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

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!

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.

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.

'Cottage by the bay', sleeps 8 near Rehoboth beach
This bayside getaway is a beautiful 'A' frame style cottage and is located along the Rehoboth bay with direct access to the water. The cottage is within the gated community of Angola by the Bay. About a block away from the front door is one of the three private crabbing/fishing docks, kayak launch and marina! Enjoy walking or biking along the water and trails throughout the community. The large pool is always a favorite too! Baywood greens golf is nearby also! Enjoy the beautiful sunsets!

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, pickle ball 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.

Cozy Condo on Silver Lake - Walk to the beach!
Located in the middle of a nature preserve on Silver Lake, and walking distance to the beach this end unit condo boasts stunning views and cozy modern decor. Enjoy the pool just steps from your lakeside patio or take a short walk to the beach or town crossing the footbridge (known by locals as turtle bridge.) Lovely boutiques and fine dining in town plus numerous family friendly restaurants. 5 minute drive to Tanger Outlets. Rehoboth Beach parking pass provided with each rental.

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.

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool
Fresh New Photos! 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.

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.

Buoyed Spirits 2 BR 2B 1st floor condo
2 bedroom, 2 bathroom ground floor apartment in a nice neighborhood, off Rt 1. 1.5 miles from the beach! The community has 3 swimming pools and tennis courts. Master has a king-sized bed, the second room has 2 twins. Sofa in living room is a pull out. Two bikes with helmets and locks also come with the rental, as well as 2 tennis rackets. Towels (including beach towels) and linens provided, BUT YOU WILL NEED TO LAUNDER THE SHEETS AND TOWELS BEFORE YOU LEAVE.

Beautiful condo in Villages of Five Points, Lewes
Welcome to our beautiful condo in the desirable family friendly community of The Villages of Five Points ! Our 2 bedroom, 2 bath condo is the perfect place for your beach vacation or any occasion. The condo has been newly painted and new flooring has been installed as well. The condo is right off east of route 1 and about 3 miles from Lewes beach. Biking trails are close by and Cape Henlopen State Park is a short ride of about 3 miles.

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

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

Mystical Cape May's Modern Farmhouse: The Widmore

Luxury Carriage House in Rehoboth Beach

Luxurious Fine Linens, Aveda Spa amenities/Hot Tub

Coastal Beauty-Bike to Beach

River Cottage with pool

Mosaic Life Escapes -Bayfront Million Dollar Views

Bayfront Oasis Vacation Rental
Apartment rentals with a pool

Right on Silver Lake walk to beach!

Bluewater Couples Escape

Salt Air Retreat - Rehoboth Beach

Classy Beach Getaway

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

1 Bedroom 1 Bath Condo on Silver Lake

Rehoboth/Dewey Coastal Condo 2bd 2ba

Oceanfront 2 Bedroom-Sleeps 6-Indoor/Outdoor Pool
Other holiday rentals with a pool

Coastal Hideaway at Five Points

Village at Five Points Condo Getaway

Studio Bedroom in the Woods

Lewes Crest Retreat | Bike Trail Access & Pool

3BD/2BA 2nd flr - Dreamy Rehoboth Beach Getaway

Luxe Lewes Townhouse: Pool, Roof Deck & Bike Trail

4br/3ba + pool, beach getaway. Pet friendly

Water Views: Balcony, Pool & Easy Parking
Quick stats about holiday rentals with a pool in Lewes

Total holiday rentals
Explore 10 holiday rentals in Lewes

Nightly prices starting at
Lewes holiday rentals start at ₹8,322 per night before taxes and fees

Verified guest reviews
Over 610 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Lewes holiday 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!
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- Ocean City Beach
- Ocean City Boardwalk
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- Assateague Island National Seashore
- Willow Creek Winery & Farm
- Jolly Roger Amusement Park
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- Cape Henlopen State Park
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