Vacation rentals with a pool in Fenwick Island

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Fenwick Island

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

1 of 1 pages1 / 1
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
4.94 out of 5 average rating, 284 reviews

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!

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.
Condo in Ocean City
5 out of 5 average rating, 111 reviews

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!

Top 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
4.93 out of 5 average rating, 137 reviews

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.

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
5 out of 5 average rating, 17 reviews

Dog friendly| community pool | gym| kayak| bayside

Welcome to your ultimate family beach escape! Nestled near Fenwick Island this 3 BDR 2 BTH home offers everything you need for a memorable vacation. Unwind with cocktails at the tiki bar, toast marshmallows around the fire pit, or make a splash in the refreshing pool. Stay in shape at the on-site gym, ensuring your fitness routine doesn't miss a beat. With its prime location just moments from the beach and an array of amenities this bayside retreat promises an unforgettable vacation experience.

Top guest favourite
Apartment in Ocean City
5 out of 5 average rating, 20 reviews

SeaGate Serenity | Oceanfront Condo with Balcony

Wake up to the sound of the waves crashing outside your window and finish your days relaxing on the private balcony as you watch the pastel skies over the ocean at sunset. Come find your serenity by the sea in our newly renovated oceanfront condo. Located in midtown, you can keep your car parked in our reserved spot and walk to many of the towns best restaurants, bars, and entertainment as well as the World Famous Ocean City Boardwalk. Morning beach strolls, pool days, and evening sips await :)

Guest favourite
A private in-ground pool features clear blue water, surrounded by a curved concrete deck. Two white lounge chairs are positioned in the shallow end, offering a relaxing spot. In the background, a tiki bar and seating area are partially visible among lush landscaping.
Home in Ocean City
4.81 out of 5 average rating, 57 reviews

Bayside Oasis *In-Ground Pool*Hot Tub*Huge Yard*

Sleeps 10 comfortably! A pristine gathering place for family & friends to enjoy a private IN-GROUND POOL & lovely HOTTUB! Nestled in the beautiful greenery of a HUGE fenced-in backyard with a hammock, grill & tiki bar! With 3 bedrooms & 2 full baths, this beautiful home is family-friendly and/or the perfect getaway for a group of pals! Take a dip in the pool or hot tub, read a book in the hammock, short walk to the beach. This gorgeous single-family in North O.C. has something for everyone

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
4.96 out of 5 average rating, 28 reviews

Anchors Away, Your Dream Getaway in Fenwick Shoals

Escape to our stunning, spacious 5-bedroom, 3.5-bathroom retreat in a gated community just 2.5 miles from the Fenwick Island/Ocean City beaches, nearby golf courses too. Our 3 story single family home sleeps up to 13. Over 3500 square feet, our house features a fully equipped kitchen, LR/DR, optional elevator, game room with pool table, slot machine, foosball, air hockey & more. Our beautiful single family home with the perfect blend of comfort & coastal charm the whole family will enjoy.

Guest favourite
Home in Selbyville
4.97 out of 5 average rating, 31 reviews

Cozy Beach Escape Mallard Lakes Resort Amenities

Located in the peaceful Mallard Lakes community just minutes from Fenwick Island, Ocean City, and Delaware Beach. This relaxing coastal retreat in Mallard Lakes combines resort-style amenities with the comfort of home — perfect for family vacations, couples getaways, beach weekends, and remote work stays. Why Guests Love Staying Here Less than 3 miles to the beach 2 pools + tennis courts Family-friendly layout Dedicated workspace + fast Wi-Fi Self check-in Outdoor shower after beach days

Top guest favourite
A serene view captures a group of ducks swimming in a calm waterway, bordered by lush green grass and small reeds. The surrounding area features a natural landscape, with distant homes visible in the background.
Townhouse in Selbyville
4.92 out of 5 average rating, 237 reviews

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.

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

Golf, Beach & Pool Escape • 6BR • Game Room

Luxury 6BR/4.5BA Bayfront custom home in Selbyville! Minutes to Fenwick & Bethany beaches. Features a King Suite, 3rd-floor SUNDECK, and a covered porch with a FIREPLACE for sunset views. Rare EV CHARGER on-site. Game lounge with ping pong. LINENS INCLUDED! Community POOL access included with your stay. Near Freeman Arts Pavilion & top golf courses. Professionally managed by local experts Sandy Steps. Perfect for large families & golf groups. Sleeps 12. Book your coastal retreat today!

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
5 out of 5 average rating, 29 reviews

Bayside Family Oasis - Perfect for Large Families

Welcome to your coastal getaway in Bayside Resort, less than a 5-minute walk to the Sunridge Pool and fitness center. Set along the 17th hole of a Jack Nicklaus golf course, this spacious 5-bedroom home sleeps up to 12 guests and is ideal for families, golf trips, and group getaways. Inside, enjoy an open-concept layout with a fully equipped kitchen, dining area, and fireplace, perfect for relaxing after the beach or pool. Step outside to unwind on the patio with golf course views.

Guest favourite
The living area features soft blue furnishings and a light wood coffee table. Floor-to-ceiling windows offer direct views of the ocean, while two lamps provide warm lighting. A coastal-themed artwork adorns the wall, enhancing the serene atmosphere of the space.
Condo in Ocean City
4.94 out of 5 average rating, 322 reviews

Direct Oceanfront 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 full 100% view of the beach and ocean.

Popular amenities for Fenwick Island rentals with a pool

Quick stats about vacation rentals with a pool in Fenwick Island

  • Nightly prices starting at

    Fenwick Island vacation rentals start at $585 CAD per night before taxes and fees

  • Verified guest reviews

    Over 10 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!