Vacation rentals with a pool in Dewey Beach

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Top-rated rentals with a pool in Dewey Beach

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Guest favorite

Home in Rehoboth Beach

4.99 out of 5 average rating, 126 reviews

Secluded beach beauty with private, heated pool

The LV home by architect Rocio Romero is a modern classic, we love it… The heated, salt water pool is open mid-May to mid-October. You can cook in the fully equipped kitchen and eat indoors or on the large deck out back, play in the pool or fenced yard, lie in the hammocks, play games, do puzzles... We are right by the Junction and Breakwater bike trail; it's about 2 miles to the Rehoboth Boardwalk, 6 miles to Lewes. There's high speed WiFi, a Sonos audio system, and a Roku smart tv (no cable).

Superhost

Home in Rehoboth Beach

4.95 out of 5 average rating, 105 reviews

Amazing Bay Vista Beauty with Private Pool!

Fabulous 7 BR, 5 BA single family home with Private in-ground 20x40 Pool, Decks, Hot Tub, Screened Porch, gas FP, Open Gourmet Kitchen, gas grill, Parking + Carriage House. This one-of-a-kind 5000 sq. ft. retreat is completely remodeled w/ hardwood floors & plenty of room for entertaining! Dining room seats 12-14. Approx. 1.8 miles to beach & downtown Rehoboth. No Smoking/No Pets. Our home is located within a QUIET family-oriented community with a noise ordinance in effect at 10 pm. No parties.

Guest favorite

Condo in Rehoboth Beach

4.95 out of 5 average rating, 139 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.

Superhost

Condo in Rehoboth Beach

4.89 out of 5 average rating, 147 reviews

Right on Silver Lake walk to the beach and town!

Completely renovated, right on Silver Lake! On the most secluded part of Rehoboth Beach watch the sun rise and wildlife sitting at your patio! Park your car and walk or bike everywhere. Steps from the pool and three blocks across Turtle Bridge to get to the less crowded part of the beach. Five blocks from Rehoboth Avenue, where most restaurants and shops are. Full kitchen, Central heat/air, Smart TV, Cable and High speed internet. Pickleball, Tennis, Basketball and Tennis courts next door

Guest favorite

Condo in Rehoboth Beach

4.95 out of 5 average rating, 386 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.

Superhost

Condo in Rehoboth Beach

4.93 out of 5 average rating, 137 reviews

Beach Front living

Enjoy your vacation in this oceanfront condo. Enjoy coffee watching the sunrise on the balcony overlooking the beach & boardwalk. Step out the front door to take a dip in the Pool (summer). Just 3 blocks from Rehoboth Avenue; an ideal location! Guests supply their own sheets, pillowcases, bath & beach towels. Priced to reflect yet to be renovated. Still comfy and well stocked for your enjoyment. A true bargain! NOTE: Check-ins are unavailable on Saturday and Sunday due to cleaning schedule.

Guest favorite

Condo in Rehoboth Beach

4.82 out of 5 average rating, 381 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 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.

Top guest favorite

Condo in Ocean City

4.96 out of 5 average rating, 255 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 favorite

Condo in Rehoboth Beach

4.93 out of 5 average rating, 107 reviews

Cozy condo, 3 pools, and 4 beds in Rehoboth Beach

Get ready to relax immediately in this cozy and bright condo in a quiet community. The condo is a WALK-UP 3rd floor with vaulted ceilings, multiple balconies, and a relaxing screened porch with a view. We provide linens for the beds, bath towels, boogie boards, beach chairs, and an umbrella. Just over a mile from the beach and within walking distance are 3 community pools, a brewery, a grocery store, seafood restaurants, a water park, and more.

Guest favorite

Home in Rehoboth Beach

4.86 out of 5 average rating, 135 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, 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.