
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.

Right on Silver Lake walk to the beach and town!
Completely renovated, right on Silver Lake! On the most secluded part of Rehoboth Beach watch the sun rise and wildlife sitting at your patio! Park your car and walk or bike everywhere. Steps from the pool and three blocks across Turtle Bridge to get to the less crowded part of the beach. Five blocks from Rehoboth Avenue, where most restaurants and shops are. Full kitchen, Central heat/air, Smart TV, Cable and High speed internet. Pickleball, Tennis, Basketball and Tennis courts next door

Comfy and Convenient 2 bedroom/2 bath condo
Bright & spacious 1st floor, 2 bedroom/2 bath condo (sleeps 6) in Eagles Landing is perfect for families, couples or friends. Recently renovated floors, appliances and countertops, new furniture. We are an easy 5-minute drive from the beach. The community has 3 pools. Our unit includes parking, a full kitchen, living room, dining room (seats 6), washer/dryer, dishwasher, wi-fi. Downtown restaurants, outlet shopping, & boardwalk are all within 2 miles. We provide necessities so you pack less!

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 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.

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool
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.

Buoyed Spirits 2 BR 2B 1st floor condo
2 bedroom, 2 bathroom ground floor apartment in a nice neighborhood, off Rt 1. 1.5 miles from the beach! The community has 3 swimming pools and tennis courts. Master has a king-sized bed, the second room has 2 twins. Sofa in living room is a pull out. Two bikes with helmets and locks also come with the rental, as well as 2 tennis rackets. Towels (including beach towels) and linens provided, BUT YOU WILL NEED TO LAUNDER THE SHEETS AND TOWELS BEFORE YOU LEAVE.

Beautiful Beach House in Rehoboth
Only two summer weeks left! July 25 - August 1. August 15 - August 22. Book now! Gorgeous modern spacious house in Rehoboth Beach with a large open floor plan on a quiet street. Five bedrooms/3.5 baths. Walk to town/beach - four blocks from beach right off Rehoboth Ave. Private pool with two levels of decks, grill and table/umbrella on top deck. Big open kitchen/dining/living area, over 3000 square feet of space overall.

Beautiful Waterfront Home-Private, Clean, Relaxing
A beautiful and peaceful get-away all year round! Bright and sunny 3 bed/2 bath waterfront home with wrap-around deck. Fully stocked, community pool, walking trails, kayaks and more! Visit Rehoboth or Lewes Beaches (10 miles away), Cape Henlopen and tax-free outlet shopping (6 miles away)! Great for families, water lovers, and bird lovers! Sunday to Sunday weekly rentals *only* and no pets from Memorial Day to Labor Day.
Popular amenities for Sussex County rentals with a pool
House rentals with a pool

Quiet 3BR Coastal Home Minutes to Bethany Beach

Rehoboth-Lewes Beach House by the Bay

Modern Beach House w/ Private Pool

Luxury Carriage House in Rehoboth Beach

Private Pool! Charming 4bdrm, BayVista Beach House

Perfect Rehoboth Beach Getaway with Hot Tub

A Bethany Beach Gem 1.5 miles to Ocean Pickle Ball

Piece of Peninsula Heaven
Apartment rentals with a pool

Cozy Condo on Silver Lake - Walk to the beach!

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

Villa Del Sol, Beautiful stay near beaches/outlets

Where the Locals Live!!

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

Consistent 5-star rating Lakefront 3BR & 2BA condo

Spacious| Modern & Cozy| Pool| Close to the Beach

Mimi’s Place @ The Villages of 5 Points in Lewes
Other holiday rentals with a pool

Village at Five Points Condo Getaway

Lakefront condo blocks from the beach

Studio Bedroom in the Woods

Velo Condo-2 BR, 2 BA, Pool view

Coastal retreat •beaches, trails & historic Lewes•

Sunny Side Cottage🌞

Casa de Cozy, Relaxing Getaway - 2BR - 3 Pools

Fenwick Island Sunset Retreat
Destinations to explore
- Pet-friendly rentals Sussex County
- Rentals with a firepit Sussex County
- Rentals with breakfast Sussex County
- Fitness-friendly rentals Sussex County
- Cottage rentals Sussex County
- Beachfront rentals Sussex County
- Rentals with a sauna Sussex County
- Rentals with a washing machine and dryer Sussex County
- Townhouse rentals Sussex County
- Private suite rentals Sussex County
- Rentals with a hot tub Sussex County
- Rentals with an accessible-height toilet Sussex County
- Rentals with an EV charger Sussex County
- Waterfront rentals Sussex County
- Rentals with a kayak Sussex County
- Flat rentals Sussex County
- Rentals with lake access Sussex County
- Rentals with outdoor seating Sussex County
- Bed and breakfasts Sussex County
- Rentals with a patio Sussex County
- Holiday home rentals Sussex County
- Family-friendly rentals Sussex County
- Rentals with a fireplace Sussex County
- Hotel rooms Sussex County
- House rentals Sussex County
- Apartment rentals Sussex County
- Guest house rentals Sussex County
- Rentals with beach access Sussex County
- Boutique hotels Sussex County
- Tiny house rentals Sussex County
- Villa rentals Sussex County
- Rentals with pools Delaware
- Rentals with pools United States
- Ocean City Beach
- Ocean City Boardwalk
- Broadkill Beach
- Cape May Beach NJ
- Chincoteague Island
- Wildwood Crest Beach New Jersey
- Assateague Island National Seashore
- Willow Creek Winery & Farm
- Jolly Roger Amusement Park
- Bayside Resort Golf Club
- Northside Park
- Bear Trap Dunes
- Cape Henlopen State Park
- Assateague State Park
- Fenwick Island State Park Beach
- Delaware Seashore State Park
- Killens Pond State Park
- Lewes Public Beach
- Gordons Pond State Park Area
- Gerry Boyle Park
- Mariner's Arcade
- Roland E Powell Convention Center
- Dover Motor Speedway
- Wildwoods Convention Center




