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 ﺩ.ﺇ 514 per night before taxes and fees

  • Verified guest reviews

    Over 840 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.

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Top guest favorite
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.
Condo in Brewster
5.0 out of 5 average rating, 109 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 favorite
Home in Brewster
4.98 out of 5 average rating, 50 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 favorite
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.
Condo in Dennis Port
4.92 out of 5 average rating, 127 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 favorite
Home in Sandwich
4.99 out of 5 average rating, 100 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 favorite
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
4.89 out of 5 average rating, 38 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 favorite
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, 40 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).

Superhost
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
4.9 out of 5 average rating, 10 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.

Superhost
The exterior of the cottage features a well-maintained lawn with lush green trees in the background. A wooden deck extends from the house, along with patio chairs overlooking a tranquil pond surrounded by vibrant flowers and plants.
Cottage in Centerville
4.89 out of 5 average rating, 107 reviews

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.

Top guest favorite
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.
Apartment in Hyannis Port
4.9 out of 5 average rating, 157 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 favorite
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.
Condo in Provincetown
4.97 out of 5 average rating, 256 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 favorite
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!

Top guest favorite
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
4.88 out of 5 average rating, 120 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