
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 ﺩ.ﺇ 845 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.

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.

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.

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.

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.

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 is 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.

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 Waterfront Home-Private, Clean, Relaxing
A beautiful and peaceful get-away all year round! Bright and sunny 3 bed/2 bath waterfront home with wrap-around deck. Fully stocked, community pool, walking trails, kayaks and more! Visit Rehoboth or Lewes Beaches (10 miles away), Cape Henlopen and tax-free outlet shopping (6 miles away)! Great for families, water lovers, and bird lovers! Sunday to Sunday weekly rentals *only* and no pets from June 14 to Labor Day.
Popular amenities for Lewes rentals with a pool
House rentals with a pool

Coastal Hideaway at Five Points

Baby friendly, walk to pool and bakery town home

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

Ruby's Retreat at the Beach

Relaxing Getaway

Lewes Carriage House-Hamptons Style Pool & Hot Tub

Luxury Retreat with direct bike access to beaches

Gorgeous 5BR, 4.5BA, in town, pool, hot tub, beach
Condo rentals with a pool

Right on Silver Lake walk to the beach and town!

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

OceanfrontJewel|DirectOceanView•NewlyRenovatedPool

Renovated Condo Near Outlets, 3.5 Miles to Beach

2b 2b condo! 2 master bedrooms! rehoboth beach

Sunrise Studio - Ocean Front, on Boardwalk, Pool!

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool

2BR Coastal Escape with Pool Near Rehoboth Beach
Other vacation rentals with a pool

Lewes Home | Pool, Dogs Welcome, Fenced Yard

Beautiful Updated Condo Waterfront, Pool, Sunsets

4BR Townhouse with pool & bike trail access

Water Views: Balcony, Pool & Easy Parking

Coastal Retreat | Lakefront | Pool | Hidden Gem

Coastal retreat •beaches, trails & historic Lewes•

Bay Retreat

Village of 5 Points Lewes Beach Condo 2BR/2B
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