
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.

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.

Gorgeous 5BR, 4.5BA, in town, pool, hot tub, beach
In town Rehoboth, with Rise Up and the boardwalk just a quick walk away, you'll love this home with a POOL AND HOT TUB (April-Oct). There's a ton of natural light, plus comfy queen and king beds, nice new linens, and more. Please note there is a security camera on the pool and in the pool equipment area for your safety. Dogs are allowed for a $75 fee per stay for first pet, $25 per additional (additional pet fee after the first will be billed after your reservation is complete). Maximum 3 dogs.

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool
Spring Break Getaway! 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.

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. Each bedroom has 1 king size bed and 1 queen size air mattress (in closet) *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)

Tiny house w/ Pool on water near Beaches / turf
Enjoy a peaceful waterfront stay in our custom-built tiny house, located on Cedar Creek just off Route 1. Conveniently situated only 10 minutes from Delaware Turf and 15 minutes from the beach. The home comfortably sleeps four and includes hot tub access. We live on-site and are happy to assist throughout your stay. Ideal for families, pets (please review rules under “The Space” section), contractors, and long-term renters. Perfect for travel nurses & remote workers – Monthly stays welcome!

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.

Teeny's Place: A Historic Milton Home.
Family friendly get-away filled with fun. All the amenities of a single family home, plus a backyard made for life at the beach. Proudly offering an in-ground pool, air-conditioned pool house with changing room, 3 season entertainment space, fire pit and deck spaces. The Pool is opened May 1st-October 1st. Walking distance to Downtown Milton's shops, restaurants, and -of course- Dogfish Head Brewery. Just a short drive to the Delaware Beaches. Newly renovated Pool House in 2024.

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.

Water Views: Balcony, Pool & Easy Parking
Why just visit the coast when you can live on the water? Experience the peaceful side of Coastal Delaware in our bright, first-floor waterfront retreat. Perched at the mouth of the Rehoboth Bay, this condo offers an escape where you can watch the tide turn from your private rocking-chair balcony. Wake up to locally roasted Rise Up coffee, spend the afternoon at the pool, and explore the dunes of Cape Henlopen just a short drive away. Your stress-free vacation starts here.

Luxurious Fine Linens/Salt Water Pool/Spa Hot Tub
Lewes Carriage House is a 5 Star, one-of-a-kind, architecturally designed luxury escape nestled on a 4-acre estate w/ resort style pool, grounds & private spa/hot tub. Perfect for private, romantic honeymoon & baby-moon escapes, anniversaries, as well as forest bathing & wellness retreats. - 5-10 minute drive to historic downtown Lewes, boutique shopping and Cape Henlopen State Park beaches. - Lush perennial gardens, an old-growth forest, native wetlands & 1-acre pond.

Surf Shack with Private inground pool
*** Note*** due to damage during storms in February the Pool opens mid- June 2026 New "surf shack" private beach cottage. Part of a restored 1940's cottage. Best sunset views around & just steps from your door! Close to Bethany Beach (6-10 minute ride) away from the noise of traffic & beach crowds. Within easy walking/biking distance of James Farm ecological park & beach. Community bay access is steps from the house. 2 adults and 2 children max capacity

Modern Beach Vibe - Rehoboth Beach
Step into a beautifully comfortable designer townhome, and relax in style just blocks from the restaurants & beach on Rehoboth Avenue. Much care has been given to all the furnishings in this 2300sq foot, 3 stories, from the Gourmet Kitchen, Great Room, 3 gorgeous bedrooms, 2 full baths, 2 half baths, patio, to the 2 balconys, large 3rd floor indoor & outdoor living, plus a pool. Every detail is of the highest quality to evoke a relaxed upscale modern beach vibe.
Popular amenities for Delaware rentals with a pool
House rentals with a pool

Spacious 5 Bedroom w/Pool, Patio and Theater

The Red Chalet

Cozy Beach Escape Mallard Lakes Resort Amenities

Gorgeous Bayfront, Pool, Hot Tub, Linens Included

Golf, Beach & Pool Escape • 6BR • Game Room

Bayside Family Oasis - Perfect for Large Families

Steady Waves | Dog-Friendly Home w/ Pool |Rehoboth

Spacious 4-bedroom house with a private pool.
Apartment rentals with a pool

Stress-Free Family Beach Stay | Pool + Kid Perks

Villa Del Sol, Beautiful stay near beaches/outlets

Right on Silver Lake walk to the beach and town!

Salt Air Retreat - Rehoboth Beach

1 Bedroom 1 Bath Condo on Silver Lake

Modern & Cozy Retreat | Pool | Close to Beaches

2b 2b condo! 2 master bedrooms! rehoboth beach

Beach Escape Condo w/ Pool - Lewes Beach 3.5 Miles
Other holiday rentals with a pool

Pool, dog friendly, private deck, fenced yard

Ocean View Paradise w/Hot Tub & Free Massages!

Family friendly house in Rehoboth Beach near pool

Dog Friendly Fenced 3BR King Bed

Condo at Eagles Landing

The Hidden Gem•Heated pool•Pickleball Court

Coastal retreat •beaches, trails & historic Lewes•

The Beach Chalet
Destinations to explore
- Farm stay rentals Delaware
- Cottage rentals Delaware
- Pet-friendly rentals Delaware
- Beachfront rentals Delaware
- Bed and breakfasts Delaware
- Flat rentals Delaware
- Rentals with beach access Delaware
- Rentals with a fireplace Delaware
- Boutique hotels Delaware
- Holiday home rentals Delaware
- Private suite rentals Delaware
- Waterfront rentals Delaware
- Mansion rentals Delaware
- Rentals with an EV charger Delaware
- Motorhome rentals Delaware
- Family-friendly rentals Delaware
- Apartment rentals Delaware
- Rentals with a washing machine and dryer Delaware
- Hotel rooms Delaware
- Villa rentals Delaware
- Rentals with breakfast Delaware
- Rentals with lake access Delaware
- Beach apartment rentals Delaware
- Rentals with outdoor seating Delaware
- Rentals with a hot tub Delaware
- Fitness-friendly rentals Delaware
- Rentals with a firepit Delaware
- Tiny house rentals Delaware
- Rentals with a kayak Delaware
- Guest house rentals Delaware
- Lakehouse rentals Delaware
- Rentals with a patio Delaware
- Rentals with an accessible-height toilet Delaware
- House rentals Delaware
- Townhouse rentals Delaware
- Rentals with pools United States





