Holiday rentals with a pool in Delaware

Gorgeous 5BR, 4.5BA, in town, pool, hot tub, beach

In town Rehoboth, with Rise Up and the boardwalk just a quick walk away, you'll love this home with a POOL AND HOT TUB (April-Oct). There's a ton of natural light, plus comfy queen and king beds, nice new linens, and more. Please note there is a security camera on the pool and in the pool equipment area for your safety. Dogs are allowed for a $75 fee per stay for first pet, $25 per additional (additional pet fee after the first will be billed after your reservation is complete). Maximum 3 dogs.

Villa Del Sol, Beautiful stay near beaches/outlets

This bright and beachy 3 br/2 bath stay in Lewes, De comfortably sleeps 6 to 8 people. Just a short drive (10-15 min) to Lewes Beach and Cape Henlopen Park. Villa del Sol is a great beach escape with plenty of parking, as well as a community pool (open 5/27 - 9/5). Rehoboth Beach is also just 5 miles away, or you can go shopping at the nearby outlets. Walk to Bushel’s or Crooked Hammock for dinner, or cook something up with enough room to seat the whole family! At least 25 years old to book.

Cozy Rehoboth Beach Condo w/ 2 bedrooms

This condo is a boho getaway tucked away in a quiet enclave conveniently located on the beachside of Highway 1. It has dedicated parking in front, plus an additional spot for a second car. This condo it is a two bedroom/two bathroom unit. Full kitchen and a dining area that seats up to six. The condo is on the second floor with one stair flight. The beach is a 20 minute walk, 10 minute bike ride, or 5 minute drive Community pool on site provides an extra place to relax and cool down.

Perfect Rehoboth Beach Getaway with Hot Tub

Discover the epitome of coastal comfort in newly remodeled home. Dive into luxury with a private hot tub, where the bubbling warmth provides the perfect escape. Unwind in the chic interiors, adorned with modern furnishings. Stay connected with complimentary Wi-Fi as you plan your outings to the nearby beaches, bustling boardwalk, and local attractions. Steps away from tax free outlet shopping. With convenience at every turn, this home ensures a perfect blend of tranquility and accessibility.

Coastal Modern Condo • Balcony, 2 Baths, East Rt 1

☀️ Your Rehoboth Beach Escape Why guests love staying here: • Community pool 🌴 • 2 full baths • Private screened balcony 🌿 • East of Route 1 • Strong central AC ❄️ • Split-bedroom layout for added privacy • Beach chairs & towels included 🏖️ • Fast WiFi + smart TVs • Plenty of FREE parking • In-unit washer & dryer • Minutes to beaches, boardwalk, restaurants & shopping • Quiet community close to everything Perfect for couples, families, girls’ weekends, and relaxing coastal getaways.

Modern & Cozy Retreat | Pool | Close to Beaches

Enjoy a relaxing Lewes getaway nestled just off Coastal Highway, with easy access to beaches, dining, and local attractions. Less than 5 miles to Lewes Beach and less than 7 miles to Rehoboth and Dewey Beach, making it easy to enjoy the ocean, boardwalk, and everything the area has to offer. Just minutes from Nassau Valley Vineyards, Georgetown-Lewes Trail, Cape Henlopen State Park, historic downtown Lewes, great restaurants, breweries, and tax-free shopping at Tanger Outlets.

Cozy Woodland Cottage

Enjoy the sounds of nature when you stay in this unique place. Located less than 5 miles from downtown Lewes and Delaware Beaches. The cottage guest house is nestled in the woods adjacent to a tree house overlooking a tranquil pond with a calming fountain sounds. On the main property guests have access to a in ground swimming pool (seasonal) with a 60 foot lap lane and slide, schedule times with hosts.. The backyard also includes an organic garden, playground and 🐔 chickens.

The Big Chill at Bethany Beach

The Big Chill at Bethany Beach is our whimsical family beach house in the Clearwater community, just two miles from the Bethany Beach boardwalk. We've thought of everything so that you don't have to. Spacious bedrooms with fine bed and bath linens; fully stocked kitchen with cookware and spices; smart TVs and Nintendo Switch; lots of books and board games; screened-in porch and open-air deck; and comfortable furnishings throughout. And bring your dogs; they're family, too!

Lewes Carriage House-Hamptons Style Pool & Hot Tub

Lewes Carriage House is a 5 Star, one-of-a-kind, architecturally designed luxury escape nestled on a 4-acre estate w/ resort style pool, grounds & private spa/hot tub. Perfect for private, romantic honeymoon & baby-moon escapes, anniversaries, as well as forest bathing & wellness retreats. - 5-10 minute drive to historic downtown Lewes, boutique shopping and Cape Henlopen State Park beaches. - Lush perennial gardens, an old-growth forest, native wetlands & 1-acre pond.

The Little house W/ Pool & Spa

Nestled in the woods and just steps from cedar creek, The little house is a charming, pet-friendly tiny house that offers a magical escape from the everyday. Thoughtfully designed and comfortably sleeping up to 6 guests, this unique hideaway is perfect for couples, families, or friends looking to unwind and relax. 10 Minutes from DE turf, 20 minutes from the beach, directly beside yogi bear. Perfect for travel nurses & remote workers – Monthly stays welcome!

Dodd House Beach Home w/private pool and hot tub

Saturday to Saturday bookings from the third week in June through mid August. Large 5 bed 3.5 Bath Luxury Home with pool and hot tub. Parking for six to eight cars. ARRIVE, STOCK UP, AND NEVER LEAVE IF YOU CHOOSE! GET YOUR FAMILY AND FRIENDS TOGETHER SAFELY! This large 4,500 square foot rental unit includes 5 private BR, 3.5 BTH, and sleeps 18! Pool opens May 15th until September 30th. Outdoor fire pit with some wood provided. 25 and older please.

Hot tub, Pool, Shop & Dine, Sleeps 8

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.