Vacation rentals with a pool in Dennis

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Top-rated rentals with a pool in Dennis

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

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Top guest favorite
A small outdoor balcony area features a grey wooden chair beside a rustic table. A screened door leads into the unit, with a decorative turtle wall plaque visible. Shades cover the window beside the door, allowing natural light into the space.
Condo in Ocean City
4.97 out of 5 average rating, 157 reviews

Boardwalk ramp condo w/designated parking & pool

*Bedding linens (sheets & pillowcases), wash, bath, AND beach towels are NOT included Saturday-only check-ins and outs June 20 -August 22, 2026, Per HOA Included are pillows & bedspreads for a queen, double, & single. Paper products are NOT guaranteed/ please bring all needed items. Pool & hot tub: (Mid May thru mid Sept/weather & staffing permitting) 4 Beach tags provided for June - Sept, required for 12yrs & up Your assigned parking space is #4 & a few feet off the boardwalk ramp :)

Top guest favorite
A serene bedroom is featured, with light blue walls and a large bed adorned with a fish-patterned quilt. Two bedside lamps flank the bed, and ocean-themed artwork hangs above it. Framed photos are displayed on the walls, contributing to a coastal atmosphere.
Guest suite in Dennis
4.98 out of 5 average rating, 222 reviews

Boutique suite, Palace in the Woods

⚽️⚽️ WELCOME FIFA ⚽️⚽️ The Palace in the Woods is a “ NO CHORES STAY AIRBNB “ just what you need for a peaceful visit to Cape May County BEACHES & BOARDWALKS . Located in the woods, just ten to fifteen minutes from Sea Isle, Avalon, and Stone Harbor, and the Cape May County ZOO - a little bit further to Ocean City, Wildwood and Cape May. A perfect location for beachgoers, birders, cyclists, and foodies. Please read house rules ( additional rules ). If you have any questions, feel free to ask.

Top guest favorite
A comfortable living room features a gray sofa across from a wooden coffee table. A large round mirror reflects light, while framed fish prints adorn the walls. Natural light floods the space, highlighting the open layout that connects to the dining area and kitchen.
Home in North Cape May
4.99 out of 5 average rating, 179 reviews

Hot Tub Backyard Oasis! Private Beach, Local Pool

Start your morning soaking in the hot tub or curled up on a heavenly chaise lounge in the sunroom. Just 9 houses from the beach, toss in a fishing line at the ferry jetty, while steps away, your group soaks up the sun on the beach. Enjoy the local pool or a beachfront eatery, both just a few blocks away! Spot a school of dolphins under a red-sky sunset before heading home for grilling & corn hole by the fire, or watching movies on the screened porch! Click our icon for our other Cape May homes!

Top guest favorite
A spacious deck is shown, featuring a large umbrella providing shade over a table with six chairs. A fenced area surrounds the deck, while a glimpse of a large above-ground pool is visible in the background, with clear blue skies overhead.
Home in Villas
4.81 out of 5 average rating, 149 reviews

Steps to the Bay | 3BR w/ Pool | Pet Friendly

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
An outdoor space features a heated swimming pool surrounded by a concrete patio. Comfortable seating options include several couches and chairs. A large umbrella provides shade, while a hot tub is positioned nearby. String lights and greenery enhance the backyard ambiance.
Home in Lower Township
4.96 out of 5 average rating, 126 reviews

Relaxing Getaway

Enjoy the shore at this fully renovated luxurious beach house. This 3 bedroom 2 bath (with sleeper Sofa) can sleep up to 12 people. The space has been recently renovated. New kitchen, new bathrooms, brand new carpets, and hardwoods. An amazing in ground heated pool, with 8ft privacy fence highlight the back yard. The back yard also features ample seating, a fire pit, and a brand new 7 person hot tub. This is the perfect getaway for any family or families looking for fun at the jersey shore.

Top guest favorite
A vibrant pool area is visible, with guests relaxing under large umbrellas. The water sparkles in the sunlight, while white poolside loungers provide seating. The surrounding fencing features a welcoming design, and the atmosphere is family-friendly, with a glimpse of traffic in the background.
Condo in North Wildwood
4.92 out of 5 average rating, 209 reviews

Cute beachfront condo with pool and 2 bedrooms!

Awesome little condo- 2 bedrooms! Quiet community with pool and parking. Directly across the street from the ocean, 7 blocks from the boardwalk, and walking distance to N Wildwood bars and restaurants. Table and chairs right outside the front door! Lots of loungers, tables, and 2 grills around the property. Newly renovated bathroom. Key will be left in lock box- unit 105. Please bring your owns linens or wash and make beds before leaving. June min -3 nights July and August min - 4 nights

Guest favorite
A spacious outdoor pool is surrounded by brightly colored buildings, featuring vibrant blue umbrellas and stacked lounge chairs. The pool reflects the sky, inviting relaxation, while the white railings create a barrier between the pool area and the well-maintained walkways.
Condo in Wildwood Crest
4.79 out of 5 average rating, 286 reviews

Cozy Wildwood Crest Beach - Poolside Condo

Sunkissed Wildwood Crest Cozy Beach Condo. This beautiful poolside first floor one bedroom condo is available for you to enjoy! Newly updated and furnished with a cottagey style. Enjoy the beach just 2 blocks away, and steps away from the pristine pool of the Alps. This unit has all the joys of home, couch, smart TVs with internet, oven, stove, fridge, freezer, and shower. Bike to beautiful Cape May. ID Verification Required Must be 21 Years or older to lease 2 Adult Max No 3rd Party leases

Top guest favorite
An aerial view showcases the expansive riverfront property surrounded by lush green fields and waterways. The deep Cohansey River meanders through the landscape, reflecting the sky. Various shades of green and water create a tranquil and serene environment.
Home in Bridgeton
4.99 out of 5 average rating, 270 reviews

THE SORA with Disco, Hot Tub & Pool

Immerse yourself in the timeless beauty of this 12 acre riverfront property. Experience the peaceful beauty of 800+ feet of direct river frontage on the deep Cohansey River. This river leads to the Delaware Bay/ Atlantic Ocean. Situated on the site of the Prestigious Sora Gun Club, this historic 4 Bedroom, 2 1/2 Baths light-filled home with magnificent great room has classical details and distinctive appointments. One of the 4 bedrooms and the 1/2 bath is in the 2 story guest house.

Guest favorite
An inviting saltwater pool is bordered by lounge chairs, with colorful floats resting on the water's surface. Surrounding scenery features lush greenery and a vibrant sunset sky, casting warm hues over the space. The area is designed for relaxation and enjoyment.
Home in Cape May
4.89 out of 5 average rating, 124 reviews

Mimosa Salt Water Pool & HOT TUB Oasis, Sleeps 8

Just Renovated!Linens and Towels INCLUDED! Perfect for 2 families a King & Queen Bedroom and the third bedroom comes w/a full/twin bunkbed that has a twin pull out in addition to a twin bed. (Sleeps 8 total) In ground Salt Water Pool perfect for relaxing all day w/your kids if beach is too much of a chore or having dinner outside. Our yard is fenced in and perfect for your furry friend. Open concept living room, dining room and kitchen. Great for coming together and socializing

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, 234 reviews

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

PRIVATE HEATED SALT WATER POOL Reopens 4/3/26- 10/30/26 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 and Wineries. Just a short walk to the Delaware bay. Beautiful fenced in back yard with outdoor grill and shower

Guest favorite
A spacious backyard features a newly constructed pool and spa surrounded by a stone border. Comfortable lounge chairs and seating areas are arranged nearby. A light blue home is visible, with a large patio door leading inside. Lush greenery adds to the inviting atmosphere.
Home in Cape May Court House
4.89 out of 5 average rating, 114 reviews

7 Bedroom| Beach| Pool| Walk to Bars & Restaurants

Enjoy your shore getaway in the center of it all! This newly renovated 7 Bedroom home can sleep the whole family and friends. This amenity filled home features a brand new pool/spa, volleyball court, outside furniture, grill, and more! Centrally located only minutes to Avalon & Stone Harbor Beaches, and walking distance to Restaurant/bars, Wineries/Breweries, and other local attractions. ****hot tub open year round**** ****pool only open from may 1stOctober 18th***

Top guest favorite
A new hot tub is featured in the image, surrounded by a landscaped yard. Water bubbles gently in the inviting space, with a child enjoying the amenities while wearing a snorkel mask. The background includes a grassy area and a white wooden deck.
Home in Villas
4.99 out of 5 average rating, 112 reviews

SeaLaVie! HotTub! BaySunsets! FirePits! HugeYard!

Pool & hot tub! Linens and towels, 10 beach tags and beach supplies included. Sea La Vie is a paradise! 3 blocks to a dog friendly bay beach w/ gorgeous sunset! 15 min to ocean beaches. Close to wineries, breweries, nature preserves & all sorts of off-season and seasonal fun! You will love grilling & enjoying the pool (seasonal), hot tub (), fire pit & yard games in the huge yard. Boutique decor. Perfect for stargazing! Stocked kitchen! Family & group friendly

Popular amenities for Dennis rentals with a pool

Quick stats about vacation rentals with a pool in Dennis

  • Total vacation rentals

    Explore 10 vacation rentals in Dennis

  • Nightly prices starting at

    Dennis vacation rentals start at G$16,725 GYD per night before taxes and fees

  • Verified guest reviews

    Over 720 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Wi-Fi availability

    10 of Dennis vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Dennis rentals

  • 4.8 Average rating

    Dennis stays are highly rated by guests—averaging 4.8 out of 5!