Family-friendly holiday rentals in Provincetown

The Farmhouse - walk everywhere -2 pkg spots

View the Pilgrim Monument from the upstairs deck, with 2 private decks to choose from. The updated interior serves a modern twist on the traditional farmhouse with a mid-century flair, all showcased under open vaulted ceilings. This townhouse is the right-hand portion of the farmhouse, which has been divided into two townhouses. Lovely open airy vaulted ceilings with plentiful natural light fill the space. Serene yet invigorating. You have TWO private parking spaces to use! The front porch & the two decks in the back are yours exclusively. Shared laundry in basement with one unit. Text us anytime. The Farmhouse is a historic property located on a quiet street right in the center of town. Shop and browse galleries on Commercial Street, and visit the nearby Long Point Light Station. Bike and hike along the Cape Cod Provincelands Trail. We have parking for 2 cars. Many guests park and walk everywhere. Some bring their bikes and or rent them. The town also has pedi-cabs which are fun - and there is also Uber and Lyft. It’s a breeze to get anywhere. Please be advised that the rate you pay/the listed rate, already includes taxes of 5.7% State Tax, 6.0% Local Tax, and 2.75% Cape Cod & Islands Water Pollution Fund Tax

The Pilgrim Monument Studio Apartment

"Great location and super clean!! Roof deck was great as well" (Thalia May 2021) Located in downtown Provincetown, this apartment has it all! Renovated in 2026 to upgrade the kitchen. You will love all the great views. Relax on the shared deck or dress and enjoy all that Commercial St has to offer. Explore the shops, restaurants, clubs, & shows. Grab the provided beach chairs because that’s right across the street! Come back to comfortable beds, close the blinds and refresh to begin another day.

Location!! Large West End House w/ parking!

Location! Beautifully renovated 1840's single family home centrally located on a quiet street in the heart of the West End! One block from Commercial Street, Boat Slip ("Tea Dance") & Joe's Coffee, very central to all bars, restaurants, galleries/shops! Fresh interior with recent major renovation while maintaining its antique charm. It has 3 bedrooms, central AC, off-street parking for 3 cars, washer/ dryer, 2.5 baths. Sunny outdoor deck & dining area, gas grill, & close to everything in PTown!

Bayshore 2:Direct waterfront/Parking/Pets welcome

Welcome to Bayshore 2: Your dream waterfront getaway in Provincetown! Stunning 1 bedroom, 1 bathroom condo boasting unparalleled views of the bay. Step onto your private covered deck, and let the breathtaking views take your breath away. We know that your pets are family too, so we welcome up to two dogs (no cats) for an additional fee of $100 per pet/per stay. For your convenience, off-street parking for one car is included. Book your stay now and make unforgettable memories in Provincetown!

Penthouse, waterviews, large deck,steps from beach

Ultra-modern 3 bedroom, 2 full bath condo in renovated 1870 Victorian. Penthouse comprises the entire 3rd floor and provides a sanctuary right on Commercial Street. Dramatic water views from every room plus exceptional views of the Pilgrim Monument. Beach access across the street. Beach gear and bikes can be securely stored in the on-site garage. Private deck with lounge seating for 8 (May-October), one-car parking on Law Street (3 min. walk), two-zone central air, wifi, 4 TVs, washer/dryer.

Modern Mid Century in West End with Parking

Newly renovated 2 bedroom 2 bath in desirable west end on 2 levels. It is close to beaches and walking distance to commercial street. The unit comes with 2 dedicated parking spaces. Upstairs, open living floor plan with direct access to large patio, outdoor shower and outdoor dining; office space with desk and additional pull out sofa bed; and main bedroom with king size bed and bath. Downstairs, bedroom suite with a queen size bed, kitchenette & bath & another direct access to small patio.

Quaint Cottage with Backyard Deck, A Perfect Getaway

Find a true Provincetown escape at this charming home. Conveniently located a short five-minute walk from Commercial Street, the cottage features all the comforts of home, an eclectic mix of furnishings and decor, an open concept living area, and a large outdoor lounge area with BBQ and hammock. Great for remote work with fast Wi-Fi and dedicated space. The house was built in 1940, and we were the first to tackle a meticulous renovation (2017). We look forward to hosting you!

A Quiet 3BR Perch in the Heart of Provincetown

This 3bed/2bath house sits amid the trees atop a quiet hill just next to the center of town with views of the Monument. Steps away from the ferry and Commercial Street, with two parking spaces, it offers a spacious open ground floor living room, dining area, and chef's kitchen along with a family / TV room, a bathroom, a patio for bikes, and a deck with table, chairs, and grill. Upstairs, three bedrooms, a second bathroom, and a second deck accommodate up to six guests.

Provincetown Pied-à-Terre

Renovated top-floor condo with two queen bedrooms and one full bath two blocks from Commercial Street and Provincetown's many attractions. Off quiet, residential Court Street, this cozy and comfortable retreat has a lovely living area, full kitchen and a breezy deck for morning coffee. Parking for one car, central heat and a/c plus in-unit laundry round out this convenient little haven. FOUR NIGHT MINIMUM 6/27 THRU 9/7. Two night minimum otherwise.

Designer West End Waterfront

This whimsical yet sophisticated waterfront penthouse in the magical West End features breathtaking 180-degree views of Provincetown Harbor, Long Point, and Cape Cod Bay. The unit is the best of both worlds: enjoy panoramic and ever-changing seascapes as you listen to waves crash onto the beach — then walk to the vibrant restaurants, bars, shopping, and galleries of Ptown. Or relax on the 200 feet of beachfront deck exclusive to the Masthead complex.

Private Beachfront, AC, EV, Kayaks, Renovated!

10% off Weeklong Off-Season bookings! Welcome to Larkspur Cottage, part of the "Days' Cottages," one of the 22 white and teal cottages located right before Provincetown, complete with its own private beach, portable AC unit and convenient located next door to an EV charging station! Enjoy majestic views and romantic sunsets. This newly updated cottage is carefully decorated to ensure a comfortable, relaxing, and memorable stay.

Modern & Cozy Apt in the Heart of Ptown w/ Parking

Welcome to our Ptown Pied-à-terre! Large penthouse at the historic Odd Fellows building in the center of town. Directly behind Town Hall and walking distance to all major attractions that Provincetown has to offer. Top floor unit with high ceilings. Many windows and skylight throughout that allows lots of light to fill the space and great view on the city, Pilgrim Monument and ocean. Easy access to huge sunny common deck.