, hot tub, beach
4.96 out of 5 average rating, 56 reviews
Lewes Carriage House: A Sanctuary for Mind & Body
5.0 out of 5 average rating, 70 reviewsApartment rentals with a pool

First Floor Comfort and Convenience
4.98 out of 5 average rating, 130 reviews
Mimi’s Place @ The Villages of 5 Points in Lewes
4.99 out of 5 average rating, 179 reviews
Newly Renovated Modern 2 Bed/2 Bath Condo w/ Pool
4.98 out of 5 average rating, 125 reviews
Beach Escape Condo w/ Pool - Lewes Beach 3.5 Miles
4.97 out of 5 average rating, 132 reviews
Bright condo-On bike trail & 1 mile to boardwalk
4.96 out of 5 average rating, 114 reviews
Condo 2 Bedroom Waterfront Lewes/Rehoboth DE
4.98 out of 5 average rating, 222 reviews
2BR Coastal Escape with Pool Near Rehoboth Beach
4.95 out of 5 average rating, 122 reviews
Bethany Bay. Sleeps 4. AC, Pool, Ground Floor
4.98 out of 5 average rating, 133 reviewsOther holiday rentals with a pool

Lewes Getaway | Pool, Dogs & Fenced Yard
5.0 out of 5 average rating, 38 reviews
Coastal retreat •beaches, trails & historic Lewes•
4.99 out of 5 average rating, 93 reviews
‘Dockside Retreat’ -pool, minutes to OC/beaches
5.0 out of 5 average rating, 67 reviews
Dog Friendly Fenced 3BR King Bed
4.97 out of 5 average rating, 67 reviews
Gorgeous Bayfront, Pool, Hot Tub, Linens Included
4.96 out of 5 average rating, 81 reviews
Resort Retreat: King Suites & Nature Trails
4.9 out of 5 average rating, 10 reviews
Cape Shores Luxury - NEW Pool, Beach, Pier, Park!
5.0 out of 5 average rating, 63 reviews
Lewes Beach Condo: 1st Floor, 2 Pools, Bike Trail
4.9 out of 5 average rating, 86 reviewsDestinations to explore
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- Chincoteague Island
- Cape May Beach NJ
- Assateague Island National Seashore
- Wildwood Crest Beach New Jersey
- Ocean City Beach
- Broadkill Beach
- Rehoboth Beach
- Bethany Beach Boardwalk
- Assateague State Park
- Cape Henlopen State Park
- Willow Creek Winery & Farm
- Dover Motor Speedway
- Northside Park
- Wildwood Boardwalk
- Delaware Seashore State Park
- Jolly Roger Amusement Park
- Fenwick Island State Park Beach
- Stone Harbor Beach
- Roland E Powell Convention Center
- Wildwoods Convention Center
- Ocean Pines Golf Club
- Mariner's Arcade
- Ocean City Boardwalk
- Funland





