
Holiday rentals with a pool in Dewey Beach
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Top-rated rentals with a pool in Dewey Beach
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Newly Renovated Modern 2 Bed/2 Bath Condo w/ Pool
Newly renovated and designer decorated 2 bedroom/2 bath beach condo with the most comfortable beds imaginable. Located in the heart of Dewey Beach with an outdoor pool and only 1 block to beach and bay. One bedroom includes a King sized bed with private bathroom. The 2nd bedroom includes a Queen and a Twin sized beds adjacent to the 2nd bathroom. The fully equipped kitchen features stainless steel appliances, granite countertops, an island w/ seating, and washer/dryer. 2 parking spots included.

Stress-Free Family Beach Stay | Pool + Kid Perks
From the moment you walk in, it just feels different. Fresh flowers, thoughtful touches, and even surprise goodies for the kids-everything is designed so your family can relax instantly. No over-packing, no stress-we've stocked it all (beach gear, snacks, games & more). Tucked in a quiet spot just minutes from the beach & boardwalk, you get the best of both worlds. This isn't just a stay--it's a place families come back to year after year. No kiddos coming-No worries! Kids items are put away.

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.

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.

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

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. Each bedroom has 1 king size bed and 1 queen size air mattress (in closet) *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)

Comfy and Convenient 2 bedroom/2 bath condo
Bright & spacious 1st floor, 2 bedroom/2 bath condo (sleeps 6) in Eagles Landing is perfect for families, couples or friends. Recently renovated floors, appliances and countertops, new furniture. We are an easy 5-minute drive from the beach. The community has 3 pools. Our unit includes parking, a full kitchen, living room, dining room (seats 6), washer/dryer, dishwasher, wi-fi. Downtown restaurants, outlet shopping, & boardwalk are all within 2 miles. We provide necessities so you pack less!

Cozy Rehoboth Beach Condo w/ 2 bedrooms
This condo is a boho getaway tucked away in a quiet enclave conveniently located on the beachside of Highway 1. It has dedicated parking in front, plus an additional spot for a second car. This condo it is a two bedroom/two bathroom unit. Full kitchen and a dining area that seats up to six. The condo is on the second floor with one stair flight. The beach is a 20 minute walk, 10 minute bike ride, or 5 minute drive Community pool on site provides an extra place to relax and cool down.

Luxury at the Beach.
Luxury accommodations at the beach, walkout to the pool from your sliders to your gated private patio with poolview. Hardwood floors, fireplace, TV, WIFI, Enjoy the rooftop outdoor pool, fire pits & propane grills on the veranda for use only by The Residences at Lighthouse Cove tenants & owners. Access to indoor pool & fitness room along with the hotel guests. Breathe the salt air, bay views and one block to ocean. Restaurants walking distance too. Walking distance to ocean and bay.

Dodd House Beach Home w/private pool and hot tub
Saturday to Saturday bookings from the third week in June through mid August. Large 5 bed 3.5 Bath Luxury Home with pool and hot tub. Parking for six to eight cars. ARRIVE, STOCK UP, AND NEVER LEAVE IF YOU CHOOSE! GET YOUR FAMILY AND FRIENDS TOGETHER SAFELY! This large 4,500 square foot rental unit includes 5 private BR, 3.5 BTH, and sleeps 18! Pool opens May 15th until September 30th. Outdoor fire pit with some wood provided. 25 and older please.

Hot tub, Pool, Shop & Dine, Sleeps 8
A convenient central location between Rehoboth/Dewey and Lewes Beaches. You can walk to the neighborhood pool (available Memorial Day- Labor Day). Stylish, clean and comfortable, our house is an entertainer's dream. A huge 11 ft island and open concept living space is perfect for gatherings. Each bedroom is curated for comfort. The peaceful, private back deck is perfect to layout. We go above and beyond to ensure the best experience for our guests.

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* and no pets from June 14 to Labor Day.
Popular amenities for Dewey Beach rentals with a pool
House rentals with a pool

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

Ocean View Paradise w/Hot Tub & Free Massages!

Beach Zen 3BR Condo w/ Pool

Amazing Bay Vista Beauty with Private Pool!

Steady Waves | Dog-Friendly Home w/ Pool |Rehoboth

4BD 4BA Carriage Home-Fenced Yard | Rehoboth Beach

Private Pool! Charming 4bdrm, BayVista Beach House

Luxurious Fine Linens/Salt Water Pool/Spa Hot Tub
Condo rentals with a pool

Cozy Condo on Silver Lake - Walk to the beach!

Consistent 5-star rating Lakefront 3BR & 2BA condo

1 Bedroom 1 Bath Condo on Silver Lake

Mimi’s Place @ The Villages of 5 Points in Lewes

2 Bedroom Condo Rehoboth Beach w/Brand New Bed

First Floor Comfort and Convenience

Direct Oceanfront with a View and Amenities Galore

Beach condo w/pool! All linens & beach supplies
Other holiday rentals with a pool

Luxurious Penthouse, King beds. Dog & ADA Friendly

Lux Dewey: Rehoboth Bay Front*1Block 2 Ocean! Pets

The Post House

Spring Lake Escape | Dog-Friendly by Trail & Beach

Bayview Oasis-Pool/Free Parking

1st Floor Condo - Walk to the Beach - Pool

Perfect Location in Dewey Beach!

Dewey Perfect 1 BR Condo with a Pool
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