Holiday rentals with a pool in Dennis Port

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.

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.

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.

Deluxe Double Room | Full Studio w/ Kitchenette

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

Heated Pool | Waterfront | A/C | Kayaks | 3 Acres

Relax at this modern, spacious, private waterfront home on Mill Pond in Yarmouth Port. This 4 bedroom (6 bed), 3 bath retreat offers beautiful water views, a private in-ground heated saltwater pool, sunroom, and expansive outdoor living space with 3 acres of land. Paddle our kayaks from the backyard, enjoy nearby bike paths and walking trails, or unwind just minutes from Cape Cod beaches. Perfect for families or peaceful group getaways. 18C - Hosted by Tuxfin Hospitality

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.

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.

Jolly Captain Lighthouse

Ever wanted to stay in a lighthouse?! Well this your opportunity. The Jolly captain lighthouse was originally built in 1960 and recently renovated in 2024-2025. Including breathtaking views of Bass River. Access to community pool is available. In addition, dock slip is available for additional cost. Please contact host privately for additional information.

Steps from Bass River Marina · Private Balcony

Wake up to marina views, kayak across the street, and hit West Dennis Beach in under 10 minutes. This cozy, beautifully decorated studio has everything you need: full kitchen, SmartTV, private balcony with seating for four, and a seasonal pool. Cook dinner, lounge outside, or end the night with a movie in bed.