Holiday rentals with a pool in Wellfleet

Find and book unique homes with a pool on Airbnb

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
Guest suite in Centerville
4.99 out of 5 average rating, 93 reviews

“The Hideaway” Private Guest Suite/Pool/Beach Pass

Enjoy a bit of Cape Cod in a friendly and walkable neighborhood of lush green trees , flower gardens, and a walking trail. Less than 1 mile from Centerville's shops and restaurants. Less than 2 miles from Craigville Beach and its beachside walk up shanty’s for lunch. A small beach on Lake Wequaquet is only 2 miles down the road . Main street Hyannis, a walkable downtown with many shops and restaurants is a quick 10-minute drive. Ocean marinas, and ferries to the islands, are a 15 minute drive.

Top guest favourite
The living area features a light-colored sofa paired with matching armchairs. A small table holds fresh flowers. Soft lighting from lamps creates a comfortable environment. Large sliding doors provide natural light and open to an outdoor patio with a dining set.
Apartment in Brewster
4.96 out of 5 average rating, 95 reviews

Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access

Enjoy this 1,000 SF, 2 bed, 2 full new marle tile bathrooms, 2 showers, at Ocean Edge, right in the middle of the golf course. This Airbnb is a full member of the Ocean Edge Resort and allows you access to Ocean Edge golf, and free resort access included up to 6 guests to swimming pools, tennis, gym & pickleball. No one lives here, it is absent of personal items. From the moment you enter, you will know that you have made a great choice and that your time here will be above your expectations.

Top guest favourite
The balcony offers a view of the lush golf course, framed by trees and natural landscape. A round table with two high stools sits center stage, accompanied by a candle, creating a peaceful outdoor setting for relaxation.
Apartment in Brewster
5 out of 5 average rating, 101 reviews

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

Top guest favourite
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.
Flat in Wellfleet
4.98 out of 5 average rating, 105 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.

Guest favourite
A light-filled living area is presented, featuring a cozy sofa and modern seating around a circular table. A well-equipped kitchen is visible in the background, complemented by large windows that open to the private deck with greenery.
Apartment in North Truro
4.81 out of 5 average rating, 70 reviews

Designer Studio Condo with peeks of Cape Cod Bay.

Beautiful, unique designer condo with custom built ins. 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 very large private deck. Near Atlantic beaches, Truro vineyards, historic lighthouse & Wellfleet. Quiet in unit, 2nd floor, no one above. Guests 21+ welcome. 4 night minimum. 10% discount for 7 nights, 15% discount for 10 nights. Please read more details in 'The Space'

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
4.91 out of 5 average rating, 115 reviews

The Sea Salt Studio - Steps to the Beach!

Gorgeous studio (Unit #1) only 175 yards from white sand Glendon Road beach. 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
Home in Chatham
5 out of 5 average rating, 13 reviews

Luxury Home w/ Salt Water Pool Overlooking Ocean

Welcome to your dream Cape Cod getaway! Our brand-new, fully renovated 4-bedroom, 5-bath luxury home offers breathtaking views of Buck’s Creek and Nantucket Sound, creating the perfect backdrop for your vacation. Inside, you'll find a stunning cathedral-ceiling living room designed for relaxation and gathering. The chef’s kitchen features a massive 15-foot eat-in island, perfect for family breakfasts or evening cocktails. Each of the spacious bedrooms offers comfort and privacy.

Top guest favourite
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.
Flat in Hyannis Port
4.9 out of 5 average rating, 144 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 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, 240 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 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
4.88 out of 5 average rating, 34 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.

Superhost
A scenic view of a coastline is presented, showcasing calm blue waters meeting a sandy beach. Rocky outcrops create a natural border, with a distant lighthouse visible along the horizon. The sky exhibits clear blue tones, enhancing the overall serene landscape.
Apartment in Provincetown
4.89 out of 5 average rating, 109 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!

Top guest favourite
The exterior of the Cape Cod cottage is shown, featuring a light-colored siding and a unique turret-like structure. Lush green landscaping surrounds the home, which is set back from a gently curved pathway. Tall trees provide natural shade in the area.
Townhouse in Brewster
4.87 out of 5 average rating, 113 reviews

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

Quick stats about holiday rentals with a pool in Wellfleet

  • Total holiday rentals

    Explore 10 holiday rentals in Wellfleet

  • Nightly prices starting at

    Wellfleet holiday rentals start at $140 SGD per night before taxes and fees

  • Verified guest reviews

    Over 750 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Wifi availability

    10 of Wellfleet holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wellfleet rentals

  • 4.7 Average rating

    Wellfleet stays receive an average rating of 4.7 out of 5 from guests