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

Total holiday rentals
Explore 10 holiday rentals in Lewes

Nightly prices starting at
Lewes holiday rentals start at $128 SGD per night before taxes and fees

Verified guest reviews
Over 620 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Lewes holiday rentals include wifi 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.

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.

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE
2 Bedroom Condo Top Floor (3rd Floor) - Waterfront in Lewes/Rehoboth Beach DE Great Scenery Views - The Residence at Rehoboth Bay. Each bedroom has 1 king size bed and 1 queen size air mattress (in closet) *Community Pool available during in-season (8am-8pm) *No cleaning fee Nearby amenities and attractions include: Rehoboth Beach Boardwalk (6 Miles) Cape Henlopen State Park (8 Miles) Dewey Beach, DE (7 Miles) Bethany Beach, DE (18 Miles) Ocean City, MD (32 Miles) Shopping Outlets (4 Miles)

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.

Cozy Lewes Retreat | Pool, Short Drive 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.

Sunset Vibes | Pond View Condo Near Beaches, Pool
Our beautiful, spacious condo has everything you and your family/friends need! Centrally located to all beaches - 4 miles to Lewes Beach, 5 miles to Rehoboth Beach, and 5.4 miles to the beautiful Cape Henlopen State Park with walking/biking trails and beach access. Our 3 bedroom, 2 bath end unit with lots of natural light is located on the 2nd floor(with elevator access) in a quiet community with plenty of free parking and a gated community pool steps away from the building!

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 will be 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

Turtle Cottage by the Bay

Mystical Cape May's Modern Farmhouse: The Widmore

Beautiful Beach House in Rehoboth

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

Dog Friendly Fenced 3BR King Bed

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

Mid-Century Milton w/heated Pool

Coastal Beauty-Bike to Beach
Apartment rentals with a pool

Stress-Free Family Beach Stay | Pool + Kid Perks

Right on Silver Lake walk to the beach and town!

Cozy Condo on Silver Lake - Walk to the beach!

Salt Air Retreat - Rehoboth Beach

Modern Beach Glam in the heart of outlets.

Renovated Condo Near Outlets, 3.5 Miles to Beach

2 Bedroom Condo Rehoboth Beach w/Brand New Bed

Beach condo w/pool! All linens & beach supplies
Other holiday rentals with a pool

Coastal Cozy “Your relaxed retreat at the beach!”

3 BR Coastal Retreat

Pool, dog friendly, deck, fenced yard, Lewes

Coastal oasis w pool, near night life and beaches

Charming Lewes Escape - Near Beaches & Bike Trails

Lewes Beach Condo: 1st Floor, 2 Pools, Bike Trail

Charming Lewes/Rehoboth Retreat, Pet Friendly!

Lewes Bright and Airy Coastal Retreat
Destinations to explore
- Norfolk Holiday rentals
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Rentals with a fireplace Lewes
- Family-friendly rentals Lewes
- Rentals with a washing machine and dryer Lewes
- House rentals Lewes
- Beach house rentals Lewes
- Rentals with outdoor seating Lewes
- Pet-friendly rentals Lewes
- Beachfront rentals Lewes
- Rentals with a patio Lewes
- Rentals with beach access Lewes
- Flat rentals Lewes
- Apartment rentals Lewes
- Cottage rentals Lewes
- Rentals with a firepit Lewes
- Beach apartment rentals Lewes
- Rentals with pools Sussex County
- Rentals with pools Delaware
- Rentals with pools United States
- Ocean City Beach
- Ocean City Boardwalk
- Ocean City Boardwalk
- Wildwood Crest Beach New Jersey
- Cape May Beach NJ
- Broadkill Beach
- Assateague Island National Seashore
- Rehoboth Beach
- Willow Creek Winery & Farm
- Northside Park
- Ocean City Boardwalk
- Assateague State Park
- Delaware Seashore State Park
- Jolly Roger Amusement Park
- Cape Henlopen State Park
- Fenwick Island State Park Beach
- Bethany Beach Boardwalk
- Dover Motor Speedway
- Ocean City Beach
- Dewey Beach Access
- Ocean Pines Golf Club
- Wildwoods Convention Center
- Wildwood Boardwalk
- Roland E Powell Convention Center





