Vacation rentals with a pool in Provincetown Harbor

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Top-rated rentals with a pool in Provincetown Harbor

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Brewster

4.97 out of 5 average rating, 186 reviews

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!

Top guest favorite

A cozy living area is furnished with a comfortable sofa adorned with decorative pillows. A dining table with seating for four is visible, alongside a well-equipped kitchen in the background. Natural light enters through the windows, highlighting the warm wood floors.

Apartment in Wellfleet

4.98 out of 5 average rating, 93 reviews

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.

Superhost

A well-maintained outdoor pool is framed by a clean concrete deck. Lounge chairs are arranged neatly along the edges, and shaded tables can be seen in the background. Surrounding greenery provides a pleasant backdrop for relaxation. The pool displays a clear blue surface with a depth marker reading '10 FT NO DIVING.'

Condo in Truro

4.81 out of 5 average rating, 68 reviews

Designer Studio Condo with peeks of Cape Cod Bay.

See 'my property'. Beautiful, unique designer condo. Photos show what makes my place stand out from others. Please view and read captions!! 10 minute walk to Bay beach, 10 minute drive to Provincetown. Peeks of blue bay from private, spacious deck. Near Atlantic beaches, Truro vineyards, historic lighthouse & Wellfleet. Quiet in unit, 2nd floor, no one above. Guests 21+ welcome, 4 night minimum 5/22 to 6/29 check ins; 5 nights 6/30 to 9/1 check ins; back to 4 nights for 9/2 to 10/31 check ins

Top guest favorite

A spacious outdoor pool is surrounded by a wooden deck, with comfortable seating arranged nearby. The two-story cottage features a large balcony above, adorned with potted plants and sun umbrellas. Lush greenery in the background enhances the tranquil setting.

Cottage in Provincetown

5 out of 5 average rating, 54 reviews

Cozy Cottage in the East End

Cozy cottage nestled in the East End of Provincetown. Enjoy this prime location just under a mile from the center of town. Plenty of shops, restaurants, galleries and activities to enjoy! Relax in our newly, fully renovated home complete with private patio and two parking spots! Outdoor dining and living areas provide even more space for you to enjoy outside. Steps to the convenient East End Market & Cafe, Berta Walker Art Gallery and Provincetown Theatre. You're guaranteed a great vacation!

Guest favorite

A charming cottage features shingle siding and a well-maintained exterior. A large deck with a grill is visible at the front. Surrounding greenery and a stone pathway lead to the entrance, which is framed by large windows allowing natural light into the interior.

Cottage in Provincetown

4.9 out of 5 average rating, 30 reviews

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 now - Sept. No smoking and no pets.

Top guest favorite

A view overlooking a well-maintained pool surrounded by green grass, with beach access visible in the distance. The landscape features a mix of trees and charming houses, set against a clear blue sky and tranquil water.

Home in Plymouth

4.9 out of 5 average rating, 287 reviews

Ocean Side, Amazing View, close to town/beach, Spa

PRICING IS FOR 2 GUESTS, 1 BEDROOM, 1 BATH ONLY, can add additional bed/bath for a fee, YOU WILL HAVE THE HOUSE TO YOURSELF. We only use this listing to fill gaps when the larger listing isn't rented & will decline ALL WEEKENDS, HOLIDAYS, PEAK times and will only accept mid-week, non summer/holidays. Please read additional info. OCEAN FRONT, HISTORIC SUMMER COTTAGE, AMAZING VIEWS, GREAT LOCATION, less than 1 mile walk to town and beach. Hot tub, fireplace, stocked kitchen, fresh linens.

Guest favorite

A shared pool area features a clear blue pool surrounded by lounge chairs in yellow and green hues. The pool is enclosed by a wooden fence, with the condo visible in the background, displaying gray shingle siding and a small porch.

Condo in Provincetown

4.93 out of 5 average rating, 44 reviews

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.

Guest favorite

A private deck is showcased with outdoor furniture, including a round table and chairs. A colorful striped umbrella provides shade, while surrounding greenery and flowers add a natural touch. The deck is well-lit by sunlight, creating a warm and inviting space.

Apartment in Hyannis

4.89 out of 5 average rating, 137 reviews

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.

Top guest favorite

Condo in Provincetown

4.97 out of 5 average rating, 227 reviews

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.

Superhost

A heated pool is seen in a sunny outdoor area, surrounded by lounge chairs. A colorful beach ball floats on the water, and umbrellas provide shade on the deck. Stairs lead to an upper deck that offers a view of the pool and surrounding greenery.

Apartment in Provincetown

4.87 out of 5 average rating, 61 reviews

15 Cottage #2 Top floor

Small complex with heated pool, spa in summer season one with parking . Located on the top floor, vaulted ceilings in LR, bedrooms are roommate style, exclusive deck, views to Bay Very bright, airy and spacious condo. Beautiful pine hardwood floors throughout. Kitchen has slate floors and granite counter tops. Excellent West End location that is quiet, easy access to shops, restaurants and entertainment. Quick walk over to bay or beach.

Top guest favorite

An inviting open-concept living area features exposed wooden beams and large windows that offer panoramic views. A round dining table with woven chairs is positioned near the windows, while a spiral staircase leads to an upper level. A cozy seating area is visible in the background.

Apartment in North Truro

5 out of 5 average rating, 42 reviews

Captains Quarters at Dune Crest Hotel

Panoramic views of Cape Cod Bay, Provincetown, Pilgrim Lake. Located on 12 acres in the National Seashore, this is the Owner's apartment at the Dune Crest Resort. 2 Ensuite bedrooms, open floor plan kitchen, dining, living room for gathering. Use of hotel amenities: Continental Breakfast, tennis court, swimming pool, hiking trails. Provincetown only a few miles away for dining, shopping, entertainment.

Superhost

A comfortable living area features a dark sectional sofa and a light wood coffee table. A large flat-screen TV is mounted on the wall. Bright natural light filters through sliding glass doors, revealing views of the ocean and outdoor deck. Light furnishings enhance the airy feel.

Condo in Provincetown

4.9 out of 5 average rating, 105 reviews

Bright Beach Condo • Walk to Sand & Shops

Soak in ocean views from this sun-filled, stylish condo just steps from the beach and a short walk to town. Enjoy brand-new beds, an open layout, and a peaceful, breezy vibe perfect for relaxing. Ideal for couples, solo adventurers, business travelers, or families with kids. Whether you're here to unwind or explore, this light-filled retreat is the perfect home base. We can’t wait to welcome you!