
Vacation 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.

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

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.

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.

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.

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.

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.

OceanfrontJewel|DirectOceanView•NewlyRenovatedPool
Oceanfront Jewel is proudly offered by RedHill Stays. Wake up to unobstructed ocean views from the top floor, just steps from the iconic Rehoboth boardwalk! Sip your morning coffee as the sun rises over the Atlantic, then fall asleep to the sound of waves at night. Designed for both romantic getaways and family escapes, this thoughtfully curated space blends comfort, style, and an unbeatable location.

Oceanfront 2 Bedroom-Sleeps 6-Indoor/Outdoor Pool
Kick back and relax in this beautiful and modern newly remodeled condo in Golden Sands! This rare 2 bedroom, 1.5 bathroom unit has an amazing Master Suite with full-length windows providing panoramic views down the coastline, and direct access to the private patio. Renowned building amenities include outdoor pool, top floor indoor pool, gym, tiki bar, sun deck & more. Linens & towels included!
Popular amenities for Dewey Beach rentals with a pool
House rentals with a pool

Family Oasis Near The Beach | Shared Pool & Tennis

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!

The Circle House, Pool, Hot tub, Firepit, Location

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

Coastal Cottage! Walk to Beach!

Luxurious Fine Linens/Salt Water Pool/Spa Hot Tub

Private Pool! Charming 4bdrm, BayVista Beach House
Condo rentals with a pool

Stress-Free Family Beach Stay | Pool + Kid Perks

Bluewater Couples Escape

Cozy Condo on Silver Lake - Walk to the beach!

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

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

1 Bedroom 1 Bath Condo on Silver Lake

Comfy and Convenient 2 bedroom/2 bath condo

Beach condo w/pool! All linens & beach supplies
Other vacation 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

Luxury Bay & Oceanview Condo in the Heart of Dewey

Perfect Location in Dewey Beach!

Golden Hour Getaway | Marina & Bay Views in Dewey
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