Vacation rentals with a pool in Sussex County

4.99 out of 5 average rating, 148 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, 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 theperson booking must be at least 25 years of age. We a4 beach chairs & umbrellas are in closet on outside porch.

Condo in Rehoboth Beach, Sussex County

A dining area is showcased with a grey table set for six, surrounded by vibrant yellow chairs and a metal wire-frame chair. A modern light fixture hangs above, and a decorative wreath adorns the wall, complemented by abstract artwork on either side.

4.98 out of 5 average rating, 192 reviews

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.

4.87 out of 5 average rating, 100 reviews

An inviting swimming pool is surrounded by a spacious patio featuring several lounge chairs. Pool floats in the shape of swans rest on the water. A shaded area provides shelter, while a lawn and trees create a serene backdrop.

Guest suite in Milford

Studio apt near DE turf, beaches, &hospital

Your family will be close to everything when you stay at our centrally-located place. We are just 2 minutes from bayhealth hospital Milford campus, 10 minutes from DE turf & 20-30 minutes from all beaches. Early check in available upon request for 12:00pm, fee $100. During the summer months we offer our pool for guest use! We welcome families & fur babies! We do have 5 dogs ourself that roam freely in our backyard. PLEASE READ CANCELLATION POLICY CAREFULLY Pets crated when unattended!

4.94 out of 5 average rating, 408 reviews

A round blue dining table is set for four, featuring neutral plates and glasses. Surrounding chairs have a classic black design. A large piece of abstract art adorns the wall, while the kitchen area is visible in the background, showcasing light cabinetry and appliances.

Condo in Rehoboth Beach

Pool, near Shopping, Clean and Comfy

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.

4.86 out of 5 average rating, 318 reviews

Tiny home in Lincoln

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!

4.97 out of 5 average rating, 124 reviews

Condo in Rehoboth Beach

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.

4.95 out of 5 average rating, 182 reviews

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

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.

A bright living area features a light-colored sofa and armchair with coastal patterns. A wooden coffee table sits on a textured rug, while a mounted television is visible on the wall opposite. The open layout allows for glimpses of a dining area with a table set for six.

4.98 out of 5 average rating, 101 reviews

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.

A balcony view captures a wide expanse of lush green fields and dense trees, framed by a soft gray sky. The natural landscape offers a serene backdrop, highlighting a peaceful atmosphere. A railing can be seen in the foreground, providing a sense of depth.

5 out of 5 average rating, 123 reviews

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)

4.99 out of 5 average rating, 202 reviews

Home in Lewes

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.

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.

4.95 out of 5 average rating, 116 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.