Holiday rentals with a pool in Fenwick Island

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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

Home in Montego Bay

4.95 out of 5 average rating, 255 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

Townhouse in Sussex County

4.98 out of 5 average rating, 51 reviews

Waterfront Haven: Moments from the Beach!

POOL IS NOW OPEN-LINENS & TOWELS PROVIDED + PREMIUM AMENITIES INCLUDED - NO ADDITIONAL COST! Welcome to FENWICK BAY VISTA! Enjoy a relaxing stay in this stunning waterfront luxury townhouse on the Little Assawoman Bay, with ample water views and only 10 minutes from the beach! This airy 2500 sq. ft., 3-level, 3-bedroom, 3.5-bath home sleeps 8 and boasts incredible views of the bay. Nestled in a boutique resort community, you’ll enjoy a bayside pool, gym, sport courts, kayaking, and plenty more!

Guest favourite

Home in Montego Bay

4.94 out of 5 average rating, 104 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.

Guest favourite

Home in Selbyville

5 out of 5 average rating, 6 reviews

Family + Pet-Friendly Home Near Fenwick Island

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

Home in Selbyville

5 out of 5 average rating, 19 reviews

Coastal Comfort: 4BR 3BH House Pool & Rooftop Deck

Welcome to your dream beach getaway in Selbyville! Immerse in luxury at our modern 4BR home, where comfort meets elegance. • Stunning rooftop deck with panoramic views • Shared outdoor swimming pool for refreshing dips • Spacious kitchen with a large island, perfect for gatherings • Two master bedrooms, each with private bathrooms • Game room with ping pong & foosball • Much more! Start each day with breathtaking sunrises from the deck. Book now for an unforgettable beachside experience!

Superhost

Condo in Montego Bay

4.73 out of 5 average rating, 26 reviews

Beach Condo 90 Steps to the beach!

Just 90 steps from the beach and a short walk to multiple restaurants and attractions! This beachfront property offers the perfect getaway. This condo includes a bathroom, living room, dining area, a fully equipped kitchen and a balcony to enjoy the refreshing ocean breeze scent. There is 2 full beds and 2 loft beds in the master room. Enjoy complimentary private parking and free WiFi. Towels and bed linens are provided, and the condo has a private entrance for added privacy. Book now!!!!

Guest favourite

Townhouse in Selbyville

4.91 out of 5 average rating, 219 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.

Superhost

Condo in Ocean City

4.82 out of 5 average rating, 274 reviews

🏖 *Ocean *Ocean *Ocean* 🏖 Beautiful Condo!!

Oceanfront OCMD! An Awesome 2 Bedroom & 2 FULL Bath Condo in the Atlantis Condominium. Perfect for Families, that sleeps 8! This Beautiful Condo is Self Check-in and is walking distance to Restaurants, Shops, Attractions & Most Importantly - only steps to THE BEACH!! Large Community Outdoor Pool is on site. Many Toys, Games, Puzzles & a Bunk Bed perfect for children. Unit is No Smoking of Any Kind. Also No Pets, large groups (8 max.) or senior week rentals permitted. Book Today!

Superhost

Condo in Ocean City

4.85 out of 5 average rating, 202 reviews

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.

Guest favourite

Home in Rehoboth Beach

4.97 out of 5 average rating, 118 reviews

Hot tub, Pool, Relax, Shop & Dine, Sleeps 8, Games

A convenient central location between Rehoboth/Dewey and Lewes Beaches. You can walk to the neighborhood pool (available Memorial Day- Labor Day). Stylish, clean and comfortable, our house is an entertainer's dream. A huge 11 ft island and open concept living space is perfect for gatherings. Each bedroom is curated for comfort. The peaceful, private back deck is perfect to layout. We go above and beyond to ensure the best experience for our guests.

Guest favourite

Condo in Ocean City

4.92 out of 5 average rating, 230 reviews

Sun, Sand & Sea | Your Cozy Oceanfront Hideaway

**2025 guests: Our pool and hot tub are in the process of being renovated and will be closed during your stay. This does not impact our condo, but you will not be able to use these amenities.** -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!

Top Guest favourite

Apartment in Ocean City

4.98 out of 5 average rating, 240 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!