
Vacation rentals with a pool in Lewes
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Lewes
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.

Where the Locals Live!!
Charming Beachy-Boho Property: Once our beloved family home, now your vacation getaway! Have a question, just ask! Thanks for checking us out, have a great day! 🚴 Ideal Location between Historic Lewes & The Boardwalk 🚗 2 Off Street Parking Spots 🦀 Local Eats: Steps from great dining, stoned throw from grocery store/dining/attractions. 🏊 Pool just steps from the unit! ⭐Balcony w/ Pool View 📺TV & board games. 🐶Pet Friendly 🌞Responsive Local Hosts 🌅 Great Charm at an unbeatable Value!

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.

Mimi’s Place @ The Villages of 5 Points in Lewes
Enjoy this 3rd floor (no elevator) renovated condo with amenities-tennis courts, walking & biking paths connecting to downtown Lewes & 2 outdoor pools in season. The condo is east of route 1, 3 miles to Lewes beach & 15+ restaurants, 5 you can walk to (2 blocks away), nail salon, a hair salon, grocery store and a CVS (4 blocks). We need pictures of everyone’s license and the person booking must be at least 25 years of age. There is 4 beach chairs and a large umbrella & 2 chair umbrellas.

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.

First Floor Comfort and Convenience
This first floor condo is conveniently located in a family-friendly community with all you need within walking distance, including several restaurants and a grocery store. A short and easy 3-mile drive to Lewes Beach and the charming town of Lewes makes this an ideal location. Amenities include access to two pools, tennis courts and kids play area. The Georgetown Lewes Biking/Walking Trail, that connects to the town of Lewes, is literally steps from our front door.

1st Floor Beach-town Condo in Lewes
Come stay at our favorite little beachtown condo in Lewes! This 1st floor 2 bedroom, 2 bath condo has everything you need for an enjoyable and relaxing vacation! You will be just a few miles to the beach and outlet malls, have access to the community pools (May-Sept), park, and sport courts, and will be within walking distance to several great restaurants and shops. While we are "pet friendly" only 1 pet (dog or cat, 40lb maximum) is allowed per the HOA rules.

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool
Perfect location to enjoy the holiday season in Southern DE for upcoming events, such as Polar Bear Plunge, Super Bowl Weekend or Dewey’s Famous Winter Gala! 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 by having everything you need for a memorable stay.

Hot tub, Relax, Shop & Dine, Sleeps 8, Games
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 Memorial Day to Labor Day.

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. *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)

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.
Popular amenities for Lewes rentals with a pool
House rentals with a pool

Artist’s Escape (2-bedrooms/3 beds/3 bathrooms)

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

Quiet 3BR Coastal Home Minutes to Bethany Beach

Wilde Rose By The Bay - Salt water Inground pool

Hot Tub Backyard Oasis, Private Beach, Local Pool

Beautiful Beach House in Rehoboth

Rehoboth-Lewes Beach House by the Bay

The Jungalow - Dog Friendly, Fenced in & Pool
Condo rentals with a pool

Right on Silver Lake walk to beach!

Classy Beach Getaway

Rehoboth Beach Canal Retreat

Renovated Condo Near Outlets, 3.5 Miles to Beach

2 Bedroom Condo Rehoboth Beach w/ No Chores

Gone Coastal *Pool* Bayside with view* Top Floor

Oceanfront Studio, King bed, Sleeps 4, Pool, Wi-Fi

Buoyed Spirits 2 BR 2B 1st floor condo
Other vacation rentals with a pool

Baby friendly, walk to pool and bakery town home

1st Floor 2BR/2BA | Pool | Peaceful & Near It All

Pool, dog friendly, fenced yard in Lewes

Lakefront condo blocks from the beach

Aw Shucks Condo | Off-Season Monthly Retreat

3 BR Coastal Retreat

Cape Shores Luxury - NEW Pool, Beach, Pier, Park!

Water Views * Balcony * Pool * Fast Wi-Fi
Quick stats about vacation rentals with a pool in Lewes

Total vacation rentals
Explore 10 vacation rentals in Lewes

Nightly prices starting at
Lewes vacation rentals start at $123 CAD per night before taxes and fees

Verified guest reviews
Over 610 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Lewes vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Lewes rentals

4.9 Average rating
Lewes stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Plainview Vacation rentals
- New York City Vacation rentals
- Long Island Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- The Hamptons Vacation rentals
- Outer Banks Vacation rentals
- Beach house rentals Lewes
- Rentals with a patio Lewes
- Family-friendly rentals Lewes
- House rentals Lewes
- Cottage rentals Lewes
- Condo rentals Lewes
- Rentals with a firepit Lewes
- Rentals with outdoor seating Lewes
- Rentals with beach access Lewes
- Rentals with a fireplace Lewes
- Beach condo rentals Lewes
- Rentals with a washer and dryer Lewes
- Pet-friendly rentals Lewes
- Beachfront rentals Lewes
- Apartment rentals Lewes
- Rentals with pools Sussex County
- Rentals with pools Delaware
- Rentals with pools United States
- Ocean City Beach
- Broadkill Beach
- Ocean City Boardwalk
- Wildwood Crest Beach New Jersey
- Cape May Beach NJ
- Assateague Island National Seashore
- Willow Creek Winery & Farm
- Jolly Roger Amusement Park
- Bayside Resort Golf Club
- Northside Park
- Bear Trap Dunes
- Cape Henlopen State Park
- Killens Pond State Park
- Assateague State Park
- Fenwick Island State Park Beach
- Delaware Seashore State Park
- Lewes Public Beach
- Gordons Pond State Park Area
- Mariner's Arcade
- Trimper Rides of Ocean City
- Ocean City Boardwalk
- Funland
- Hawk Haven Vineyard & Winery
- Longport Dog Beach




