
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 ﺩ.ﺇ 331 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.

House on Cape Cod with pool close to beach
This single family house is located at the end of a cul de sac in a quite neighborhood in walking distance to Mayflower and Bayview beaches. You enter through the bright and open kitchen, looking out over the patio and the pool. The open living and dining room open up to a sun room where you can relax after a fun day at the beach. The two smaller bedrooms share a big bathroom with tub and double sink, whereas the master bedroom has its own bathroom. A big dining table can host up to 8 people.

Bright and Lovely Cottage With Community Pool
(Reservations avail as of my 5/14/27 season opening. Prices now INCLUDE the Airbnb Guest Fee! Only state/local taxes added.) Skylights & lots of windows make this contemporary cottage appealing. A loved location. Just over 1/2 mile to the ocean! Quiet community w/ pool. One bedroom - queen bed. Loft - twin bed. WIFI, outside shower, locking shed, private deck, fenced yard. Come. Relax! Some flexibility re dates and arrival times. Will try to help. Incredible bike path nearby!!

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

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

Beachwalk cozy studio with pool!
Your family will be close to everything at this central located studio in the heart of Dennis Port. Walkable 1/2 mile to Haigis Beach or relax by the shared pool! This furnished apt is perfect for 2 people/ baby with a queen bed, a newly renovated full kitchen with stove, fridge, Keurig, microwave and all essentials. Studio has air conditioning, smart TV with cable, Wifi, and access to back patio area with grill and furniture. Parking on premises. Beach chairs and beach wagon 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!
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!

ShoestringBayHouse, waterfront & pool in Cotuit

Luxury Historic Estate with Expansive Grounds

Coastal Charm New Seabury: 5BRs with Private Pool

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

Private Pool, near beaches, 3 BR/3 BA, Central Air

Luxury retreat, in-ground pool, 10-person hot tub
Condo rentals with a pool

Cozy Studio Just Steps Away From the Beach!

Comfy Cape Escape! Spacious, Cozy, Close to Beach!

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

Mid Cape Cod, 3 Season Haven by Bass River
Other vacation rentals with a pool

Renovated Cape Oasis W/ New Pool and Game Room!

Beach house in Hyannis with pool

Popponesset, Exclusive, 3-Bdrm, 4-Bths, Sleeps 6,

Fenced Pool, Fire pit, Outside dining, Coffee bar

Sagamore Manor | Pool | Hot Tub | 5min to Beach!

Town House for Cape Cod fun, by Bass River.

Breezy Pool Retreat Near Mayflower Beach

Pool. Hot Tub. Game Room. Walk to Beach. Luxury!
When is the best time to visit Dennis Port?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 613 | ﺩ.ﺇ 771 | ﺩ.ﺇ 1,212 | ﺩ.ﺇ 716 | ﺩ.ﺇ 624 | ﺩ.ﺇ 944 | ﺩ.ﺇ 1,730 | ﺩ.ﺇ 1,770 | ﺩ.ﺇ 1,318 | ﺩ.ﺇ 742 | ﺩ.ﺇ 573 | ﺩ.ﺇ 661 |
| 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 patio Dennis Port
- Rentals with a fire pit Dennis Port
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- Pet-friendly rentals Dennis Port
- Boutique hotels Dennis Port
- Cottage rentals Dennis Port
- Rentals with a hot tub Dennis Port
- House rentals 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
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- Onset Beach
- East Sandwich Beach
- Duxbury Beach
- Sandy Neck Beach
- New Silver Beach
- Saquish Beach
- Pinehills Golf Club
- Nauset Beach
- Skaket Beach
- Falmouth Heights Beach
- Coast Guard Beach
- Race Point Beach
- Cape Cod Canal
- Popponesset Peninsula
- Cape Cod Inflatable Park
- Nickerson State Park
- Inkwell Beach
- Sea Gull Beach
- Cahoon Hollow Beach
- Marconi Beach





