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.

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Top 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, 276 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!

Guest favourite
The living room features a spacious seating arrangement with a red armchair and a gray chair facing a wooden TV stand. Large sliding glass doors lead to the private oceanfront balcony, allowing natural light to fill the space and offering views of the ocean.
Apartment in Ocean City
4.79 out of 5 average rating, 121 reviews

Spacious Direct Oceanfront 1BR Condo w/Balconies

Spacious 1 bdr, 1bath direct oceanfront condo w/ private oceanfront balcony for sunrises and a private bayside balcony for sunsets! 15th floor. 1 min walk to beach. Outdoor pool. Fountainhead Towers Condo is located on 116th St off Coastal Hwy on the oceanfront. Food lion, CVS, DD, ice cream, wawa, convenient stores & restaurants all within close walking distance WEEKLY RENTALS ONLY: Sat to Sat GUESTS PROVIDE SHEETS & TOWELS Plus on arrival $50 CASH fee that includes parking for a week NO PETS

Superhost
A spacious living area is furnished with a light-colored couch and an armchair, complemented by a ceiling fan above. A flat-screen TV sits on a wooden media console, while a dining table is positioned in the background, leading towards an updated kitchen area.
Apartment in Ocean City
4.83 out of 5 average rating, 179 reviews

☀️ Enjoy the Beachlife!! —>2Bed & 2Bath Condo ☀️

Relax with the whole family at this peaceful OCEANFRONT Condo in OCMD! Updated 2 Bedroom & 2 Full Bath on the 1st floor Atlantis High-Rise that sleeps 8. Most Importantly- Only Steps to THE BEACH! Unit is Self-Checkin & is walking distance/short drive to many Restaurants, Shops, Attractions, etc. Large Outdoor Pool is on site (seasonal). Toys, Games, Puzzles & is perfect for families with children. NO Smoking allowed. No Pets or Large groups(8 max) or senior week rentals permitted. Book Today!

Top guest favourite
The living area features comfortable electric reclining sofas facing a coffee table. Large windows provide views of the ocean, while a dining area and modern kitchen are visible in the background, creating a spacious and inviting atmosphere.
Apartment in Ocean City
5 out of 5 average rating, 119 reviews

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

Top guest favourite
A multi-story condo building showcases a modern architectural design with a light yellow exterior. The structure features multiple balconies with white railings and has a teal roof. The ground level offers covered parking beneath the building, enhancing accessibility.
Apartment in Ocean City
4.95 out of 5 average rating, 120 reviews

BEST SPOT IN OCEAN CITY

Beautiful spacious 3 bedroom 2.5 bath penthouse condo that offers it all. Tall ceilings, open floor plan, spectacular ocean view and gorgeous sunrise and sunsets. Rooftop pool, full kitchen access with a large bar and new appliances. Steps away from the beach. Enjoy great food from one of the many restaurants ocean city has to offer. Great for family vacation. Many activities to choose from including clubs, boardwalk, water park, mini golf, amusement park, indoor ice skating rink, and shopping,

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
4.97 out of 5 average rating, 138 reviews

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.

Guest favourite
Apartment in Ocean City
4.87 out of 5 average rating, 211 reviews

🌊Oceanfront studio w/ amazing views & amenities🏖

Efficiency/studio condo oceanfront in Golden Sands. Queen size Murphy bed (has 13 inch thick serta mattress, same as a regular bed), couch, loveseat, full kitchen, bathroom, washer & dryer, ac/heat, parking, awesome amenities. This building is beautiful with amazing views. We clean & stock this condo ourselves so you'll get the owners personal touch without the crazy extra fees that rental companies charge. I love to make everyone's stay as wonderful as possible. Please read entire listing.

Top guest favourite
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.
Apartment in Ocean City
4.96 out of 5 average rating, 107 reviews

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! 🌊☀️

Superhost
A spacious living area features a large wall-mounted entertainment center with a flat-screen TV. Comfortable seating options include a striped sofa and a patterned armchair. Sliding glass doors provide unobstructed ocean views and natural light, enhancing the inviting atmosphere of the space.
Apartment in Ocean City
4.85 out of 5 average rating, 106 reviews

Luxurious Oceanfront Retreat with Amazing Views!

Beautifully renovated oceanfront condo with panoramic ocean views and direct beach access. Building indoor pool and hot tub are closed for a full HOA renovation and upgrade, scheduled to reopen in May 2026 and be refreshed and like new for the 2026 season. By booking, you acknowledge the pool and hot tub may be unavailable during your stay and agree no discounts or compensation will be provided for this closure unless confirmed in writing in advance of your reservation and booking.

Guest favourite
A modern living area features a spacious gray sofa and a wooden coffee table, complemented by a cozy area rug. Large glass doors open to a private oceanfront balcony, allowing natural light to fill the space. Decorative accents include a wall-mounted surfboard and a round mirror.
Flat in Ocean City
4.98 out of 5 average rating, 266 reviews

OceanFront-Fireplace-sleeps4-Balcony-King-Disney+

Welcome to Salty Shark - direct oceanfront studio! This remodeled studio sleeps 4 and is in North Ocean City near great restaurants, bars, and 58 acre North Side Park. The park has sports fields, a recreation center, a walking/biking path, crabbing pier, playground, and outdoor fitness area. Building has outdoor pool in summer too! The unit features a King Murphy bed, and a Queen sofa bed. There's also an outdoor pool open in summer months!

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
4.88 out of 5 average rating, 163 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!

Top guest favourite
The kitchen area features modern cabinetry and stainless steel appliances. A large kitchen island with seating is complemented by woven bar stools. Natural light enters through a window, enhancing the open space and inviting atmosphere.
Flat in Frankford
4.98 out of 5 average rating, 126 reviews

Sunshine By The Sea near Bethany Beach

Enjoy Southern Delaware and everything it has to offer in this stylish, family friendly condo located just 1.5 miles from the beach. Completely remodeled in 2022 and thoughtfully furnished to create modern, relaxing coastal getaway. Pool access 2026 Opens Memorial Day Weekend Closes TBD (through LDW possibly still open first week in September) Hours: 11am-7:45pm

Popular amenities for Fenwick Island rentals with a pool

Quick stats about holiday rentals with a pool in Fenwick Island

  • Nightly prices starting at

    Fenwick Island holiday rentals start at £345 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!