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 favourite

Home in Ocean City

4.94 out of 5 average rating, 219 reviews

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

Jan. 19 – 26

$197 CAD per night

Guest favourite

Home in Rehoboth Beach

4.99 out of 5 average rating, 119 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).

Sep. 15 – 22

$1,009 CAD per night

Guest favourite

Condo in Dewey Beach

4.95 out of 5 average rating, 105 reviews

Luxury water-view condo with high-end finishes

Luxury 2-bedroom condo at The Residences at Lighthouse Cove located in the heart of Dewey Beach. This unit features great views of Rehoboth Bay and is only 1 block from the Atlantic Ocean. Easy walk to Dewey Beach’s shops, restaurants, and nightlife. This unit sleeps up to 6. There is a master bedroom with a king bed and in suite bathroom. The second bedroom has a full bunkbed bottom & twin top with trundle that can sleep 5. Lounge at private rooftop pool, fire pits, & grills for Residences

Mar. 12 – 19

$251 CAD per night

Guest favourite

Condo in Rehoboth Beach

4.89 out of 5 average rating, 120 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

Dec. 17 – 24

$230 CAD per night

Guest favourite

Condo in Rehoboth Beach

4.96 out of 5 average rating, 337 reviews

The Artist's Hideaway *Community Pool*

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.

Sep. 23 – 30

$396 CAD per night

Superhost

Condo in Ocean City

4.85 out of 5 average rating, 100 reviews

2 Bdrm Oceanfront-Pool, Xbox, Pickleball, Gym, HBO

Stunning newly renovated 2 bedroom oceanfront condo in the premiere Golden Sands! Blue Wave is known for its unique 3-tiered wave wall and incredible ocean views from the living room and primary bedroom. SmartTV w/Xbox! Wake up to the sun rising over the ocean right out your bedroom window, and after a cup of coffee on the balcony (included!) head to the building's sun deck,fitness center, lounge, arcades, tennis court, pickleball court,beach volleyball,or indoor/outdoor pools and tiki bar.

Oct. 25 – Nov. 1

$253 CAD per night

Guest favourite

Condo in Rehoboth Beach

4.99 out of 5 average rating, 168 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.

Sep. 28 – Oct. 5

$194 CAD per night

Guest favourite

Townhouse in Millville

4.97 out of 5 average rating, 170 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 (12 people max.) or Senior Week rentals permitted. Book Today!

Oct. 25 – Nov. 1

$219 CAD per night

Guest favourite

Condo in Ocean City

4.97 out of 5 average rating, 226 reviews

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

Nov. 27 – Dec. 4

$308 CAD per night

Superhost

Condo in Ocean City

4.89 out of 5 average rating, 164 reviews

🌊Oceanfront studio w/ amazing views & amenities🏖

Efficiency/studio condo oceanfront. Queen size Murphy bed, couch, loveseat, full kitchen, bathroom, washer & dryer, ac/heat, parking, awesome amenities. This building is beautiful with amazing views. We clean & stock this condo ourselves so you'll get the owners personal touch without the crazy extra fees that rental companies charge. I love to make everyone's stay as wonderful as possible. Please read entire listing.

Nov. 26 – Dec. 3

$253 CAD per night

Guest favourite

Condo in Bethany Beach

4.93 out of 5 average rating, 280 reviews

Sea Colony Premier Family Resort

Sea Colony is a beach/tennis resort. There are 10 swimming pools, 4 at the beach. The Fitness Center is new and has an indoor and outdoor pool. The Tennis Center has hard and soft courts as well as 6 indoor courts. The condo is on the East side which is a 10 minute scenic walk to beach. If one brings or rents bicycles, there are a number of paths which are safe and one can ride to beach in 5 minutes.

Oct. 6 – 13

$254 CAD per night

Guest favourite

Condo in Rehoboth Beach

4.92 out of 5 average rating, 143 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.

Feb. 15 – 22

$197 CAD per night