Holiday rentals with a pool in Lewes

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Top-rated rentals with a pool in Lewes

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Condo in Rehoboth Beach, Sussex County

4.98 out of 5 average rating, 170 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.

Guest favourite

Condo in Rehoboth Beach

4.96 out of 5 average rating, 113 reviews

Sunrise Studio - Ocean Front Boardwalk Sanctuary

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 favourite

Condo in Lewes

4.98 out of 5 average rating, 115 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 favourite

Condo in Rehoboth Beach

4.82 out of 5 average rating, 365 reviews

2 Bedroom Condo Rehoboth Beach w/ No Chores

2 Bedrooms Condo. Great for families or couples. Walking distance to restaurants, beach, bars & other entertainment. Driving distance to 5 different golf courses within 15 minutes. Walking distance to water park & amusement park. Pool on site. Bike & running trail behind the condo. Roku on every TV with Xfinity app for local TV & a Spectrum app for premium channels. We have MGM +& you can add any of your own streaming services during your stay. Smoking area on deck. No chores for you to do!

Guest favourite

Condo in Rehoboth Beach

4.98 out of 5 average rating, 197 reviews

Comfy and Convenient 2 bedroom/2 bath condo

Our bright and spacious 1st floor, 2 bedroom/2 bath condo (sleeps 6) in Eagles Landing is perfect for couples, friends, or a family. Recently renovated floors, appliances and countertops. We are an easy 5-minute drive from the beach. If you don't like the sand, the community offers 3 pools. Our unit includes parking, a full kitchen, living room, dining room (seats 6), washer/dryer, dishwasher, cable/wi-fi. Downtown restaurants, outlet shopping, & boardwalk are all within 2 miles.

Guest favourite

Tiny home in Lewes

4.96 out of 5 average rating, 135 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 favourite

Condo in Ocean City

4.96 out of 5 average rating, 225 reviews

Caramar Couples Retreat

This cute little first floor efficiency condo is ocean front for a perfect vacation to the beach. It’s an older building but has been partially renovated and updated. You can get to the beach by a very short walk through a private walkway from the condo building. The view from the private balcony is perfect and relaxing. WiFi provided upon check in- xfinity, Netflix, and internet. Indoor and outdoor dining areas and a full kitchen. Closet and dresser for storage use.

Guest favourite

Condo in Rehoboth Beach

4.9 out of 5 average rating, 198 reviews

Charming Beach Condo

Conveniently located in less than two miles to Rehoboth and Dewey Beach. A first floor end unit provides easy access. The community boasts 3 pools, tennis courts, grilling area, and is a short bike ride from the beach and all that Rehoboth and Dewey has to offer. It is walkable distance (1.5 miles) to downtown Rehoboth, where you'll find a variety of restaurants, shopping, and a world class boardwalk. There is something for everyone here! Sorry not pets

Guest favourite

Guest suite in Rehoboth Beach

4.98 out of 5 average rating, 122 reviews

*Radcliffe Retreat* Studio, Pool & RB Parking Pass

*Book your 2025 stay before Jan 1 to avoid the new state rental tax* Updated 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.

Guest favourite

Condo in Lewes

4.95 out of 5 average rating, 112 reviews

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.

Guest favourite

Home in Lewes

4.98 out of 5 average rating, 175 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 favourite

Condo in Rehoboth Beach

4.92 out of 5 average rating, 157 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.