
Vacation rentals with a pool in Wellfleet
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Wellfleet

Total vacation rentals
Explore 20 vacation rentals in Wellfleet

Nightly prices starting at
Wellfleet vacation rentals start at G$23,012 GYD per night before taxes and fees

Verified guest reviews
Over 820 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Wi-Fi availability
20 of Wellfleet vacation rentals include wi-fi 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.

Ocean Edge Resort-Pool Access-CentralAC-2 bdr/2bth
Modern 2nd floor 2 bed/2 full bath Ocean Edge condo located in the heart of Brewster with balcony overlooking the resort golf course. Access to OE resort amenities (additional fees apply). Easy access to Cape Cod Rail Trail. Scenic route 6A offers arts & crafts galleries, coffee places 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. 15 minute walk to Ellis Landing Beach, great sunsets! Central A/C and heat

Private Pool, near beaches, 3 BR/3 BA, Central Air
Enjoy the Barnstable historic seaside village of Cotuit in this sprawling house with central air, nestled in the pines on a quiet street with private gated (unheated) pool, lg. backyard, firepit, ample parking, just blocks from Main St, Ropes Beach, scenic ocean views, fort playground, and Kettleer baseball. Each bedroom has a TV and ensuite bathroom! Relax in the seasonal sunroom overlooking the pool; grill burgers on the patio. Max. 9 (6 adults). Pool open 6/20-9/15/26. The reviews tell all!

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 available year-round. Vast serene private 1.5 acres adjacent to conservation land. Lighted Private heated saltwater pool Mid May to End 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.

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.

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.

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.

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.

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.

New Seabury Cape Condo | Pool & Beach Escape
Welcome to your coastal getaway at The Mews in New Seabury, Mashpee—a refined Cape-style condo tucked within an intimate golf course community. This exclusive enclave of just 15 residences offers a peaceful, private escape with access to a shared association pool reserved solely for residents. Enjoy nearby beaches like South Cape Beach State Park and Mashpee Town Beach, both just minutes away, for the perfect Cape Cod retreat.

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!

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.

Ocean Edge Cape House with Beach, Pool, and AC
Your dream Cape Cod getaway awaits! This classic Cape Cod cottage is nestled in the heart of Brewster, offering a perfect blend of comfort, relaxation, and outdoor adventure. With access to a private beach, resort-style amenities, and iconic local attractions, this is the ultimate retreat for families, couples, or groups looking to experience the best of the Cape.
Popular amenities for Wellfleet rentals with a pool
House rentals with a pool

Harwich Haven: Pool & Fire Pit

5-bedroom Cape with a pool and yard games.

House on Cape Cod with pool close to beach

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

4 BD slice of Harwich Heaven

Winslow Acres [heated] Pool Escape; pool May-Oct

Jolly Captain Lighthouse
Condo rentals with a pool

Cozy Studio Just Steps Away From the Beach!

1BR 2nd Floor Condo with pool

Luxury Waterfront Getaway

Ocean Edge: 2 bed/2 bath - Pools & Resort Access

Stylish & Modern Studio Condo - Steps to the Beach

Hidden Hideaway

Mary's Cape Escape

Newly Updated Condo w/ Pool - Steps to Boatslip!
Other vacation rentals with a pool

Spacious, newly updated condo

Fenced Pool, Fire pit, Outside dining, Coffee bar

Mashpee Manor Pool House

Modern A-Frame Farm Stay! One bedroom+ loft

Overlook Poolside Getaway Heated Pool (May - Oct 2

Bright Beach Condo • Walk to Sand & Shops

Cape Cod Luxury: Heated Pool, Game Room, Bike Path

New Seabury Oasis with Pool!
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