
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.

Mimi’s Place @ The Villages of 5 Points in Lewes
You will 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 theperson booking must be at least 25 years of age. We a4 beach chairs & umbrellas are in closet on outside porch.

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.

Pines Getaway - Berlin Tree Light & Ice Ice 11/28
Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool
Perfect location to enjoy the holiday season in Southern DE for upcoming events, ie. Rehoboth Beach Parade, Rehoboth and Dewey Beach Tree Lighting, NYE Celebrations and 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.

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.

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 and kids play area. The Georgetown Lewes Biking/Walking Trail, that connects to the town of Lewes, is literally steps from our front door.

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.

WraparoundBalcony-2 Bed-Sleeps 8-Pool-Laundry-WiFi
Welcome to our stunning oceanfront retreat! This luxurious property offers the perfect combination of comfort, style, and breathtaking views. With a spacious J-shaped wraparound balcony, you can indulge in panoramic vistas of the sparkling ocean waves from every angle. Ideal for groups of up to 8 guests, this two-bedroom, two-bathroom getaway provides ample space for everyone to unwind. Book today for the vacation you'll never forget!

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)

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* from Memorial Day to Labor Day.
Popular amenities for Lewes rentals with a pool
House rentals with a pool

Coastal Hideaway at Five Points

Village at Five Points Condo Getaway

Family & Pet-friendly Beach House with Pool

Hot Tub Holiday Escape! Fireplace + backyrd oasis!

Beautiful Beach House in Rehoboth

Thalassofili: Curated by the Sea

Relaxing Getaway

Dog Friendly Fenced 3BR King Bed
Apartment rentals with a pool

Right on Silver Lake walk to beach!

Family Friendly Top Floor Condo Near Boardwalk

Luxury water-view condo with high-end finishes

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Where the Locals Live!!

Classy Beach Getaway

Cozy condo, 3 pools, and 4 beds in Rehoboth Beach

Clean and Comfy, Close to Schellville and Shopping
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Dog friendly, fenced yard, pool, Lewes

Lakefront condo blocks from the beach

Studio Bedroom in the Woods

The Little house W/ Pool & Spa

Water Views * Balcony * Pool * Fast Wi-Fi

Spacious, Conveniently Located Townhouse

Beach getaway: perfect for off season enjoyment

Modern-Coastal Lewes Beach 1st Floor Condo
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 € 103 per night before taxes and fees

Verified guest reviews
Over 590 verified reviews to help you choose

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

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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