Holiday rentals with a pool in Provincetown

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.

Family · Value · Comfort

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!

Family · Value · Comfort

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

Family · Location · Pool

Beachside cottage with pool in Provincetown

Relax with family or friends at this cottage at Beach Point Club. Enjoy a BBQ on the large deck or walk to the beach on the boardwalk, which is steps away from the cottage. Take in the water view from the side of the deck, hop on the shuttle to downtown Provincetown, or relax by the pool. Bedrooms contain queen beds. There are mini splits in the living room and bedrooms. Open-concept kitchen contains cooking basics and a Keurig. Linens provided. Pool open July to Sept. No smoking & no pets.

Location · Family · Getting around

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

Value · Family · Accuracy

Luxury Waterfront Getaway

Enjoy direct water views of Cape Cod Bay in our beautiful 1st floor condo with central air. Our home is steps from the beach with an approx. 1 mile walk through the dunes to the Atlantic Ocean. We are perfectly situated on the East End with beach accessibility. Enjoy Provincetown’s great restaurants, many art galleries, shows and unique shops. Enjoy our home anytime of the year. This past year our association upgraded our siding, lighting and entrance to offer a fresh new look.

Location · Family · Beach

Newly Updated Condo w/ Pool - Steps to Boatslip!

This newly updated 2-bed, 1-bath condo, which sleeps 4, is the perfect escape for your Ptown vacation. This first floor condo is only a short walk from Commercial Street and steps to the beach and embodies the best of the Ptown experience! You will love spending time lounging around the lovely pool and exploring all that Commercial Street has to offer! As this property is only steps from the beach, you won't have to venture far to breathe in that relaxing ocean breeze.

Family · Location · Kitchen

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.

Value · Location · TV

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.

Location · Family · Air conditioning

P-Town Beach Beauty on the Bay. Water View!

Beautiful Water View East End 2 bedroom condo across the street from the beach on the bay. Just cross the road and take the association maintained steps down to the beach. This beach boasts a nice tidal swing where you can walk out in the shallows during low tide. The condo is in the perfect East End location, combining closeness to the center of town, with your own beach and not having the noise and parking issues of downtown Provincetown.

Value · Family · Long stay

Wellfleet~Beautiful One Day Perfect The Next

Are you looking for the perfect getaway in charming Wellfleet? This two-bedroom cottage is located in a private, detached cottage village. Enjoy the beautiful SEASONAL in-ground pool (OPENS July 4th & CLOSES LABOR DAY) and a welcoming family-friendly atmosphere. The cottage is centrally located with a five-minute drive to both bay and ocean side beaches, freshwater kettle ponds, Wellfleet center, and the rail trail!

Location · Value · Amenities

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.

Family · Location · Shared spaces