
Holiday rentals with a pool in Delaware
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Delaware
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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.
LocationValuePool
4.96 out of 5 average rating, 55 reviews
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.
LocationValueCheckout
4.97 out of 5 average rating, 241 reviews
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.
ValueFamilyAccuracy
4.99 out of 5 average rating, 174 reviews
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.
LocationFamilyBeach
4.94 out of 5 average rating, 106 reviews
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.
LocationFamilyCheck-in
4.99 out of 5 average rating, 118 reviews
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.
FamilyValueNearby
4.95 out of 5 average rating, 322 reviews
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.
ValueFamilyLaundry
4.94 out of 5 average rating, 235 reviews
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!
FamilyValueKitchen
4.98 out of 5 average rating, 101 reviews
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.
FamilyLocationAir conditioning
5.0 out of 5 average rating, 67 reviews
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!
LocationFamilyAccess
4.91 out of 5 average rating, 112 reviews
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.
ValueLocationAir conditioning
4.88 out of 5 average rating, 249 reviews
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.
LocationFamilyBarbecue
4.94 out of 5 average rating, 184 reviewsPopular amenities for Delaware rentals with a pool
House rentals with a pool

A Bethany Beach Gem 1.5 miles to Ocean Pickle Ball
ValueLocationHospitality
4.94 out of 5 average rating, 218 reviews
Modern Beach House w/ Private Pool
LocationValueHospitality
4.97 out of 5 average rating, 102 reviews
The Hidden Gem•Heated pool•Pickleball Court
FamilyValueAir conditioning
4.99 out of 5 average rating, 86 reviews
Spacious 5 Bedroom w/Pool, Patio and Theater
LocationFamilyBiking
4.81 out of 5 average rating, 81 reviews
Ruby's Retreat at the Beach
LocationFamilyCleanliness
4.9 out of 5 average rating, 29 reviews
Private Pool! Charming 4bdrm, BayVista Beach House
LocationFamilyBathroom
5.0 out of 5 average rating, 78 reviews
Coastal Cottage! Walk to Beach!
FamilyValueBarbecue
5.0 out of 5 average rating, 90 reviews
Dog Friendly Fenced 3BR King Bed
ValueFamilyComfort
4.97 out of 5 average rating, 65 reviewsCondo rentals with a pool

Beautiful condo in Villages of Five Points, Lewes
FamilyLocationGetting around
4.95 out of 5 average rating, 159 reviews
Renovated Condo Near Outlets, 3.5 Miles to Beach
FamilyLocationCleanliness
4.98 out of 5 average rating, 220 reviews
Cozy Creekwood Condo - Relaxing Getaway - W/ Pool
ValueFamilyDecor
4.98 out of 5 average rating, 307 reviews
Condo 2 Bedroom Waterfront Lewes/Rehoboth DE
ValueLocationDecor
4.99 out of 5 average rating, 219 reviews
2BR Coastal Escape with Pool Near Rehoboth Beach
FamilyLocationCheck-in
4.95 out of 5 average rating, 119 reviews
SeaRenity, beach, pool, biking, outlets shopping
LocationFamilyWi-Fi
4.96 out of 5 average rating, 142 reviews
Sunrise Studio - Ocean Front, on Boardwalk, Pool!
ValueLocationLayout
4.94 out of 5 average rating, 198 reviews
Beach Escape Condo w/ Pool - Lewes Beach 3.5 Miles
LocationValueAccess
4.97 out of 5 average rating, 131 reviewsOther holiday rentals with a pool

Lewes Home | Pool, Dogs Welcome, Fenced Yard
FamilyValueHospitality
5.0 out of 5 average rating, 36 reviews
‘Dockside Retreat’ -pool, minutes to OC/beaches
LocationFamilyAmenities
5.0 out of 5 average rating, 63 reviews
Mi Casa at Bay Knolls
FamilyLocationHospitality
5.0 out of 5 average rating, 9 reviews
The Beach Chalet
FamilyLocationPool
4.67 out of 5 average rating, 21 reviews
Anchors Away, Your Dream Getaway in Fenwick Shoals
FamilyLocationAccuracy
4.97 out of 5 average rating, 33 reviews
Cozy Coastal Haven: Beach Community Charm
FamilyLocationAmenities
4.98 out of 5 average rating, 94 reviews
Spacious Family Beach House with Private Hot Tub
ValueLocationSleep quality
4.93 out of 5 average rating, 29 reviews
Water Views: Balcony, Pool & Easy Parking
FamilyValueDecor
4.99 out of 5 average rating, 92 reviewsDestinations to explore
- Tiny house rentals Delaware
- Family-friendly rentals Delaware
- Pet-friendly rentals Delaware
- Villa rentals Delaware
- Private suite rentals Delaware
- Condo rentals Delaware
- Rentals with a hot tub Delaware
- Beachfront rentals Delaware
- Rentals with breakfast Delaware
- Boutique hotels Delaware
- Waterfront rentals Delaware
- Rentals with lake access Delaware
- Rentals with a kayak Delaware
- House rentals Delaware
- Rentals with a sauna Delaware
- Apartment rentals Delaware
- RV rentals Delaware
- Cottage rentals Delaware
- Rentals with an accessible height toilet Delaware
- Hotel rooms Delaware
- Mansion rentals Delaware
- Bed and breakfasts Delaware
- Beach condo rentals Delaware
- Holiday home rentals Delaware
- Guesthouse rentals Delaware
- Lakehouse rentals Delaware
- Farmstay rentals Delaware
- Townhouse rentals Delaware
- Rentals with beach access Delaware
- Rentals with pools United States





