
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.

CapeSearenity-Large Pool-Beach Passes-Family Fun!
Visit Cape SeaRenity–a stunning home w/solar heated pool and outdoor lounge, perfect for a memorable family vacation and a fabulous Cape Cod experience. Escape to Cape SeaRenity—a beautifully updated home near Barnstable Village with a pool, outdoor lounge, & stylish interiors. Minutes from beaches, shops, dining, & whale-watching. Enjoy a modern kitchen, game-filled garage, bikes & kayaks. With thoughtful design & ProHost® support, it’s the perfect base for exploring Cape Cod with your family.

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 6/20-9/15/24. 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.

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth
2nd floor Ocean Edge end unit condo located in the heart of Brewster with access to OE resort amenities: pools, gyms, tennis courts, as well as access to resort activities (fees apply). Easy access to Cape Cod Rail Trail for bicycles. Scenic route 6A offers arts & crafts galleries 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. A 30 minute ride to Cape Cod National Sea Shore. Welcome to your Happy Place!

Rock on Wellfleet!
A wonderful Wellfleet location! This second floor rental has a spacious bedroom with a queen bed, bathroom with a tub and living area with a well stocked kitchen. You would have the whole upstairs to yourself with a private door to come and go. You are also invited to use our pool at anytime! We're located very close to the Cape Cod Rail Trail for miles of bike riding, PB Boulangerie Bistro, Marconi Beach, the iconic Wellfleet drive-in and so much more. Bedding, towels and essentials provided.

The Sea Salt Studio - Steps to the Beach!
Gorgeous studio (Unit #1) only 175 yards from white sand Glendon Road beach. 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.

Barnstable, Relaxing, Great Location, Clean!
🏡 Charming historic home blends comfort, privacy, & a prime Cape Cod location, making it the perfect spot for your family retreat. ☀️ Spend your summer days swimming in the pool (open through Sept 9), cooking meals in the well-equipped kitchen, or exploring the area’s beautiful beaches, local breweries, and dining spots. 🌳 Our well-kept home sits on a full acre of land, bordering the Cape Cod Organic Farms, offering a peaceful and scenic backdrop for relaxation after a day of adventure.

Luxury Home w/ Salt Water Pool Overlooking Ocean
Welcome to your dream Cape Cod getaway! Our brand-new, fully renovated 4-bedroom, 5-bath luxury home offers breathtaking views of Buck’s Creek and Nantucket Sound, creating the perfect backdrop for your vacation. Inside, you'll find a stunning cathedral-ceiling living room designed for relaxation and gathering. The chef’s kitchen features a massive 15-foot eat-in island, perfect for family breakfasts or evening cocktails. Each of the spacious bedrooms offers comfort and privacy.

Family Fun- Games, Pool & HotTub, Dogs ok! Slps 10
Welcome to Sesuit Harbor Hideaway – your perfect Cape Cod getaway! This spacious 4-bedroom, 3-bathroom home offers a relaxing escape, complete with all the amenities you need for an unforgettable vacation. Nestled in a quiet, charming neighborhood, it’s ideal for families, friends, or groups looking to enjoy the best of the Cape. 6min to Cold Storage beach 5min to Sesuit Harbor Café 3min to Dennis Pines Golf Course 3min to Scargo Tower 10 minutes to Mayflower Beach

Hidden Hideaway
Welcome to Mid Cape Cod. Location, Location, Location. Wake up in the morning and have coffee on your private patio. The view overlooks the well manicured back yard bordered by tress and bunnies running around. After coffee, walk down main street for breakfast and more coffee at 3 Fins. Now that you are hyped, walk across the street and rent a Kayak or SUP for the day. Paddle out the Bass river down to the Nantucket sound. Have lunch next door at Sundancers.

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.

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

Beachside Retreat pool&spa bball court

Sauna, Hot Tub, Walk to Beach -Seaglass Cottage

XL Cape Retreat - Pool - Hot Tub - 5min to Beach!

49 Clover Lane, 3 beds, 3.5 baths, pool & firepit

ShoestringBayHouse, waterfront & pool in Cotuit

Sunny Cape w/Private Pool, Steps to Private Lake

4 BD slice of Harwich Heaven

Sippewissett Forest Magic by the Sea
Condo rentals with a pool

Cozy Studio Just Steps Away From the Beach!

1BR 2nd Floor Condo with pool

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

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

InnSeason Resorts Surfside

Ocean Edge Resort/Pool access/2bedroom-2bath Condo

Oct + Nov Discount | Central | Private Balcony

Escape to the Cape
Other vacation rentals with a pool

Renovated Cape Oasis W/ New Pool and Game Room!

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

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

Mansion with Heated Pool Near Ocean

Ocean Edge Townhouse/Pool Access

Getaway with pool

New Construction Home with Pool in N. Falmouth

Cute Dennis Port Cottage with pool & A/C
When is the best time to visit Dennis?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 389 | € 401 | € 389 | € 378 | € 278 | € 322 | € 396 | € 394 | € 302 | € 249 | € 388 | € 389 |
| 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 |
Quick stats about vacation rentals with a pool in Dennis

Total vacation rentals
Explore 230 vacation rentals in Dennis

Nightly prices starting at
Dennis vacation rentals start at € 34 per night before taxes and fees

Verified guest reviews
Over 2,990 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
230 of Dennis vacation rentals include wi-fi 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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