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

Total vacation rentals
Explore 270 vacation rentals in Dennis

Nightly prices starting at
Dennis vacation rentals start at ﺩ.ﺇ 331 per night before taxes and fees

Verified guest reviews
Over 2,930 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
110 properties have a dedicated workspace

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

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

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

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!

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.

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.

Beach Pass Included! Brand New Spa! Central AC!
Welcome to your Italian Villa in the center of Cape Cod! My father, Sal, created this property to make memories that will last a lifetime. What could be better than a secluded yard that feels like a hidden oasis, but is also walking distance or a short drive to tourism? Walk 0.2mi to ice cream and mini golf. Or, drive 10 mins to local beaches, Hyannis Main Street, island ferries, fishing excursions, whale watching, The Cape Cod Melody Tent, the mall, rt 6, Cape Cod Gateway Airport, and more!

"Cape Escape" luxury home w/pool & beach access.
Welcome to the Cape Escape! Enjoy views of Spectacle Pond from the 70 ft. deck of this recently renovated 5 bed/3 bath spacious home meeting all your needs! Relax by the in-ground pool in the private enclosed yard. Enjoy nights around the fire-pit. Directly across the driveway you can enjoy kayaking, sunbathing & swimming at the neighborhood beach. Within 6 miles of the home you will find the historic Sandwich boardwalk, Ocean beaches, Cape Cod Canal and more! Perfect for family gatherings!

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!

ShoestringBayHouse, waterfront & pool in Cotuit
September: FIVE (5) night minimum stay. NOTE: airbnb has given the hosts notice that they are raising the fees, this will be passed onto the guest. Welcome to ShoestringBayHouse, waterfront on Popponesset Bay. It's all about the views. Our home overlooks the pool, beach and bay. We include: 2-Bikes, 2-Kayaks, and a Barnstable beach pass with beach chairs. Pet friendly and spacious with 4 BR/ 4.5 baths is priced for six adult guests plus children. Pool closes: Columbus Day

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.

Seaview Summit | Ocean Views, Indoor Pool, Beach
Perched above the coastline with panoramic Atlantic views, Seaview Summit House is Plymouth's premier oceanfront retreat. Designed for discerning travelers seeking serenity, space, and sophistication. With a heated indoor pool, expansive outdoor living areas, and direct beach access just moments away, this stunning property delivers a five-star experience in every season. Book your stay today. You'll be glad you did.

Waterfront Bass River Jolly Captain
Not only will you enjoy your stay surrounded by waterfront views from two floors of living space, you’ll be centrally-located to dining, shopping, nightlife, outdoor activities, on-site heated pool, but you’ll be staying next to a Cape Cod landmark! The iconic Lighthouse with the Jolly Captain perched above, has been welcoming visitors over the Bass River Bridge since 1960!
Popular amenities for Dennis rentals with a pool
House rentals with a pool

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

Private Pool, Large Deck, and Game Room!

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

Lovely villa w pool/hottub, central AC, near beach

Charming Cape Escape with Pool, Hot Tub & Fire Pit

Luxury retreat, in-ground pool, 10-person hot tub

Beach house in Hyannis with pool

Pool Escape in East Falmouth
Condo rentals with a pool

New Seabury Cape Condo | Pool & Beach Escape

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

1BR 2nd Floor Condo with pool

Mary's Cape Escape

Hidden Hideaway

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

Cozy Studio Just Steps Away From the Beach!

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

Beachside Condo with Balcony - Oceanside Condos

Skip to Beach, Cape Cod Condo!

Wellfleet~Beautiful One Day Perfect The Next

King Bed Suite (Pet Friendly) in a great location

Cottage at the Escape Inn

Bright and Lovely Cottage With Community Pool

The Captain's Quarters Suite - #10

Townhouse at Ocean Edge 2B/2B + Loft
When is the best time to visit Dennis?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 826 | ﺩ.ﺇ 790 | ﺩ.ﺇ 1,212 | ﺩ.ﺇ 1,609 | ﺩ.ﺇ 1,183 | ﺩ.ﺇ 1,374 | ﺩ.ﺇ 1,686 | ﺩ.ﺇ 1,678 | ﺩ.ﺇ 1,285 | ﺩ.ﺇ 771 | ﺩ.ﺇ 808 | ﺩ.ﺇ 1,102 |
| 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 |
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- 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
- Horseneck Beach
- Sea Gull Beach
- Cahoon Hollow Beach





