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 Mashpee

4.97 out of 5 average rating, 103 reviews

Sleep 6 @ New Seabury w/ Pool Access, All Seasons!

Welcome to our beautiful Cape Condo located in The Mews at New Seabury Country Club in Mashpee, MA. Our unit provides access to a private condo association pool a 3 min walk from the unit. Also, we have: -5 min bike/car ride to beach -2 bicycles available for use -Central air, wifi, cable, gas grill -Located on Championship Golf Course -Beach chairs, beach towels/toys -New Seabury Village restaurants, mini-golf, bowling, museums -20 min drive to Hy-Line Ferry to Nantucket/Martha's Vineyard

Apr 14 – 21

G$32,339 GYD per night

Guest favorite

Condo in Brewster

4.97 out of 5 average rating, 158 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!

Oct 26 – Nov 2

G$53,567 GYD per night

Guest favorite

Cottage in Provincetown

4.91 out of 5 average rating, 11 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 private 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 community pool. Bedrooms contains queen beds, and there are mini splits in the living room and bedrooms. Open-concept kitchen contains cooking basics and a Keurig. Linens provided. Pool open July-September

Mar 9 – 16

G$62,138 GYD per night

Guest favorite

Cottage in Sandwich

4.95 out of 5 average rating, 123 reviews

Gold Anchor Cottage - private hot tub getaway!

This newly renovated cottage is an amenity-filled launching point to explore all of Cape Cod! Just 0.4miles to the beach and with our own salt water pool plus private hot tub, you’ll be able to fully enjoy the Cape. Some of our favorites nearby: 2min- your local coffee shop 2min- great fish tacos + bar 2min- nice conservation area hike 2min- local convenience store 7min- downtown Sandwich 7min- golf course 9min- Sandwich Boardwalk 10min- Heritage Museums & Gardens 22min- Cape Cod Rail Trail

Sep 18 – 25

G$85,965 GYD per night

Guest favorite

Cottage in Provincetown

5.0 out of 5 average rating, 11 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!

Dec 2 – 9

G$66,326 GYD per night

Guest favorite

Apartment in Provincetown

4.9 out of 5 average rating, 41 reviews

15 Cottage #2 Top floor

Small complex with heated pool, spa in summer season one with parking We accept 7 days reservations during season July/Aug 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.

Apr 7 – 14

G$51,691 GYD per night

Guest favorite

Home in Plymouth

4.9 out of 5 average rating, 213 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.

Nov 17 – 24

G$118,172 GYD per night

Guest favorite

Apartment in Hyannis

4.89 out of 5 average rating, 102 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, and kettle. This studio has air conditioning.

Sep 29 – Oct 6

G$39,252 GYD per night

Superhost

Cottage in Provincetown

4.87 out of 5 average rating, 15 reviews

(Beachfront) 2BR/2BA Cottage w/ Front & Back Deck

Nestled within the Beach Point Club complex, this two-bedroom/two-bathroom cottage has all the amenities needed for an unforgettable Cape Cod vacation. A short 2-minute walk along a private boardwalk brings you to the stunning and serene Cape Cod bay beachfront. After watching the painting-like Sunsets, you can unwind on the Private Back Deck or in the Private Front Yard. World-class dining, shopping, and entertainment in the heart of Provincetown is accessible via a 6 minute shuttle.

Mar 10 – 17

G$84,541 GYD per night

Superhost

Apartment in Provincetown

4.9 out of 5 average rating, 10 reviews

Spectacular Waterfront Condo

Beautifully waterfront condo renovated in spring 2023. Newly appointed Kitchen features driftwood cabinetry with white quartz counters and center island. Enjoy water views from the kitchen/living room. New leather sofa and 65" TV in the loving room. The main bedroom features a king size bed and 43" TV and quest room appointed with a queen size bed and 43" TV. New bathroom features a walk in shower. Enjoy the sunsets on the deck or on the beach while enjoying an evening beverage.

Jan 18 – 25

G$60,469 GYD per night

Guest favorite

Condo in Provincetown

4.97 out of 5 average rating, 33 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.

Nov 13 – 20

G$99,009 GYD per night

Guest favorite

Home in Barnstable

4.93 out of 5 average rating, 105 reviews

Magical pool home with windmill/new kitchen

This magical, luxurious property has 6 bedrooms, 5 bathrooms & sleeping arrangements for 14 – it’s an excellent choice for a family, an offsite business meeting or a group of close friends looking for the ultimate beachside, pool experience with a four story windmill tower. The welcoming home has everything you’ll need for a comfortable stay, including wireless internet, central A/C, & a new pool. Its 4 story magical windmill will amaze you and your guests.

Nov 26 – Dec 3

G$235,993 GYD per night