
Holiday 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.

2BRCapri: Indoor Pool, Game Room, Massage Chair
ALL THE COMFORTS OF HOME AT THE BEACH! BRAND NEW RENOVATED BATHROOMS! -ALL LINENS INCLUDED -Comfortable electric-reclining sofas -65-in smart Roku TV with soundbar. -Massage chair in master bedroom -Balcony & Dining Area w/ Ocean +Bay Views -In-unit W/D -Many conventional & USB Outlets -Arcade level features b-ball hoop, pool tables, ping-pong, shuffleboard, air-hockey -Outdoor tennis court -Large heated indoor pools -can swim full laps -Sauna and Gym -Board games in unit -Fast Wifi

Gone Coastal *Pool* Bayside with view* Top Floor
Welcome to Gone Coastal! Relax in this beautiful 2BR/2BA getaway featuring: 🛏 1 King (Master) | 1 Twin-over-Full Bunk | 1 Sleeper Sofa 🏊♂️ Outdoor Community Pools – Lap & Family Pool (Directly Across!) 🔑 Keyless, Contactless Check-in 🌅 Spacious Deck – Outdoor Dining + Bay & Pool Views 📺 Smart TVs + YouTube TV 🛒 1-Minute to Grocery Store 🍽 Fully Equipped Kitchen 📍 Prime Location – 120th St, Heron Harbor 🚗 Ample Free Onsite Parking A perfect retreat for families & beach lovers! 🌊☀️

Right behind Alley Oops & Crab Bag. Walk to beach
Look no further! With Alley OOps in the backyard and a 5-minute walk to the beach, pool, tennis, and shopping, the fun is endless. This 3 bedroom, 2 bathroom house has high-end furniture, fast wifi, 4 flat screens and 2 free parking spots with street parking when available. Our Community offers all of these amenities included in your rental and free putt-putt too! Enjoy our natural wood-burning fireplace and large porch to take in the sunset through the trees. We do not rent to under 25.

Beautiful Cottage W/ shared pool & close 2 beach
"Beautifully decorated & completely renovated 3 BR/2 BA/ plus den. The home is 2 blocks from the bay and a 20 min. walk to the beach! Enjoy this entire home in the quiet neighborhood of Montego Bay which boasts 2 pools, tennis courts, a fishing pier, a walking pond, mini golf and Northside Park. The kitchen is fully stocked and the house is kid-friendly. There are 2 parking spaces & off-street parking. Finally, enjoy the sunset on the large deck complete with an area for al fresco dining.

Oceanfront Studio, King bed, Sleeps 4, Pool, Wi-Fi
Wake up with ocean views right from your king-sized bed! This stunning ocean front studio comfortably sleeps 4 guests and offers a restful retreat in N. Ocean City. Whether you order carry-out or cook at home the kitchen has everything you need! Enjoy your coffee with the sun rise over the Atlantic or sip a cocktail on the balcony while gazing at the beach during the "golden hours" of evening. Located away from the hustle and bustle of the boardwalk, but only a short drive/bus ride away!

Newly built bright and airy guest suite!!!!
FREE oceanfront parking pass with bookings. 2nd floor private suite with parking, patio/firepit, and self check-in private entry. We are located just minutes from the Ocean City beaches, quaint small town of Berlin, Ocean Downs Casino, Assateague, Windmill Creek Winery, restaurants, and outlets. Enjoy neighborhood amenities such as a waterfront Yacht Club with restaurant and live music (seasonal), golf, farm market, playgrounds, 5 pools/fee, (no pool on property) racquet club.

Love Above the Waves-Best Ocean View & Heated Pool
🥂 Complimentary champagne, endless ocean views, private balcony, breathtaking sunrises, warm swimming pool and beach strolls await you at this romantic retreat. Love Above the Waves is more than a stay—it’s an unforgettable celebration of love and romance, perfect for birthdays, anniversaries, engagements, or quiet escapes for two. Let the ocean be your witness, the champagne your spark, and the sunrise your reminder that some moments are meant to stay with you forever.

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.

Nice 2 BR Oceanfront, Year Round Fun & Amenities!
Gorgeous kitchen & main areas renovated March ‘22. 2 bedroom, 1.5 bath, direct oceanfront condo on 7th floor of Golden Sands building in OC. It’s clean, comfy, stylish, full of amenities & in a great location. Great WiFi, 3 TVs with cable, DVD, well stocked kitchen & stunning ocean view with large balcony. Top floor has indoor pool, fitness room, sauna & game room. Outdoor pool, tiki bar, gift shop, market & deli open weather permitting in May, then daily by Memorial Day.

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.

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!

Bayside - Best Deal in Bayside!
Best Location In Bayside! This beautiful, luxury town home is the best vacation value on the shore! We are located right across the street form the Sunridge pool/fitness/tennis/basketball/playground facility! So you do not have to walk far or drive to the pool! In the Peak season, we require a 4 night minimum if you have a Saturday Overnight, or 3 night minimum when you can check in or check our on a Saturday.
Popular amenities for Fenwick Island rentals with a pool
House rentals with a pool

2 BR Ocean Front Condo w/Pool, Expansive Views

Quiet 3BR Coastal Home Minutes to Bethany Beach

Family + Pet-Friendly Home Near Fenwick Island

Ocean View Paradise w/Hot Tub & Free Massages!

Upscale House Steps 2 Ocean 3 Balconies Pool Bikes

Ocean Breeze

Beautiful Waterfront Home-Private, Clean, Relaxing

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines
Apartment rentals with a pool

Oceanfront Carousel building, Swimming Pools!

Beautiful Beach-View Condo

Ocean Block - Clean, cozy 1 Bedroom. Pool, Wifi

Oceanfront Balcony Overlooking Pool + Sandy Shores

Oceanview Oasis with 2 private balconies

Clean and Comfy, Close to Beach and Shopping

Oceanfront Bldg.| 2 pools | Tennis | Game Room

2b 2b condo! 2 master bedrooms! rehoboth beach
Other holiday rentals with a pool

Fabulous Ocean Block Condo!

Renovated townhouse 2 miles to Ocean City/Fenwick!

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

Stunning views from Beautiful 2 BR Condo

2BR Waterfront | 1st Floor | Patio | Pool | W/D

Bayside Family Oasis - Perfect for Large Families

North OC- short walk 2 beaches and park

Waves 203 Oceanside 3BR 2BA Condo by the Ocean
Quick stats about holiday rentals with a pool in Fenwick Island

Nightly prices starting at
Fenwick Island holiday rentals start at € 387 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!
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