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

Renovated Condo Near Outlets, 3.5 Miles to Beach
Enjoy your stay in this recently renovated and beautifully furnished two-bedroom, two-bathroom 3rd-floor condo conveniently located 3.5 miles from the Rehoboth Beach boardwalk, and 4.5 miles from Lewes Beach. The proximity to the beaches, stores, and restaurants make this condo a great spot to spend a fun-filled vacation at the beach. Our condo amenities include a community pool*( seasonal), free parking, free WiFi, smart TV, washer, and dryer. We supply all the sheets & towels for your stay.

Sunrise Studio - Ocean Front, on Boardwalk, Pool!
Our quiet ocean front studio has all the comforts of home with amazing views, a balcony hovering over a serene stretch of the Boardwalk, and is just steps away from restaurants, shops, arcades, rides and all of the best boardwalk foods! Walkable to everywhere in town! If you want to venture out further, a bike rental shop is just a few doors away! Enjoy a bike ride through town or to Dewey Beach. If you are looking for a scenic ride, enjoy the bike trails to Cape Henlopen State Park and Lewes.

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool
Spring Break Getaway! Fresh New Photos! Perfect location to enjoy the holiday season in Southern DE for upcoming events, such as Polar Bear Plunge, Super Bowl Weekend or Dewey’s Famous Winter Gala! Whether you're planning a beach vacation, a business trip, or a shopping spree at the nearby Outlets, this condo is the ideal retreat. Conveniently located near dining, shopping, scenic trails, and just a short drive to Lewes, Rehoboth, and Dewey by having everything you need for a memorable stay.

Tiny house w/ Pool on water near Beaches / turf
Enjoy a peaceful waterfront stay in our custom-built tiny house, located on Cedar Creek just off Route 1. Conveniently situated only 10 minutes from Delaware Turf and 15 minutes from the beach. The home comfortably sleeps four and includes hot tub access. We live on-site and are happy to assist throughout your stay. Ideal for families, pets (please review rules under “The Space” section), contractors, and long-term renters. Perfect for travel nurses & remote workers – Monthly stays welcome!

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.

First Floor Comfort and Convenience
This first floor condo is conveniently located in a family-friendly community with all you need within walking distance, including several restaurants and a grocery store. A short and easy 3-mile drive to Lewes Beach and the charming town of Lewes makes this an ideal location. Amenities include access to two pools, tennis courts, pickle ball courts and kids play area. The Georgetown Lewes Biking/Walking Trail, that connects to the town of Lewes, is literally steps from our front door.

Luxury water-view condo with high-end finishes
Luxury 2-bedroom condo at The Residences at Lighthouse Cove located in the heart of Dewey Beach. This unit features great views of Rehoboth Bay and is only 1 block from the Atlantic Ocean. Easy walk to Dewey Beach’s shops, restaurants, and nightlife. This unit sleeps up to 6. There is a master bedroom with a king bed and ensuite bathroom. The second bedroom has a queen bed. There are 2 twin-size fold-away beds. Lounge at private rooftop pool, fire pits, & grills for Residences

Cozy Lewes Retreat | Pool, Short Drive 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.

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE
2 Bedroom Condo Top Floor (3rd Floor) - Waterfront in Lewes/Rehoboth Beach DE Great Scenery Views - The Residence at Rehoboth Bay. *Community Pool available during in-season (8am-8pm), typically opens Labor Day weekend **No cleaning fee Nearby amenities and attractions include: Rehoboth Beach Boardwalk (6 Miles) Cape Henlopen State Park (8 Miles) Dewey Beach, DE (7 Miles) Bethany Beach, DE (18 Miles) Ocean City, MD (32 Miles) Shopping Outlets (4 Miles)

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.

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.
Popular amenities for Sussex County rentals with a pool
House rentals with a pool

The Red Chalet

PRiVATE Pool, Peaceful, and Close to Bethany Beach

Bayside Family Oasis - Perfect for Large Families

A Wave from it All - Beach, Bike Trail & Shopping

Coastal Retreat | Lakefront | Pool | Hidden Gem

Coastal Charm-Bethany Beach/Golf Home in Bear Trap

The Jungalow - Dog Friendly, Fenced in & Pool

Dog Friendly Fenced 3BR King Bed
Apartment rentals with a pool

Family Friendly Top Floor Condo Near Boardwalk

Cozy Condo on Silver Lake - Walk to the beach!

Villa Del Sol, Beautiful stay near beaches/outlets

Salt Air Retreat - Rehoboth Beach

Where the Locals Live!!

10 mins to beach-2 BR-Sleep Six-Pool-Beach PK pass

Mimi’s Place @ The Villages of 5 Points in Lewes

2b 2b condo! 2 master bedrooms! rehoboth beach
Other holiday rentals with a pool

Beautiful Updated Condo Waterfront, Pool, Sunsets

Luxury Dewey: Rehoboth Bay Front*1 Block to Ocean!

Lakefront condo blocks from the beach

Coastal Cozy “Your relaxed retreat at the beach!”

Dog friendly| community pool | gym| kayak| bayside

Luxe Lewes Townhouse: Pool, Roof Deck & Bike Trail

The Peach at the Beach ~ nice pool!

Family friendly house in Rehoboth Beach near pool
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- Rentals with pools United States
- Ocean City Beach
- Ocean City Boardwalk
- Chincoteague Island
- Cape May Beach NJ
- Wildwood Crest Beach New Jersey
- Broadkill Beach
- Assateague Island National Seashore
- Rehoboth Beach
- Willow Creek Winery & Farm
- Bayside Resort Golf Club
- Jolly Roger Amusement Park
- Northside Park
- Cape Henlopen State Park
- Assateague State Park
- Fenwick Island State Park Beach
- Delaware Seashore State Park
- Wildwoods Convention Center
- Dover Motor Speedway
- Gerry Boyle Park
- Roland E Powell Convention Center
- Mariner's Arcade
- Ocean City Boardwalk
- Hawk Haven Vineyard & Winery
- Bethany Beach Boardwalk




