
Vacation 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.

Clean and Comfy, Close to Schellville and Shopping
This newly updated condo is perfect for your next beach vacation. A convenient central location between Rehoboth/Dewey and Lewes Beaches. You can walk to the neighborhood pool. Stylish, clean and comfortable, the unit has two bedrooms, one on either side of the kitchen, an ideal layout for privacy for two couples or a family. Each bedroom has it’s own full bathroom. The screened in porch has a view full of trees. Located right off of Route 1, 3.6 miles from downtown Rehoboth and the boardwalk.

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.

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool
Perfect location to enjoy the holiday season in Southern DE for upcoming events, ie. Rehoboth Beach Parade, Rehoboth and Dewey Beach Tree Lighting, NYE Celebrations and 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.

Mimi’s Place @ The Villages of 5 Points in Lewes
Enjoy this 3rd floor (no elevator) renovated condo with amenities-tennis courts, walking & biking paths connecting to downtown Lewes & 2 outdoor pools in season. The condo is east of route 1, 3 miles to Lewes beach & 15+ restaurants, 5 you can walk to (2 blocks away), nail salon, a hair salon, grocery store and a CVS (4 blocks). We need pictures of everyone’s license and the person booking must be at least 25 years of age. There is 4 beach chairs and a large umbrella & 2 chair umbrellas.

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.

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 and kids play area. The Georgetown Lewes Biking/Walking Trail, that connects to the town of Lewes, is literally steps from our front door.

1st Floor Beach-town Condo in Lewes
Come stay at our favorite little beachtown condo in Lewes! This 1st floor 2 bedroom, 2 bath condo has everything you need for an enjoyable and relaxing vacation! You will be just a few miles to the beach and outlet malls, have access to the community pools (May-Sept), park, and sport courts, and will be within walking distance to several great restaurants and shops. While we are "pet friendly" only 1 pet (dog or cat, 40lb maximum) is allowed per the HOA rules.

Farm Cottage - POOL - 30 Min to BEACH
Enjoy this beautiful cottage/studio apartment. Perfect little getaway space for 2 (or 3). Our little cottage is surrounded by fields and the quiet sound of country sunrise. You'll wake up to chickens anxious to get out of their coop or Lucy, the turkey, peeking in your window. In the evenings, light the firepit or enjoy and a quiet nighttime swim with our duck. And our very friendly dog, Tanka (Cane Corso) will welcome you to our family.

Beautiful condo in Villages of Five Points, Lewes
Welcome to our beautiful condo in the desirable family friendly community of The Villages of Five Points ! Our 2 bedroom, 2 bath condo is the perfect place for your beach vacation or any occasion. The condo has been newly painted and new flooring has been installed as well. The condo is right off east of route 1 and about 3 miles from Lewes beach. Biking trails are close by and Cape Henlopen State Park is a short ride of about 3 miles.

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) *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)

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* from Memorial Day to Labor Day.
Popular amenities for Sussex County rentals with a pool
House rentals with a pool

Spacious Family-Friendly Beach Home w/Hot Tub

Fire Island-Style chic getaway with Pool & Linens!

New 3‑BR Ranch by DE Turf & Beaches

Gorgeous Bayfront, Pool, Hot Tub, Linens Included

Beachtown getaway

Boho Beach Golf Villa- holiday discount!

The Jungalow - Dog Friendly, Fenced in & Pool

Piece of Peninsula Heaven
Condo rentals with a pool

Family Friendly Top Floor Condo Near Boardwalk

Right on Silver Lake walk to the beach and town!

Villa Del Sol, Beautiful stay near beaches/outlets

Classy Beach Getaway

Featured on HGTV! Bethany Beach Ocean Front Condo

Renovated Condo Near Outlets, 3.5 Miles to Beach

Comfy and Convenient 2 bedroom/2 bath condo

Beach Escape Condo w/ Pool - Lewes Beach 3.5 Miles
Other vacation rentals with a pool

1st Floor 2BR/2BA | Pool | Peaceful & Near It All

Cozy, 3 BR, Lewes condo w/ Pool

Peninsula Golf & Country Club 2Bd/2bth Windswept

Village at Five Points Condo Getaway

Eastern Shore Getaway: Bethany Bay

Rehoboth-Lewes Beach House by the Bay

OceanViewBeachClub-minutes from Bethany Beach/Golf

Charming Lewes Escape - Near Beaches & Bike Trails
Destinations to explore
- Townhouse rentals Sussex County
- Rentals with an EV charger Sussex County
- Rentals with an accessible height toilet Sussex County
- Private suite rentals Sussex County
- Condo rentals Sussex County
- Rentals with a firepit Sussex County
- Villa rentals Sussex County
- Hotel rooms Sussex County
- Fitness-friendly rentals Sussex County
- Rentals with breakfast Sussex County
- Waterfront rentals Sussex County
- Rentals with a patio Sussex County
- Rentals with a fireplace Sussex County
- Bed and breakfasts Sussex County
- Rentals with a hot tub Sussex County
- Cottage rentals Sussex County
- Rentals with a kayak Sussex County
- House rentals Sussex County
- Family-friendly rentals Sussex County
- Rentals with a sauna Sussex County
- Rentals with a washer and dryer Sussex County
- Vacation home rentals Sussex County
- Pet-friendly rentals Sussex County
- Apartment rentals Sussex County
- Boutique hotels Sussex County
- Rentals with beach access Sussex County
- Rentals with lake access Sussex County
- Rentals with outdoor seating Sussex County
- Tiny house rentals Sussex County
- Guesthouse rentals Sussex County
- Beachfront rentals Sussex County
- Rentals with pools Delaware
- Rentals with pools United States
- Ocean City Beach
- Broadkill Beach
- Fortescue Beach
- Wildwood Crest Beach New Jersey
- Cape May Beach NJ
- Ocean City Boardwalk
- Assateague Island National Seashore
- Dewey Beach Access
- Willow Creek Winery & Farm
- Peninsula Golf & Country Club
- Big Stone Beach
- Pearl Beach
- Jolly Roger Amusement Park
- Cape Henlopen State Park
- Northside Park
- Poodle Beach
- Bayside Resort Golf Club
- Bear Trap Dunes
- Poverty Beach
- Higbee Beach
- Stone Harbor Beach
- Baywood Greens Golf Maintenance
- Miami Beach
- Towers Beach




