
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.

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.

Sunrise Studio - Ocean Front, on Boardwalk, Pool!
Our quiet ocean front studio has all the comforts of home with amazing views, a balcony hovering over a serene stretch of the Boardwalk, and is just steps away from restaurants, shops, arcades, rides and all of the best boardwalk foods! Walkable to everywhere in town! If you want to venture out further, a bike rental shop is just a few doors away! Enjoy a bike ride through town or to Dewey Beach. If you are looking for a scenic ride, enjoy the bike trails to Cape Henlopen State Park and Lewes.

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 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.

Beautiful condo in Villages of Five Points, Lewes
Welcome to our beautiful condo in the desirable family friendly community of The Villages of Five Points ! Our 2 bedroom, 2 bath condo is the perfect place for your beach vacation or any occasion. The condo has been newly painted and new flooring has been installed as well. The condo is right off east of route 1 and about 3 miles from Lewes beach. Biking trails are close by and Cape Henlopen State Park is a short ride of about 3 miles.

Beautifully renovated 2BR 2BA Condo w/ pool!
Renovated and beautifully decorated 3rd floor condo (no elevator) with a comfortable, beachy feel! Across from the Tanger Outlets, you are close to tax free shopping, restaurants, bars and numerous activities for the kiddos! Rental includes full kitchen with stainless steel appliances, washer/dryer, updated bathrooms, all linens and access to the pool. Less than 1/2 hour from Sports at the Beach and DE Turf Sports Complex.

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.

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. *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)

*Radcliffe Retreat* Studio, Pool & RB Parking Pass
Spacious pet friendly guest suite with Rehoboth parking permit provided. The suite is near outlets, beaches, dining, & Rehoboth boardwalk. Large community pool next door. Charming neighborhood that is a great base to explore all the nearby attractions! Rehoboth boardwalk & beach- 4 mi Outlets- 1 mi Lewes downtown- 4 mi Cape Henlopen State Park- 6 mi 1 dog is allowed with permission.

Sand & Surf Condo with Pool
Completely remodeled luxury beach condo. No detail has been left untouched. Conveniently located to all the outlets and restaurants on Rt 1 and just 2 stop lights from Rehoboth Ave businesses, nightlife and beach. We are Super host in the area with 5 other properties. This is our newest one to hit the vacation rental market! Look forward to hosting you!
Popular amenities for Lewes rentals with a pool
House rentals with a pool

Cozy Bethany Beach Retreat

Baby friendly, walk to pool and bakery town home

Village at Five Points Condo Getaway

Gorgeous Bayfront, Pool, Hot Tub, Linens Included

Mystical Cape May's Modern Farmhouse: The Widmore

Coastal Retreat | Lakefront | Pool | Hidden Gem

The Jungalow - Dog Friendly, Fenced in & Pool

Thalassofili: Curated by the Sea
Apartment rentals with a pool

Luxury water-view condo with high-end finishes

Spacious Direct Oceanfront 1BR Condo w/Balconies

Salt Air Retreat - Rehoboth Beach

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

Comfy and Convenient 2 bedroom/2 bath condo

2 Bedroom Condo Rehoboth Beach w/Brand New Bed
Other holiday rentals with a pool

Pool, dog friendly, fenced yard in Lewes

3 BR Coastal Retreat

Coastal retreat •beaches, trails & historic Lewes•

Coastal Modern Condo • Cozy Winter Getaways

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

Beach getaway: perfect for off season enjoyment

Modern-Coastal Lewes Beach 1st Floor Condo

Waterfront! Downtown historic Lewes walk to beach
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 £67 per night before taxes and fees

Verified guest reviews
Over 610 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!
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