Holiday rentals with a pool in Lewes

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Top-rated rentals with a pool in Lewes

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Top Guest favourite
A dining area is showcased with a grey table set for six, surrounded by vibrant yellow chairs and a metal wire-frame chair. A modern light fixture hangs above, and a decorative wreath adorns the wall, complemented by abstract artwork on either side.
Condo in Rehoboth Beach
4.99 out of 5 average rating, 200 reviews

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.

Top Guest favourite
A bright living area features a comfortable sofa and a blue accent chair, complemented by a wooden coffee table. A large flat-screen TV is positioned on a white media unit. Natural light enters through sliding glass doors, leading to a small balcony with outdoor seating.
Condo in Lewes
4.99 out of 5 average rating, 155 reviews

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.

Top Guest favourite
A bright living area features a light-colored sofa and armchair with coastal patterns. A wooden coffee table sits on a textured rug, while a mounted television is visible on the wall opposite. The open layout allows for glimpses of a dining area with a table set for six.
Condo in Lewes
4.98 out of 5 average rating, 113 reviews

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.

Superhost
Condo in Lewes
4.87 out of 5 average rating, 100 reviews

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!

Guest favourite
A cozy sleeping area features a spacious bed with a quilted grey coverlet. Two decorative yellow pillows are positioned at the head of the bed. A small bedside table holds a lamp and books, while a colorful area rug adds warmth to the space.
Tiny home in Lewes
4.95 out of 5 average rating, 188 reviews

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 šŸ” chickens.

Guest favourite
The living area features soft blue furnishings and a light wood coffee table. Floor-to-ceiling windows offer direct views of the ocean, while two lamps provide warm lighting. A coastal-themed artwork adorns the wall, enhancing the serene atmosphere of the space.
Condo in Ocean City
4.95 out of 5 average rating, 309 reviews

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

Guest favourite
A spacious kitchen is highlighted by an 11 ft island with four round bar stools. Pendant lighting above creates a warm ambiance. Modern appliances and a stylish backsplash are featured, enhancing the functionality of the space. Neutral tones and open shelving provide a clean, inviting atmosphere.
Home in Rehoboth Beach
4.94 out of 5 average rating, 154 reviews

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.

Top Guest favourite
A comfortable living area features a dark sofa adorned with patterned throw pillows. A coffee table sits atop a patterned area rug, while natural light enters through multiple windows adorned with wooden blinds. A TV is positioned on an entertainment unit across from the seating area.
Condo in Lewes
4.94 out of 5 average rating, 143 reviews

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.

Top Guest favourite
A wrap-around deck overlooks a tranquil waterfront view, featuring lush greenery and calm waters. A seating arrangement includes four chairs with cushioned backs, positioned for relaxation. The scene is punctuated by nearby trees, contributing to a serene atmosphere.
Home in Lewes
4.99 out of 5 average rating, 214 reviews

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.

Top Guest favourite
A balcony view captures a wide expanse of lush green fields and dense trees, framed by a soft gray sky. The natural landscape offers a serene backdrop, highlighting a peaceful atmosphere. A railing can be seen in the foreground, providing a sense of depth.
Condo in Lewes
4.99 out of 5 average rating, 169 reviews

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)

Top Guest favourite
A single-story home is set amidst a grassy lawn, featuring a light exterior and a welcoming front porch. A large tree provides shade in the foreground, while a paved driveway leads to the garage. The surrounding area is landscaped with a mix of greenery.
Guest suite in Rehoboth Beach
4.98 out of 5 average rating, 158 reviews

*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.

Top Guest favourite
An open living area showcases a modern kitchen with dark cabinets and a marble countertop. A wooden dining table is set for six, and large windows allow natural light to fill the space. The seating area features a comfortable sofa and a small side table.
Apartment in Rehoboth Beach
4.92 out of 5 average rating, 128 reviews

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

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 $149Ā NZD 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 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, Wi-Fi 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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