Holiday rentals with a pool in Ocean View

The entrance to Bear Trap Dunes is highlighted by a brick sign adorned with the name, framed by vibrant flower beds featuring pink and white blooms. Tall trees line the pathway, contributing to a well-maintained and inviting landscape.

4.94 out of 5 average rating, 118 reviews

10VG at Bear Trap/Bethany Beach - Owner Managed

Welcome to your second home! Our bright & comfortably furnished 5 BR, 4 1/2 BA end unit rowhome sleeps 14 (+ baby) in a resort-like setting. You won't find a more generously appointed Airbnb with all of the comforts of home so pack lightly! We're ideally situated just steps away from Bear Trap's optional amenities, including a 27 hole golf course, restaurant, clubhouse, indoor & outdoor pools, tennis, pickleball, basketball, fitness, tot playground, & seasonal shuttle to nearby Bethany Beach.

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.

4.96 out of 5 average rating, 28 reviews

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, 193 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.

Apartment 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.

4.9 out of 5 average rating, 104 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.

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!

The living room features ample seating on a sectional couch, complemented by an area rug and coffee table. Natural light streams through large windows, illuminating the space. A TV and sound bar are mounted on the wall, enhancing the entertainment options.

4.9 out of 5 average rating, 39 reviews

Boho Beach Golf Villa

🌞🦀🏘️⛳️- Relax, Explore, Repeat Step into an airy, stylish space designed for easy, laid-back days. Spend your time discovering local beaches, playing a round of golf, or exploring restaurants and shops. When it’s time to unwind, kick back on the patio, enjoy the fresh air, and settle into a cozy space. Boho Beach Golf Villa offers optional add-ons and thoughtful touches to make your stay even more memorable. Book your getaway today and start counting down to the shore!

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

This cute little first floor efficiency condo is ocean front for a perfect vacation to the beach. It’s an older building but has been partially renovated and updated. You can get to the beach by a very short walk through a private walkway from the condo building. The view from the private balcony is perfect and relaxing. WiFi provided upon check in- xfinity, Netflix, and internet. Indoor and outdoor dining areas and a full kitchen. Closet and dresser for storage use.

A serene ocean view is presented from a private balcony, featuring two teal chairs. The sandy beach stretches into the distance, with gentle waves lapping at the shore. A clear sky completes the tranquil coastal scene, creating a peaceful atmosphere.

4.92 out of 5 average rating, 252 reviews

Sun, Sand & Sea | Your Cozy Oceanfront Hideaway

-Oceanfront -Indoor pool & Hot tub -Walk to local dining and shopping -Elevator accessible plus luggage carts -Full kitchen for cooking meals -Fast Wifi and Streaming TVs -Fully Stocked Home: Clean linens, towels, toilet paper, paper towels & more! **2025 guests: Our pool and hot tub are in the process of being renovated and will be closed during your stay. This does not impact our condo, but you will not be able to use these amenities.**

An open-concept living space features comfortable seating, including a cozy sofa and accent chair. A dining area with modern chairs complements an equipped kitchen, showcasing stylish cabinetry and stainless-steel appliances. Large windows offer expansive views of the ocean and bright natural light.

4.93 out of 5 average rating, 136 reviews

WraparoundBalcony-2 Bed-Sleeps 8-Pool-Laundry-WiFi

Welcome to our stunning oceanfront retreat! This luxurious property offers the perfect combination of comfort, style, and breathtaking views. With a spacious J-shaped wraparound balcony, you can indulge in panoramic vistas of the sparkling ocean waves from every angle. Ideal for groups of up to 8 guests, this two-bedroom, two-bathroom getaway provides ample space for everyone to unwind. Book today for the vacation you'll never forget!

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

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A bright living area features a light blue accent wall, a spacious gray sofa, and a dark blue couch. Two side tables with lamps provide soft lighting. A coffee table with a slatted design occupies the center, while a framed coastal artwork hangs above.

5 out of 5 average rating, 11 reviews

Coastal Chill Condo at Bethany Bay

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

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

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

5 out of 5 average rating, 5 reviews

The exterior of a single-story home is presented, featuring a light gray facade with dark shutters. A two-car garage is visible on the left, while a welcoming front porch offers seating. Well-maintained landscaping with green shrubs frames the entrance, completing the inviting curb appeal.

Home in Clarksville

Gorgeous Home at Ocean View Beach Club

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!

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!

Apartment 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.

Apartment in Frankford

Pondview Villa: Beach Club Gem

Apartment in Sussex County

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.

4.95 out of 5 average rating, 91 reviews

Eastern Shore Getaway: Bethany Bay

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, 330 reviews

Oceanfront Family Oasis: Pool, Beach & Parking!

Apartment in Bethany Beach

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.

4.88 out of 5 average rating, 128 reviews

Featured on HGTV! Bethany Beach Ocean Front Condo

Apartment in Rehoboth Beach

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.

4.94 out of 5 average rating, 413 reviews

Clean and Comfy, Longer Term Stay available, Quiet

A spacious balcony offers unobstructed ocean views, featuring two comfortable wooden chairs and a small circular table. The bright blue waters and clear sky create a serene backdrop, enhancing the feeling of open outdoor space.

4.98 out of 5 average rating, 101 reviews

Beautiful 2BR 2BA oceanfront condo at the Atlantis

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

Apartment in Rehoboth Beach

A balcony view showcases the ocean, with serene waves and sandy shores. Large glass doors allow natural light to flood the interior, while outdoor seating and potted flowers add a charming touch to the space.

4.96 out of 5 average rating, 161 reviews

Sunrise Studio - Ocean Front, on Boardwalk, Pool!

Other holiday rentals with a pool

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, 19 reviews

A spacious living area features a large sectional sofa in soft blue tones, paired with a round coffee table. Sunlight streams through multiple windows adorned with plantation shutters, illuminating the open floor plan that connects to the dining area in the background.

Home in Millville

Shore to Please!

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

Holiday home in Frankford

A screened-in porch features a picnic table center and two reclining chairs arranged for comfort. An inviting hammock hangs nearby, with windows offering views of the serene outdoors. The space is illuminated by natural light, creating a relaxing environment for gatherings.

4.98 out of 5 average rating, 57 reviews

Spacious Vacation Home near Bethany Beach

5 out of 5 average rating, 20 reviews

A welcoming entrance is framed by a brick pathway lined with soft green grass and small white lights. Lush trees and vibrant shrubs provide a pleasant contrast to the exterior. Large windows invite natural light into the home, enhancing the overall charm.

Home in Millsboro

Bayfront Oasis Vacation Rental

A welcoming living area is highlighted by a large window, allowing natural light to fill the space. Comfortable seating includes a sectional sofa and accent chairs around a coffee table. Decorative elements such as wall art and nautical accents add charm. A ceiling fan provides airflow.

4.94 out of 5 average rating, 48 reviews

Beach Vibes Only – Cozy, Clean, & Close to Shore

5 out of 5 average rating, 27 reviews

A garage gameroom features a bright blue table tennis table centered in the space. The wall behind is adorned with the text 'The Villa On Calm Water.' Bicycles are mounted on racks, providing easy storage. The concrete floor adds a functional touch to the area.

Townhouse in Millville

Beach Shuttle + 3 Pools Near Bethany Beach