Holiday rentals with a pool in Delaware

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Delaware

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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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).

15–22 Sep

€ 691 per night

Superhost

Flat in Rehoboth Beach

4.8 out of 5 average rating, 5 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!

3–10 Dec

€ 105 per night

Guest favourite

Flat in Lincoln

4.83 out of 5 average rating, 195 reviews

Waterfront apt. w/ pool - shopping and beaches!

Beautiful studio apartment located on Cedar creek, directly off of route one with Hot tub access.. 10 minutes from Delaware Turf and 15minutes from the beach area. apartment comfortably sleeps four people, you can squeeze six! Waterfront view from apartment. We live on the property and are happy to help with your entire stay! We are contractor and long term rental friendly :) we also welcome Families with children or pets :) WE ARE PET FRIENDLY READ RULES IN "THE SPACE SECTION" BEFORE BOOKING

5–12 May

€ 119 per night

Guest favourite

Apartment in Dewey Beach

4.95 out of 5 average rating, 105 reviews

Luxury water-view condo with high-end finishes

Luxury 2-bedroom condo at The Residences at Lighthouse Cove located in the heart of Dewey Beach. This unit features great views of Rehoboth Bay and is only 1 block from the Atlantic Ocean. Easy walk to Dewey Beach’s shops, restaurants, and nightlife. This unit sleeps up to 6. There is a master bedroom with a king bed and in suite bathroom. The second bedroom has a full bunkbed bottom & twin top with trundle that can sleep 5. Lounge at private rooftop pool, fire pits, & grills for Residences

12–19 Dec

€ 183 per night

Guest favourite

Apartment 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

25 Sep – 2 Oct

€ 206 per night

Guest favourite

Apartment in Rehoboth Beach

4.96 out of 5 average rating, 337 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.

2–9 Aug

€ 461 per night

Guest favourite

Townhouse in Bethany Beach

4.84 out of 5 average rating, 328 reviews

Spacious Bethany Beach Retreat

Imagine walking into your own fully equipped beach condo. Listed as one of Delaware's top Airbnb's! This is a perfect place to get away and retreat with family and friends. The beach is 1.5 miles away and the amazing pool is a 2 minute walk. The kitchen is fully equipped and the gas grill, patio and yard add space for your stay. The condo is fully equipped. Linens, paper products coffee and everything you may have forgotten. Families and friends return again and again to make memories.

23–30 Dec

€ 161 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.

4–11 Sep

€ 211 per night

Guest favourite

Apartment in Rehoboth Beach

4.99 out of 5 average rating, 168 reviews

Comfy and Convenient 2 bedroom/2 bath condo

Our bright and spacious 1st floor, 2 bedroom/2 bath condo (sleeps 6) in Eagles Landing is perfect for couples, friends, or a family. Recently renovated floors, appliances and countertops. We are an easy 5-minute drive from the beach. If you don't like the sand, the community offers 3 pools. Our unit includes parking, a full kitchen, living room, dining room (seats 6), washer/dryer, dishwasher, cable/wi-fi. Downtown restaurants, outlet shopping, & boardwalk are all within 2 miles.

22–29 Sep

€ 176 per night

Guest favourite

Tiny home in Lewes

4.94 out of 5 average rating, 89 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.

25 Mar – 1 Apr

€ 149 per night

Guest favourite

Apartment 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.

14–21 Nov

€ 137 per night

Guest favourite

Home in Lewes

4.98 out of 5 average rating, 156 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.

13–20 Oct

€ 242 per night