
Vacation rentals with a pool in Dennis Port
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Dennis Port

Total vacation rentals
Explore 140 vacation rentals in Dennis Port

Nightly prices starting at
Dennis Port vacation rentals start at G$18,827 GYD per night before taxes and fees

Verified guest reviews
Over 890 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
130 of Dennis Port vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Dennis Port rentals

4.7 Average rating
Dennis Port stays receive an average rating of 4.7 out of 5 from guests
Top-rated rentals with a pool in Dennis Port
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Beachside Condo with Balcony - Oceanside Condos
Charming Cape Cod oceanside condominium unit, located just steps from the warm waters of Nantucket Sound. Queen bed, futon, heated pool, BBQ grill with outdoor table, high-speed wifi, cable, & 2 TVs. Do your own cooking with fully-furnished kitchenette (stove, fridge, microwave, coffeemaker, & utensils), or go out to local restaurants, ice cream sundaes, go-carts, mini-golf, kayaking, or jetskiing. 2nd floor, no elevators; not handicap-friendly. No pets. Bring own linens. Pool closes mid-Sep.

Skip to Beach, Cape Cod Condo!
Adorable condo with ocean views! We are across the street from Glendon Beach, less than 100 feet away! One private bedroom with a queen bed and a full size pull out couch in the living room that sleeps 2. Kitchen includes full size stovetop, sink, and large fridge. Bathroom is a full bath with shower and tub. Heated pool is right outside the door. Next door to Sailing Cow Cafe for breakfast, lunch and dinner and down the road from the Dog House. No pets! LINENS ARE NOT PROVIDED. Over 25 only.

Sea Salt Studio - Steps to Glendon Rd Beach
Funky studio (Unit #1) only 175 yards from a white sand beach on Nantucket Sound. Soak up the sun at the beach, relax by the pool or enjoy a relaxing cocktail on your own private patio. This studio is equipped with a fridge, microwave and gas stove as well as a fully stocked kitchenette and cable/Roku TV. A futon couch offers extra sleeping space, if needed. Outside, enjoy a natural gas grill. Walk or bike to multiple restaurants, ice cream shops and all the amenities Dennis Port has to offer.

Modern Oasis, Heated Saltwater Pool, Beach, Golf
Welcome to an exceptional modern Cape Oasis on a private & quiet cul-de-sac Mins. to Golf, beaches, lakes, bike path Bright airy, spacious, central AC, modern/new furnishing,enjoyable year-round Expansive deck, pool lounge & yard Fenced in w/full privacy Thoughtfully curated for multi families/groups Resort style retreat w/tranquility & fun games Location is virtually close to everything Pool heat: Memorial day weekend -last Sun. of Sept. All essentials provided 6+ free parking

Poolside studio home! A walk to the beach!
Your family will be close to everything when you stay at this central located studio in the heart of Dennis Port. The shared pool is located right outside your door! You’ll find all kitchen essentials, full stove and propane grill. The floor plan offers a large living area with a queen size bed and 2 pull out queen sofas. Step outside via sliders to outdoor seating. Condo is less than 1/4 mile from and within walking distance to the beach. Beach chairs and tent included. Parking on premises.

Dennis Deluxe King Room | Full Studio w/ Kitchenet
Dennis Port Surf Club Boutique Hotel – Your ideal Cape Cod getaway at 329 Main Street. Newly renovated and family-friendly, we’re just 5 minutes from the beach and located on Route 28 near top dining, shopping, and attractions. Enjoy our outdoor pool, Jacuzzi, and mini arcade. Rooms include free Wi-Fi, microwave, and mini fridge. Steps from mini golf, arcade, bumper cars, and ice cream. Free parking and a welcoming stay for couples, families, and beach lovers. $85 pet fee not included

The Holly Cottage
Welcome to Centerville, enjoy this fully equipped 1 bedroom 1 bath home with an easy walk or ride to just about everything. Enjoy the nearby ocean and beaches, or take a ride downtown to Main Street for dining and entertainment. Only a short distance to the ferries for a day trip to the islands and you can be back in time to catch a concert at the Melody Tent. Enjoy your days by the pool and your evenings grilling out on the large deck or chatting with the koi fish.

Great Location. Near Beach & Main Street. Unit M1
Our home-away-from-home accommodations include this charming studio with lawn space, a private deck with outdoor furniture and a gas grill. The cottage is comfortably furnished and features a small kitchen. This cottage has a queen bed and a table with sitting area. The kitchen is nicely updated with updated with beautiful granite countertops and stainless steel appliances including an stove/oven, microwave, mini-fridge, toaster, coffee maker. Keurig, and kettle.

X Marks the spot
X marks the spot for your perfect Cape Cod getaway. This renovated 3BR, 2BA cottage in Dennis Port is just steps to Inman Beach, Sea Street Park, and local favorites. Enjoy a bright open living area, modern kitchen, A/C, heat, and in-unit laundry. Outside features a private patio with grill, fire pit, and outdoor shower. Includes parking, and classic Cape charm—perfect for a relaxing coastal stay just moments from the sand.

Cozy cottage steps to the beach!
PLEASE NOTE BED LINENS (QUEEN) AND TOWELS NOT PROVIDED. You’ll treasure your time at this memorable place that is steps from a heated outdoor pool, gas grills, and the beach! Close to shopping and restaurants and everything mid Cape Cod has to offer. The complex is located directly across the street from Glendon Road Beach and next to the Sailing Cow restaurant. Relax onsite or explore, it is up to you!

Comfy Cape Escape! Spacious, Cozy, Close to Beach!
Come stay at the Cape and enjoy this comfortable, DOUBLE-UNIT condominium to do so! Bring your family, or even your friends, and sleep well on the three queen-sized beds in this space! Enjoy breakfast in the 5-chair nook after preparing it in the quaint yet amenable kitchen. Then, walk 5 minutes down to the beach and relax. Come back and cook-out on the large grill on the spacious, private patio.

Ocean Edge Cape House with Beach, Pool, and AC
Your dream Cape Cod getaway awaits! This classic Cape Cod cottage is nestled in the heart of Brewster, offering a perfect blend of comfort, relaxation, and outdoor adventure. With access to a private beach, resort-style amenities, and iconic local attractions, this is the ultimate retreat for families, couples, or groups looking to experience the best of the Cape.
Popular amenities for Dennis Port rentals with a pool
House rentals with a pool

Harwich Haven: Pool & Fire Pit

In-Ground Pool Oasis | 5 Min to Cape Cod Beaches!

Sleeps 14 Home w/ Pool Great for Families!

Beach house in Hyannis with pool

House on Cape Cod with pool close to beach

ShoestringBayHouse, waterfront & pool in Cotuit

Winslow Acres [heated] Pool Escape; pool May-Oct

Cape Cod Oasis: pool, hot tub, firepit & grill!
Condo rentals with a pool

Resort Pools & Golf Views · Walk to Bay Beaches

Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access

Hidden Hideaway

Ocean Edge Resort-Pool Access-CentralAC-2 bdr/2bth

Mary's Cape Escape

Happy Daze are here again! Cute condo by the Bay!

Mid Cape Cod, 3 Season Haven by Bass River

Oceanfront 1-Bedroom Condo w/ Balcony Views
Other vacation rentals with a pool

Fenced Pool, Fire pit, Outside dining, Coffee bar

Town House for Cape Cod fun, by Bass River.

Breezy Pool Retreat Near Mayflower Beach

Pool. Hot Tub. Game Room. Walk to Beach. Luxury!

Coastal Retreat in East Sandwich - Dogs OK!

Bright and Lovely Cottage With Community Pool

Summer Serenity on Cape Cod (heated pool)

Coastal Charm New Seabury: 5BRs with Private Pool
When is the best time to visit Dennis Port?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$34,934 GYD | G$43,929 GYD | G$69,031 GYD | G$101,873 GYD | G$67,358 GYD | G$80,327 GYD | G$98,526 GYD | G$100,828 GYD | G$75,098 GYD | G$42,256 GYD | G$32,633 GYD | G$37,653 GYD |
| Avg. temp | 0°C | 0°C | 3°C | 7°C | 12°C | 17°C | 21°C | 21°C | 18°C | 13°C | 8°C | 3°C |
Destinations to explore
- Rentals with lake access Dennis Port
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- Rentals with a fire pit Dennis Port
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- Boutique hotels Dennis Port
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- Rentals with a fireplace Dennis Port
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- Rentals with a hot tub Dennis Port
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- Family-friendly rentals Dennis Port
- Rentals with breakfast Dennis Port
- Rentals with pools Dennis
- Rentals with pools Barnstable County
- Rentals with pools Massachusetts
- Rentals with pools United States
- Cape Cod
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- Cape Cod Canal
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- Marconi Beach





