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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Guest favourite
A cozy bedroom features a spacious bed with a patterned gray comforter and a pink accent pillow. Two framed artworks are mounted on the wall above the bed. Light emanates from bedside lamps, and a window with blinds offers views of a twilight sky.
Apartment in Lewes
4.82 out of 5 average rating, 106 reviews

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!

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.
Apartment 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.
Apartment in Lewes
4.99 out of 5 average rating, 157 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.

Guest favourite
A welcoming entrance to Angola by the Bay is captured at sunset, featuring a large, well-lit sign with the community's name. Soft hues of orange and purple fill the sky, and the surroundings include neatly landscaped greenery and a paved road leading into the community.
Cottage in Lewes
4.85 out of 5 average rating, 121 reviews

'Cottage by the bay', sleeps 8 near Rehoboth beach

This bayside getaway is a beautiful 'A' frame style cottage and is located along the Rehoboth bay with direct access to the water. The cottage is within the gated community of Angola by the Bay. About a block away from the front door is one of the three private crabbing/fishing docks, kayak launch and marina! Enjoy walking or biking along the water and trails throughout the community. The large pool is always a favorite too! Baywood greens golf is nearby also! Enjoy the beautiful sunsets!

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.
Apartment in Lewes
4.98 out of 5 average rating, 114 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.

Guest favourite
A modern kitchen area features wooden cabinets, stainless steel appliances, and a stone accent wall. A circular glass dining table is surrounded by wicker chairs, providing a cozy space for meals. The overall layout is bright and inviting, with natural light highlighting the contemporary decor.
Apartment in Rehoboth Beach
4.94 out of 5 average rating, 122 reviews

Cozy Condo on Silver Lake - Walk to the beach!

Located in the middle of a nature preserve on Silver Lake, and walking distance to the beach this end unit condo boasts stunning views and cozy modern decor. Enjoy the pool just steps from your lakeside patio or take a short walk to the beach or town crossing the footbridge (known by locals as turtle bridge.) Lovely boutiques and fine dining in town plus numerous family friendly restaurants. 5 minute drive to Tanger Outlets. Rehoboth Beach parking pass provided with each rental.

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 🐔 chickens.

Top guest favourite
Apartment in Rehoboth Beach
4.98 out of 5 average rating, 283 reviews

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool

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.

Guest favourite
A spacious living area features a comfortable sectional sofa with decorative pillows, complemented by a large area rug. A television is positioned on a stylish media console, while large glass doors provide access to a private patio, framed by blue curtains. A ceiling fan is present above.
Apartment in Lewes
4.97 out of 5 average rating, 119 reviews

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.

Top guest favourite
A small outdoor patio area features two colorful, striped chairs and one neutral-colored chair. The concrete floor holds potted flowers and a decorative wall planter. Sliding glass doors provide access to the interior, while a welcoming wreath adorns the door nearby.
Apartment in Rehoboth Beach
4.96 out of 5 average rating, 195 reviews

Buoyed Spirits 2 BR 2B 1st floor condo

2 bedroom, 2 bathroom ground floor apartment in a nice neighborhood, off Rt 1. 1.5 miles from the beach! The community has 3 swimming pools and tennis courts. Master has a king-sized bed, the second room has 2 twins. Sofa in living room is a pull out. Two bikes with helmets and locks also come with the rental, as well as 2 tennis rackets. Towels (including beach towels) and linens provided, BUT YOU WILL NEED TO LAUNDER THE SHEETS AND TOWELS BEFORE YOU LEAVE.

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.
Apartment in Lewes
4.94 out of 5 average rating, 144 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, 216 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.

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 ₹8,322 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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