
Holiday rentals with a pool in Henlopen Acres
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Henlopen Acres
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.

Sunrise Studio - Ocean Front, on Boardwalk, Pool!
Our quiet ocean front studio has all the comforts of home with amazing views, a balcony hovering over a serene stretch of the Boardwalk, and is just steps away from restaurants, shops, arcades, rides and all of the best boardwalk foods! Walkable to everywhere in town! If you want to venture out further, a bike rental shop is just a few doors away! Enjoy a bike ride through town or to Dewey Beach. If you are looking for a scenic ride, enjoy the bike trails to Cape Henlopen State Park and Lewes.

Downtown RB Townhome-Great Location-WALK TO BEACH
Great location in downtown Rehoboth Beach-walk everywhere! Tucked away in a quite residential community, yet close to all of RB's favorite attractions: 4 blocks to the beach and boardwalk, less than 1/2 block to Rehoboth Avenue. No need to drive once you arrive-walk to the beach, boardwalk, Funland, and all of the restaurants and shopping in town. Also close to the bike trails. This 2 level townhome overlooks the salt water pool and includes 2 parking spaces and 2 additional parking passes.

Clean and Comfy, Longer Term Stay available, Quiet
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.

Family Friendly Top Floor Condo Near Boardwalk
Located just 2 miles from the Rehoboth Beach boardwalk, yet nestled in a peaceful community. Condo offers a comfortable & well-equipped space Primary Bedroom: King w/ en-suite bathroom Second Bedroom: Queen w/ en-suite bathroom Living Area: Sofa & comfy chairs for relaxing For the Littles: Pack 'n Play, high chair, & many kid-friendly extras—see the last few photos for all the thoughtful touches! Whether you're here to explore Rehoboth’s charm or simply unwind, this is the perfect home base!

Modern 2BR/2BA – Beach Pass + Bikes, 5 Min Drive
This spacious, clean, and modern 2-bedroom, 2-bath condo is the perfect place to unwind after a road trip or a sun-soaked day at the beach. With a King bed, Queen bed, beach parking pass, and bikes included, getting to Rehoboth Beach is as easy as it gets. And when you're back home, parking is a breeze — with hundreds of open spots right outside the condo. We even provide you recommendations to restaurants, fun activities and even what to order! Beach, Outlets, Parks and Good Food.

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.

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.

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.

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.

Beautiful Beach House in Rehoboth
Last minute cancellation so July 20 week open! Gorgeous modern spacious house in Rehoboth Beach with large open floor plan on quiet street. Five bedrooms/3.5 baths. Walk to town/beach - four blocks from beach right off Rehoboth Ave. Private pool with two levels of decks, grill and table/umbrella on top deck. Big open kitchen/dining/living area, over 3000 square feet of space overall.
Popular amenities for Henlopen Acres rentals with a pool
House rentals with a pool

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

Family & Pet-friendly Beach House with Pool

Relaxing Getaway

Modern Beach House w/ Private Pool

Dog Friendly Fenced 3BR King Bed

Private pool in BayVista! 4bdrm family beach house

Cheerful 3-Bedroom Home in Rehoboth Beach

Sandbar Coastal Escape
Condo rentals with a pool

Oceanfront Condo | NEW Retro Design | Beach + Pool

Bluewater Couples Escape

Villa Del Sol, Beautiful stay near beaches/outlets

10 mins to beach-2 BR-Sleep Six-Pool-Beach PK pass

Classy Beach Getaway

Cozy condo, 3 pools, and 4 beds in Rehoboth Beach

Spacious| Modern &Cozy| Pool| Close to the Beaches

Condo Reho -1st fl/2 bed/2 bath, centrally located
Other holiday rentals with a pool

Stunning views from Beautiful 2 BR Condo

Spring Lake Escape-dog friendly, monthly available

Luxury Bay & Oceanview Condo in the Heart of Dewey

Velo Condo-2 BR, 2 BA, Pool view

Direct Ocean View*Walk to Lake Gerar, Playground

Water Views * Balcony * Pool * Fast Wi-Fi

Charming Oceanfront Condo

Lovely 2 BR/2Ba in Reho Beach!
Quick stats about holiday rentals with a pool in Henlopen Acres
Total rentals
50 properties
Nightly prices starting at
$154 AUD before taxes and fees
Total number of reviews
940 reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wi-Fi availability
40 properties include access to Wi-Fi
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Philadelphia Holiday rentals
- Mount Pocono Holiday rentals
- Jersey Shore Holiday rentals
- Outer Banks Holiday rentals
- Ocean City Holiday rentals
- The Hamptons Holiday rentals
- Family-friendly rentals Henlopen Acres
- Rentals with beach access Henlopen Acres
- Rentals with outdoor seating Henlopen Acres
- Condo rentals Henlopen Acres
- Pet-friendly rentals Henlopen Acres
- Townhouse rentals Henlopen Acres
- Rentals with a fireplace Henlopen Acres
- Apartment rentals Henlopen Acres
- Rentals with a washing machine and dryer Henlopen Acres
- House rentals Henlopen Acres
- Waterfront rentals Henlopen Acres
- Rentals with a patio Henlopen Acres
- Rentals with pools Sussex County
- Rentals with pools Delaware
- Rentals with pools United States
- Ocean City Beach
- Assateague Island National Seashore
- Broadkill Beach
- Wildwood Crest Beach New Jersey
- Cape May Beach NJ
- Fortescue Beach
- Ocean City Boardwalk
- Dewey Beach Access
- Ocean City Beach
- Willow Creek Winery & Farm
- Cape Henlopen State Park
- Pearl Beach
- Jolly Roger Amusement Park
- Big Stone Beach
- Peninsula Golf & Country Club
- Poodle Beach
- Poverty Beach
- Higbee Beach
- Assateague State Park
- Bear Trap Dunes
- Northside Park
- Bayside Resort Golf Club
- Stone Harbor Beach
- Towers Beach