Holiday rentals with a pool in Ocean View

4.96 out of 5 average rating, 28 reviews

An aerial view of a well-appointed beach club showcases a spacious outdoor pool surrounded by lounge chairs and umbrellas. A tennis and pickleball court is visible, along with a serene pond nearby. The surrounding landscape features neatly arranged homes and lush greenery.

Townhouse in Ocean View

OceanViewBeachClub-minutes from Bethany Beach/Golf

Enjoy this spacious, 3br 2ba 1,300 sq ft NEW condo with 12ft ceilings 1.5 miles to Bethany Beach, a 5 min drive or a 10 min bike ride. Minutes from Bear Trap Dunes Golf Course and boardwalk This condo is part of the highly sought after Ocean View Beach Club, the first new construction beach club in Ocean View as you drive from Bethany beach. OVBC offers an amazing large outdoor pool- great for kids! Plus sauna, steam room, fitness center, billiards, basketball/pickleball court and more

4.97 out of 5 average rating, 192 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

Spacious Rental - Winterfest of Lights 11 mi.

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 coastal home features a welcoming façade with a light pink exterior and white railings. Lush green grass surrounds the property, while vibrant pink flowers add a pop of color in the front garden. A spacious front porch invites relaxation with multiple entry points.

4.87 out of 5 average rating, 111 reviews

Coastal Charm-Bethany Beach/Golf Home in Bear Trap

Welcome to our coastal home in the charming community of Bear Trap Dunes! Bright, cheery home near beach, golf & activities! -On the golf course -Short drive to Bethany Beach -Great front porch with rockers -Screened back porch for dining & lounging -4 bedrooms, sleeps 7 -Community pool, tennis/pickleball, beach shuttle, gym, basketball, playground are available with purchase of community amenity pass The perfect place to chill & access all the beach area fun! Weekly Rentals are Sun-Sun.

Superhost

The exterior of a charming end-unit townhome is shown, featuring a covered front porch with seating. Trees frame the home, and a well-maintained lawn extends from the front to the side. The inviting architecture showcases a classic white facade with a dark roof.

Townhouse in Ocean View

4.9 out of 5 average rating, 103 reviews

Sleeps 14 - Enjoy Golf, Shuttle to beach and pools

The best mix of beach, golf, fun and relaxation. Just 3 miles away from Bethany beach. Resort shuttle (in season) is available to take you just steps from the beach. For the golfers, a beautiful 27 holes. Steps from the front door, the Pavilion includes gyms, an indoor olympic pool, hot tub and sauna. An outdoor pool, clay tennis and pickleball courts are all located just steps from the home. Pet friendly with many families and dogs always walking! Wonderful restaurant in resort.

A modern kitchen features a spacious island with four black bar stools positioned around it. White cabinetry is paired with stainless steel appliances, including a refrigerator and microwave. Natural light is provided by recessed lighting and a large window, creating a bright, inviting cooking space.

5 out of 5 average rating, 12 reviews

Ocean View Paradise w/Hot Tub & Free Massages!

Our special place is close to everything for your DE beach visit! Make memories at our unique, updated Sharp Ocean View Paradise. Free access to a zero gravity, full body massage chair as you relax. Short discount to Bethany Beach and pools, gym, sports court and beach club community access. Enjoy a private hot tub, full range of games & arcade systems for your family sleeping up to 14. Enjoy grilling, large outdoor dining & access to full range of kayaks for canal access near our backyard!

4.91 out of 5 average rating, 145 reviews

An open living space features high cathedral ceilings with two large windows allowing natural light. A wooden coffee table sits in front of a full couch and loveseat. A fireplace is centered on the wall, with a TV positioned nearby. Elegant rugs cover the hardwood floor.

Home in Bethany Beach

Bright Open Floor Plan Family Beach Retreat

Everything you need to enjoy your time in Bethany! Our family home is a bright beautiful retreat to relax and enjoy yourself. Located on the 1st tee of the Salt Pond Golf Course. Community Pool & Gym just a two minute walk! Basketball, Tennis, Shuffleboard, Sand volleyball court, and Children's Playground access included. Grocery Store & Restaurants at entrance to the neighborhood (2 min drive or a 10 min walk!) Just minutes drive to multiple beaches, shopping, restaurants & family fun!

A spacious living area features a light-colored sofa and armchairs arranged around a circular coffee table. A modern fireplace is centered on the wall, with a large screen displaying coastal imagery above it. Natural light streams through large windows, illuminating the room.

5 out of 5 average rating, 14 reviews

5BR Beauty Near Bethany-Community Pool; Linens

This 5-bed, 4.5-bath home in Ocean View, DE has been professionally and lovingly designed for optimum comfort and style. This 2,850 square foot home can easily accommodate 10 guests - with large rooms, multiple hangout areas - both indoors and outdoors, and plenty of upgraded features and amenities. The community features a pool for guests! This luxury home is perfect for multi-family groups or groups of friends reuniting for a memorable week at the beach. Stay in style at Tibbetts Point!

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

Beautifully updated and recently renovated, rancher on a great street in Ocean Pines perfect for families and adults looking for a relaxing stay. We offer 3 bedrooms and 2 bathrooms on one level, with new large flat screen TV's, stainless appliances, and everything you'll need for your stay. We have a large driveway and a screened patio. Ocean Pines boasts over a dozen parks and walking trails, a public Yacht Club, 5 pools, 2 marinas, and a championship golf course - 10 min to the beach!

A spacious living area features a large sectional sofa and is anchored by a flat-screen TV. Soft lighting is provided by ceiling fixtures, while light blue walls create an airy atmosphere. A staircase leads to a lofted space, enhancing the open concept design.

4.98 out of 5 average rating, 59 reviews

Serenity&Peace Minutes to Beach!

Relax with the whole family at this peaceful place to stay. As you enter this everyday oasis, you'll feel instant "vacation mode!" This home offers a serene atmosphere with a pond view! Minutes from Bethany Beach, shopping, and restaurants- this location is the perfect combination of Beach Town and Calm Escape. The house is equipped with a full kitchen, laundry room, and a game room. Each bedroom has a smart TV, the home is equipped with high speed internet, and all you need is close by.

An aerial view showcases a modern house surrounded by lush greenery. A private pool is visible in the backyard, accompanied by a spacious patio area. The screened porch and wood deck feature comfortable seating, inviting relaxation in a tranquil outdoor setting.

4.89 out of 5 average rating, 82 reviews

PRiVATE Pool, Peaceful, and Close to Bethany Beach

Private Pool is OPEN until October Unexpected oasis close to Bethany Beach, all the modern comforts, & private pool! This all-season rental includes a double fireplace, so be sure to pack your swimsuit in summer and favorite heavy books in winter. Equally perfect for family vacation or couple’s romantic getaway! New & comfortable mattresses, Internet, SmartTVs in living room, gameroom, master. Alexa in kitchen, RING doorbell, ECOBEE thermostat, parking, screened porch, unique artwork.

A modern kitchen is complemented by a spacious dining area and cozy living room with ocean views. White cabinetry and stainless steel appliances enhance the kitchen, while large windows allow natural light to fill the space, highlighting the wood-paneled ceiling.

4.96 out of 5 average rating, 159 reviews

Oceanfront 1 Bedroom, Balcony, Sitting Room, Pool

Opal Osprey: This OVERSIZE one-bedroom condo has been completely remodeled... giant oceanfront balcony PLUS a large patio room on the bayside! Expansive ocean views from every angle, super easy beach access, wonderful atmosphere in the quiet north end of OC. Linens included! Property Amenities - King size bed & queen sleeper - Large outdoor pool - Elevators - Dedicated high-speed WiFi and router w/ ethernet (Xfinity 100Mbps) - 2 Smart TVS with Xfinity, Roku - Keyless check-in 24/7

5 out of 5 average rating, 8 reviews

Ocean View Retreat-off-season monthly availability

Unwind with the whole family at this tranquil 4-bedroom home in Ocean View, just 2.9 miles from downtown Bethany Beach and the Boardwalk. Enjoy a day by the ocean or take a short walk to the community pool for a more laid-back experience. Conveniently located near local restaurants and parks, this peaceful retreat is ideal for a relaxing getaway with family and friends! - All guests must be at least 25 years old, except for children with parents.

Popular amenities for Ocean View rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 79 reviews

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

Steps to pool and bakery, baby friendly town home

The exterior of a house is framed by tall trees and greenery, showcasing a patio area with a stone surface. A seating arrangement of black chairs surrounds a circular table, while potted plants add elegance to the space. The entrance features a welcoming porch.

4.96 out of 5 average rating, 91 reviews

Private Bungalow near Bethany Beach

4.91 out of 5 average rating, 23 reviews

An aerial view captures a row of charming homes situated along a sandy beach, with the Indian River Bay visible in the background. Neatly manicured lawns and driveways are observed in front of each house, framed by tall trees and grassy areas.

Home in Dagsboro

Beauty On The Bay

A spacious living area features a large sectional sofa with nautical-themed cushions, complemented by a blue area rug. A dining table is set with place settings, while three framed coastal prints adorn the wall above. Natural light streams in from windows, enhancing the airy feel.

5 out of 5 average rating, 20 reviews

4BR|3BA Yard+Pool Bethany, Rehoboth, Ocean City MD

5 out of 5 average rating, 105 reviews

The exterior of the single-family home is shown, featuring a welcoming entrance with a striped awning. A well-maintained front yard with shrubs and a tree provides shade, while the attached garage is visible on the left.

Home in Frankford

3BR single family house close to Bethany Beach

4.85 out of 5 average rating, 240 reviews

A wooded area features tall pine trees casting shadows on the soft ground covered with pine needles. In the background, the still water of a pond is visible, surrounded by foliage and gently reflecting the sky.

Home in Bethany Beach

Condo Villa 2B 2B, Walk 2 Beach Sl6

5 out of 5 average rating, 12 reviews

A spacious living area features a comfortable sectional couch in soft gray, arranged around a round coffee table. A ceiling fan hangs above, contributing to airflow. A wall-mounted TV is positioned opposite, with colorful storage and toys visible on a nearby shelf.

Home in Frankford

8 Beds 10 min to Beach & Golf! Great for Groups!

4.94 out of 5 average rating, 199 reviews

The living area features a comfortable arrangement of seating including a gray sofa, an armchair with patterned upholstery, and a coffee table at the center. A television is mounted on the wall, and soft light is provided by a lamp on a side table. Large windows allow natural light to fill the space.

Home in Frankford

A Bethany Beach Gem 1.5 miles to Ocean Pickle Ball

Condo rentals with a pool

4.99 out of 5 average rating, 156 reviews

A serene bedroom features a spacious bed adorned with a textured navy quilt, flanked by two bedside tables with lamps. Natural light enters through a window, illuminating the light blue walls. A dresser and decorative mirror complement the calming atmosphere.

Condo in Rehoboth Beach

Family Friendly Top Floor Condo Near Boardwalk

The living area features a modern design with a sleek Italian leather sofa and a wall-mounted flat-screen TV. An electric fireplace is installed beneath the TV, while a coffee table and a single chair complement the space. Ample natural light enters through a nearby window.

4.97 out of 5 average rating, 299 reviews

Bluewater Couples Escape

A light-filled living area features a soft, neutral-toned sectional sofa facing a wooden coffee table. Floor-to-ceiling windows showcase ocean views, with sunlight reflecting off the water. A flat-screen TV is mounted on a wooden entertainment unit, complementing the room's modern design.

4.91 out of 5 average rating, 329 reviews

Oceanfront Family Oasis: Pool, Beach & Parking!

A spacious living area is displayed featuring comfortable navy blue sofas and patterned armchairs. A large coffee table rests on a textured rug, with a view of the ocean visible through floor-to-ceiling windows. An electric fireplace adds warmth, while a dining table invites gatherings.

4.86 out of 5 average rating, 224 reviews

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

4.88 out of 5 average rating, 128 reviews

A partial view of the ocean is visible from the balcony, showcasing the sandy beach and a section of the pool below. Beach umbrellas and chairs are arranged along the shore, set against a clear blue sky.

Condo in Bethany Beach

Featured on HGTV! Bethany Beach Ocean Front Condo

4.94 out of 5 average rating, 285 reviews

A light-filled living area features a comfortable seating arrangement with two red chairs and a cozy couch, accompanied by a round coffee table. A wall-mounted TV is situated above an electric fireplace, enhancing the space's inviting atmosphere. Large windows offer views of the outside.

Condo in Lewes

Spacious| Modern &Cozy| Pool| Close to the Beaches

4.98 out of 5 average rating, 195 reviews

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

An open-concept living and dining area features a wooden dining table set for six, complemented by modern chairs. A comfortable seating arrangement with light-colored couches is situated near large windows, offering views of the surrounding area. A mounted TV and decorative elements enhance the space.

4.96 out of 5 average rating, 121 reviews

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

Other holiday rentals with a pool

4.86 out of 5 average rating, 22 reviews

A scenic view of a pond is presented, bordered by residential homes that reflect a serene atmosphere. The sky is adorned with clouds, casting varying shades of blue and orange as the sun sets. A fountain can be seen in the pond, adding to the tranquil setting.

Condo in Frankford

Pondview Villa: Beach Club Gem

5 out of 5 average rating, 17 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

4.98 out of 5 average rating, 61 reviews

A spacious living room features a comfortable blue sofa, a wooden coffee table, and a media console with a TV. Large windows provide natural light and showcase distant views. A decorative rug adds texture underfoot, while a small table with plants enhances the inviting atmosphere.

Condo in Dewey Beach

Stunning views from Beautiful 2 BR Condo

4.95 out of 5 average rating, 91 reviews

A spacious living area is furnished with a cozy blue accent chair and a large TV set atop a light-colored console. A woven bench adds texture, while a dining area with a table and woven chairs is visible in the background, enhancing the functional layout.

Condo in Sussex County

Eastern Shore Getaway: Bethany Bay

5 out of 5 average rating, 54 reviews

A cozy family room is presented with a large flat-screen TV mounted above a stone fireplace, featuring comfortable seating options, including a spacious sofa and a futon. Vibrant arcade games are visible against the textured wall, enhancing the entertainment options.

Home in Bethany Beach

Coastal Cottage! Walk to Beach!

A community pool is featured, surrounded by a white picket fence. Several lounge chairs are positioned around the pool area, with sun umbrellas providing shade. The water is clear and inviting, reflecting the blue sky above.

5 out of 5 average rating, 21 reviews

The Sea Salt Retreat: Pool, Beach, Family Fun!

5 out of 5 average rating, 40 reviews

A wooden walkway lined with lush greenery leads toward a tranquil water view, framed by trees. The sky is painted with hues of orange and pink, suggesting a beautiful sunset. A sign indicates safety regulations, enhancing awareness of the natural surroundings.

Townhouse in Selbyville

‘Dockside Retreat’ -pool, minutes to OC/beaches