Vacation rentals with a pool in Lewes

A cozy living area features a stone fireplace as a focal point. Comfortable leather seating surrounds a coffee table, with a TV visible nearby. Natural light is allowed through multiple windows, and a dining area is positioned in the foreground with elegant lighting.

4.91 out of 5 average rating, 131 reviews

Luxury Carriage House in Rehoboth Beach

Luxury carriage house with 4 bedrooms / 4 baths. Private fenced in backyard with wrought-iron fence and paver patio with iron dining furniture. Great kitchen with Dacor double ovens, built-in gas range in two-tier island, subzero wine refrigerator. First floor is open floor plan with kitchen, living area, TV/sitting area with two sliders leading to furnished screen porch. Floors are mainly stone & hardwood, except two bedrooms. Master - jacuzzi & dual showerhead stone shower. Enjoy firepit

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.

4.99 out of 5 average rating, 152 reviews

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.

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.

4.96 out of 5 average rating, 131 reviews

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.

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.

4.98 out of 5 average rating, 197 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.

4.97 out of 5 average rating, 198 reviews

A serene waterfront scene is captured at sunset, with vibrant colors reflected in the calm water. A charming building with large windows is illuminated, surrounded by lush trees, and boats are docked along the waterfront, creating a peaceful atmosphere.

Condo in Ocean Pines

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

The living room features two full couches facing a coffee table, with a Smart TV mounted on a console nearby. A ceiling fan rotates above, while natural light filters through the sheer curtains. A dark accent wall contrasts with light walls, enhancing the space's depth.

4.97 out of 5 average rating, 273 reviews

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.

4.95 out of 5 average rating, 187 reviews

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.

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.

4.98 out of 5 average rating, 110 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 and kids play area. The Georgetown Lewes Biking/Walking Trail, that connects to the town of Lewes, is literally steps from our front door.

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.

4.97 out of 5 average rating, 115 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.

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.

4.95 out of 5 average rating, 138 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.

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.

5 out of 5 average rating, 148 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)

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.

4.99 out of 5 average rating, 212 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* from Memorial Day to Labor Day.

Popular amenities for Lewes rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.93 out of 5 average rating, 135 reviews

A charming two-story home is framed by vibrant flower beds and lush greenery. The front porch features white railings and a welcoming entrance, while blooming flowers add color to the outdoor space. Sunlight brightens the façade, emphasizing the inviting atmosphere of the property.

Home in Villas

Wilde Rose By The Bay - Salt water Inground pool

A round wooden dining table surrounded by eight woven chairs is positioned in a well-lit dining area. Soft natural light enters through large windows adorned with white blinds. A coastal-themed wall art piece enhances the serene ambiance, and a smaller table can be seen in the background.

5 out of 5 average rating, 214 reviews

Beautiful Beach House in Rehoboth

4.96 out of 5 average rating, 120 reviews

An outdoor space features a heated swimming pool surrounded by a concrete patio. Comfortable seating options include several couches and chairs. A large umbrella provides shade, while a hot tub is positioned nearby. String lights and greenery enhance the backyard ambiance.

Home in Lower Township

Relaxing Getaway

5 out of 5 average rating, 10 reviews

Tranquility Corner at Rehoboth Beach

A bright living room is featured with a nautical theme. A large sectional sofa faces a decorative fireplace beneath a sailboat model. Light streams in through multiple windows adorned with shutters, while a white cabinet and an additional sailboat display complete the space.

5 out of 5 average rating, 16 reviews

Coastal Beauty-Bike to Beach

5 out of 5 average rating, 11 reviews

5 min to beach Spacious coastal home, game room

4.99 out of 5 average rating, 102 reviews

A spacious living room features a comfortable dark sofa, two brown chairs, and a cozy fireplace. Natural light enters through large windows adorned with light blue drapes. A ceiling fan and recessed lighting contribute to a bright and airy atmosphere, complemented by modern decor.

Home in Ocean Pines

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines

4.99 out of 5 average rating, 229 reviews

A spacious outdoor area features a private saltwater pool surrounded by a paved patio. Several lounge chairs and umbrellas offer shaded seating around a dining table. Neatly maintained gardens enhance the atmosphere, providing a serene backdrop for relaxation.

Home in North Cape May

The Villa By the Bay-Private Heated Pool & Hot Tub

Condo rentals with a pool

A patio space is displayed, featuring a round table surrounded by four cushioned chairs. Lush greenery frames the scene, offering a view of Silver Lake in the background, where trees stand along the water's edge, enhancing the serene atmosphere.

4.79 out of 5 average rating, 307 reviews

Right on Silver Lake walk to beach!

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.

4.97 out of 5 average rating, 219 reviews

Villa Del Sol, Beautiful stay near beaches/outlets

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.

4.82 out of 5 average rating, 106 reviews

Where the Locals Live!!

A spacious bedroom features a large bed with a patterned comforter and multiple decorative pillows. Natural light floods the room through a glass door leading to a balcony. A bedside table with a lamp and a potted plant add to the calming atmosphere.

4.94 out of 5 average rating, 114 reviews

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

A welcoming living room features a modern design with a circular mirror and stylish light fixture. Comfortable seating includes a round chair and plush sofas configured around a wooden coffee table. Natural light enters through large windows, illuminating the space and providing a view of the outside.

4.97 out of 5 average rating, 129 reviews

Modern 2BR/2BA – Beach Pass + Bikes, 5 Min Drive

A living area is presented with a gray sofa and wooden coffee table, featuring decorative items. A flat-screen television rests on a wooden console, while a clock and window with sheer curtains provide a bright atmosphere. A doorway leads to an adjacent bedroom.

4.97 out of 5 average rating, 104 reviews

Beach Escape Condo w/ Pool - Lewes Beach 3.5 Miles

4.84 out of 5 average rating, 219 reviews

Condo in Ocean City

Beachfront with a View and Amenities Galore

4.96 out of 5 average rating, 282 reviews

A cozy living area displays a light blue color scheme. A white sofa is positioned beside a coffee table on a patterned rug, while a dining table is set nearby. Floor-to-ceiling sliding doors open to a balcony, offering views of the ocean.

Condo in Ocean City

Caramar Couples Retreat

Other vacation rentals with a pool

An open kitchen features warm wooden cabinetry, stainless steel appliances, and a spacious granite countertop. Natural light fills the area through windows, illuminating a cozy living space in the background, which includes a comfortable seating arrangement and decorative light fixtures.

5 out of 5 average rating, 11 reviews

Coastal Hideaway at Five Points

4.91 out of 5 average rating, 35 reviews

The exterior of a light blue house is surrounded by tall trees, providing ample shade. A welcoming front porch features a railing and four chairs, inviting relaxation. The roof is gently sloped, and the home showcases a chimney at the peak.

Cottage in Lewes

Relaxing Beach Cottage

5 out of 5 average rating, 18 reviews

A spacious living area features a cozy arrangement of light-toned sofas and an accent chair, facing a modern fireplace below a large television. A coffee table lies centrally, with decorative coastal accents. Light blue walls and natural wood floors complement the open design that flows into the dining area.

Home in Millsboro

Peninsula Golf & Country Club 2Bd/2bth Windswept

Apartment in Rehoboth Beach

Two white Adirondack chairs are positioned on a patio overlooking a serene lake. Lush green grass surrounds the area, while trees offer shade. The calm water reflects the greenery, creating a peaceful outdoor setting.

4.9 out of 5 average rating, 62 reviews

Lakefront condo blocks from the beach

An expansive view of the sandy beach stretches towards the horizon, revealing sunbathers under colorful umbrellas. The shoreline is framed by a wooden boardwalk. The balcony offers a glimpse of the tranquil ocean, with waves lapping gently against the shore under a clear blue sky.

4.96 out of 5 average rating, 57 reviews

Oceanfront Sanctuary - On Boardwalk! Pool!

4.9 out of 5 average rating, 49 reviews

The exterior of the tiny house features a welcoming front porch with wooden steps. A small, round table with two chairs is positioned under a gabled roof, accompanied by playful garden decor. The house is surrounded by lush greenery, creating a peaceful woodland atmosphere.

Tiny home in Lincoln

The Little house W/ Pool & Spa

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.

4.99 out of 5 average rating, 67 reviews

Water Views * Balcony * Pool * Fast Wi-Fi

A sunlit sunroom features a dark futon and light armchair, surrounded by large windows with treatments. A patterned area rug lies beneath a coffee table. A decorative plant adds a touch of greenery, while a friendly dog rests on the rug, creating a relaxed atmosphere.