Holiday rentals with a pool in Wellfleet

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Wellfleet

  • Total holiday rentals

    Explore 20 holiday rentals in Wellfleet

  • Nightly prices starting at

    Wellfleet holiday rentals start at £103 per night before taxes and fees

  • Verified guest reviews

    Over 840 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Wifi availability

    20 of Wellfleet holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wellfleet rentals

  • 4.6 Average rating

    Wellfleet stays receive an average rating of 4.6 out of 5 from guests

Top-rated rentals with a pool in Wellfleet

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

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Top guest favourite
An open living area features large glass doors that provide views of the golf course. A comfortable seating arrangement includes a recliner and a sectional sofa. A spiral staircase leads to the loft above, and a mounted television is positioned above a modern fireplace.
Apartment in Brewster
5.0 out of 5 average rating, 101 reviews

Ocean Edge Resort/Pool access/2bedroom-2bath Condo

Recently renovated end unit townhouse located in the heart of The OE Villages. Beautiful views towards the golf course, and southern exposure with lots of natural light, A/C, W/D and private patio with Weber grill and outdoor furniture. Sports Membership so Guest passes are available for purchase at Linx for use of pools, hot tubs and gyms. Additional costs for use of courts may apply. Bike rail trail, Ice cream store, great restaurants, coffee, beaches and Kayak/Bike rentals are all close by.

Top guest favourite
Home in Brewster
4.98 out of 5 average rating, 53 reviews

Modern Cape, Private Heated Pool, Beach, Golf

Welcome to your perfect vacation/reunion in the center of the Cape. Min. to 3 golf courses, 5 ocean beaches, lakes, park, trails. Bright modern quality home, AC, enjoyable year-round. Vast serene private 1.5 acres adjacent to conservation land. Pool heated Memorial day weekend- last Sunday of Sept. Bocce Court, Putting green, Corn hole, Hammock, Outdoor shower, AC. Expansive double deck with awning. Beautiful indoor/outdoor dining/entertaining. All essentials provided. 7+ free parking.

Top guest favourite
A communal pool area features a clear blue pool surrounded by concrete decking. Lounge chairs are arranged neatly on the sides, with greenery visible in the background. A wooden fence encloses the area, providing a private atmosphere.
Apartment in Dennis Port
4.92 out of 5 average rating, 133 reviews

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.

Top guest favourite
A spacious living area features a light-colored sofa and a patterned accent chair. A dining table for four and a coffee table are present. Large windows allow natural light, showcasing the balcony view. A ceiling fan provides ventilation, and an air conditioning unit is visible.
Apartment in Brewster
5.0 out of 5 average rating, 99 reviews

Ocean Edge Resort-Pool Access-Golf View-2 bdr/2bth

Newly renovated 2nd floor 2bed/2 full baths condo located within Ocean Edge Resort, with balcony overlooking the golf course. Access to OE resort amenities (additional fees apply) and restaurants. Easy access to Cape Cod Rail Trail . Scenic route 6A offers arts & crafts galleries, coffee/tea spots and local shops. A 10 minute car ride to a 36 hole Captains Golf course. Short ride to 10 Brewster bay beaches famous for their tidal flats. 15 minute walk to Ellis Landing Beach, great sunsets!

Top guest favourite
Home in Sandwich
4.99 out of 5 average rating, 102 reviews

"Cape Escape" luxury home w/pool & beach access.

Welcome to the Cape Escape! Enjoy views of Spectacle Pond from the 70 ft. deck of this recently renovated 5 bed/3 bath spacious home meeting all your needs! Relax by the in-ground pool in the private enclosed yard. Enjoy nights around the fire-pit. Directly across the driveway you can enjoy kayaking, sunbathing & swimming at the neighborhood beach. Within 6 miles of the home you will find the historic Sandwich boardwalk, Ocean beaches, Cape Cod Canal and more! Perfect for family gatherings!

Guest favourite
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, 40 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 July to Sept. No smoking & no pets.

Guest favourite
The backyard features an inground pool illuminated at night, surrounded by wooden decking. Nearby, a shed with white shutters enhances the outdoor space, while lush greenery provides a serene backdrop.
Home in Orleans
4.93 out of 5 average rating, 43 reviews

5-bedroom Cape with a pool and yard games.

Five-bedroom and three-bath Cape style home with large fenced backyard and an inground pool. Various yard games are available - outdoor ping pong table and corn toss. Short distance to Pleasant Bay, freshwater ponds, and the ocean. Approximately five miles from downtown Chatham and Orleans Center. A variety of local shops, and restaurants, and catch the Cape Cod Baseball under the lights just minutes away. (Our pool is not heated - the opening and closing is weather dependent).

Top guest favourite
Bright and airy living space is highlighted by a spiral staircase leading to an open loft. A plush light grey sofa faces a coffee table on a woven area rug, while a dining table and chairs are visible in the background. Modern kitchen cabinetry offers a sleek contrast.
Flat in Brewster
5.0 out of 5 average rating, 35 reviews

Townhouse at Ocean Edge 2B/2B + Loft

Experience resort-style living at its finest! Tucked away just a 10-minute drive to the beach, this delightful townhouse offers the perfect blend of comfort and convenience. With two bedrooms, two baths, and an additional cozy loft space, there's ample room for relaxation. Enjoy lounging on the patio, take a refreshing dip in one of the resort pools (for an additional fee paid directly to Ocean Edge) or head to the beach for some sun and surf. Your ultimate getaway awaits!

Guest favourite
A distinctive A-frame cottage is situated among tall trees, surrounded by natural greenery. The entrance features a wooden deck with a picnic table and two chairs, inviting relaxation in the outdoors. Clear skies provide ample sunlight, enhancing the cottage's inviting atmosphere.
Cottage in Wellfleet
4.91 out of 5 average rating, 11 reviews

The Cottages at Even'tide Resort - Seagull

Seagull cottage is one of 8 cottages located at the Even'tide Resort. Where else on Cape Cod can you rent a private cottage and enjoy a huge heated indoor pool and direct access to a 22 mile paved bike path? A 1 mile hike through the woods takes you to Marconi National Seashore beach. You have access to all the amenities at the motel including ping pong, billiards, 5 hole mini golf, shuffleboard, corn hole, fitness room, playground, basketball court, and coin op laundry.

Guest favourite
A scenic view showcasing the bay with gently rippling waters and distant land on the horizon. The foreground features coastal vegetation, including pines and shrubs, along a wooden pathway leading toward the beach. Nearby, a stop sign indicates road access.
Apartment in Provincetown
4.97 out of 5 average rating, 262 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.

Guest favourite
A charming cottage exterior is showcased, featuring natural wood shingles and red shutters. A bright orange door provides a welcoming entrance. Lush green leaves frame the image, highlighting the serene surroundings of the property against a clear sky.
Cottage in Wellfleet
4.87 out of 5 average rating, 67 reviews

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!

Guest favourite
A light-filled living area features a beige sofa and a matching loveseat, accented by navy and white decorative pillows. A round wooden coffee table sits in the center, surrounded by a patterned area rug. Sliding glass doors provide access to the outdoor space.
Townhouse in Brewster
4.86 out of 5 average rating, 43 reviews

Ocean Edge Townhouse/Pool Access

End unit townhouse located in heart of OE Villages with private patio, A/C & W/D. There’s no better way to experience all that Brewster has to offer than taking your family to stay at the Ocean Edge Resort. Just minutes off the property you will find yourself at the beach, on the golf course, or at one of the many excellent local restaurants. Unit has pool & fitness access for additional fees.

Popular amenities for Wellfleet rentals with a pool