
Holiday rentals with a pool in Dennis Port
Find and book unique homes with a pool on Airbnb
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. World Cup fans welcome, combine football with a beach holiday. 90 min drive to stadium/matches!

Stylish & Modern Studio Condo - Steps to the Beach
Stay in a renovated modern, cozy studio style condo with walking distance to Glendon Beach. This stylish airy & bright poolside retreat is perfect for couples and solo travelers. A slider door offers direct access to the shared pool area. The kitchenette features quartz counters, a sink, refrigerator, 2-burner cooktop, and a microwave. Enjoy a restful night's sleep with a memory foam mattress and black-out curtains. The home also has a 24" Roku Smart TV for you to enjoy your favorite shows.

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.

Fenced Pool, Fire pit, Outside dining, Coffee bar
Our family friendly home which has three bedrooms and 2 1/2 bathrooms with an open floor plan. A electric fireplace in the living room. Seating enough for 10 in the living and dinning room. Renovated kitchen with coffee/tea bar Our backyard is equipped with a fenced in in-ground heated pool, lounge chairs with free standing umbrellas, patio with fire table and comfortable, fire pit with Adirondack chairs. Outside grill. Outside dinning table for 10 with canopy for shade and bug screen.

Cottage at the Escape Inn
Guests will have a special experience as this cottage provides a fireplace. Featuring a private entrance, this air-conditioned cottage is consisted of 1 living room, 2 separate bedrooms and 1 bathroom with a bath and a shower. The well-equipped kitchen features a stovetop, a refrigerator, a dishwasher and kitchenware. The spacious chalet offers a tea and coffee maker, a seating area, a wardrobe, a sofa, as well as a flat-screen TV with cable channels. The unit offers 3 beds.

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.

Charming Cape Escape with Pool, Hot Tub & Fire Pit
Welcome to Searside Retreat, your ultimate Cape Cod escape in South Dennis! This charming home offers a private pool, open layout, and modern comforts just minutes from top beaches, restaurants, and shops. Relax in a quiet neighborhood in the heart of the Cape. Mayflower Beach - 10min Chapin Beach - 6 min Cape Cod Rail Trail – 10min The Marshside Restaurant – 2min Sesuit Harbor Cafe - 5 min Scargo Cafe - 5 min Smugglers Ice Cream - 5 min Learn more below!

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 Port rentals with a pool
House rentals with a pool

Harwich Haven: Pool & Fire Pit

Renovated Cape Oasis W/ New Pool and Game Room!

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

House on Cape Cod with pool close to beach

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

4 BD slice of Harwich Heaven

CapeSearenity-Large Pool-Beach Passes-Family Fun!

Private Pool, near beaches, 3 BR/3 BA, Central Air
Apartment rentals with a pool

1BR 2nd Floor Condo with pool

Resort Pools & Golf Views · Walk to Bay Beaches

Hidden Hideaway

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

Mary's Cape Escape

Mid Cape Cod, 3 Season Haven by Bass River

Cape Cod, South Yarmouth July 18-25. Sleeps 8

Ocean Edge Resort/Pool access/2bedroom-2bath Condo
Other holiday rentals with a pool

Our families slice of heaven

Town House for Cape Cod fun, by Bass River.

Breezy Pool Retreat Near Mayflower Beach

Ocean Edge Townhouse/Pool Access

Steps to the Beach & Heated Pool!

Family Friendly Hideaway

Skip to Beach, Cape Cod Condo!

Townhouse on the beach, pool, walk to Main St.
When is the best time to visit Dennis Port?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €144 | €181 | €284 | €419 | €277 | €331 | €406 | €415 | €309 | €174 | €134 | €155 |
| 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 holiday rentals with a pool in Dennis Port

Total holiday rentals
Explore 130 holiday rentals in Dennis Port

Nightly prices starting at
Dennis Port holiday rentals start at €78 per night before taxes and fees

Verified guest reviews
Over 770 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
130 of Dennis Port holiday rentals include wifi 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
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- Onset Beach
- East Sandwich Beach
- Duxbury Beach
- Pinehills Golf Club
- Sandy Neck Beach
- New Silver Beach
- Coast Guard Beach
- Nauset Beach
- Falmouth Heights Beach
- Skaket Beach
- Saquish Beach
- Race Point Beach
- Cape Cod Inflatable Park
- Nickerson State Park
- Lighthouse Beach
- Cahoon Hollow Beach
- Popponesset Peninsula
- Cape Cod Canal
- Sea Gull Beach
- Inkwell Beach





