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.

0 of 0 items showing

1 of 3 pages

Guest favourite

Home in Rehoboth Beach

4.99 out of 5 average rating, 119 reviews

Secluded beach beauty with private, heated pool

The LV home by architect Rocio Romero is a modern classic, we love it… The heated, salt water pool is open mid-May to mid-October. You can cook in the fully equipped kitchen and eat indoors or on the large deck out back, play in the pool or fenced yard, lie in the hammocks, play games, do puzzles... We are right by the Junction and Breakwater bike trail; it's about 2 miles to the Rehoboth Boardwalk, 6 miles to Lewes. There's high speed WiFi, a Sonos audio system, and a Roku smart tv (no cable).

Sep. 15 – 22

$1,014 CAD per night

Superhost

Apartment in Rehoboth Beach

4.83 out of 5 average rating, 6 reviews

Cozy Condo at Creekwood

Enjoy this beautiful, quiet,2-bedroom condo centrally located on the route 1 corridor. Whether you are away for a 'Couples Retreat' or beaching with the family, this condo will have you relaxed from the minute you arrive. Enjoy the lazy days around the pool or venture a few minutes out of the community and enjoy all the shops, restaurants, bars and entertainment this area has to offer. Creekwood is in the heart of it all but nestled quietly away from the noise. We can't wait to have you. Cheers!

Oct. 25 – Nov. 1

$154 CAD per night

Guest favourite

Condo in Lewes

4.97 out of 5 average rating, 36 reviews

Newly Renovated 2BR Condo w/ Pools Trails & Linens

NEW Updates in 2022! Get ready for a relaxing beach getaway in the newly renovated Boho Beach Condo - just mins from the beach! With all new furnishings, appliances, & kitchen updates, enjoy a pond view & free amenities steps from your door! Linens inc'd Situated in the highly desirable Five Points community you'll have access to pools, tennis courts, bike + walking trails. Comfortably sleeps 5. Just mins from historic downtown Lewes and walkable to restaurants + shops. Plenty of free parking.

Dec. 16 – 23

$230 CAD per night

Guest favourite

Condo in Rehoboth Beach

4.89 out of 5 average rating, 120 reviews

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

Dec. 20 – 27

$231 CAD per night

Guest favourite

Condo in Rehoboth Beach

4.96 out of 5 average rating, 338 reviews

The Artist's Hideaway *Community Pool*

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.

May 12 – 19

$314 CAD per night

Guest favourite

Condo in Ocean Pines

4.96 out of 5 average rating, 109 reviews

Waterview Retreat

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

Feb. 23 – Mar. 2

$210 CAD per night

Superhost

Condo in Lewes

4.8 out of 5 average rating, 35 reviews

Blue Crab Condo - pool, pet friendly- Lewes

Your relaxing Delaware beach vacation at this pet friendly and centrally-located 2 bedroom condo in Lewes with pond view. Features 2 community pools(open seasonally), tennis courts, pickle ball, and community playground for guest use. 0.4 mi to the Lewes/Georgetown trail 0.4 mi to restaurants in the Village 3.6 mi to Lewes Beach 6 mi to the beautiful Cape Henlopen State Park 6.6 mi to Rehoboth Beach/Boardwalk 11 mi to Sports at the Beach complex *Can be rented out monthly in off season*

Nov. 1 – 8

$207 CAD per night

Guest favourite

Guest suite in Lewes

4.93 out of 5 average rating, 118 reviews

Lewes, DE guest suite with pool

Newly built house in Lewes. Rental is an upstairs guest suite with separate outdoor entrance. The owner lives downstairs in a separate space, and there is a second upstairs 1BR rental on the other side of the house. -Children over 12 please. -Responsible adults only, no pets, no visitors/parties. *2 BR *in-ground swimming pool shared with the owner and other guests. (May 12- Sept 15, not heated) *6 miles to the beach THERE IS NO CABLE TV. TV has Wi-Fi *close to shopping and restaurants.

Sep. 16 – 23

$317 CAD per night

Guest favourite

Tiny homes in Lewes

4.94 out of 5 average rating, 90 reviews

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.

Mar. 4 – 11

$215 CAD per night

Guest favourite

Apartment in Lewes

4.95 out of 5 average rating, 20 reviews

Modern-Coastal Lewes Beach 1st Floor Condo

Enjoy a stylish, coastal stay at our two bed, two bath condo in the private community of The Villages of Five Points, minutes from the charming downtown and family-friendly beach of Lewes, Delaware. Easily accessible, super quiet location, east of Route 1, outside of the hustle of Rehoboth traffic. You're welcome to use all resort amenities such as the two outdoor saltwater pools and tennis courts. Right next door is the popular Lewes-Georgetown Trail to bike or walk downtown.

Jan. 25 – Feb. 1

$266 CAD per night

Guest favourite

Condo in Lewes

4.96 out of 5 average rating, 55 reviews

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.

Nov. 19 – 26

$201 CAD per night

Guest favourite

Home in Lewes

4.98 out of 5 average rating, 157 reviews

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.

Oct. 18 – 25

$355 CAD per night