
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.

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.

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.

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)

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.

Cozy Rehoboth Beach Condo w/ 2 bedrooms
This condo is a boho getaway tucked away in a quiet enclave conveniently located on the beachside of Highway 1. It has dedicated parking in front, plus an additional spot for a second car. This condo it is a two bedroom/two bathroom unit. Full kitchen and a dining area that seats up to six. The condo is on the second floor with one stair flight. The beach is a 20 minute walk, 10 minute bike ride, or 5 minute drive Community pool on site provides an extra place to relax and cool down.

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.

Top floor, overlooking Love Creek at Rehoboth Bay
Our unit is on the waterfront of Love Creek, the boat docks, and the access path to the Rehoboth Bay. Offsite, but accessible via walking path you will find a fishing pier. The unit has one assigned parking spot, however, additional parking spots are easily accessible to the building. The condo is on the top floor (3rd) in gated community with elevators, community pool and charcoal BBQ grills. Bring Kayaks or paddle boards - or have them delivered on-site by our recommended vendor.

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.

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

Baby friendly, walk to pool and bakery town home

Relaxing Getaway

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

Lewes Carriage House /Salt Water Pool/Spa Hot Tub

Beach Getaway, minutes away from everything!!

New Modern Beach Home, Close to Beaches

Ruby's Retreat at the Beach

Cape Shores Luxury - NEW Pool, Beach, Pier, Park!
Condo rentals with a pool

Mimi’s Place @ The Villages of 5 Points in Lewes

2BR Coastal Escape with Pool Near Rehoboth Beach

Right on Silver Lake walk to the beach and town!

OceanfrontJewel|DirectOceanView•NewlyRenovatedPool

Sunrise Studio - Ocean Front, on Boardwalk, Pool!

Lovely Two bedroom condo with community pool.

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

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

Beautiful Updated Condo Waterfront, Pool, Sunsets

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

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

Water Views: Balcony, Pool & Easy Parking

Pondside Paradise | Dog-Friendly, Pond Views, Pool

Waterfront! Downtown historic Lewes walk to beach

Gorgeous 5BR, 4.5BA, in town, pool, hot tub, beach

Village of 5 Points Lewes Beach Condo 2BR/2B
Destinations to explore
- New York Vacation rentals
- Philadelphia Vacation rentals
- Washington Vacation rentals
- Ocean City Vacation rentals
- Pittsburgh Vacation rentals
- Virginia Beach Vacation rentals
- Raleigh Vacation rentals
- Jersey City Vacation rentals
- Newark Vacation rentals
- Baltimore Vacation rentals
- Richmond Vacation rentals
- Atlantic City Vacation rentals
- Rentals with a fire pit Lewes
- Condo rentals Lewes
- Family-friendly rentals Lewes
- Rentals with a fireplace Lewes
- Cottage rentals Lewes
- Rentals with beach access Lewes
- Beach condo rentals Lewes
- Beachfront rentals Lewes
- House rentals Lewes
- Rentals with a patio Lewes
- Apartment rentals Lewes
- Pet-friendly rentals Lewes
- Beach house rentals Lewes
- Rentals with pools Sussex County
- Rentals with pools Delaware
- Rentals with pools United States
- Cape May Beach NJ
- Assateague Island National Seashore
- Ocean City Beach
- Wildwood Crest Beach New Jersey
- Ocean City Boardwalk
- Broadkill Beach
- Rehoboth Beach
- Ocean City Boardwalk
- Assateague State Park
- Cape Henlopen State Park
- Bethany Beach Boardwalk
- Willow Creek Winery & Farm
- Northside Park
- Dover Motor Speedway
- Ocean City Boardwalk
- Delaware Seashore State Park
- Jolly Roger Amusement Park
- Stone Harbor Beach
- Fenwick Island State Park Beach
- Wildwood Boardwalk
- Roland E Powell Convention Center
- Longport Dog Beach
- Wildwoods Convention Center
- Mariner's Arcade





