Vacation rentals with a pool in Fenwick Island

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.

4.94 out of 5 average rating, 278 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!

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.

5 out of 5 average rating, 102 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!

Multiple Condo units stand adjacent to calm waters, featuring private boat slips. Each unit is accessible by a balcony, surrounded by well-kept greenery. Cloudy skies reflect on the water's surface, while a few boats are visible moored nearby.

4.86 out of 5 average rating, 148 reviews

Bayfront Family Friendly Beach Condo w/BoatSlip

Come enjoy our Cozy Bay/Canal Water Front Beach Condo. 1 bedroom, 1 bath condo with a Boat Slip & Pool and just a few blocks from the Beach and Northside Park, in the desired Hidden Harbor Community. Also just a short walk to the Beach Bus Stop. ** For July and August we try to rent Saturday to Saturday, 7 night stays! ** Contact me if you're interested in shorter stays. Pool Open Memorial Day to Labor Day Xfinity WiFi and Smart TV for your streaming needs. New Mattress and TV added 2024!

A spacious common area is designed with high-end leather sofas and armchairs, arranged around a central coffee table. Bright natural light enters through large windows, highlighting the tasteful decor. A dining area is visible in the background, creating a warm and inviting environment.

4.88 out of 5 average rating, 132 reviews

Upscale House Steps 2 Ocean 3 Balconies Pool Bikes

Book 2 nights, get 1 night FREE stays thru April 16. inquire before booking This is a Ocbeachfrontrentals .com premier property 24/7 SUPPORT LINEN & TOWELS PROVIDED This spacious 3-level beach home is perfect for family & friends. Relax on 3 balconies, hang out poolside, go for a bike ride or walk to the beach. With 5BD/3.5BA, high-end furniture, high-speed WiFi, 6 flat screens, a Weber grill, and a foosball table, there's room for everyone! Must be 25 or older unless accompanied by adult

4.92 out of 5 average rating, 235 reviews

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

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.

A comfortable living area features a gray sofa with blue accent pillows and a textured rug. Large sliding glass doors offer a view of the ocean and access to a private balcony with outdoor seating. Natural light fills the space, creating a welcoming atmosphere.

4.98 out of 5 average rating, 244 reviews

Cozy oceanfront condo with stunning ocean views

Fully updated 1 bed/1 bath oceanfront condo in a quiet, mid-rise building with a beachfront pool in uptown OC. The perfect unit for a quick romantic getaway, long weekend, or family vacation. We are happy to accommodate the dates and timeframes that meet the needs of our guests. If possible, please consider these recommended timeframes for your booking: Memorial Day - Labor Day -7 Nights, Fri-Fri or Mon-Mon -3 Nights, Fri-Mon -4 Nights, Mon-Fri Labor Day - Memorial Day -Any 2 Nights

4.82 out of 5 average rating, 114 reviews

Lovely beach-front condo with pool and views

Kick back and relax in this calm, stylish space. This one-bedroom condo is the perfect space for 1-2 couples, or a family. You have floor-to-ceiling beach views, plus amazing sunrises and sunsets from the two separate balconies. The kitchen is well equipped to cook every meal, or eat out at Ocean City's many restaurants. Your stay also comes with 4 pool passes for accessing the onsite seasonal outdoor pool (viewable from the unit) and access to the building’s tennis/pickleball courts!

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.

4.95 out of 5 average rating, 167 reviews

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

Guest suite in Ocean Pines

A bright, open kitchen area is visible, featuring modern appliances and a spacious countertop. Large windows allow natural light to fill the room. A comfortable chair sits beside a decorative rug, while a sleek ceiling fan contributes to the airy atmosphere.

4.99 out of 5 average rating, 135 reviews

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.

Townhouse in Bethany Beach

A spacious living area is furnished with a comfortable gray sofa, an armchair, and a coffee table. Natural light enters through windows, while a ceiling fan offers a cooling breeze. A television is mounted on the wall, and a cozy fireplace adds warmth to the space.

4.85 out of 5 average rating, 374 reviews

Spacious Bethany Beach Retreat Pool Pickle Ball

Fully Equipped, all you need is a beach towel! Listed as one of Delaware's top Airbnb's! This is a perfect get away for family and friends. The beach is 1.5 miles away and the amazing pool is a 2 minute walk. The kitchen is fully equipped and the patio and yard add space for your stay. Tennis and Pickleball court access. Linens included and everything you may have forgotten. Families and friends return again and again to make memories.

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.

4.88 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!

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, 268 reviews

Oceanfront Paradise | Pool | Hot Tub | Beach

-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! **2026 guests: Our pool and hot tub are in the process of being renovated and will be closed during your stay. They will re-open after Memorial Day**

Popular amenities for Fenwick Island rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 35 reviews

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

5 out of 5 average rating, 12 reviews

A charming house with a light blue exterior is surrounded by lush greenery. A spacious deck features potted plants and outdoor seating. Colorful Adirondack chairs in red and blue are placed around a small fire pit on a patterned stone patio, inviting relaxation.

Home in Ocean Pines

Cozy beach home away from home!

A screened-in room features a comfortable sectional sofa adorned with pillows, alongside a glass-topped table. Two high-backed chairs are positioned at a small table, with a view of a serene landscape and sunset reflected in the glass doors.

4.97 out of 5 average rating, 30 reviews

Waterfront View | Mallard Lakes | Resort Amenities

The exterior of a two-story house is showcased, featuring a modern design with blue shingles and white trim accents. Landscaping includes small shrubs and decorative gravel, while a pathway leads to the entrance. The mailbox is visible near the curb, adding to the welcoming appearance.

4.89 out of 5 average rating, 53 reviews

Welcome to the Pearl of the Oyster!

A spacious living area is furnished with two dark leather sofas, providing ample seating. A ceiling fan enhances airflow. The open layout connects to a dining area featuring wooden chairs, while the kitchen is visible in the background, showcasing modern appliances and cabinetry.

4.94 out of 5 average rating, 232 reviews

Right behind Alley Oops & Crab Bag. Walk to beach

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.

5 out of 5 average rating, 27 reviews

Bayside Family Oasis - Perfect for Large Families

A sunlit room features a checkered table surrounded by wooden chairs, with a woven basket at its center. A comfortable sofa is positioned against the wall, and large windows with bamboo shades offer a view of the outdoors, enhancing the airy atmosphere.

4.94 out of 5 average rating, 17 reviews

Ocean Breeze

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

Condo rentals with a pool

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.

4.79 out of 5 average rating, 121 reviews

Spacious Direct Oceanfront 1BR Condo w/Balconies

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, 345 reviews

Oceanfront Family Oasis: Pool, Beach & Parking!

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.

4.86 out of 5 average rating, 102 reviews

Oceanview Oasis with 2 private balconies

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.

4.96 out of 5 average rating, 125 reviews

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

Superhost

4.84 out of 5 average rating, 178 reviews

Love Above the Waves-OceanView/Rooftop Heated Pool

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.

4.94 out of 5 average rating, 315 reviews

Direct Oceanfront with a View and Amenities Galore

4.96 out of 5 average rating, 177 reviews

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.

Condo in Rehoboth Beach

Sunrise Studio - Ocean Front, on Boardwalk, Pool!

The kitchen is equipped with modern appliances including a refrigerator, stove, microwave, and dishwasher. White cabinetry provides ample storage, and a light-colored countertop offers workspace. The back wall features a decorative tiled backsplash, while various kitchen items are displayed on top of the cabinets.

4.74 out of 5 average rating, 124 reviews

2 bed/2 bath/3 blocks from beach in Ocean city MD

Other vacation rentals with a pool

An outdoor courtyard features a round table surrounded by six mesh chairs under a blue umbrella. A patterned area rug adds color to the space. Wooden steps lead to the entrance of the unit, complemented by the blue siding of the building.

5 out of 5 average rating, 10 reviews

Welcome to Splash Pad-pools, beach + private patio

5 out of 5 average rating, 12 reviews

Guesthouse in Lewes

Pool, dog friendly, fenced yard in Lewes

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.

5 out of 5 average rating, 87 reviews

Modern coastal beach home in West Fenwick Island

A large swimming pool is surrounded by a spacious deck featuring several lounge chairs. The clear blue water is inviting, and the area is enclosed by a fence. A few trees are visible in the background, providing a touch of greenery against the blue sky.

4.96 out of 5 average rating, 73 reviews

Canal Front Condo 2 Blocks 2 Beach & Park Sleeps 4

4.97 out of 5 average rating, 31 reviews

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.

Apartment in Ocean City

2 BR 2BA North Ocean City Condo

5 out of 5 average rating, 16 reviews

A well-lit bedroom features two full-size beds with colorful bedding displaying floral patterns. A dresser, a ceiling fan, and a large wall-mounted mirror are visible, contributing to the room's spacious feel. Natural light enters from a window, enhancing the bright atmosphere.

Apartment in Ocean City

Let's go to the Beach!

5 out of 5 average rating, 34 reviews

A chef’s kitchen showcases high-end appliances and granite countertops, with a dining area visible in the background. Colorful wall decor features beach-themed art and decorations. Natural light streams through the windows, enhancing the welcoming vibe of the space.

Townhouse in Ocean City

Large Family Oasis Steps from the Sand