
Vacation rentals with a pool in Rehoboth Beach
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Top-rated rentals with a pool in Rehoboth Beach
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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!

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.

Clean and Comfy, Longer Term Stay available, Quiet
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.

Family Friendly Top Floor Condo Near Boardwalk
Located just 2 miles from the Rehoboth Beach boardwalk, yet nestled in a peaceful community. Condo offers a comfortable & well-equipped space Primary Bedroom: King w/ en-suite bathroom Second Bedroom: Queen w/ en-suite bathroom Living Area: Sofa & comfy chairs for relaxing For the Littles: Pack 'n Play, high chair, & many kid-friendly extras—see the last few photos for all the thoughtful touches! Whether you're here to explore Rehoboth’s charm or simply unwind, this is the perfect home base!

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.

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.

Sun, Sand & Sea | Your Cozy Oceanfront Hideaway
-Oceanfront -Indoor pool & Hot tub -Walk to local dining and shopping -Elevator accessible plus luggage carts -Full kitchen for cooking meals -Fast Wifi and Streaming TVs -Fully Stocked Home: Clean linens, towels, toilet paper, paper towels & more! **2025 guests: Our pool and hot tub are in the process of being renovated and will be closed during your stay. This does not impact our condo, but you will not be able to use these amenities.**

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.

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.

*Radcliffe Retreat* Studio, Pool & RB Parking Pass
Spacious 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.

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool
Pool opens May 24th 2025!!! The Perfect Family Getaway! Whether you're planning a beach vacation, a business trip, or a shopping spree at the nearby Outlets, this condo is the ideal retreat. Conveniently located near dining, shopping, scenic trails, and just a short drive to Lewes, Rehoboth, and Dewey beaches, you'll have everything you need for a memorable stay.

1st Floor 2BR/2BA | Pool | Quiet & Convenient
Step into our beautifully appointed 1,000 sq ft beach condo, where comfort meets convenience! Located on the first floor, this stylish retreat is easily accessible and designed for relaxation. Whether you're here for a beach getaway or to explore local shops and restaurants, our condo is your perfect home away from home!
Popular amenities for Rehoboth Beach rentals with a pool
House rentals with a pool

Cozy updated cottage with private heated pool.

Family & Pet-friendly Beach House with Pool

Dodd House Beach Home w/private pool and hot tub

Rehoboth Beach Retreat- 4BR, monthly available

Modern Beach House w/ Private Pool

Dog Friendly Fenced 3BR King Bed

Private pool in BayVista! 4bdrm family beach house

Lewes Carriage House- Reflect. Recenter. Renew.
Condo rentals with a pool

Salt Air Retreat - Rehoboth Beach

Classy Beach Getaway

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

1 Bedroom 1 Bath Condo on Silver Lake

Beach Front living

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

Condo Reho -1st fl/2 bed/2 bath, centrally located

Beautiful 2BR 2BA oceanfront condo at the Atlantis
Other vacation rentals with a pool

Blue Skies

Lakefront condo blocks from the beach

Spring Lake Escape-dog friendly, monthly available

Luxury Bay & Oceanview Condo in the Heart of Dewey

Gorgeous Bayfront, Pool, Hot Tub, Linens Included

Direct Ocean View*Walk to Lake Gerar, Playground

5 bed 5.5 bath w/ heated pool, 5min walk to beach

Cozy Condo at Creekwood
Quick stats about vacation rentals with a pool in Rehoboth Beach
Total vacation rentals
Explore 560 vacation rentals in Rehoboth Beach
Nightly prices starting at
Rehoboth Beach vacation rentals start at $14 CAD per night before taxes and fees
Verified guest reviews
Over 18,470 verified reviews to help you choose
Family-friendly vacation rentals
460 properties offer extra space and kid-friendly amenities
Pet-friendly vacation rentals
Find 100 rentals that welcome pets
Rentals with dedicated workspaces
300 properties have a dedicated workspace
Wifi availability
560 of Rehoboth Beach vacation rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Rehoboth Beach rentals
4.8 Average rating
Rehoboth Beach stays are highly rated by guests—averaging 4.8 out of 5!
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