
Vacation rentals with a pool in Lewes
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Lewes

Total vacation rentals
Explore 20 vacation rentals in Lewes

Nightly prices starting at
Lewes vacation rentals start at R 3,685 ZAR per night before taxes and fees

Verified guest reviews
Over 640 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Lewes vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Lewes rentals

4.9 Average rating
Lewes stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated rentals with a pool in Lewes
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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!

SeaRenity, beach, pool, biking, outlets shopping
We offer you a large,/modern,/comfortable,/functional beach,/vacation, office work space that was renovated in March '24. SeaRenity is located between Lewes - Rehoboth, in a quiet apartment building. It's located 5 miles from Rehoboth Beach by car and 4.3 miles by bike/trail. Lewes Beach is 4 miles away. SeaRenity has unlimited free parking and is well equipped for shorter/longer stays. Walking distance to Lefty's (bowling, arcade, restaurant, drive-in movies), Matts Fish Camp restaurant.

Mimi’s Place @ The Villages of 5 Points in Lewes
Enjoy this 3rd floor (no elevator) renovated condo with amenities-tennis courts, walking & biking paths connecting to downtown Lewes & 2 outdoor pools in season. The condo is east of route 1, 3 miles to Lewes beach & 12 restaurants, 4 you can walk to, nail & a hair salon, grocery store and a CVS (3 blocks). We need pictures of everyone’s license per our condo association & the person booking must be at least 25 years of age. There are 4 beach chairs and a large umbrella & 2 chair umbrellas.

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.

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.

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.

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.

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.

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.

Hot tub, Pool, Shop & Dine, Sleeps 8
A convenient central location between Rehoboth/Dewey and Lewes Beaches. You can walk to the neighborhood pool (available Memorial Day- Labor Day). Stylish, clean and comfortable, our house is an entertainer's dream. A huge 11 ft island and open concept living space is perfect for gatherings. Each bedroom is curated for comfort. The peaceful, private back deck is perfect to layout. We go above and beyond to ensure the best experience for our guests.

Beautiful condo in Villages of Five Points, Lewes
Welcome to our beautiful condo in the desirable family friendly community of The Villages of Five Points ! Our 2 bedroom, 2 bath condo is the perfect place for your beach vacation or any occasion. The condo has been newly painted and new flooring has been installed as well. The condo is right off east of route 1 and about 3 miles from Lewes beach. Biking trails are close by and Cape Henlopen State Park is a short ride of about 3 miles.
Popular amenities for Lewes 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

Ruby's Retreat at the Beach

Cape Shores Luxury - NEW Pool, Beach, Pier, Park!

Beautiful Beach House in Rehoboth

A Wave from it All - Beach, Bike Trail & Shopping

Designer Lewes Beach Retreat w/ Private Pool

Modern Beach House w/ Private Pool

Lewes Carriage House-Hamptons Style Pool & Hot Tub
Condo rentals with a pool

Right on Silver Lake walk to the beach and town!

Cozy Condo on Silver Lake - Walk to the beach!

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

OceanfrontJewel|DirectOceanView•NewlyRenovatedPool

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

Sunset Vibes | Pond View Condo Near Beaches, Pool

Renovated Condo Near Outlets, 3.5 Miles to Beach

1st Floor Beach-town Condo in Lewes
Other vacation rentals with a pool

Coastal Hideaway at Five Points

Beautiful Updated Condo Waterfront, Pool, Sunsets

Lewes, Dog Friendly w/Pool, Deck & Fenced Yard

Water Views: Balcony, Pool & Easy Parking

Dog Friendly Fenced 3BR King Bed

Coastal retreat •beaches, trails & historic Lewes•

Slipper Shell Sanctuary

Coastal Zen Condo | Relaxing Condo w/ Pool
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