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, 145 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.

Top guest favorite

A spacious outdoor pool is surrounded by lounge chairs and umbrellas, providing a relaxing environment. A two-story building with a balcony overlooks the pool area, while modern structures stand in the background, emphasizing the setting's inviting atmosphere.

Condo in Rehoboth Beach

4.95 out of 5 average rating, 148 reviews

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.

Guest favorite

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

4.94 out of 5 average rating, 398 reviews

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.

Guest favorite

The exterior of a custom-built tiny house is displayed, featuring a combination of horizontal siding and large windows. Two yellow chairs with a small table sit on the porch, framed by surrounding greenery, creating a connection to the natural environment.

Tiny home in Lincoln

4.86 out of 5 average rating, 309 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. Perfect for travel nurses & remote workers – Monthly stays welcome!

Top guest favorite

A bright bedroom is presented with a spacious bed dressed in crisp white bedding. Natural light streams through several windows adorned with woven shades, revealing views of the lush outdoors. A large mirror and decorative tray add to the room's charming décor.

Home in Lewes

5 out of 5 average rating, 31 reviews

Lewes Carriage House: Unwind. Recenter. Indulge.

Lewes Carriage House offers a one-of-a-kind, architecturally designed boutique luxury stay nestled on a picturesque 4-acre estate. Ideally located just a 5-10 minute drive from downtown Lewes and Cape Henlopen beaches, the property offers the perfect balance of proximity and seclusion for romantic retreats, special occasions, or a unique escape. The grounds feature lush perennial gardens, an old-growth forest, native wetlands, and a serene 1-acre pond. Estate sized pool & private spa/hot tub.

Top guest favorite

A private pool is framed by a stone patio, with several lounge chairs positioned nearby. Lush greenery surrounds the area, providing a relaxing atmosphere. A potted plant adds a touch of color to the space, inviting guests to unwind by the water.

Home in Rehoboth Beach

5 out of 5 average rating, 58 reviews

Private pool in BayVista! 4bdrm family beach house

This charming property is tucked away in the quiet neighborhood of Bay Vista, beneath a beautiful canopy of pine trees. The home is minutes to the beaches in Rehoboth and Dewey and shopping at the Tanger Outlets. The home is 4 bedroom, 2.5 bath. The first floor is a beautiful open concept kitchen, dining, and living area, with a sunroom and side den. You’ll enjoy a fully-fenced backyard with a private pool (unheated, open Memorial Day-Labor Day), outdoor dining, grill and outdoor shower.

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, 172 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.

Top guest favorite

A serene outdoor scene features a sparkling pool in the foreground, surrounded by lush green grass and a colorful landscape. In the distance, a tranquil water view is framed by trees, while a rainbow arcs gracefully across the sky.

Home in Lewes

5 out of 5 average rating, 20 reviews

Coastal Retreat | Lakefront | Pool | Hidden Gem

Unwind at your scenic get-away on the water, with a pool, dock, and relaxing backyard spaces. You’re just minutes from Historic Lewes, Cape Henlopen State Park, and the Bike Trail. Step into your vaulted living & dining room, where a large farmhouse table, a fully equipped kitchen, and stunning views await you! Breathe in the air on the covered porch, enjoy games in the backyard, or cozy up indoors with a good book. Everything you need for a perfect stay is here.

Top 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, 107 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.

Superhost

An outdoor patio area features a shaded pergola adorned with hanging plants. A lounge seating arrangement is positioned around a table, while a barbecue grill is nearby. In the background, a swimming pool is enclosed by a fence, surrounded by a manicured lawn.

Tiny home in Millsboro

4.82 out of 5 average rating, 146 reviews

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.

Guest favorite

An in-ground pool is set within a stone patio, surrounded by a lush garden featuring various plants. Two lounge chairs are positioned beside the pool, and a tree provides natural shade, enhancing the backyard's inviting atmosphere.

Home in Rehoboth Beach

4.86 out of 5 average rating, 137 reviews

Hot Tub + Pool, Fire Pit, Cottage by Dogfish Head

This adorable beach cottage has it all, and it's bigger than it looks! With 3 full-size bedrooms, 2 full baths, and an enormous back yard with an IN-GROUND POOL, big back deck, huge HOT TUB, gas fire-pit, and dual charcoal and gas-burning BBQ, this home has everything you need for an unforgettable beach trip. You'll love the 3 KING SIZE BEDS, two of which are tempur-pedic, plus the two twin beds are great for kids.

Top guest favorite

Home in Lewes

4.98 out of 5 average rating, 195 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.