
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 130 vacation rentals in Dennis Port

Nightly prices starting at
Dennis Port vacation rentals start at G$18,828 GYD per night before taxes and fees

Verified guest reviews
Over 770 verified reviews to help you choose

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

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.

Ocean Edge Resort-Pool Access-CentralAC-2 bdr/2bth
Modern 2nd floor 2 bed/2 full bath Ocean Edge condo located in the heart of Brewster with balcony overlooking the resort golf course. Access to OE resort amenities (additional fees apply). Easy access to Cape Cod Rail Trail. Scenic route 6A offers arts & crafts galleries, coffee places and local shops. A 10 minute car ride to a 36 hole Captains Golf course. Short ride to 10 Brewster bay beaches famous for tidal flats. 15 minute walk to Ellis Landing Beach, great sunsets! Central A/C and heat

Steps to the Beach & Heated Pool!
World Cup visitors - Only 1.5 hours to Boston Stadium! Great Cape Cod /Boston Location! Sleeps 4. Super cute, remodeled 1 bedroom/ 1 bath, 1st floor condo! Partial Ocean Views! Steps away from Glendon Beach & Heated Pool. Master bedroom with queen-sized bed & large closet; queen sleeper sofa & smart tv in living area; fully equipped kitchen w/Keurig & dining space; cable tv, Strong Wi-Fi!; ac/heat; outdoor barbeque and seating area. Heated pool is open from Memorial weekend to mid September.

Private Pool, near beaches, 3 BR/3 BA, Central Air
Enjoy the Barnstable historic seaside village of Cotuit in this sprawling house with central air, nestled in the pines on a quiet street with private gated (unheated) pool, lg. backyard, firepit, ample parking, just blocks from Main St, Ropes Beach, scenic ocean views, fort playground, and Kettleer baseball. Each bedroom has a TV and ensuite bathroom! Relax in the seasonal sunroom overlooking the pool; grill burgers on the patio. Max. 9 (6 adults). Pool open 6/20-9/15/26. The reviews tell all!

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.

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.

Walk to the beach or sit poolside! Updated studio!
Adorable condo in the heart of vacationland in Dennis Port! This studio unit is full of natural light and comfortable for two people! The floor plan offers a living area with a queen sized bed and a pull out full sofa. Step out the sliders onto a deck with outdoor seating. There is a shared pool open late June- Aug. All this and right in the middle of the summer fun of Dennis Port and all its activities. The beach is under 1/4 mile away in walking distance. Beach chairs and 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.

Bright and Lovely Cottage With Community Pool
Skylights and lots of windows make this contemporary cottage appealing. Just over 1/2 mile to the ocean! Quiet community with pool. One bedroom with queen bed. Loft with twin bed. WIFI, outside shower, locking shed, private deck, fenced yard. Come and relax. Please inquire for any possible flexibility in calendar dates and arrival or check-out times. We will try to help. Incredible bike path nearby!! Sorry - no smoking and no pets.

New Seabury Cape Condo | Pool & Beach Escape
Welcome to your coastal getaway at The Mews in New Seabury, Mashpee—a refined Cape-style condo tucked within an intimate golf course community. This exclusive enclave of just 15 residences offers a peaceful, private escape with access to a shared association pool reserved solely for residents. Enjoy nearby beaches like South Cape Beach State Park and Mashpee Town Beach, both just minutes away, for the perfect Cape Cod retreat.

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.
Popular amenities for Dennis Port rentals with a pool
House rentals with a pool

Harwich Haven: Pool & Fire Pit

Water Views Private Pool, Hot Tub, Access to Cove!

Fenced Pool, Fire pit, Outside dining, Coffee bar

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

Modern Cape, Private Heated Pool, Beach, Golf

4 BD slice of Harwich Heaven

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

Jolly Captain Lighthouse
Condo rentals with a pool

Peaceful Retreat on Chilton Lane

Ocean Edge: 2 bed/2 bath - Pools & Resort Access

Stylish & Modern Studio Condo - Steps to the Beach

Hidden Hideaway

Mary's Cape Escape

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

Mid Cape Cod, 3 Season Haven by Bass River

Cape Cod, South Yarmouth July 18-25. Sleeps 8
Other vacation rentals with a pool

Adorable 2BR cottage with pool.

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

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

1 bedroom apartment located 5 minute walk to beach

Hyannis Port Coastal Escape – Pool & Walk to Beach

Cape Cod Resort|Cabin w/Pool & Private Beach

Cute Dennis Port Cottage with pool & A/C

New Seabury Oasis with 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$97,278 GYD | G$97,278 GYD | G$97,278 GYD | G$101,881 GYD | G$67,363 GYD | G$80,333 GYD | G$98,534 GYD | G$100,835 GYD | G$75,103 GYD | G$42,259 GYD | G$32,635 GYD | G$37,656 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
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- Rentals with pools Barnstable County
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- Rentals with pools United States
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- East Sandwich Beach
- Duxbury Beach
- Onset Beach
- Coast Guard Beach
- Pinehills Golf Club
- Sandy Neck Beach
- New Silver Beach
- Nickerson State Park
- Popponesset Peninsula
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- Saquish Beach
- Lighthouse Beach
- Cape Cod Inflatable Park
- Race Point Beach
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- Falmouth Heights Beach
- Marconi Beach
- Inkwell Beach




