
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 3,739 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.

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.
ValueLocationDecor
4.97 out of 5 average rating, 146 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, remote workers, girls’ weekends, and relaxing getaways.
FamilyLocationBeach
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!
ValueFamilyBeach
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.
ValueFamilySleep quality
4.98 out of 5 average rating, 224 reviews
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.
LocationValueParking
4.99 out of 5 average rating, 179 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.
ValueLocationTV
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.
ValueLocationQuiet
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!
LocationFamilyDecor
5.0 out of 5 average rating, 101 reviews
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.
ValueFamilyGetting around
4.98 out of 5 average rating, 130 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.
FamilyValueHospitality
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.
LocationFamilyHospitality
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.
LocationFamilyHeating
4.94 out of 5 average rating, 239 reviewsPopular amenities for Lewes rentals with a pool
House rentals with a pool

Modern Beach House w/ Private Pool
LocationFamilySleep quality
4.97 out of 5 average rating, 103 reviews
Bay Pearl House! (grill, screened porch, crabbing)
LocationValueCondition
4.93 out of 5 average rating, 121 reviews
Baby friendly, walk to pool and bakery town home
FamilyLocationLayout
4.9 out of 5 average rating, 103 reviews
Ruby's Retreat at the Beach
LocationValueBathroom
4.84 out of 5 average rating, 32 reviews
Lewes Carriage House: A Sanctuary for Mind & Body
FamilyLocationGetting around
5.0 out of 5 average rating, 70 reviews
Cape Shores Luxury - NEW Pool, Beach, Pier, Park!
LocationFamilyNearby
5.0 out of 5 average rating, 63 reviews
Beach Getaway, minutes away from everything!!
LocationValueCondition
4.98 out of 5 average rating, 43 reviews
Gorgeous 5BR, 4.5BA, in town, pool, hot tub, beach
ValueFamilyCheck-in
4.96 out of 5 average rating, 56 reviewsCondo rentals with a pool

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE
LocationValueWalkability
4.98 out of 5 average rating, 222 reviews
Cozy Creekwood Condo - Relaxing Getaway - W/ Pool
ValueLocationGetting around
4.98 out of 5 average rating, 310 reviews
1st Floor Beach-town Condo in Lewes
LocationFamilyBeach
4.95 out of 5 average rating, 133 reviews
Bright condo-On bike trail & 1 mile to boardwalk
FamilyLocationCleanliness
4.96 out of 5 average rating, 114 reviews
2BR Coastal Escape with Pool Near Rehoboth Beach
FamilyLocationHospitality
4.95 out of 5 average rating, 122 reviews
Top floor, overlooking Love Creek at Rehoboth Bay
ValueLocationBeach
4.97 out of 5 average rating, 105 reviews
Sunset Vibes | Pond View Condo Near Beaches, Pool
FamilyLocationIndoor spaces
4.88 out of 5 average rating, 108 reviews
Modern Beach Glam in the heart of outlets.
ValueLocationHospitality
4.89 out of 5 average rating, 294 reviewsOther vacation rentals with a pool

Cozy Rehoboth Beach Condo w/ 2 bedrooms
ValueFamilyParking
4.99 out of 5 average rating, 180 reviews
Waterfront! Downtown historic Lewes walk to beach
FamilyValueQuiet
4.71 out of 5 average rating, 254 reviews
Lewes Beach Condo: 1st Floor, 2 Pools, Bike Trail
ValueLocationLong stay
4.9 out of 5 average rating, 86 reviews
Lewes Getaway | Pool, Dogs & Fenced Yard
ValueFamilyComfort
5.0 out of 5 average rating, 38 reviews
Coastal retreat •beaches, trails & historic Lewes•
FamilyLocationHeating
4.99 out of 5 average rating, 93 reviews
Beach getaway: perfect for off season enjoyment
LocationValueQuiet
4.87 out of 5 average rating, 67 reviews
4BR Townhouse with pool & bike trail access
ValueFamilyGetting around
5.0 out of 5 average rating, 18 reviews
Dog Friendly Fenced 3BR King Bed
FamilyValuePets
4.97 out of 5 average rating, 67 reviewsDestinations to explore
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