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Holiday rentals with a pool in Fenwick Island

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Quick stats about holiday rentals with a pool in Fenwick Island

  • Nightly prices starting at

    Fenwick Island holiday rentals start at €397 per night before taxes and fees

  • Verified guest reviews

    Over 20 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Fenwick Island rentals

  • 4.9 Average rating

    Fenwick Island stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated rentals with a pool in Fenwick Island

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
A light and airy deck features a rectangular dining table surrounded by aqua-colored chairs. A calm water view is visible beyond the railing, with flags gently waving in the breeze. Soft lighting is provided by string lights overhead, enhancing the inviting atmosphere.
Home in Ocean City

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

4.94 out of 5 average rating, 287 reviews
Guest favourite
A back deck features a seating area composed of a sofa and ottoman with soft cushions, facing a calm canal. A wooden table is positioned nearby. A red umbrella is closed and stands beside the seating, while a sunset casts gentle hues across the water.
Home in Ocean City

3 BR Waterfront Home, Minutes to the Beach

Recently updated waterfront house located in the family-friendly Montego Bay community. Enjoy beautiful sunsets on the back deck or hop in one of the kayaks for a paddle around the wide-open canal. Try your hand at crabbing or fishing off the dock to catch your dinner. Within easy walking distance of the beach and Northside Park (about 10 minutes walk to both). Beach chairs, toys, boogie boards, and umbrellas are yours to use for fun in the sand and surf. The dock is available for boat tie-ups.

4.93 out of 5 average rating, 150 reviews
Top guest favourite
The living area is spacious, featuring a light blue wall color and a large sectional sofa. Natural light floods through windows, illuminating the decorative rug. The outdoor porch includes dining furniture and offers views of the canal and neighboring buildings.
Apartment in Ocean City

Beautiful waterview 2B condo w/Dock&Close to Beach

Welcome to the Canal Bungalow! A stylish 1000 sq. foot retreat to enjoy all the fun & relaxation of the coastal lifestyle in North Oc. Bring your boat with you and dock alongside your back porch, enjoy pool access in a private gated community, or bring your sports gear for Northside Park. We are tucked away on the quiet bayside of OC & only a few minutes walk to the beach. Unwind on our beautiful balcony while watching the boats go by & finally understand the true meaning of a coastal lifestyle!

5.0 out of 5 average rating, 120 reviews
Top guest favourite
A spacious living area features two sofas, one in dark leather and the other in a light fabric, arranged around a low wooden coffee table. A flat-screen TV is mounted on a light wall above a stone fireplace, adding a cozy touch to the room.
Home in Ocean City

Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.

Relax with the family in this comfortable and charming home. There is room for 8 to sleep comfortably. The dining room and breakfast nook offer plenty of seating for all with a spacious kitchen. Our corner lot offers the option for outdoor fun like slip and slide, corn hole, frisbee, and more! Nearby: Beach, Bay, Wildlife sanctuary surrounded by a walking trail, Pool, Tennis, restaurants & Eventful Northside Park! Quiet and peaceful location to make family or romantic memories of a lifetime.

4.97 out of 5 average rating, 160 reviews
Guest favourite
Townhouse in Selbyville

Beach house on lake!

2 miles from the beach in a complex called Mallard Lakes in Fenwick Island, DE.Close to great views, restaurants, beach, and family activities.Bird watching outside screened-in porch, fishing, crabbing, two outdoor pools/hot tub (open Memorial Day-Labor Day), tennis, volleyball and basketball courts, tot lot, horseshoe pit, shuffleboard, grilling area and a shopping center across the street.Free water aerobics, outside shower, fireplace, umbrella and chairs for beach, comfortable sofa bed.

4.91 out of 5 average rating, 251 reviews
Top guest favourite
A spacious living room features two comfortable sofas arranged around a wooden coffee table. A flat-screen TV is mounted above a cozy gas fireplace. Natural light enters through multiple windows, while a dining area is visible in the background, furnished with a long table and chairs.
Home in Selbyville

Modern coastal beach home in West Fenwick Island

Welcome to Two Buoys At The Beach, a bright and beautiful open-concept home just 7 minutes from feet in the sand at Fenwick Island State Park. Our family-friendly beach house comfortably sleeps 10, with plenty of space to relax and unwind. Entertain with ease with a fully stocked kitchen, private gas grill, and furnished deck, and enjoy the outdoor shower after a day of fun in the sand or at our community pool. We hope you enjoy the quiet serenity of the Delaware beaches as much as we do!

5.0 out of 5 average rating, 102 reviews
Guest favourite
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.
Apartment in Ocean City

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

4.95 out of 5 average rating, 187 reviews
Guest favourite
A private balcony is showcased overlooking the ocean, featuring two comfortable chairs and a small table. The scene is framed by large sliding doors, allowing natural light to brighten the space. Green turf flooring complements the outdoor seating area.
Apartment in Ocean City

Luxury Oceanfront Oasis!

Welcome to Marigot Beach, one of the most coveted building in OC. This stunning condo boasts 2 spacious bedrooms and 2 bathrooms, ideal for a large family or a large group up to 8 guests. The master bedroom features an en-suite bathroom, while the second bedroom offers two full-size beds. Included: free WiFi, smart TVs in every room, fully equipped kitchen, large-capacity washer/dryer, and elevator. PLUS, take advantage of TWO designated parking spots! Pool/hot tub are now OPEN!

4.95 out of 5 average rating, 103 reviews
Top guest favourite
A panoramic view of the ocean is visible, with gentle waves lapping at the sandy beach. Below, an outdoor pool is surrounded by lounge chairs and clear pathways, providing a peaceful atmosphere. Skies are blue, enhancing the serene coastal setting.
Apartment in Ocean City

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

Sea Watch Condo's is an ideal family location with tons of amenities. The until is a recently updated 3 bedroom 2 bathroom condo that sleeps 6 people in 2 queen beds, 2 twin beds . The unit is ocean front with a large oceanfront balcony. The amenities Include, basketball court, tennis courts, playground, arcade, movie theater, billiard room, indoor pool and outdoor pool as well as a restaurant. The condo has 24 hour security and plenty of parking. Pools closed in off season

4.88 out of 5 average rating, 142 reviews
Top guest favourite
A charming beach house is set on stilts, featuring a pink exterior with white shutters. The front porch offers a welcoming entry, surrounded by a landscaped yard with trees. Gravel driveway and a white picket fence enhance the appealing exterior in a tranquil neighborhood.
Home in Frankford

The Big Chill at Bethany Beach

The Big Chill at Bethany Beach is our whimsical family beach house in the Clearwater community, just two miles from the Bethany Beach boardwalk. We've thought of everything so that you don't have to. Spacious bedrooms with fine bed and bath linens; fully stocked kitchen with cookware and spices; smart TVs and Nintendo Switch; lots of books and board games; screened-in porch and open-air deck; and comfortable furnishings throughout. And bring your dogs; they're family, too!

4.98 out of 5 average rating, 101 reviews
Guest favourite
Apartment in Ocean City

Beachfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with a breathtaking view of the beach and ocean.

4.83 out of 5 average rating, 252 reviews
Top guest favourite
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.
Home in Lewes

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* and no pets from June 14 to Labor Day.

4.99 out of 5 average rating, 235 reviews

Popular amenities for Fenwick Island rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favourite
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

4.94 out of 5 average rating, 106 reviews
Top guest favourite
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

4.94 out of 5 average rating, 218 reviews
Top guest favourite
A large, inviting pool area features clear blue water surrounded by lounge chairs and umbrellas. The pool is equipped for swimming laps, with marked lanes. A spacious building with numerous windows provides a welcoming atmosphere adjacent to the pool.
Home in Selbyville

Dog friendly| community pool | gym| kayak| bayside

5.0 out of 5 average rating, 24 reviews
Top guest favourite
The spacious three-story home features a welcoming facade with a combination of blue and white hues. A broad driveway leads to large garage doors beneath an expansive covered porch. Multiple balconies create an inviting atmosphere, framed by neatly landscaped grounds.
Home in Selbyville

Anchors Away, Your Dream Getaway in Fenwick Shoals

4.97 out of 5 average rating, 33 reviews
Top guest favourite
The exterior of a charming two-story home features a light beige facade with white trim and a welcoming front porch. Spacious balconies extend from the second floor, and the well-maintained lawn complements the overall inviting appearance. A three-car garage is visible on the right.
Home in Selbyville

Bayside Family Oasis - Perfect for Large Families

5.0 out of 5 average rating, 35 reviews
Top guest favourite
Home in Selbyville

Mi Casa at Bay Knolls

5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Ocean City

North OC 3BR + Loft Sleeps 12 Walk to Pool & Beach

5.0 out of 5 average rating, 14 reviews
Top guest favourite
The exterior of a modern house is presented at dusk, featuring a welcoming porch with multiple seating areas. Illuminated windows reflect warm light, while a lamp post adds ambiance. A tidy driveway leads up to the home, framed by well-maintained landscaping.
Home in Ocean City

Upscale Family Home in North OC

5.0 out of 5 average rating, 65 reviews

Apartment rentals with a pool

Top guest favourite
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.
Apartment in Ocean City

Beautiful 2BR 2BA oceanfront condo at the Atlantis

4.98 out of 5 average rating, 111 reviews
Guest favourite
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.
Apartment in Ocean City

Oceanfront Paradise | Pool | Hot Tub | Beach

4.92 out of 5 average rating, 290 reviews
Guest favourite
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.
Apartment in Ocean City

Water Front Condo w/Pool Short Walk to Beach

4.89 out of 5 average rating, 186 reviews
Guest favourite
A view from the 14th floor balcony is presented, showcasing the ocean and sandy beach under clear blue skies. The sparkling water reflects sunlight, while a glass table and chairs provide a space for relaxation. Coastal vegetation can be seen along the shore.
Apartment in Ocean City

Oceanview Oasis with 2 private balconies

4.86 out of 5 average rating, 125 reviews
Top guest favourite
An open floor plan presents a well-lit living area featuring comfortable seating and light blue accents. A subtle sunburst mirror is mounted on the wall, while a patterned area rug adds texture to the space. Kitchen cabinetry and bar seating create an inviting atmosphere.
Apartment in Ocean City

Entire beautifully updated Condo with Ocean Views!

4.93 out of 5 average rating, 105 reviews
Superhost
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.
Apartment in Ocean City

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

4.93 out of 5 average rating, 138 reviews
Guest favourite
Apartment in Ocean City

Oceanfront Bldg.| 2 pools | Tennis | Game Room

4.96 out of 5 average rating, 125 reviews
Top guest favourite
A bright living area features a blue sofa, a striped armchair, and a wooden coffee table. Natural light flows through sliding glass doors that lead to a balcony with ocean views. Light curtains frame the view, and a TV is mounted on a light-colored media console.
Apartment in Ocean City

21st Floor Carousel - 2 BR Oceanfront & Bay View

4.96 out of 5 average rating, 115 reviews

Other holiday rentals with a pool

Top guest favourite
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

5.0 out of 5 average rating, 63 reviews
Top guest favourite
Apartment in Ocean City

Oceanfront Balcony • Pool • North Ocean City

5.0 out of 5 average rating, 23 reviews
Guest favourite
A cozy bedroom features a bunk bed with a Twin bed above a Full bed, all adorned with striped bedding in shades of blue and green. Natural light entering through the window highlights the soft carpeted floor and simple furnishings.
Flat in Ocean City

2 BR 2BA North Ocean City Condo

4.93 out of 5 average rating, 56 reviews
Top guest favourite
A serene view of the Little Assawoman Bay is showcased at sunset, with soft pastel colors reflecting off the water. Marshland and grasses frame the landscape, and charming homes line the opposite shore, creating a tranquil atmosphere.
Townhouse in Sussex County

Waterfront Haven: Moments from the Beach!

4.96 out of 5 average rating, 69 reviews
Guest favourite
The entrance to the condo is framed by lush green shrubs and a well-maintained garden. The pathway leads to a welcoming door, with a small balcony above. Soft natural light filters through the nearby windows, enhancing the inviting atmosphere of the entryway.
Holiday home in Fenwick Island

Cozy, updated condo. Pool, tennis, walk to beach.

4.94 out of 5 average rating, 50 reviews
Top guest favourite
A community pool is showcased, featuring a spacious deck and surrounded by a secure white fence. The water is clear, reflecting the blue sky above. Nearby, three multi-story buildings provide a backdrop, characterized by a variety of exterior colors and balconies.
Home in Ocean City

Beach House | 1 Block to Beach | Pool | OC MD

5.0 out of 5 average rating, 34 reviews
Top guest favourite
An open floor plan is showcased, featuring a modern kitchen with a central island and white cabinetry. Large sliding glass doors allow for natural light and ocean views. A cozy seating area includes a coffee table and comfortable blue couches, inviting relaxation in a bright environment.
Flat in Ocean City

NEW: Oceanfront End-Unit Condo w/ 100ft Balcony

5.0 out of 5 average rating, 10 reviews
Top guest favourite
A cozy living area features a light blue sectional couch adorned with patterned cushions. A round, patterned coffee table is positioned in front, complemented by a lamp and artwork on a neutral wall. A small decorative plant brings a touch of greenery.
Home in Bethany Beach

Cozy Bethany Beach Retreat

4.98 out of 5 average rating, 54 reviews

Destinations to explore