
Holiday rentals with a pool in Lewes
Find and book unique homes with a pool on Airbnb
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.

Where the Locals Live!!
Charming Beachy-Boho Property: Once our beloved family home, now your vacation getaway! Have a question, just ask! Thanks for checking us out, have a great day! 🚴 Ideal Location between Historic Lewes & The Boardwalk 🚗 2 Off Street Parking Spots 🦀 Local Eats: Steps from great dining, stoned throw from grocery store/dining/attractions. 🏊 Pool just steps from the unit! ⭐Balcony w/ Pool View 📺TV & board games. 🐶Pet Friendly 🌞Responsive Local Hosts 🌅 Great Charm at an unbeatable Value!

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.

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.

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 & 15+ restaurants, 5 you can walk to (2 blocks away), nail salon, a hair salon, grocery store and a CVS (4 blocks). We need pictures of everyone’s license and the person booking must be at least 25 years of age. There is 4 beach chairs and a large umbrella & 2 chair umbrellas.

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.

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, Relax, Shop & Dine, Sleeps 8, Games
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 Memorial Day to Labor Day.
Popular amenities for Lewes rentals with a pool
House rentals with a pool

Hot Tub Backyard Oasis! Private Beach, Local Pool

Gorgeous Bayfront, Pool, Hot Tub, Linens Included

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

Coastal Retreat | Lakefront | Pool | Hidden Gem

Rehoboth-Lewes Beach House by the Bay

Amazing Bay Vista Beauty with Private Pool!

The Jungalow - Dog Friendly, Fenced in & Pool

Designer Lewes Beach Retreat w/ Private Pool
Condo rentals with a pool

Luxury water-view condo with high-end finishes

Family Friendly Top Floor Condo Near Boardwalk

Cozy Condo on Silver Lake - Walk to the beach!

Salt Air Retreat - Rehoboth Beach

Classy Beach Getaway

10 mins to beach-2 BR-Sleep Six-Pool-Beach PK pass

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

1 Bedroom 1 Bath Condo on Silver Lake
Other holiday rentals with a pool

Baby friendly, walk to pool and bakery town home

3 BR Coastal Retreat

Luxe Lewes Townhouse: Pool, Roof Deck & Bike Trail

Family friendly house in Rehoboth Beach near pool

Water Views: Balcony, Pool & Easy Parking

Coastal retreat •beaches, trails & historic Lewes•

CondoReho • Central location, pool, porch

Charming Lewes Escape - Near Beaches & Bike Trails
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 $141 AUD 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 and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Lewes holiday 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!
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