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, 13 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!

The living area showcases a spacious arrangement of light-colored furniture, including an orange sectional and inviting armchairs. Large windows allow natural light to fill the room, complemented by a cozy fireplace. An elegant rug anchors the space, providing a comfortable atmosphere for relaxation.

5 out of 5 average rating, 14 reviews

Quiet & Cozy Beach House

Welcome to your perfect beach escape! Nestled in the quiet cul-de-sac within an upscale community of Ocean View, DE, this peaceful retreat offers the ideal blend of privacy, comfort, and coastal charm. Just minutes from the sandy shores of Bethany Beach and steps from the renowned Bear Trap Dunes golf course, this home is the ultimate getaway for rest and relaxation. Tucked away on a serene cul-de-sac, this home offers a sense of seclusion while still being conveniently close to everything.

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!

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

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

Listed as one of Delaware's top Airbnb's this fully equipped condo feels like your own personal beach home! This is a perfect getaway for family and friends. The beach is 1.5 miles away and the pool a 2 minute walk. The kitchen is fully equipped for cooking and children. Sunroom with pullout bed and play area. Deck for relaxing. Tennis and Pickleball court access. Located 5 miles from Ocean City and Dewey, 10 miles to Rehoboth Beach. located n the Quiet Beaches of Bethany.

4.97 out of 5 average rating, 114 reviews

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

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.

An open-plan kitchen and living area feature a light wooden counter with three stools. A fully equipped kitchen is visible, including a refrigerator, while a comfortable seating area with a cream-colored armchair and a coffee table is also present. Natural light enhances the inviting space.

4.89 out of 5 average rating, 158 reviews

Water Front Condo w/Pool Short Walk to Beach

FIRST FLOOR UNIT Bayside Condominium Sleeps 4 - 6 max Walking Distance to Northside Park Walk to the Ocean , don't worry about beach parking NON SMOKING 1 Bedroom 1 Bath condo, First floor unit with an outside deck This Air Conditioned, One Bedroom Condo has a fully equipped kitchen, washer/dryer, full refrigerator. There is a Queen bed and a full bed along with 1 Queen Sleep sofa in the living room *MUST BE 21 OR OVER* No Pets!

Popular amenities for Ocean View rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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!

5 out of 5 average rating, 9 reviews

An elegant entrance is showcased with a wide staircase leading to a grand front door framed by tall windows. Flanking the entrance, stacked stone pillars support the roof, and a patterned stone walkway is bordered by landscaped areas, enhancing the welcoming ambiance.

Home in Dagsboro

Pristine 4+ acre waterfront in Bethany Beach area

The open-concept living area features a modern kitchen with stainless steel appliances and light wood cabinetry. A dining table is situated alongside a plush couch, all set against a soothing blue wall. Natural light brightens the space, which is adorned with a patterned rug.

5 out of 5 average rating, 9 reviews

Welcome to Blue Tide Escape

Condo rentals with a pool

4.99 out of 5 average rating, 157 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

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, 413 reviews

A round blue dining table is set for four, featuring neutral plates and glasses. Surrounding chairs have a classic black design. A large piece of abstract art adorns the wall, while the kitchen area is visible in the background, showcasing light cabinetry and appliances.

Condo in Rehoboth Beach

Clean and Comfy, Longer Term Stay available, Quiet

An open living area is highlighted by large windows that offer views of the bay and pool. A comfortable sectional sofa is positioned adjacent to a smart TV, while a modern dining table for four is visible next to the kitchen. The space features light-colored walls and natural wood flooring.

4.96 out of 5 average rating, 107 reviews

Gone Coastal *Pool* Bayside with view* Top Floor

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.

4.96 out of 5 average rating, 279 reviews

Caramar Couples Retreat

4.97 out of 5 average rating, 269 reviews

The living room features two full couches arranged around a coffee table, providing ample seating. A ceiling fan is mounted overhead, and natural light floods the space through multiple windows. A Smart TV is positioned on a console, and a dining area is visible in the background.

Condo in Rehoboth Beach

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool

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

4.92 out of 5 average rating, 37 reviews

A charming studio cabin, nestled among tall trees, features a brown exterior with white trim. Large windows allow natural light to fill the interior. A stone pathway leads to a main entrance, framed by a serene woodland setting.

Guesthouse in Lewes

Studio Bedroom in the Woods

Superhost

A spacious living area is depicted, featuring a large sectional sofa and two accent chairs. A coffee table sits at the center, with a modern stone fireplace adorned by a flat-screen television. Natural light enters through window panes, highlighting the plush area rug.

4.92 out of 5 average rating, 37 reviews

Luxury Single Family, Waterfront w/Linens Included

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

4.89 out of 5 average rating, 19 reviews

Home in Rehoboth Beach

Dog Friendly Fenced 3BR King Bed

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!