
Vacation rentals with a pool in Dennis
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Dennis
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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.

500ft to Private Beach! Hot tub-Local Pool-Fireplc
Start your morning soaking in the hot tub, or sipping coffee in rocking chairs on the front porch. Relax on the private beach, just 8 houses away, or head over to the local pool! Go for a stroll along the waterfront sidewalk & grab a bite at the beachfront eatery. Spot a school of dolphins under a red-sky sunset, before returning for a seafood boil & fire pit marshmallows roast. End the night with a movie and games cozy in front of the fire. Click our icon to check out our other Cape May homes!

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.

Open 6/28-7/1. Beautiful condo. 1 Block to beach
Perfect Avalon/Stone Harbor location. Beautiful renovated 2nd floor end unit 1 bedroom , 1 and 1/2 bath condo comfortably sleeps 6. Two queen beds in bedroom and a pull out queen sleeper sofa in living room.. Located across the street from recreation fields and the Windrift and Icona Resorts . Features 2 swimming pools , indoor + outdoor, elevator and an onsite laundry (not in the unit). 4 beach tags. Bath towels and linens provided. You must be 25 years old to reserve this condo. No pets.

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!

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.

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.

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

OASIS Stone Harbor for 12 People + Pool
OASIS Stone Harbor is an authentic "vintage chic" beach house, that is just a block from the ocean and a quick walk or bike ride into town, and it's pet friendly. The OASIS experience is great all summer and as an off-season “retreat” to re-energize mind, body, and spirit. Get your toes in the sand! The swimming pool with the integrated waterfall and hot tub are typically open from early-April through early-December. Interior and outside videos are online at oasis stone harbor.

Mystical Cape May's Modern Farmhouse: The Widmore
Mystical Cape May's "The Widmore" Incredible brand-new modern farmhouse situated on over 1.2 acres, on a culd-de-sac, neighboring the Isaac Smith Vineyard and with no neighbors! (Well, they live across the street) 4 Bedroom, 2.5 Bath, large kitchen, oversized dining room, in ground swimming pool, Fireplace, outdoor fire pit, endless parking and completely quarantine and social distance friendly. 10 minute bike ride to the beautiful beaches of Cape May (4 min by car)

Villa By the Bay NOW OPEN Heated Pool & Hot Tub
PRIVATE HEATED SALT WATER POOL NOW OPEN UNTIL 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

Wilde Rose By The Bay - Salt water Inground pool
Quaint 3 bedroom home, 2 queen size beds, downstairs and 1 queen size bed and a full size bed upstairs full bath downstairs and half bath upstairs.spiral stairs to get upstairs or outside steps. out door shower also. Sleeps 6. salt water inground pool (12x26) Large back deck, with gas grill Covered front porch, and second floor open deck with view of amazing sunsets from either deck. Across the street from the bay.Pool will open May and close first week in october.
Popular amenities for Dennis rentals with a pool
House rentals with a pool

The Ranch. Heated Pool

The Perfect Escape with Gorgeous In-ground Pool

7 Bedroom, Pool, Bar, Beach, Avalon | Stone Harbor

Perfect Rehoboth Beach Getaway with Hot Tub

Mid-Century Milton w/heated Pool

Cape May Salt Water Pool Retreat

Cape May · Private Hot Tub +$100 Off-Season GIFT!

Serenity near Long Beach
Condo rentals with a pool

Oceanfront Condo | NEW Retro Design | Beach + Pool

Where the Locals Live!!

Where your toughest decision is beach or pool!

Boardwalk ramp condo w/designated parking & pool

Cozy Lewes Retreat | Pool, Short Drive to Beaches

Renovated Condo Near Outlets, 3.5 Miles to Beach

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool

Beach & Boardwalk - Endless Summer Sunrise Studio
Other vacation rentals with a pool

Beach House* Pool/Game Room/Grill/Outdoor space

Bright & relaxing beach home

Cape May Backyard Oasis with Pool, Bocce & More

AV Beach Block Condo & Pool (East)

Back Bay Bliss! - Pool, Dock and Stunning Sunsets!

Cape Getaway: Pool, Spa & Comfort on the 2nd Floor

Stone Harbor Gem! Charming 3-bedroom beach house

Pool, Beach & Family Retreat! Fully Stocked!
Quick stats about vacation rentals with a pool in Dennis

Total vacation rentals
Explore 20 vacation rentals in Dennis

Nightly prices starting at
Dennis vacation rentals start at $110 CAD per night before taxes and fees

Verified guest reviews
Over 730 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities

Wifi availability
10 of Dennis vacation rentals include wifi 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!
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