Holiday rentals with a pool in Wellfleet

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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
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, 100 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
The expansive pool, surrounded by a landscaped yard, features a vibrant blue surface reflecting the clear sky. Comfortable lounge chairs are positioned alongside, inviting relaxation. A floating inflatable adds a playful touch to the tranquil setting.
Home in Cotuit
4.95 out of 5 average rating, 128 reviews

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 6/20-9/15/24. The reviews tell all!

Guest favourite
The studio features a spacious bed adorned with colorful decorative pillows. A seating area with a small table and golden chairs is visible. Light pours in through sheer curtains, complemented by three framed art pieces on the wall, adding character to the bright space.
Apartment in Dennis Port
4.88 out of 5 average rating, 75 reviews

Stylish & Modern Studio Condo - Steps to the Beach

Stay in a renovated modern, cozy studio style condo with walking distance to Glendon Beach. This stylish airy & bright poolside retreat is perfect for couples and solo travelers. A slider door offers direct access to the shared pool area. The kitchenette features quartz counters, a sink, refrigerator, 2-burner cooktop, and a microwave. Enjoy a restful night's sleep with a memory foam mattress and black-out curtains. The home also has a 24" Roku Smart TV for you to enjoy your favorite shows.

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, 104 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.

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

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
A private outdoor pool area is enclosed by a white fence and surrounded by greenery. The inviting blue water is complemented by sun loungers, an umbrella, and Adirondack chairs positioned for relaxation. The pool area features a spacious patio for sunbathing and outdoor enjoyment.
Home in North Eastham
5 out of 5 average rating, 19 reviews

Heated Pool, Game Room, Projector Room, Private

Relax at this peaceful newly renovated home with every amenity! Come to your very own private resort on Cape Cod, located on a quiet cul-de-sac in Eastham with tons to offer. Central A/C, heated pool, projector theater, game room, fire pit, outdoor grill w/ dining area and much more! Gimlet Getaway, as we have coined this oasis, is the perfect mix of relaxing Cape Cod and every ounce of a good time w/ all modern comforts and amenities. Message me for details! POOL IS SEASONAL (May-Sept)

Top guest favourite
An aerial view showcases a tranquil swimming pool surrounded by a spacious lawn. Adjacent seating areas, including sun loungers and a fire pit with chairs, are positioned within the private fenced yard. Lush greenery and garden beds enhance the outdoor space.
Home in Harwich Center
5 out of 5 average rating, 32 reviews

Harwich Haven: Pool & Fire Pit

Welcome to The Harwich Haven! This 4-bed, 3.5-bath retreat in Harwich, MA offers a spacious family room, modern kitchen, swimming pool, fire pit, two decks with outdoor dining, an outdoor grill, private fenced in yard, two newly renovated ensuite bathrooms with spa amenities and more. With easy access to beaches, restaurants, and shops, it's your perfect vacation getaway! Saturday to Saturday weekly rentals only July & August. 4 night Thursday to Sunday minimum in June.

Top guest favourite
An aerial view of a spacious colonial home surrounded by lush greenery and a well-maintained garden. A sparkling pool is visible, framed by deck chairs and umbrellas, while a small shed is nestled in the garden. The well-manicured landscape enhances the serene setting.
Home in Brewster
5 out of 5 average rating, 20 reviews

Cape Cod Oasis: pool, hot tub, firepit & grill!

Over 4500 sqft of living space in the heart of Cape Cod, with an inviting pool, a hot tub, magnificent garden and expansive outdoor living space big enough to fit your entire party. Welcome to your own private resort! This beautiful custom-built center entrance colonial has room to roam, both inside and out. 5 beds, 5 baths, eco pool, The building is surrounded by lush landscape and tastefully decorated. Fully equipped chef's kitchen. Short drive to the beach!

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, 237 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.

Top guest favourite
A welcoming living area features a comfortable sectional sofa and two wooden armchairs arranged around a circular coffee table. Natural light fills the space, highlighting a large area rug on the hardwood floor. A well-equipped kitchen is visible in the background.
Apartment in New Seabury
4.97 out of 5 average rating, 161 reviews

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

Welcome to Your Coastal Getaway at The Mews, New Seabury – Mashpee, MA Tucked inside the beautiful New Seabury Country Club, our cozy Cape-style condo offers the perfect balance of relaxation and adventure on Cape Cod. Enjoy access to a private condo association pool just a 3-minute walk away, and a beach that is 5 min drive or 10 min bike ride or 30 min walk (walk cuts through golf course-ask host for directions).

Guest favourite
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
4.9 out of 5 average rating, 108 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!

Popular amenities for Wellfleet rentals with a pool

Quick stats about holiday rentals with a pool in Wellfleet

  • Total rentals

    20 properties

  • Nightly prices starting at

    £52 before taxes and fees

  • Total number of reviews

    770 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi and Pool