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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 R 3,719 ZAR 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.

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Top guest favorite
A spacious dining area features a large rectangular table surrounded by eight black chairs, set against a warm yellow wall. In the background, a modern kitchen with white cabinetry and appliances is partially visible, providing a functional and inviting atmosphere.
Condo in Lewes

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.

4.96 out of 5 average rating, 142 reviews
Top guest favorite
A light-filled living room features a cozy seating arrangement with two patterned chairs and a soft sofa. A coffee table with a checkerboard design sits atop a textured area rug, with a flat-screen TV positioned nearby. Soft blue walls complement the space.
Townhouse in Lewes

Spacious, Conveniently Located Townhouse

Beautifully updated townhouse located in quiet community of Eagle Point offers 4 bedrooms, 2.5 bathrooms and 2,500 SF. The 1st floor offers open concept layout with living and dining rooms, large set up kitchen with breakfast area, 1/2 bath, laundry room, and master suite with king bed. The 2nd floor offers 3 bedrooms (2 queen beds and 1 full size bunk bed) and full bath. In addition, the 2nd floor presents another living space with TV and pullout sofa. Plenty of room for cozy family gatherings!

4.98 out of 5 average rating, 103 reviews
Top guest favorite
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

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 & 12 restaurants, 4 you can walk to, nail & a hair salon, grocery store and a CVS (3 blocks). We need pictures of everyone’s license per our condo association & the person booking must be at least 25 years of age. There are 4 beach chairs and a large umbrella & 2 chair umbrellas.

4.99 out of 5 average rating, 177 reviews
Top guest favorite
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

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.

4.98 out of 5 average rating, 220 reviews
Top guest favorite
Two spacious beds with white bedding are positioned against a clean, white wall. A lamp and a small plant rest on a bedside table situated between the beds. Framed botanical artwork is displayed above each bed, adding a touch of nature to the serene space.
Condo in Lewes

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.

4.97 out of 5 average rating, 241 reviews
Top guest favorite
An open-concept living area features a light-colored sectional sofa adorned with textured pillows. A round coffee table sits on a soft area rug. The dining area, equipped with a sizable wooden table and stylish woven chairs, is visible in the background alongside modern kitchen appliances.
Apartment in Rehoboth Beach

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.

4.99 out of 5 average rating, 174 reviews
Top guest favorite
A private hot tub is set on a paved patio beneath a shaded gazebo. Wooden decking surrounds the area, enhancing the serene outdoor setting. Lush greenery provides privacy, while outdoor lighting can be seen strung above, creating a welcoming space for relaxation.
Home in Rehoboth Beach

Perfect Rehoboth Beach Getaway with Hot Tub

Discover the epitome of coastal comfort in newly remodeled home. Dive into luxury with a private hot tub, where the bubbling warmth provides the perfect escape. Unwind in the chic interiors, adorned with modern furnishings. Stay connected with complimentary Wi-Fi as you plan your outings to the nearby beaches, bustling boardwalk, and local attractions. Steps away from tax free outlet shopping. With convenience at every turn, this home ensures a perfect blend of tranquility and accessibility.

4.94 out of 5 average rating, 106 reviews
Top guest favorite
A spacious bedroom is presented, featuring a four-poster bed with a light-colored bedding set. Flanking the bed are two bedside tables, each with a lamp. Natural light filters through the window, illuminating the soft, neutral tones of the room.
Condo in Rehoboth Beach

Coastal Modern Condo • Balcony, 2 Baths, East Rt 1

☀️ Your Rehoboth Beach Escape Why guests love staying here: • Community pool 🌴 • 2 full baths • Private screened balcony 🌿 • East of Route 1 • Strong central AC ❄️ • Split-bedroom layout for added privacy • Beach chairs & towels included 🏖️ • Fast WiFi + smart TVs • Plenty of FREE parking • In-unit washer & dryer • Minutes to beaches, boardwalk, restaurants & shopping • Quiet community close to everything Perfect for couples, families, girls’ weekends, and relaxing coastal getaways.

4.99 out of 5 average rating, 118 reviews
Top guest favorite
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

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.

4.98 out of 5 average rating, 128 reviews
Top guest favorite
Condo in Lewes

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.

4.95 out of 5 average rating, 322 reviews
Top guest favorite
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

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.

4.94 out of 5 average rating, 235 reviews
Guest favorite
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

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.

4.94 out of 5 average rating, 184 reviews

Popular amenities for Lewes rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favorite
Home in Lewes

Bay Pearl House! (grill, screened porch, crabbing)

4.91 out of 5 average rating, 120 reviews
Guest favorite
The living room features a high ceiling and light-colored walls, creating an open atmosphere. A large flat-screen TV is mounted on the wall opposite a comfortable dark leather couch. Natural light fills the space through large windows, alongside a stylish coffee table and accent chair.
Home in Lewes

Baby friendly, walk to pool and bakery town home

4.92 out of 5 average rating, 100 reviews
Top guest favorite
An open-concept kitchen and living area features a large wooden island with a sink, surrounded by modern cabinetry. Natural light floods the space through wide windows, showcasing cozy seating and a vibrant dining area with a round table. Bookshelves line a portion of the wall.
Home in Rehoboth Beach

Modern Beach House w/ Private Pool

4.97 out of 5 average rating, 103 reviews
Top guest favorite
A modern coastal-style home is pictured, featuring a spacious two-story structure with a covered front porch. Lush green landscaping surrounds the property, and a light-colored facade complements the clear blue sky. Driveway access is visible beneath the elevated home.
Home in Lewes

Cape Shores Luxury - NEW Pool, Beach, Pier, Park!

5.0 out of 5 average rating, 63 reviews
Top guest favorite
Home in Lewes

Ruby's Retreat at the Beach

4.9 out of 5 average rating, 29 reviews
Top guest favorite
An open-concept living space is presented, featuring a dining area with a wooden table and chairs. Comfortable seating arrangements are located in the foreground, complemented by natural light entering through nearby windows. Wood accents and nautical decor add to the atmosphere of the room.
Home in Rehoboth Beach

Beach Getaway, minutes away from everything!!

4.98 out of 5 average rating, 42 reviews
Top guest favorite
The outdoor space features a rectangular saltwater pool, surrounded by a smooth stone patio. Reclining loungers and teak umbrellas provide shaded seating. Lush greenery, including trees and shrubs, creates a serene backdrop, enhancing the overall tranquility of the setting.
Home in Lewes

Lewes Carriage House: A Sanctuary for Mind & Body

5.0 out of 5 average rating, 68 reviews
Guest favorite
A serene outdoor area features a sparkling pool accompanied by a hot tub. Surrounding the space are several lounge chairs and a shaded patio with a large umbrella. Colorful flowers in planters add to the lush greenery and natural surroundings.
Home in Rehoboth Beach

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

4.96 out of 5 average rating, 55 reviews

Condo rentals with a pool

Guest favorite
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.
Condo in Lewes

1st Floor Beach-town Condo in Lewes

4.95 out of 5 average rating, 131 reviews
Top guest favorite
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

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

4.99 out of 5 average rating, 219 reviews
Top guest favorite
Condo in Rehoboth Beach

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool

4.98 out of 5 average rating, 307 reviews
Top guest favorite
A spacious living area is presented, featuring a comfortable green sofa and a matching armchair. A large television is positioned on a low cabinet. Natural light streams through sliding glass doors, leading to a screened-in porch, enhancing the atmosphere with a view of greenery.
Condo in Rehoboth Beach

2BR Coastal Escape with Pool Near Rehoboth Beach

4.95 out of 5 average rating, 119 reviews
Guest favorite
A modern kitchen and dining area are showcased, featuring a granite countertop with three black stools, and a dining table with dark chairs. Striped wallpaper adds a bold touch, complemented by a wall art piece and decorative accents, creating a cohesive aesthetic.
Condo in Rehoboth Beach

Modern Beach Glam in the heart of outlets.

4.89 out of 5 average rating, 292 reviews
Top guest favorite
A cozy living room is depicted, featuring a light-colored sofa adorned with decorative cushions. A matching armchair is positioned nearby. Unique starfish-themed wall decor enhances the space, while a large clock and soft lighting add to the inviting atmosphere. A balcony door leads to outdoor seating.
Condo in Lewes

Top floor, overlooking Love Creek at Rehoboth Bay

4.97 out of 5 average rating, 102 reviews
Top guest favorite
A spacious outdoor pool area features a large swimming pool with a vibrant blue interior and a jacuzzi nearby. Lounge chairs are arranged around the pool for relaxation. Fountains are visible at one end, adding a calming water feature to the setting.
Condo in Rehoboth Beach

Bright condo-On bike trail & 1 mile to boardwalk

4.96 out of 5 average rating, 112 reviews
Guest favorite
A private balcony is shown, featuring two black wicker chairs and a small table positioned on a tiled floor. The view overlooks a serene body of water, with greenery and landscaped buildings visible in the background.
Condo in Rehoboth Beach

Lovely Two bedroom condo with community pool.

4.86 out of 5 average rating, 109 reviews

Other vacation rentals with a pool

Guest favorite
A modern open-concept living area is presented, featuring comfortable seating arrangements and large windows that provide ample natural light. The space includes a dining area with barstools and a kitchen counter. Views of the waterfront are visible through the sliding glass doors.
Condo in Lewes

Beautiful Updated Condo Waterfront, Pool, Sunsets

4.91 out of 5 average rating, 98 reviews
Guest favorite
A scenic view captures the tranquil waterway at sunset, with boats docked along a waterfront marina. The silhouette of downtown Lewes is visible in the distance, framed by lush greenery and a clear sky, creating a serene atmosphere.
Condo in Lewes

Waterfront! Downtown historic Lewes walk to beach

4.71 out of 5 average rating, 253 reviews
Top guest favorite
Apartment in Lewes

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

4.9 out of 5 average rating, 86 reviews
Top guest favorite
Guesthouse in Lewes

Lewes Home | Pool, Dogs Welcome, Fenced Yard

5.0 out of 5 average rating, 36 reviews
Top guest favorite
A welcoming living area features a leather sectional sofa with colorful accent pillows, set before a wooden coffee table. A flat-screen television is mounted on the wall, while a fireplace adds warmth. Sliding glass doors lead to a dining area, allowing natural light to flow in.
Townhouse in Lewes

Coastal retreat •beaches, trails & historic Lewes•

4.99 out of 5 average rating, 93 reviews
Top guest favorite
A bright living area features a spacious sofa paired with accent chairs. Natural light floods through large windows, enhancing the serene atmosphere. A wooden coffee table rests on a textured rug, while a wall-mounted TV adds modern convenience.
Condo in Lewes

Water Views: Balcony, Pool & Easy Parking

4.99 out of 5 average rating, 92 reviews
Guest favorite
A light-filled living area features a soft blue sofa and a wooden coffee table centered on a plush rug. A ceiling fan provides airflow, while large windows allow natural light. A small desk with a chair is positioned near the transition to the dining area.
Apartment in Lewes

Beach getaway: perfect for off season enjoyment

4.86 out of 5 average rating, 66 reviews
Top guest favorite
Apartment in Lewes

Slipper Shell Sanctuary

5.0 out of 5 average rating, 23 reviews

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