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.

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Top guest favorite

Condo in Lewes

4.99 out of 5 average rating, 134 reviews

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

You will 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, 3 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. 4 beach chairs & umbrella are in closet on outside porch.

Guest favorite

Condo in Rehoboth Beach

4.96 out of 5 average rating, 113 reviews

Modern 2BR/2BA – Beach Pass + Bikes, 5 Min Drive

This spacious, clean, and modern 2-bedroom, 2-bath condo is the perfect place to unwind after a road trip or a sun-soaked day at the beach. With a King bed, Queen bed, beach parking pass, and bikes included, getting to Rehoboth Beach is as easy as it gets. And when you're back home, parking is a breeze — with hundreds of open spots right outside the condo. We even provide you recommendations to restaurants, fun activities and even what to order! Beach, Outlets, Parks and Good Food.

Guest favorite

The exterior of a twinhome is showcased, featuring a stone-accented garage with two doors. Lush green landscaping surrounds the entrance, while large windows with black shutters offer a glimpse of the welcoming interior. A paved driveway leads up to the garage.

Townhouse in Millville

4.95 out of 5 average rating, 228 reviews

⛱ Quiet 3 Bed Twinhome just 3 miles from Beach! ⛱

Enjoy this Beautiful 3 Bedroom & 2.5 Bath Twinhome in Millville, DE. Perfect for Families! This home is within walking distance or short drive to Restaurants, Shops, Grocery Store and other Attractions & Most Importantly - only 3 miles to THE BEACH!! There is a Community Pool in the neighborhood. Many Toys, Games, Puzzles available for children. Home is No Smoking of Any Kind. Also No Pets, No Large groups/parties (10 people max.) or Senior Week rentals permitted. Book Today!

Guest favorite

A seasonal swimming pool is framed by a spacious deck featuring multiple lounge chairs. Lush greenery surrounds the pool area, providing a serene backdrop. Play equipment is visible in the distance, enhancing the outdoor recreational space.

Tiny home in Lewes

4.95 out of 5 average rating, 163 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.

Guest favorite

A spacious living area features a comfortable sectional sofa with decorative pillows, complemented by a large area rug. A television is positioned on a stylish media console, while large glass doors provide access to a private patio, framed by blue curtains. A ceiling fan is present above.

Condo in Lewes

4.97 out of 5 average rating, 102 reviews

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.

Guest favorite

A spacious kitchen is highlighted by an 11 ft island with four round bar stools. Pendant lighting above creates a warm ambiance. Modern appliances and a stylish backsplash are featured, enhancing the functionality of the space. Neutral tones and open shelving provide a clean, inviting atmosphere.

Home in Rehoboth Beach

4.98 out of 5 average rating, 121 reviews

Hot tub, Pool, Relax, Shop & Dine, Sleeps 8, Games

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.

Superhost

Tiny home in Lincoln

4.85 out of 5 average rating, 294 reviews

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.

Top guest favorite

Home in Lewes

4.98 out of 5 average rating, 190 reviews

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.

Guest favorite

An aerial view captures a community equipped with multiple tennis courts, all featuring green surfaces and blue lines. A swimming pool is nearby, surrounded by lounge chairs and shaded areas. Residential buildings are visible in the background, accentuating the family-friendly environment.

Condo in Lewes

4.94 out of 5 average rating, 102 reviews

Cozy condo in the Villages of Five Points, Lewes

Located in the Villages of Five Points Lewes, east of route 1, our condo is the perfect spot for your weekend gateway or a family beach vacation. Lewes beach is about 3 miles, biking paths and trails that connect to downtown Lewes are in close proximity. Within walking distance from the property enjoy the restaurants, have a splash in the pool in the summer time, or hit the tennis courts for some fun.

Guest favorite

A gated pool area is visible, featuring a curved shape with light blue water and surrounding lounge chairs. Sunlight reflects off the surface, creating a serene atmosphere. The backdrop includes a light-colored building with large windows, further enhancing the tranquil setting.

Condo in Rehoboth Beach

4.92 out of 5 average rating, 158 reviews

Welcome to The Getaway at Rehoboth Beach

Welcome to the Getaway ! This clean, cozy and comfortable 2 Bedroom , 2 Bath second floor condo was totally renovated in July of 2019 with all new Furniture, Flooring, Bedding, Kitchen Cabinetry and Appliances, not to mention a fresh coat of paint throughout. The property is just 3 short miles to the Rehoboth Boardwalk and centrally located within walking distance to some really great restaurants.

Top guest favorite

A fenced community pool is visible, surrounded by lounge chairs under a clear blue sky. A nearby building provides changing facilities. Lush greenery frames the area, contributing to a relaxing environment for guests.

Guest suite in Rehoboth Beach

4.98 out of 5 average rating, 131 reviews

*Radcliffe Retreat* Studio, Pool & RB Parking Pass

Spacious pet friendly guest suite with Rehoboth parking permit provided. The suite is near outlets, beaches, dining, & Rehoboth boardwalk. Large community pool next door. Charming neighborhood that is a great base to explore all the nearby attractions! Rehoboth boardwalk & beach- 4 mi Outlets- 1 mi Lewes downtown- 4 mi Cape Henlopen State Park- 6 mi 1 dog is allowed with permission.

Top guest favorite

The living room features two full couches arranged around a coffee table, providing ample seating. A ceiling fan is mounted overhead, and natural light floods the space through multiple windows. A Smart TV is positioned on a console, and a dining area is visible in the background.

Condo in Rehoboth Beach

4.98 out of 5 average rating, 235 reviews

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool

Pool opens May 24th 2025!!! The Perfect Family Getaway! 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 beaches, you'll have everything you need for a memorable stay.