Vacation 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.

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Guest favorite

A spacious yard is viewed, featuring three modern wooden lounge chairs and two decorative side tables. In the background, a contemporary house with large glass doors is illuminated, creating a welcoming ambiance as twilight sets in among the trees.

Home in Rehoboth Beach

4.99 out of 5 average rating, 126 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).

Guest favorite

A spacious outdoor area is highlighted by a glistening pool, with a backdrop of a yellow two-story home. Red lounge chairs are arranged around the pool, and a large red umbrella provides shade. Fencing surrounds the pool, ensuring a private retreat.

Home in Cape May

4.82 out of 5 average rating, 131 reviews

Beautiful 5BR house with inground salt water pool

Beautiful custom build home with an in-ground pool on two acres. This property is located around 10 minutes from Cape May and Wildwood, 20 minutes from Stone Harbor, Avalon and about 40 minutes from Atlantic City. If you are looking for a quiet and relaxing place with good nights sleep and the comfort of a spacious single home but close to all attractions, this is your place. This place is surrounded by a lot of trees, where you can breathe clean air and a lot of space for walking and sports.

Superhost

A spacious deck features a dining table with six chairs, shaded by an umbrella. The deck overlooks a large above-ground pool, surrounded by greenery and a white fence, creating a private outdoor space ideal for relaxation.

Home in Wildwood Villas

4.76 out of 5 average rating, 105 reviews

Bayside Beach Home with a pool-New Deck for 2025

Welcome to your perfect vacation getaway, just 4 houses from the beautiful Delaware Bay beaches! Famous for its breathtaking sunsets, this inviting 3BR home features a large above-ground pool and a lovely deck, ideal for relaxation. Start your day with coffee with loved ones or kick back with a cool drink in the afternoon sun. Plus, it’s pet-friendly, complete with a fenced yard where your furry friends can play. - Only 7 miles to the Cape May Beaches. - Only 8 miles to the Wildwood Boardwalk.

Top guest favorite

A spacious outdoor area features a private saltwater pool surrounded by a paved patio. Several lounge chairs and umbrellas offer shaded seating around a dining table. Neatly maintained gardens enhance the atmosphere, providing a serene backdrop for relaxation.

Home in North Cape May

4.99 out of 5 average rating, 203 reviews

The Villa By the Bay-Private Heated Pool & Hot Tub

THE POOL IS NOW OPEN FOR 2025! PRIVATE HEATED SALT WATER POOL. HOT TUB OPEN YEAR ROUND! EVERYTHING YOU NEED FOR THE PERFECT VACATION ALL LINENS/TOWELS PROVIDED. We offer you a coffee and Tea Bar, Snacks to get your vacation off to the right start and a Welcome Gift to thank you for coming! Just mins from the Bay & the Heart of Cape May! We are close to restaurants, wineries & Cape May Ferry. Just a short walk to the Delaware bay. Beautiful fenced in back yard with outdoor grill and shower

Guest favorite

The exterior of a two-story vacation home is visible, surrounded by greenery. A fenced-in saltwater pool is situated on the left, with several lounge chairs positioned nearby. A patio area features a grill and outdoor seating under a shaded tent, inviting relaxation.

Home in Lower Township

4.88 out of 5 average rating, 69 reviews

Cape May Pool Paradise *Hot Tub* Sleeps 10

Escape to a paradise of relaxation and retreat in our charming vacation home in Cape May, New Jersey. This 4-bedroom rental boasts a beautifully designed saltwater pool, hot tub, outdoor tv/and deck, WiFi, a fire pit for cozy evenings under the stars, and a warm indoor pot belly stove to enjoy during cooler months. Centrally located between wineries, breweries, distilleries and only a few minutes drive from the beach, this is a vacation stay will ensure memories that will last a lifetime.

Guest favorite

Condo in Dewey Beach

4.98 out of 5 average rating, 44 reviews

Stunning 2 bedroom with pool

Beautiful 2 bedroom condo in Dewey's most desired location. This condo is located at the Residences of Light House Cove with a stunning view of the bay and marina from your private balcony. The master suite boasts a king bed with a spacious private master bath. The comfortable 2nd bedroom has a queen bed with full bath easily accessible. The open floor plan allows ample room to spread out including a well equipped kitchen. The building has elevators for easy access and private parking.

Top guest favorite

A spacious outdoor area features an inviting private pool with a floating lounger, surrounded by seating arrangements including colorful chairs and dining tables. Vibrant umbrellas offer shade, while the deck connects to the modern home, enhancing the outdoor living experience.

Home in North Cape May

5 out of 5 average rating, 26 reviews

Heated Pool Paradise - North Cape May

Sunny Oasis with HEATED Private Pool - Steps from the Bay! Welcome to coastal paradise in North Cape May! This inviting home offers a perfect blend of modern comfort and relaxation, an ideal getaway for anyone seeking a sun-soaked retreat. Nestled just steps away from the bay, this home provides you with the ultimate beachside experience - a HEATED IN-GROUND POOL. Enjoy tranquil mornings and vibrant sunsets by the water, and easily access the sandy shores for a day of and relaxation.

Guest favorite

A heated salt water pool is set within a private fenced area, featuring a unique shape. Surrounding the pool are several lounge chairs arranged on a patio of square pavers, offering a spacious area for relaxation. Bright sunlight illuminates the scene.

Home in North Cape May

4.98 out of 5 average rating, 97 reviews

Bay block home w heated saltwater pool

Brand new heated salt water pool was just completed April 2022. Our home is close to family-friendly activities, restaurants, & Bay block. My place is good for families and big groups. Walking distance to Harpoon’s and one block walk from AMAZING sunset views!! Close to wineries, breweries & distilleries. We are also Dog friendly and have a dog friendly beach block. (200/per dog non-refundable, fee is not included with booking). Pool opening May 2024; closing October 2024

Guest favorite

The heated saltwater pool is surrounded by a laid stone patio, with a well-maintained lawn and vibrant flowers nearby. Expansive windows of the main house provide a view of the pool, enhancing the outdoor space's tranquil atmosphere.

Home in Rehoboth Beach

4.96 out of 5 average rating, 71 reviews

Modern Home with Private Pool in Rehoboth Beach

Stunning modern home within biking or walking distance to Downtown Rehoboth. Location is key! We are just a stones throw from grocery stores, shopping, and many great restaurants! Our home features a large main house with 3 bedrooms (each with its own full bath), spacious living room, dining room, custom kitchen, a large screened porch, and heated saltwater pool. The property also includes a separate studio/4th bedroom with a powder room and outdoor shower area!

Superhost

A dining area features a wooden table surrounded by metal chairs, complementing the open concept design. Natural light filters through a large window, illuminating the space. A staircase leads to the upper level, while decorative plants add a touch of greenery.

Condo in Ocean City

4.8 out of 5 average rating, 56 reviews

Renovated Downtown Townhome W/ Pool & Shuffleboard

Update- Outdoor pool closes 9/23/24 Modern, downtown Bayside 2-level townhouse w/ large community pool. Prepare to relax and unwind in this 2-level beach house! This central location makes it very easy to walk to the beach, boardwalk, and many restaurants & shops. The kitchen is fully stocked with all your cooking needs. Enjoy the pool view from right outside your sliding door. There isn't much more you could ask for. Bath and bed linens provided.

Guest favorite

Condo in Rehoboth Beach

4.93 out of 5 average rating, 102 reviews

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

Get ready to relax immediately in this cozy and bright condo in a quiet community. The condo is a WALK-UP 3rd floor with vaulted ceilings, multiple balconies, and a relaxing screened porch with a view. We provide linens for the beds, bath towels, boogie boards, and beach chairs. Just over a mile from the beach and within walking distance are 3 community pools, a brewery, a grocery store, seafood restaurants, a water park, and more.

Guest favorite

A spacious pool area features neatly arranged lounge chairs and umbrellas, surrounded by neatly trimmed shrubs. A well-maintained lawn provides ample green space, and a gated entrance ensures security. The background highlights a tall tree and low-rise buildings, under a blue sky with scattered clouds.

Condo in Ocean City

4.94 out of 5 average rating, 16 reviews

Condo with Pool in the Heart of OC

First floor family friendly condominium with pool located within walking distance to the boardwalk, beach, amusement park, mini golf, and many restaurants. It has one bedroom with 2 queen beds and a pull-out sofa in the living room. Linens, bath towels, washcloths, and beach towels are provided for your convenience. The pool is located in the middle of the beautiful courtyard. There is a patio to enjoy the sunrise or sunsets.